Retinol - Knowledge (XXG)

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increasing vitamin A in the body, such as food modification, fortification, and supplementation, all of which are used to combat vitamin A deficiency. Toxicity is classified into two categories: acute and chronic. The former occurs a few hours or days after ingestion of a large amount of vitamin A. Chronic toxicity takes place when about 4,000 IU/kg or more of vitamin A is consumed for a long time. Symptoms of both include nausea, blurred vision, fatigue, weight-loss, and menstrual abnormalities.

844:, into vitamin A as it is needed, so high levels of carotene are not toxic, whereas the ester (animal) forms are. The livers of certain animals, especially those adapted to polar environments, such as polar bears and seals, often contain amounts of vitamin A that would be toxic to humans. Thus, vitamin A toxicity is typically reported in Arctic explorers and people taking large doses of synthetic vitamin A. The first documented death possibly caused by vitamin A poisoning was that of 924:

pattern of Homeobox (Hox) genes that encode different homeodomain transcription factors which in turn can turn on cell type specific genes. Deletion of the Homeobox (Hox-1) gene from rhombomere 4 makes the neurons growing in that region behave like neurons from rhombomere 2. Retinoic acid is not required for patterning of the retina as originally proposed, but retinoic acid synthesized in the retina is secreted into surrounding

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eight other companies developed their own processes. β-ionone, synthesized from acetone, is the essential starting point for all industrial syntheses. Each process involves elongating the unsaturated carbon chain. Pure retinol is extremely sensitive to oxidization and is prepared and transported at low temperatures and oxygen-free atmospheres. When prepared as a dietary supplement or food additive, retinol is stabilized as the

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manifestations of deficiency as follows: "ancient" accounts; 18th- to 19th-century clinical descriptions (and their purported etiologic associations); early 20th-century laboratory animal experiments, and clinical and epidemiologic observations that identified the existence of this unique nutrient and manifestations of its deficiency.

1787:. When struck by light, 11-cis retinal undergoes photoisomerization to all-trans retinal and via signal transduction cascade send a nerve signal to the brain. The all-trans retinal is reduced to all-trans retinol and travels back to the retinal pigment epithelium to be recycled to 11-cis retinal and conjugated to opsin. 867:. This seems to happen at much lower doses than those required to induce acute intoxication. Only preformed vitamin A can cause these problems, because the conversion of carotenoids or retinyl esters into vitamin A is downregulated when physiological requirements are met; but excessive uptake of carotenoids can cause 3743: 875:

foods containing beta carotene and that they ensure that they consume no more than 5,000 IU of preformed vitamin A (if any) per day. Although vitamin A is necessary for fetal development, most women carry sufficient stores of vitamin A in their liver cells, so over-supplementation should be strictly avoided.

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and each rhombomere has a specific pattern of genes being expressed. If retinoic acid is not present the last four rhombomeres do not develop. Instead, rhombomeres 1–4 grow to cover the same amount of space as all eight would normally occupy. Retinoic acid has its effects by turning on a differential

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Retinoic acid via the retinoic acid receptor influences the process of cell differentiation, hence, the growth and development of embryos. During development, there is a concentration gradient of retinoic acid along the anterior-posterior (head-tail) axis. Cells in the embryo respond to retinoic acid

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Studies emerging from developing countries India, Bangladesh, and Indonesia strongly suggest that, in populations in which vitamin A deficiency is common and maternal mortality is high, dosing expectant mothers with retinol can greatly reduce maternal mortality. Similarly, dosing newborn infants with

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The world market for synthetic retinol is primarily for animal feed, leaving approximately 13% for a combination of food, prescription medication and dietary supplement use. The first industrialized synthesis of retinol was achieved by the company Hoffmann-La Roche in 1947. In the following decades,

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Vitamin A acute toxicity occurs when a person ingests vitamin A in large amounts more than the daily recommended value in the threshold of 25,000 IU/kg or more. Often, the patient consumes about 3–4 times the RDA's specification. Toxicity of vitamin A is believed to be associated with the methods of

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Vitamin A deficiency is common in developing countries but rarely seen in developed countries. Approximately 250,000 to 500,000 malnourished children in the developing world go blind each year from a deficiency of vitamin A. Vitamin A deficiency in expecting mothers increases the mortality rate of

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Excess preformed vitamin A during early pregnancy is associated with a significant increase in birth defects. These defects may be severe, even life-threatening. Even twice the daily recommended amount can cause severe birth defects. The FDA recommends that pregnant women get their vitamin A from

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This vitamin plays an essential role in vision, particularly night vision, normal bone and tooth development, reproduction, and the health of skin and mucous membranes (the mucus-secreting layer that lines body regions such as the respiratory tract). While Vitamin A is often considered to be an

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Although vitamin A was not confirmed as an essential nutrient and a chemical structure described until the 20th century, written observations of conditions created by deficiency of this nutrient appeared much earlier in history. Sommer classified historical accounts related to vitamin A and/or

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Retinol or other forms of vitamin A are needed for eyesight, maintenance of the skin, and human development. Other than for vision, which requires 11-cis retinal, the active compound is retinoic acid, synthesized from retinal, in turn synthesized from retinol. The differing biological roles of

1577:. The non-visual functions of vitamin A are essential in the immunological function, reproduction and embryonic development of vertebrates as evidenced by the impaired growth, susceptibility to infection and birth defects observed in populations receiving suboptimal vitamin A in their diet. 3341:

Goodman GE, Thornquist MD, Balmes J, Cullen MR, Meyskens FL, Omenn GS, et al. (December 2004). "The Beta-Carotene and Retinol Efficacy Trial: incidence of lung cancer and cardiovascular disease mortality during 6-year follow-up after stopping beta-carotene and retinol supplements".

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controlled 96% of global vitamin A sales. In 2001, the European Commission imposed total fines of 855.22 Euros on these and five other companies for their participation in eight distinct market-sharing and price-fixing cartels that dated back to 1989. Roche sold its vitamin division to

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in skin cells respond to pathogens and cell damage by inducing a pro-inflammatory immune response which includes increased RA production. The epithelium of the skin encounters bacteria, fungi and viruses. Keratinocytes of the epidermal layer of the skin produce and secrete

1696: 1375:, the most well-known being β-carotene. For this reason, amounts of vitamin A are measured in Retinol Equivalents (RE). One RE is equivalent to 0.001 mg of retinol, or 0.006 mg of β-carotene, or 3.3 International Units of vitamin A. 830:(RDA) for preformed supplemental vitamin A for adult men and women is 900 and 700 Retinol Activity Units(RAE)/day, respectively, or about 3,000 IU and 2,300 IU. In pregnancy, the vitamin A RDA is 750–770 RAE/day (about 2,500–2,550 IU). During 1378:

Vitamin A is fat-soluble and is stored in the liver and fat tissue. When required by a particular part of the body, the liver releases some vitamin A, which is carried by the blood and delivered to the target cells and tissues.

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of stem cells to more committed fates, echoing retinoic acid's importance in natural embryonic developmental pathways. It is thought to initiate differentiation into a number of different cell lineages through activation of the

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By giving high-doses of vitamin A to the targeted deficient population, a method known as supplementation. In regions where deficiency is common, a single large dose is recommended to those at high risk twice a

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mortality by 5% and 16%, respectively. This effect has been attributed to the role of retinol and retinoic acid in increasing circulating cholesterol and triglycerides as well as promoting cancer incidence.

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precursors, also known as provitamins, which must be converted to active forms by the body. These are obtained from fruits and vegetables containing yellow, orange and dark green pigments, known as

1410:. Liver cells store vitamin A as the ester, and when retinol is needed in other tissues, it is de-esterifed and released into the blood as the alcohol. Retinol then attaches to a serum carrier, 837:

Retinol Activity Units can only be converted to IU (International Units) when the source of the vitamin A is known. The IU values listed above do not apply to food sources of vitamin A.

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secretion, which is a nutrient source for bacteria. Retinol has been the subject of clinical studies related to its ability to reduce the appearance of fine lines on the face and neck.

5660: 5166: 1755:, also in 1913, which suggested a fat-soluble nutrient in butterfat. The "accessory factors" were termed "fat soluble" in 1918 and later "vitamin A" in 1920. In 1931, Swiss chemist 1206:(IU). IU refers to biological activity and therefore is unique to each individual compound, however 1 IU of retinol is equivalent to approximately 0.3 micrograms (300 nanograms). 1610:. This epoxide is then attacked by water creating two hydroxyl groups in the center of the structure. The cleavage occurs when these alcohols are oxidized to the aldehydes using 140: 2671:

Klemm RD, Labrique AB, Christian P, Rashid M, Shamim AA, Katz J, et al. (July 2008). "Newborn vitamin A supplementation reduced infant mortality in rural Bangladesh".

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was a co-recipient of the Nobel Prize in Physiology and Medicine "..."for their discoveries concerning the primary physiological and chemical visual processes in the eye."

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Mucida D, Park Y, Kim G, Turovskaya O, Scott I, Kronenberg M, et al. (July 2007). "Reciprocal TH17 and regulatory T cell differentiation mediated by retinoic acid".

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Retinoids are found naturally only in foods of animal origin. Each of the following contains at least 0.15 mg of retinoids per 1.75–7 oz (50–198 g):

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where it is required to prevent overgrowth of perioptic mesenchyme which can cause microphthalmia, defects in the cornea and eyelid, and rotation of the optic cup.

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Enriching commonly eaten and affordable foods with vitamin A, a process called fortification. It involves addition of synthetic vitamin A to staple foods like

3741:, Herloff IH, Horst P, "Compounds with the carbon skeleton of beta-carotene and process for the manufacture thereof", published 2 September 1952. 1847:"75 Years of Vitamin A Production: A Historical and Scientific Overview of the Development of New Methodologies in Chemistry, Formulation, and Biotechnology" 856:

expedition that had lost its food supplies and fell to eating its sled dogs. Mertz may have consumed lethal amounts of vitamin A by eating the dogs' livers.

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protein (either rod opsin or blue, red or green cone opsins). The process of vision relies on the light-induced isomerisation of the chromophore from 11-

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is one of the first signs of vitamin A deficiency. Vitamin A deficiency contributes to blindness by depleting the necessary form needed for rhodopsin.

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Through dietary modification involving the adjustment of menu choices of affected persons from available food sources to optimize vitamin A content.

1414:, for transport to target tissues. A binding protein inside cells, cellular retinoic acid binding protein, serves to store and move retinoic acid 3722:, Wittig G, Pommer H, "Compounds of the vitamin A series", issued 1959, assigned to Badische Anilin- & Soda-Fabrik Akt.-Ges. 1141:

Deficiencies in vitamin A have been linked to an increased susceptibility to skin infection and inflammation. Vitamin A appears to modulate the

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The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023)

763: 1603: 2048: 1728: 945:. It has numerous applications in the experimental induction of stem cell differentiation; amongst these are the differentiation of human 3703:, Wittig G, Pommer H, "Verfahren zur Herstellung von best-Carotin bzw. 15,15'-Dehydro-beta-carotin", issued 13 December 1956. 2018: 1759:

described the chemical structure of vitamin A. Retinoic acid and retinol were first synthesized in 1946 and 1947 by two Dutch chemists,

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InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

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Vitamin A is involved in maintaining a number of immune cell types from both the innate and acquired immune systems. These include the

4112: 3684: 2275: 2488:"Mortality in randomized trials of antioxidant supplements for primary and secondary prevention: systematic review and meta-analysis" 2209: 2042: 2012: 1985: 667: 2332: 1930:"A comparative study of the effects of retinol and retinoic acid on histological, molecular, and clinical properties of human skin" 1573:

Many of the non-visual functions of vitamin A are mediated by retinoic acid, which regulates gene expression by activating nuclear

774:. In 2021, vitamin A was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions. 2419: 1364:

antioxidant that prevents cancers, it does not have antioxidant activity and is shown to promote the development of many cancers.

2396: 2518: 1015:-retinal. The change in the shape of the molecule in turn changes the configuration of the opsin in a cascade that leads to the 4427: 233: 200: 80: 2098: 1367:

There are two sources of dietary vitamin A. Retinyl ester or retinol forms, which are immediately available to the body or

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Blaner WS, Shmarakov IO, Traber MG (October 2021). "Vitamin A and Vitamin E: Will the Real Antioxidant Please Stand Up?".

1744: 1232: 5600: 5665: 5586: 379: 5416: 5202: 4755: 4436: 4418: 495: 2632:"Newborn vitamin A dosing reduces the case fatality but not incidence of common childhood morbidities in South India" 99: 5650: 4787: 2189: 2062: 1704: 5534: 1093:

synthesis requires adequate vitamin A status. In severe vitamin A deficiency, lack of glycoproteins may lead to

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are less affected. The cones are less abundant than rods and come in three types, each contains its own type of

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differently depending on the amount present. For example, in vertebrates, the hindbrain transiently forms eight

4249: 3306:"The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers". 1388: 937: 827: 1719:

were necessary for growth in rats. Hopkins received a Nobel Prize for this discovery in 1929. One year later,

328: 1391:(DRI) Recommended Daily Amount (RDA) for vitamin A for a 25-year-old male is 900 micrograms/day, or 3000 IU. 5635: 4743: 4068: 4064: 3986: 1499:

Many different geometric isomers of retinol, retinal and retinoic acid are possible as a result of either a

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Parker GL, Smith LK, Baxendale IR (February 2016). "Development of the industrial synthesis of vitamin A".

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Burri BJ, Clifford AJ (October 2004). "Carotenoid and retinoid metabolism: insights from isotope studies".

712:. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and 534: 5186: 4105: 1760: 1590: 1574: 1155: 1142: 1047:-retinol in a sequence of chemical transformations that occurs primarily in the pigment epithelial cells. 942: 897:

50,000 IU (15 mg) of vitamin A within two days of birth can significantly reduce neonatal mortality.

879: 736:. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging. 5640: 5630: 3046:"Illuminating the Role of Vitamin A in Skin Innate Immunity and the Skin Microbiome: A Narrative Review" 1615: 1551: 319: 215: 5133: 3095: 2630:

Tielsch JM, Rahmathullah L, Thulasiraj RD, Katz J, Coles C, Sheeladevi S, et al. (November 2007).

1190:. Vitamin A is needed to produce the red blood cells from stem cells through retinoid differentiation. 834:, the RDA increases to 1,200–1,300 RAE/day (about 4,000–4,300 IU, with differences depending on age). 5454: 5335: 3738: 3719: 456: 5449: 4780: 4704: 4484: 4208: 3942: 3887: 3700: 3207:"Vitamin A and beta-carotene can improve nonheme iron absorption from rice, wheat and corn by humans" 1427: 1118: 783: 721: 3878:

Arens JF, Van Dorp DA (February 1946). "Synthesis of some compounds possessing vitamin A activity".

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daily recommended values are slightly lower at 700 micrograms for men and 600 micrograms for women.

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occurs. Night blindness, the inability to see well in dim light, is associated with a deficiency of

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García-Casal MN, Layrisse M, Solano L, Barón MA, Arguello F, Llovera D, et al. (March 1998).

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Oren T, Sher JA, Evans T (November 2003). "Hematopoiesis and retinoids: development and disease".

5178: 4377: 4272: 4037: 3968: 3911: 3819: 3510: 3146: 2977: 2696: 1959: 1903: 1772: 1203: 1166:, are promoted by RA. Another way that vitamin A helps maintain a healthy skin and hair follicle 1146: 988: 972: 821: 767: 744: 709: 5355: 5123: 3414:"Adipocyte HSL is required for maintaining circulating vitamin A and RBP4 levels during fasting" 2439:"Adipocyte HSL is required for maintaining circulating vitamin A and RBP4 levels during fasting" 2348:"Adipocyte HSL is required for maintaining circulating vitamin A and RBP4 levels during fasting" 963:

Retinol is an essential compound in the cycle of light-activated chemical reactions called the "

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Akhtar S, Ahmed A, Randhawa MA, Atukorala S, Arlappa N, Ismail T, et al. (December 2013).

2032: 1019:, which signals the detection of light. The opsin then splits into the protein component (such 477: 5655: 5524: 5494: 5380: 5370: 5221: 5175: 4664: 4639: 4098: 4029: 3960: 3903: 3860: 3811: 3680: 3642: 3567: 3492: 3443: 3394: 3359: 3323: 3288: 3228: 3187: 3138: 3077: 3019: 2957: 2926: 2869:

Purves D, Augustine GJ, Fitzpatrick D, Katz LC, LaMantia AS, McNamara JO, et al. (2001).

2851: 2799: 2747: 2716:"The pathogenic role of retinoid nuclear receptor signaling in cancer and metabolic syndromes" 2688: 2653: 2612: 2568: 2537:"The pathogenic role of retinoid nuclear receptor signaling in cancer and metabolic syndromes" 2510: 2468: 2377: 2256: 2205: 2168: 2038: 2008: 2002: 1981: 1951: 1868: 1845:

Bonrath W, Gao B, Houston P, McClymont T, Müller MA, Schäfer C, et al. (September 2023).

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Steinhoff JS, Wagner C, Dähnhardt HE, Košić K, Meng Y, Taschler U, et al. (July 2024).

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Steinhoff JS, Wagner C, Dähnhardt HE, Košić K, Meng Y, Taschler U, et al. (July 2024).

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Steinhoff JS, Wagner C, Dähnhardt HE, Košić K, Meng Y, Taschler U, et al. (July 2024).

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and mucosa through its metabolite, retinoic acid (RA). As part of the innate immune system,

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Too much vitamin A in retinoid form can be harmful. The body converts the dimerized form,

4327: 4322: 4317: 4312: 1133:). Vitamin A maintains immune barriers in the gut through its activity as retinoic acid. 3946: 3891: 3438: 3413: 2742: 2715: 2563: 2536: 2463: 2438: 2372: 2347: 2324: 1570:

resulting in a change of the conformation and activation of the photoreceptor molecule.

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Retinol was discovered in 1909, isolated in 1931, and first made in 1947. It is on the

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Amengual J, Zhang N, Kemerer M, Maeda T, Palczewski K, Von Lintig J (October 2014).

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Amengual J, Zhang N, Kemerer M, Maeda T, Palczewski K, Von Lintig J (October 2014).

3150: 2700: 1963: 1614:. This compound is called retinal. Retinal is then reduced to retinol by the enzyme 1432: 5459: 5421: 5325: 5305: 5300: 5207: 5113: 5093: 5015: 4977: 4967: 4947: 4932: 4859: 4724: 4644: 4603: 4556: 4523: 4503: 4498: 4359: 4287: 4277: 4267: 4125: 4041: 3972: 1708: 1535:

isomers are found naturally and carry out essential functions. For example, the 11-

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Thompson J, Manore M (2005). "Ch. 8: Nutrients involved in antioxidant function".

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Kong R, Cui Y, Fisher GJ, Wang X, Chen Y, Schneider LM, et al. (March 2016).

37: 3182: 3165: 2953: 1823: 1058:, a class of compounds that includes retinol and retinal. In the early stages of 1050:

Without adequate amounts of retinol, regeneration of rhodopsin is incomplete and

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A review of all randomized controlled trials in the scientific literature by the

72: 5340: 5295: 5108: 4972: 4952: 4937: 4907: 4889: 4879: 4869: 4656: 4513: 4334: 4226: 4074: 3319: 3134: 2120: 1906:. Office of Dietary Supplements, National Institutes of Health. 15 December 2023 1826:. Drugs.com, The American Society of Health-System Pharmacists. 12 December 2024 1776: 1768: 1756: 1695: 1555: 1540: 1512: 1403: 1126: 1122: 1106: 920: 868: 849: 5144: 3585: 3429: 2870: 2837: 2785: 2454: 2363: 46: 5439: 5330: 5290: 5118: 5103: 5098: 4982: 4962: 4942: 4803: 4594: 4586: 4579: 4543: 4536: 4463: 4409: 4391: 4307: 4282: 4256: 4231: 4190: 3777: 3390: 1724: 1650:. The two major suppliers, DSM and BASF, are believed to use total synthesis. 1554:

molecule. Rhodopsin is composed of the 11-cis-retinal covalently linked via a

1548: 1479: 1372: 1222: 1167: 925: 853: 716:, immune function and reproductive development. Dietary sources include fish, 575: 359: 128: 5570:

6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid

3628: 2648: 2631: 2607: 2590: 2163: 2146: 1872: 1863: 1846: 257:)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol 5488: 5430: 5390: 5319: 5236: 5231: 5226: 5128: 5088: 5040: 4699: 4691: 4608: 4574: 4400: 4369: 4299: 4176: 4166: 4143: 3015: 1736: 1544: 1454: 1399: 1275: 1263: 1251: 1239: 1199: 1071: 1067: 1059: 1055: 996: 831: 797: 748: 705: 66: 4033: 3964: 3907: 3864: 3855: 3838: 3815: 3646: 3571: 3496: 3447: 3398: 3363: 3292: 3223: 3206: 3191: 3142: 3081: 3023: 2930: 2855: 2803: 2751: 2692: 2684: 2657: 2616: 2572: 2514: 2506: 2486:

Bjelakovic G, Nikolova D, Gluud LL, Simonetti RG, Gluud C (February 2007).

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as the ester form, and it is these particles that mediate transport to the

3355: 3327: 3232: 2895:"Retinol Dehydrogenases Regulate Vitamin A Metabolism for Visual Function" 5080: 5025: 4874: 4864: 4854: 4811: 4477: 3553: 3478: 2732: 2553: 1368: 1159: 1075: 1063: 992: 841: 789:

Three approaches may be used when populations have low vitamin A levels:

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Starck T (1997). "Severe Corneal Ulcerations and Vitamin A Deficiency".

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The Role of Food, Agriculture, Forestry and Fisheries in Human Nutrition

1626: 967:" that underlies vertebrate vision. Retinol is converted by the protein 348: 29: 5060: 4121: 3062: 2201: 1946: 1929: 1712: 1607: 1516: 1114: 1110: 809: 752: 701: 294: 133: 20: 3807: 2911: 2397:"Caution Urged With Vitamin A in Pregnancy: But Beta-Carotene is Safe" 2242: 1707:

demonstrated that unknown accessory factors found in milk, other than

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Frederick Gowland Hopkins, 1929 Nobel Prize for Physiology or Medicine

1027:-retinal. The regeneration of active opsin requires conversion of all- 5035: 4957: 4634: 4621: 4551: 3955: 3930: 3899: 1679:

in 2003. DSM and BASF have the major share of industrial production.

1484: 1468: 984: 976: 447: 2591:"Vitamin a deficiency and clinical disease: an historical overview" 910:

and whether it is present in the all-trans, 9-cis or 13-cis forms.

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in 2007 found that supplementation with beta carotene or vitamin A

416: 5020: 2822:"Retinoic acid synthesis and signaling during early organogenesis" 2770:"Retinoic acid synthesis and signaling during early organogenesis" 1780: 1694: 1686: 1655: 1625: 1589: 1559: 1431: 1407: 1346: 1171: 1000: 968: 598: 589: 483: 427: 4090: 4012:

Ebrey T, Koutalos Y (January 2001). "Vertebrate photoreceptors".

3538:"STRA6 is critical for cellular vitamin A uptake and homeostasis" 3463:"STRA6 is critical for cellular vitamin A uptake and homeostasis" 1003:

protein and acts as a light-activated molecular switch. When 11-

1667: 1639: 1618:. Retinol dehydrogenase is an enzyme that is dependent on NADH. 1611: 1488: 739:

Retinol at normal doses is well tolerated. High doses may cause

407: 5148: 4776: 4094: 1980:(69 ed.). British Medical Association. 2015. p. 701. 800:, bread, flours, cereals, and infant formula during processing. 209: 89: 4772: 1716: 1531:-retinol shown at the top of this page). Nevertheless, some 808:

Retinol is also used to reduce the risk of complications in

720:, and meat. As a supplement it is used to treat and prevent 500: 2227:"The vitamin A content and toxicity of bear and seal liver" 1606:

cleaves β-carotene at the central double bond, creating an

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isomers are less stable and can readily convert to the all-

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George Wald, 1967 Nobel Prize for Physiology or Medicine

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World Health Organization's List of Essential Medicines

5598: 1039:-retinal occurs in vertebrates via conversion of all- 983:-retinal. This molecule is then transported into the 863:

Excess vitamin A is suspected to be a contributor to

3794:

Semba RD (2012). "On the 'discovery' of vitamin A".

2276:"Man's best friend? (An account of Mertz's illness)" 5399: 5185: 5079: 5049: 4996: 4888: 4810: 4717: 4690: 4462: 4453: 4368: 4298: 4175: 4142: 4133: 3586:"Micronutrient deficiencies - Vitamin A deficiency" 3166:"Regulation of hematopoiesis by retinoid signaling" 633: 619: 609: 587: 574: 550: 545: 526: 494: 466: 446: 426: 406: 378: 358: 338: 327: 318: 293: 265: 224: 199: 194: 139: 127: 109: 79: 61: 56: 3839:"Vitamin A as "anti-infective" therapy, 1920-1940" 2037:. John Wiley & Sons. 2016. p. Chapter 2. 1062:deficiency, the more light-sensitive and abundant 2007:. Vol. IV. EOLSS Publications. p. 121. 751:may harm the fetus. The body converts retinol to 3987:"The Nobel Prize in Physiology or Medicine 1967" 1904:"Vitamin A: Fact Sheet for Health Professionals" 307: 2815: 2813: 2714:Esposito M, Amory JK, Kang Y (September 2024). 2535:Esposito M, Amory JK, Kang Y (September 2024). 2192:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.). 1527:configuration (as seen in the structure of all- 282: 274: 5187: 2978:"Vitamin A directs immune cells to intestines" 5661:World Health Organization essential medicines 5160: 4788: 4106: 4075:NIH Office of Dietary Supplements – Vitamin A 3759: 3757: 3755: 3753: 1598:Retinol is synthesized from the breakdown of 1170:, especially on the face, is by reduction of 1078:, the opsins of the cones. The cones mediate 1035:-retinal via retinol. The regeneration of 11- 8: 3617:Journal of Health, Population, and Nutrition 3039: 3037: 3035: 3033: 98: 28: 5401: 1923: 1921: 1082:, and vision in bright light (day vision). 708:family that is found in food and used as a 5167: 5153: 5145: 4795: 4781: 4773: 4459: 4232:Calcitriol (1,25-dihydroxycholecalciferol) 4139: 4113: 4099: 4091: 3044:Roche FC, Harris-Tryon TA (January 2021). 2312:. Pearson Education Inc. pp. 276–283. 2196:. World Health Organization. p. 500. 2184: 2182: 1851:Organic Process Research & Development 1436:Prevalence of vitamin A deficiency in 1995 852:scientist, who died in January 1913 on an 655:OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)/CCCC1(C)C 537: 514: 367: 45: 36: 3954: 3854: 3636: 3561: 3486: 3437: 3222: 3181: 3071: 3061: 2920: 2910: 2845: 2793: 2741: 2731: 2647: 2606: 2584: 2582: 2562: 2552: 2462: 2371: 2323:Mohsen SE, Mckinney K, Shanti MS (2008). 2250: 2162: 2074: 1945: 1862: 1666:. Prior to 1999, three companies, Roche, 395: 387: 3789: 3787: 3344:Journal of the National Cancer Institute 1978:British national formulary : BNF 69 1213: 1202:science, retinol is usually measured in 1198:When referring to dietary allowances or 5605: 3662:Vitamins and Your Health. Nutrition Now 3379:Archives of Biochemistry and Biophysics 2295:Advanced Nutrition and Human Metabolism 2293:Gropper SS, Smith JL, Groff JL (2009). 1818: 1816: 1814: 1812: 1810: 1808: 1806: 1804: 1800: 999:cells in mammals) where it binds to an 672: 652: 510: 347: 238: 528: 27: 4085:Merck Manual of Diagnosis and Therapy 4062:", Micronutrient Information Center, 3929:Van Dorp DA, Arens JF (August 1947). 2948:. Springer, Boston, MA. p. 558. 2888: 2886: 2884: 2763: 2761: 2524:from the original on 4 February 2016. 2069:. Geneva: World Health Organization. 2051:from the original on 5 November 2017. 2034:Ullmann's Food and Feed, 3 Volume Set 2021:from the original on 5 November 2017. 1898: 1896: 1894: 1892: 1890: 1888: 1886: 1884: 1882: 1735:identified a fat-soluble nutrient in 1398:During the absorption process in the 1186:; deficiency causes abnormalities in 1070:, have impaired sensitivity, and the 476: 455: 435: 71: 7: 5388:Retinoic acid metabolism inhibitors: 4014:Progress in Retinal and Eye Research 3993:from the original on 4 December 2013 3796:Annals of Nutrition & Metabolism 2720:The Journal of Experimental Medicine 2541:The Journal of Experimental Medicine 2101:from the original on 15 January 2024 482: 182: 172: 162: 152: 3511:"Vitamins and minerals - Vitamin A" 3308:The New England Journal of Medicine 2877:(2nd ed.). Sinauer Associates. 2422:. United States FDA. Archived from 2121:"Vitamin A - Drug Usage Statistics" 1638:using either a method developed by 1476:(beef, pork, chicken, turkey, fish) 1441:children shortly after childbirth. 1182:Vitamin A may be needed for normal 936:Synthetic retinoic acid is used in 724:, especially that which results in 625:137–138 °C (279–280 °F) ( 415: 298: 4428:2-Methylnaphthalene-1,4-diamine (K 3381:. Highlight issue on Carotenoids. 3285:10.1146/annurev-nutr-082018-124228 2335:from the original on 23 July 2013. 2297:(5th ed.). pp. 373–1182. 1511:configuration of four of the five 14: 3931:"Synthesis of vitamin A aldehyde" 2893:Sahu B, Maeda A (November 2016). 2401:The Nutrition Reporter Newsletter 1634:Retinol is made industrially via 5608: 639:0.000017 mg/mL (20 °C) 562: 2225:Rodahl K, Moore T (July 1943). 1934:Journal of Cosmetic Dermatology 1743:. Their work confirmed that of 1729:University of Wisconsin–Madison 1604:β-carotene 15,15'-monooxygenase 1402:, retinol is incorporated into 1271:RDA upper limit (adult female) 1121:), as well as many myelocytes ( 949:to posterior foregut lineages. 680:Key:FPIPGXGPPPQFEQ-OVSJKPMPSA-N 615:62–64 °C (144–147 °F) 5192:Tooltip Retinoic acid receptor 4437:4-Amino-3-methyl-1-naphthol (K 4419:4-Amino-2-methyl-1-naphthol (K 3664:(3rd ed.). pp. 1–20. 2310:Nutrition: An Applied Approach 2145:Schultink W (September 2002). 568: 556: 1: 5587:Receptor/signaling modulators 5426:-Retinoic acid (alitretinoin) 5212:-Retinoic acid (alitretinoin) 4026:10.1016/S1350-9462(00)00014-8 3314:(15): 1029–1035. April 1994. 2420:"Vitamin A and Birth Defects" 1259:RDA upper limit (adult male) 1145:and maintains homeostasis of 3183:10.1016/j.exphem.2005.06.007 2954:10.1007/978-1-4615-5389-2_46 2946:Advances in Corneal Research 2820:Duester G (September 2008). 2768:Duester G (September 2008). 906:retinoic acid depend on its 766:. Retinol is available as a 5406:Tooltip Retinoid X receptor 3320:10.1056/NEJM199404143301501 3135:10.1080/1042819031000116661 3096:"Vitamin A and Skin Health" 1763:and Jozef Ferdinand Arens. 1158:(AMPs). Production of AMPs 5682: 5535:LE135 (RAR beta selective) 5435:-Retinoic acid (tretinoin) 5241:-Retinoic acid (tretinoin) 3677:Medicinal Natural Products 3430:10.1038/s44319-024-00158-x 3273:Annual Review of Nutrition 3164:Evans T (September 2005). 2838:10.1016/j.cell.2008.09.002 2786:10.1016/j.cell.2008.09.002 2455:10.1038/s44319-024-00158-x 2418:Stone B (6 October 1995). 2364:10.1038/s44319-024-00158-x 2079:. WHO/MHP/HPS/EML/2023.02. 1452: 1425: 1007:-retinal absorbs light it 956: 819: 759:, through which it acts. 546:Chemical and physical data 18: 5578: 4733: 4227:25-hydroxycholecalciferol 3778:10.1016/j.tet.2016.02.029 3590:World Health Organization 3391:10.1016/j.abb.2004.04.028 2589:Sommer A (October 2008). 2190:World Health Organization 2063:World Health Organization 1705:Frederick Gowland Hopkins 1343: 1338: 1311: 1306: 1287: 1282: 1216: 782:Retinol is used to treat 663: 643: 229: 44: 35: 3843:The Journal of Nutrition 3629:10.3329/jhpn.v31i4.19975 3542:Human Molecular Genetics 3467:Human Molecular Genetics 3211:The Journal of Nutrition 2636:The Journal of Nutrition 2595:The Journal of Nutrition 2194:WHO Model Formulary 2008 2157:(9 Suppl): 2881S–2883S. 2151:The Journal of Nutrition 1864:10.1021/acs.oprd.3c00161 1779:composed of the protein 1455:Vitamin_A § Sources 1389:Dietary Reference Intake 1184:red blood cell formation 828:Recommended Daily Intake 741:enlargement of the liver 19:Not to be confused with 4069:Oregon State University 4065:Linus Pauling Institute 3837:Semba RD (April 1999). 3170:Experimental Hematology 3123:Leukemia & Lymphoma 3100:Linus Pauling Institute 3016:10.1126/science.1145697 2231:The Biochemical Journal 1575:retinoic acid receptors 1539:-retinal isomer is the 1412:retinol binding protein 1393:National Health Service 1023:) and the cofactor all- 734:injection into a muscle 5050:Vitamin A retinoids (C 3247:"Carotenoid Oxygenase" 2685:10.1542/peds.2007-3448 2649:10.1093/jn/137.11.2470 2608:10.1093/jn/138.10.1835 2507:10.1001/jama.297.8.842 2164:10.1093/jn/132.9.2881S 1761:David Adriaan van Dorp 1700: 1692: 1631: 1595: 1594:Vitamin A biosynthesis 1437: 1332:(suspected, long-term) 1156:antimicrobial peptides 1143:innate immune response 1086:Glycoprotein synthesis 943:Retinoic acid receptor 880:Cochrane Collaboration 4250:Dihydroergocalciferol 2091:"The Top 300 of 2021" 1775:in the eye contain a 1698: 1690: 1629: 1616:retinol dehydrogenase 1593: 1435: 5450:Docosahexaenoic acid 4705:Dehydroascorbic acid 4209:7-Dehydrocholesterol 4080:Vitamin A Deficiency 3989:. Nobel Foundation. 3856:10.1093/jn/129.4.783 3224:10.1093/jn/128.3.646 2733:10.1084/jem.20240519 2554:10.1084/jem.20240519 2407:on 1 September 2004. 2325:"Vitamin A toxicity" 1622:Industrial synthesis 1428:Vitamin A deficiency 1283:Deficiency symptoms 1194:Units of measurement 1119:natural killer cells 1031:-retinal back to 11- 947:embryonic stem cells 784:vitamin A deficiency 747:. High doses during 722:vitamin A deficiency 5666:Ophthalmology drugs 4599:Pyridoxal phosphate 3947:1947Natur.160..189V 3892:1946Natur.157..190A 3356:10.1093/jnci/djh320 2871:"Phototransduction" 2426:on 4 February 2004. 2282:on 29 January 2007. 2001:Squires VR (2011). 1773:Photoreceptor cells 1745:Thomas Burr Osborne 1247:RDA (adult female) 1217:Vitamin properties 1204:international units 1151:toll-like receptors 989:photoreceptor cells 700:, is a fat-soluble 635:Solubility in water 32: 4760:Never to phase III 4273:Dihydrotachysterol 3675:Dewick PM (2009). 3554:10.1093/hmg/ddu258 3479:10.1093/hmg/ddu258 3063:10.3390/nu13020302 2395:Challem J (1995). 1947:10.1111/jocd.12193 1701: 1693: 1632: 1596: 1438: 1147:epithelial tissues 973:pigment epithelium 822:Hypervitaminosis A 768:generic medication 745:hypervitaminosis A 710:dietary supplement 5596: 5595: 5176:Retinoid receptor 5142: 5141: 5134:Zuretinol acetate 4770: 4769: 4713: 4712: 4665:Adenosylcobalamin 4640:Dihydrofolic acid 4449: 4448: 3886:(3981): 190–191. 3808:10.1159/000343124 3660:Brown JE (2002). 3548:(20): 5402–5417. 3517:. 23 October 2017 3473:(20): 5402–5417. 3350:(23): 1743–1750. 3129:(11): 1881–1891. 3102:. 7 November 2016 3010:(5835): 256–260. 2963:978-1-4613-7460-2 2912:10.3390/nu8110746 2642:(11): 2470–2474. 2601:(10): 1835–1839. 2243:10.1042/bj0370166 1664:retinyl palmitate 1644:Grignard reaction 1361: 1360: 1097:or liquefaction. 932:Stem cell biology 688: 687: 600:Interactive image 496:CompTox Dashboard 213: 92: 16:Chemical compound 5673: 5651:Primary alcohols 5613: 5612: 5611: 5604: 5455:Fluorobexarotene 5407: 5403: 5336:Tazarotenic acid 5193: 5189: 5169: 5162: 5155: 5146: 4797: 4790: 4783: 4774: 4675:Hydroxocobalamin 4650:Levomefolic acid 4570:Pantothenic acid 4460: 4383:Phylloquinone (K 4140: 4115: 4108: 4101: 4092: 4046: 4045: 4009: 4003: 4002: 4000: 3998: 3983: 3977: 3976: 3958: 3956:10.1038/160189a0 3926: 3920: 3919: 3900:10.1038/157190a0 3875: 3869: 3868: 3858: 3834: 3828: 3827: 3791: 3782: 3781: 3761: 3748: 3747: 3746: 3742: 3735: 3729: 3728: 3727: 3723: 3716: 3710: 3709: 3708: 3704: 3697: 3691: 3690: 3672: 3666: 3665: 3657: 3651: 3650: 3640: 3608: 3602: 3601: 3599: 3597: 3582: 3576: 3575: 3565: 3533: 3527: 3526: 3524: 3522: 3507: 3501: 3500: 3490: 3458: 3452: 3451: 3441: 3424:(7): 2878–2895. 3409: 3403: 3402: 3374: 3368: 3367: 3338: 3332: 3331: 3303: 3297: 3296: 3268: 3262: 3261: 3259: 3257: 3243: 3237: 3236: 3226: 3202: 3196: 3195: 3185: 3176:(9): 1055–1061. 3161: 3155: 3154: 3118: 3112: 3111: 3109: 3107: 3092: 3086: 3085: 3075: 3065: 3041: 3028: 3027: 2999: 2993: 2992: 2990: 2988: 2974: 2968: 2967: 2941: 2935: 2934: 2924: 2914: 2890: 2879: 2878: 2866: 2860: 2859: 2849: 2817: 2808: 2807: 2797: 2765: 2756: 2755: 2745: 2735: 2711: 2705: 2704: 2679:(1): e242–e250. 2668: 2662: 2661: 2651: 2627: 2621: 2620: 2610: 2586: 2577: 2576: 2566: 2556: 2532: 2526: 2525: 2523: 2492: 2483: 2477: 2476: 2466: 2449:(7): 2878–2895. 2434: 2428: 2427: 2415: 2409: 2408: 2403:. Archived from 2392: 2386: 2385: 2375: 2358:(7): 2878–2895. 2343: 2337: 2336: 2320: 2314: 2313: 2305: 2299: 2298: 2290: 2284: 2283: 2278:. Archived from 2271: 2265: 2264: 2254: 2222: 2216: 2215: 2186: 2177: 2176: 2166: 2142: 2136: 2135: 2133: 2131: 2117: 2111: 2110: 2108: 2106: 2087: 2081: 2080: 2078: 2059: 2053: 2052: 2029: 2023: 2022: 1998: 1992: 1991: 1974: 1968: 1967: 1949: 1925: 1916: 1915: 1913: 1911: 1900: 1877: 1876: 1866: 1842: 1836: 1835: 1833: 1831: 1820: 1749:Lafayette Mendel 1733:Marguerite Davis 1731:, and colleague 1648:Hoffman-La Roche 1349:and other organs 1307:Excess symptoms 1214: 901:Biological roles 772:over the counter 743:, dry skin, and 714:mucous membranes 628: 602: 582: 570: 564: 558: 541: 530: 519: 518: 504: 502: 486: 480: 459: 439: 419: 399: 391: 371: 351: 331: 311: 301: 300: 286: 278: 211: 208: 186: 176: 166: 156: 102: 91: 88: 75: 49: 40: 33: 31: 5681: 5680: 5676: 5675: 5674: 5672: 5671: 5670: 5621: 5620: 5619: 5609: 5607: 5599: 5597: 5592: 5574: 5405: 5395: 5191: 5181: 5173: 5143: 5138: 5075: 5053: 5045: 5003: 4992: 4895: 4884: 4817: 4806: 4801: 4771: 4766: 4765: 4750:Clinical trials 4729: 4709: 4686: 4680:Methylcobalamin 4660: 4631: 4618: 4590: 4566: 4547: 4533: 4488: 4474: 4455: 4445: 4440: 4431: 4422: 4413: 4404: 4395: 4392:Menaquinones (K 4386: 4364: 4294: 4260: 4246: 4237:Calcitroic acid 4222:Cholecalciferol 4217: 4205: 4187: 4171: 4135: 4129: 4119: 4055: 4050: 4049: 4011: 4010: 4006: 3996: 3994: 3985: 3984: 3980: 3928: 3927: 3923: 3877: 3876: 3872: 3836: 3835: 3831: 3793: 3792: 3785: 3772:(13): 1645–52. 3763: 3762: 3751: 3744: 3737: 3736: 3732: 3725: 3718: 3717: 3713: 3706: 3699: 3698: 3694: 3687: 3674: 3673: 3669: 3659: 3658: 3654: 3610: 3609: 3605: 3595: 3593: 3592:. 18 April 2018 3584: 3583: 3579: 3535: 3534: 3530: 3520: 3518: 3509: 3508: 3504: 3460: 3459: 3455: 3411: 3410: 3406: 3376: 3375: 3371: 3340: 3339: 3335: 3305: 3304: 3300: 3270: 3269: 3265: 3255: 3253: 3245: 3244: 3240: 3204: 3203: 3199: 3163: 3162: 3158: 3120: 3119: 3115: 3105: 3103: 3094: 3093: 3089: 3043: 3042: 3031: 3001: 3000: 2996: 2986: 2984: 2976: 2975: 2971: 2964: 2943: 2942: 2938: 2892: 2891: 2882: 2868: 2867: 2863: 2819: 2818: 2811: 2767: 2766: 2759: 2713: 2712: 2708: 2670: 2669: 2665: 2629: 2628: 2624: 2588: 2587: 2580: 2534: 2533: 2529: 2521: 2490: 2485: 2484: 2480: 2436: 2435: 2431: 2417: 2416: 2412: 2394: 2393: 2389: 2345: 2344: 2340: 2322: 2321: 2317: 2307: 2306: 2302: 2292: 2291: 2287: 2273: 2272: 2268: 2224: 2223: 2219: 2212: 2188: 2187: 2180: 2144: 2143: 2139: 2129: 2127: 2119: 2118: 2114: 2104: 2102: 2089: 2088: 2084: 2061: 2060: 2056: 2045: 2031: 2030: 2026: 2015: 2000: 1999: 1995: 1988: 1976: 1975: 1971: 1927: 1926: 1919: 1909: 1907: 1902: 1901: 1880: 1844: 1843: 1839: 1829: 1827: 1822: 1821: 1802: 1797: 1766: 1685: 1660:retinyl acetate 1636:total synthesis 1624: 1588: 1583: 1497: 1457: 1451: 1443:Night blindness 1430: 1424: 1416:intracellularly 1385: 1339:Common sources 1291:Night blindness 1212: 1196: 1188:iron metabolism 1180: 1178:Red blood cells 1139: 1131:dendritic cells 1103: 1088: 1052:night blindness 1043:-retinol to 11- 1017:neuronal firing 961: 955: 938:differentiation 934: 916: 908:stereochemistry 903: 824: 818: 780: 698: 684: 681: 676: 671: 670: 659: 656: 651: 650: 626: 605: 580: 567: 561: 522: 498: 490: 462: 442: 422: 402: 374: 354: 334: 314: 297: 289: 261: 258: 237: 236: 220: 190: 112: 105: 52: 24: 17: 12: 11: 5: 5679: 5677: 5669: 5668: 5663: 5658: 5653: 5648: 5643: 5638: 5636:Apocarotenoids 5633: 5623: 5622: 5618: 5617: 5594: 5593: 5591: 5590: 5583: 5579: 5576: 5575: 5573: 5572: 5567: 5562: 5557: 5552: 5547: 5542: 5537: 5532: 5527: 5522: 5517: 5512: 5507: 5498: 5497: 5492: 5482: 5477: 5472: 5467: 5462: 5457: 5452: 5447: 5442: 5437: 5428: 5419: 5410: 5408: 5397: 5396: 5394: 5393: 5384: 5383: 5378: 5373: 5368: 5363: 5358: 5349: 5348: 5343: 5338: 5333: 5328: 5323: 5313: 5308: 5303: 5298: 5293: 5288: 5283: 5278: 5273: 5268: 5263: 5258: 5253: 5248: 5243: 5234: 5229: 5224: 5219: 5214: 5205: 5196: 5194: 5183: 5182: 5174: 5172: 5171: 5164: 5157: 5149: 5140: 5139: 5137: 5136: 5131: 5126: 5121: 5116: 5111: 5106: 5101: 5096: 5091: 5085: 5083: 5081:Retinoid drugs 5077: 5076: 5074: 5073: 5068: 5063: 5057: 5055: 5051: 5047: 5046: 5044: 5043: 5038: 5033: 5028: 5023: 5018: 5013: 5007: 5005: 5001: 4998:Apocarotenoids 4994: 4993: 4991: 4990: 4985: 4980: 4975: 4970: 4965: 4960: 4955: 4950: 4945: 4940: 4935: 4930: 4928:Diadinoxanthin 4925: 4920: 4918:Citranaxanthin 4915: 4910: 4905: 4903:Antheraxanthin 4899: 4897: 4893: 4886: 4885: 4883: 4882: 4877: 4872: 4867: 4862: 4857: 4852: 4847: 4842: 4837: 4832: 4827: 4821: 4819: 4815: 4808: 4807: 4802: 4800: 4799: 4792: 4785: 4777: 4768: 4767: 4764: 4763: 4762: 4761: 4758: 4747: 4741: 4735: 4734: 4731: 4730: 4728: 4727: 4721: 4719: 4715: 4714: 4711: 4710: 4708: 4707: 4702: 4696: 4694: 4688: 4687: 4685: 4684: 4683: 4682: 4677: 4672: 4670:Cyanocobalamin 4667: 4658: 4654: 4653: 4652: 4647: 4642: 4637: 4629: 4626: 4625: 4624: 4616: 4613: 4612: 4611: 4606: 4601: 4588: 4584: 4583: 4582: 4577: 4572: 4564: 4561: 4560: 4559: 4554: 4545: 4541: 4540: 4539: 4531: 4528: 4527: 4526: 4521: 4516: 4511: 4506: 4501: 4496: 4486: 4482: 4481: 4480: 4472: 4468: 4466: 4457: 4451: 4450: 4447: 4446: 4444: 4443: 4438: 4434: 4429: 4425: 4420: 4416: 4411: 4407: 4402: 4398: 4393: 4389: 4384: 4380: 4378:Naphthoquinone 4374: 4372: 4366: 4365: 4363: 4362: 4357: 4356: 4355: 4352: 4347: 4342: 4332: 4331: 4330: 4325: 4320: 4315: 4304: 4302: 4296: 4295: 4293: 4292: 4291: 4290: 4285: 4280: 4275: 4270: 4262: 4258: 4254: 4253: 4252: 4244: 4241: 4240: 4239: 4234: 4229: 4224: 4219: 4215: 4211: 4203: 4200: 4199: 4198: 4196:Ergocalciferol 4193: 4185: 4181: 4179: 4173: 4172: 4170: 4169: 4164: 4159: 4154: 4148: 4146: 4137: 4131: 4130: 4120: 4118: 4117: 4110: 4103: 4095: 4089: 4088: 4077: 4072: 4058:Jane Higdon, " 4054: 4053:External links 4051: 4048: 4047: 4004: 3978: 3921: 3870: 3849:(4): 783–791. 3829: 3802:(3): 192–198. 3783: 3749: 3730: 3711: 3692: 3686:978-0470741672 3685: 3667: 3652: 3623:(4): 413–423. 3603: 3577: 3528: 3502: 3453: 3404: 3385:(1): 110–119. 3369: 3333: 3298: 3263: 3238: 3217:(3): 646–650. 3197: 3156: 3113: 3087: 3029: 2994: 2969: 2962: 2936: 2880: 2861: 2832:(6): 921–931. 2809: 2780:(6): 921–931. 2757: 2706: 2663: 2622: 2578: 2527: 2501:(8): 842–857. 2478: 2429: 2410: 2387: 2338: 2315: 2300: 2285: 2266: 2237:(2): 166–168. 2217: 2210: 2178: 2137: 2112: 2082: 2054: 2043: 2024: 2013: 1993: 1986: 1969: 1917: 1878: 1857:(9): 1557–84. 1837: 1799: 1798: 1796: 1793: 1785:11-cis retinal 1721:Elmer McCollum 1684: 1681: 1623: 1620: 1587: 1584: 1582: 1579: 1496: 1493: 1492: 1491: 1482: 1477: 1471: 1466: 1450: 1447: 1426:Main article: 1423: 1420: 1384: 1383:Dietary intake 1381: 1359: 1358: 1357: 1356: 1354:Dairy products 1350: 1341: 1340: 1336: 1335: 1334: 1333: 1327: 1321: 1318: 1315: 1314:Liver toxicity 1309: 1308: 1304: 1303: 1302: 1301: 1300:Pale, dry skin 1298: 1293: 1285: 1284: 1280: 1279: 1272: 1268: 1267: 1260: 1256: 1255: 1248: 1244: 1243: 1236: 1229: 1228: 1225: 1219: 1218: 1211: 1208: 1195: 1192: 1179: 1176: 1138: 1135: 1129:, and myeloid 1102: 1099: 1095:corneal ulcers 1087: 1084: 957:Main article: 954: 951: 933: 930: 915: 912: 902: 899: 817: 814: 806: 805: 801: 794: 779: 776: 728:. It is taken 718:dairy products 696: 693:, also called 686: 685: 683: 682: 679: 677: 674: 666: 665: 664: 661: 660: 658: 657: 654: 646: 645: 644: 641: 640: 637: 631: 630: 623: 617: 616: 613: 607: 606: 604: 603: 595: 593: 585: 584: 578: 572: 571: 565: 559: 554: 548: 547: 543: 542: 532: 524: 523: 521: 520: 507: 505: 492: 491: 489: 488: 472: 470: 464: 463: 461: 460: 452: 450: 444: 443: 441: 440: 432: 430: 424: 423: 421: 420: 412: 410: 404: 403: 401: 400: 394:mixture: 392: 384: 382: 376: 375: 373: 372: 364: 362: 356: 355: 353: 352: 344: 342: 336: 335: 333: 332: 324: 322: 316: 315: 313: 312: 304: 302: 291: 290: 288: 287: 281:mixture: 279: 271: 269: 263: 262: 260: 259: 240: 232: 231: 230: 227: 226: 222: 221: 219: 218: 205: 203: 197: 196: 192: 191: 189: 188: 145: 143: 137: 136: 131: 125: 124: 115: 113:administration 107: 106: 104: 103: 85: 83: 77: 76: 69: 59: 58: 54: 53: 50: 42: 41: 15: 13: 10: 9: 6: 4: 3: 2: 5678: 5667: 5664: 5662: 5659: 5657: 5654: 5652: 5649: 5647: 5644: 5642: 5639: 5637: 5634: 5632: 5629: 5628: 5626: 5616: 5606: 5602: 5589: 5588: 5584: 5581: 5580: 5577: 5571: 5568: 5566: 5563: 5561: 5558: 5556: 5553: 5551: 5548: 5546: 5543: 5541: 5538: 5536: 5533: 5531: 5528: 5526: 5523: 5521: 5518: 5516: 5513: 5511: 5508: 5506: 5503: 5500: 5499: 5496: 5493: 5490: 5486: 5483: 5481: 5480:Retinoic acid 5478: 5476: 5473: 5471: 5468: 5466: 5463: 5461: 5458: 5456: 5453: 5451: 5448: 5446: 5443: 5441: 5438: 5436: 5434: 5429: 5427: 5425: 5420: 5418: 5415: 5412: 5411: 5409: 5404: 5398: 5392: 5389: 5386: 5385: 5382: 5379: 5377: 5374: 5372: 5369: 5367: 5364: 5362: 5359: 5357: 5354: 5351: 5350: 5347: 5344: 5342: 5339: 5337: 5334: 5332: 5329: 5327: 5324: 5321: 5317: 5314: 5312: 5311:Retinoic acid 5309: 5307: 5304: 5302: 5299: 5297: 5294: 5292: 5289: 5287: 5284: 5282: 5279: 5277: 5274: 5272: 5269: 5267: 5264: 5262: 5259: 5257: 5254: 5252: 5249: 5247: 5244: 5242: 5240: 5235: 5233: 5230: 5228: 5225: 5223: 5220: 5218: 5215: 5213: 5211: 5206: 5204: 5201: 5198: 5197: 5195: 5190: 5184: 5180: 5177: 5170: 5165: 5163: 5158: 5156: 5151: 5150: 5147: 5135: 5132: 5130: 5127: 5125: 5122: 5120: 5117: 5115: 5112: 5110: 5107: 5105: 5102: 5100: 5097: 5095: 5092: 5090: 5087: 5086: 5084: 5082: 5078: 5072: 5069: 5067: 5066:Retinoic acid 5064: 5062: 5059: 5058: 5056: 5048: 5042: 5039: 5037: 5034: 5032: 5031:Food orange 7 5029: 5027: 5024: 5022: 5019: 5017: 5014: 5012: 5011:Abscisic acid 5009: 5008: 5006: 4999: 4995: 4989: 4986: 4984: 4981: 4979: 4976: 4974: 4971: 4969: 4966: 4964: 4961: 4959: 4956: 4954: 4951: 4949: 4946: 4944: 4941: 4939: 4936: 4934: 4931: 4929: 4926: 4924: 4923:Cryptoxanthin 4921: 4919: 4916: 4914: 4913:Canthaxanthin 4911: 4909: 4906: 4904: 4901: 4900: 4898: 4891: 4887: 4881: 4878: 4876: 4873: 4871: 4868: 4866: 4863: 4861: 4858: 4856: 4853: 4851: 4848: 4846: 4843: 4841: 4838: 4836: 4833: 4831: 4828: 4826: 4823: 4822: 4820: 4813: 4809: 4805: 4798: 4793: 4791: 4786: 4784: 4779: 4778: 4775: 4759: 4757: 4754: 4753: 4751: 4748: 4745: 4742: 4740: 4737: 4736: 4732: 4726: 4725:Multivitamins 4723: 4722: 4720: 4716: 4706: 4703: 4701: 4700:Ascorbic acid 4698: 4697: 4695: 4693: 4689: 4681: 4678: 4676: 4673: 4671: 4668: 4666: 4663: 4662: 4661: 4655: 4651: 4648: 4646: 4643: 4641: 4638: 4636: 4633: 4632: 4627: 4623: 4620: 4619: 4614: 4610: 4607: 4605: 4602: 4600: 4596: 4593: 4592: 4591: 4585: 4581: 4578: 4576: 4573: 4571: 4568: 4567: 4562: 4558: 4555: 4553: 4550: 4549: 4548: 4542: 4538: 4535: 4534: 4529: 4525: 4522: 4520: 4519:Prosultiamine 4517: 4515: 4512: 4510: 4509:Fursultiamine 4507: 4505: 4502: 4500: 4497: 4495: 4494:Acefurtiamine 4492: 4491: 4490: 4483: 4479: 4476: 4475: 4470: 4469: 4467: 4465: 4461: 4458: 4452: 4442: 4435: 4433: 4426: 4424: 4417: 4415: 4408: 4406: 4399: 4397: 4390: 4388: 4381: 4379: 4376: 4375: 4373: 4371: 4367: 4361: 4358: 4353: 4351: 4348: 4346: 4343: 4341: 4338: 4337: 4336: 4333: 4329: 4326: 4324: 4321: 4319: 4316: 4314: 4311: 4310: 4309: 4306: 4305: 4303: 4301: 4297: 4289: 4286: 4284: 4281: 4279: 4276: 4274: 4271: 4269: 4266: 4265: 4263: 4261: 4255: 4251: 4248: 4247: 4242: 4238: 4235: 4233: 4230: 4228: 4225: 4223: 4220: 4218: 4212: 4210: 4207: 4206: 4201: 4197: 4194: 4192: 4189: 4188: 4183: 4182: 4180: 4178: 4174: 4168: 4165: 4163: 4160: 4158: 4155: 4153: 4150: 4149: 4147: 4145: 4141: 4138: 4132: 4127: 4123: 4116: 4111: 4109: 4104: 4102: 4097: 4096: 4093: 4087: 4086: 4081: 4078: 4076: 4073: 4071: 4070: 4066: 4061: 4057: 4056: 4052: 4043: 4039: 4035: 4031: 4027: 4023: 4019: 4015: 4008: 4005: 3992: 3988: 3982: 3979: 3974: 3970: 3966: 3962: 3957: 3952: 3948: 3944: 3941:(4058): 189. 3940: 3936: 3932: 3925: 3922: 3917: 3913: 3909: 3905: 3901: 3897: 3893: 3889: 3885: 3881: 3874: 3871: 3866: 3862: 3857: 3852: 3848: 3844: 3840: 3833: 3830: 3825: 3821: 3817: 3813: 3809: 3805: 3801: 3797: 3790: 3788: 3784: 3779: 3775: 3771: 3767: 3760: 3758: 3756: 3754: 3750: 3740: 3734: 3731: 3721: 3715: 3712: 3702: 3696: 3693: 3688: 3682: 3678: 3671: 3668: 3663: 3656: 3653: 3648: 3644: 3639: 3634: 3630: 3626: 3622: 3618: 3614: 3607: 3604: 3591: 3587: 3581: 3578: 3573: 3569: 3564: 3559: 3555: 3551: 3547: 3543: 3539: 3532: 3529: 3516: 3512: 3506: 3503: 3498: 3494: 3489: 3484: 3480: 3476: 3472: 3468: 3464: 3457: 3454: 3449: 3445: 3440: 3435: 3431: 3427: 3423: 3419: 3415: 3408: 3405: 3400: 3396: 3392: 3388: 3384: 3380: 3373: 3370: 3365: 3361: 3357: 3353: 3349: 3345: 3337: 3334: 3329: 3325: 3321: 3317: 3313: 3309: 3302: 3299: 3294: 3290: 3286: 3282: 3278: 3274: 3267: 3264: 3252: 3248: 3242: 3239: 3234: 3230: 3225: 3220: 3216: 3212: 3208: 3201: 3198: 3193: 3189: 3184: 3179: 3175: 3171: 3167: 3160: 3157: 3152: 3148: 3144: 3140: 3136: 3132: 3128: 3124: 3117: 3114: 3101: 3097: 3091: 3088: 3083: 3079: 3074: 3069: 3064: 3059: 3055: 3051: 3047: 3040: 3038: 3036: 3034: 3030: 3025: 3021: 3017: 3013: 3009: 3005: 2998: 2995: 2983: 2979: 2973: 2970: 2965: 2959: 2955: 2951: 2947: 2940: 2937: 2932: 2928: 2923: 2918: 2913: 2908: 2904: 2900: 2896: 2889: 2887: 2885: 2881: 2876: 2872: 2865: 2862: 2857: 2853: 2848: 2843: 2839: 2835: 2831: 2827: 2823: 2816: 2814: 2810: 2805: 2801: 2796: 2791: 2787: 2783: 2779: 2775: 2771: 2764: 2762: 2758: 2753: 2749: 2744: 2739: 2734: 2729: 2725: 2721: 2717: 2710: 2707: 2702: 2698: 2694: 2690: 2686: 2682: 2678: 2674: 2667: 2664: 2659: 2655: 2650: 2645: 2641: 2637: 2633: 2626: 2623: 2618: 2614: 2609: 2604: 2600: 2596: 2592: 2585: 2583: 2579: 2574: 2570: 2565: 2560: 2555: 2550: 2546: 2542: 2538: 2531: 2528: 2520: 2516: 2512: 2508: 2504: 2500: 2496: 2489: 2482: 2479: 2474: 2470: 2465: 2460: 2456: 2452: 2448: 2444: 2440: 2433: 2430: 2425: 2421: 2414: 2411: 2406: 2402: 2398: 2391: 2388: 2383: 2379: 2374: 2369: 2365: 2361: 2357: 2353: 2349: 2342: 2339: 2334: 2330: 2326: 2319: 2316: 2311: 2304: 2301: 2296: 2289: 2286: 2281: 2277: 2270: 2267: 2262: 2258: 2253: 2248: 2244: 2240: 2236: 2232: 2228: 2221: 2218: 2213: 2211:9789241547659 2207: 2203: 2199: 2195: 2191: 2185: 2183: 2179: 2174: 2170: 2165: 2160: 2156: 2152: 2148: 2141: 2138: 2126: 2122: 2116: 2113: 2100: 2096: 2092: 2086: 2083: 2077: 2072: 2068: 2064: 2058: 2055: 2050: 2046: 2044:9783527695522 2040: 2036: 2035: 2028: 2025: 2020: 2016: 2014:9781848261952 2010: 2006: 2005: 1997: 1994: 1989: 1987:9780857111562 1983: 1979: 1973: 1970: 1965: 1961: 1957: 1953: 1948: 1943: 1939: 1935: 1931: 1924: 1922: 1918: 1905: 1899: 1897: 1895: 1893: 1891: 1889: 1887: 1885: 1883: 1879: 1874: 1870: 1865: 1860: 1856: 1852: 1848: 1841: 1838: 1825: 1819: 1817: 1815: 1813: 1811: 1809: 1807: 1805: 1801: 1794: 1792: 1788: 1786: 1782: 1778: 1774: 1770: 1764: 1762: 1758: 1754: 1750: 1746: 1742: 1741:cod liver oil 1738: 1734: 1730: 1726: 1722: 1718: 1714: 1710: 1709:carbohydrates 1706: 1697: 1689: 1682: 1680: 1678: 1673: 1672:Rhone-Poulenc 1669: 1665: 1661: 1657: 1651: 1649: 1645: 1641: 1637: 1630:β-ionone ring 1628: 1621: 1619: 1617: 1613: 1609: 1605: 1602:. First, the 1601: 1592: 1585: 1580: 1578: 1576: 1571: 1569: 1565: 1561: 1557: 1553: 1552:photoreceptor 1550: 1546: 1542: 1538: 1534: 1530: 1526: 1522: 1518: 1515:found in the 1514: 1510: 1509: 1504: 1503: 1494: 1490: 1486: 1483: 1481: 1478: 1475: 1472: 1470: 1467: 1465: 1464:Cod liver oil 1462: 1461: 1460: 1456: 1448: 1446: 1444: 1434: 1429: 1421: 1419: 1417: 1413: 1409: 1405: 1401: 1396: 1394: 1390: 1382: 1380: 1376: 1374: 1370: 1365: 1355: 1351: 1348: 1345: 1344: 1342: 1337: 1331: 1328: 1325: 1324:Teratological 1322: 1319: 1316: 1313: 1312: 1310: 1305: 1299: 1297: 1296:Keratomalacia 1294: 1292: 1289: 1288: 1286: 1281: 1277: 1273: 1270: 1269: 1265: 1261: 1258: 1257: 1253: 1249: 1246: 1245: 1241: 1237: 1235:(adult male) 1234: 1231: 1230: 1226: 1224: 1221: 1220: 1215: 1209: 1207: 1205: 1201: 1193: 1191: 1189: 1185: 1177: 1175: 1173: 1169: 1165: 1161: 1157: 1152: 1148: 1144: 1136: 1134: 1132: 1128: 1124: 1120: 1116: 1112: 1108: 1101:Immune system 1100: 1098: 1096: 1092: 1085: 1083: 1081: 1077: 1073: 1069: 1066:, which have 1065: 1061: 1057: 1053: 1048: 1046: 1042: 1038: 1034: 1030: 1026: 1022: 1021:metarhodopsin 1018: 1014: 1010: 1006: 1002: 998: 994: 990: 986: 982: 978: 974: 970: 966: 960: 952: 950: 948: 944: 939: 931: 929: 927: 922: 913: 911: 909: 900: 898: 894: 891: 887: 886: 882:published in 881: 876: 872: 870: 866: 861: 857: 855: 851: 847: 843: 838: 835: 833: 829: 823: 815: 813: 811: 802: 799: 795: 792: 791: 790: 787: 785: 777: 775: 773: 769: 765: 760: 758: 757:retinoic acid 754: 750: 746: 742: 737: 735: 731: 727: 726:xerophthalmia 723: 719: 715: 711: 707: 703: 699: 692: 678: 673: 669: 662: 653: 649: 642: 638: 636: 632: 627:10 mm Hg 624: 622: 621:Boiling point 618: 614: 612: 611:Melting point 608: 601: 597: 596: 594: 591: 586: 579: 577: 573: 555: 553: 549: 544: 540: 536: 533: 531: 529:ECHA InfoCard 525: 517: 513: 512:DTXSID3023556 509: 508: 506: 497: 493: 485: 484:RCSB PDB 479: 474: 473: 471: 469: 465: 458: 454: 453: 451: 449: 445: 438: 434: 433: 431: 429: 425: 418: 414: 413: 411: 409: 405: 398: 393: 390: 386: 385: 383: 381: 377: 370: 366: 365: 363: 361: 357: 350: 346: 345: 343: 341: 337: 330: 326: 325: 323: 321: 317: 310: 306: 305: 303: 296: 292: 285: 280: 277: 273: 272: 270: 268: 264: 256: 252: 248: 244: 239: 235: 228: 223: 217: 207: 206: 204: 202: 198: 193: 185: 180: 175: 170: 165: 160: 155: 150: 147: 146: 144: 142: 138: 135: 132: 130: 126: 123: 122:intramuscular 119: 116: 114: 108: 101: 96: 87: 86: 84: 82: 78: 74: 70: 68: 64: 60: 57:Clinical data 55: 48: 43: 39: 34: 26: 22: 5641:Cyclohexenes 5631:Antioxidants 5585: 5502:Antagonists: 5501: 5484: 5460:Isotretinoin 5432: 5423: 5413: 5387: 5353:Antagonists: 5352: 5326:Tamibarotene 5315: 5306:Palovarotene 5301:Isotretinoin 5238: 5209: 5199: 5114:Isotretinoin 5094:Alitretinoin 5070: 5016:Apocarotenal 4988:Zeinoxanthin 4978:Violaxanthin 4968:Rhodoxanthin 4948:Flavoxanthin 4933:Diatoxanthin 4890:Xanthophylls 4860:Neurosporene 4718:Combinations 4645:Folinic acid 4604:Pyridoxamine 4575:Dexpanthenol 4524:Sulbutiamine 4504:Benfotiamine 4499:Allithiamine 4401:Menadione (K 4360:Tocofersolan 4288:Paricalcitol 4278:Calcipotriol 4268:Alfacalcidol 4264:D analogues 4214:Previtamin D 4161: 4083: 4063: 4020:(1): 49–94. 4017: 4013: 4007: 3995:. Retrieved 3981: 3938: 3934: 3924: 3883: 3879: 3873: 3846: 3842: 3832: 3799: 3795: 3769: 3765: 3733: 3714: 3695: 3676: 3670: 3661: 3655: 3620: 3616: 3606: 3594:. Retrieved 3589: 3580: 3545: 3541: 3531: 3519:. Retrieved 3514: 3505: 3470: 3466: 3456: 3421: 3418:EMBO Reports 3417: 3407: 3382: 3378: 3372: 3347: 3343: 3336: 3311: 3307: 3301: 3276: 3272: 3266: 3254:. Retrieved 3250: 3241: 3214: 3210: 3200: 3173: 3169: 3159: 3126: 3122: 3116: 3104:. Retrieved 3099: 3090: 3053: 3049: 3007: 3003: 2997: 2985:. Retrieved 2982:ScienceDaily 2981: 2972: 2945: 2939: 2902: 2898: 2875:Neuroscience 2874: 2864: 2829: 2825: 2777: 2773: 2723: 2719: 2709: 2676: 2672: 2666: 2639: 2635: 2625: 2598: 2594: 2544: 2540: 2530: 2498: 2494: 2481: 2446: 2443:EMBO Reports 2442: 2432: 2424:the original 2413: 2405:the original 2400: 2390: 2355: 2352:EMBO Reports 2351: 2341: 2328: 2318: 2309: 2303: 2294: 2288: 2280:the original 2274:Nataraja A. 2269: 2234: 2230: 2220: 2193: 2154: 2150: 2140: 2128:. Retrieved 2124: 2115: 2103:. Retrieved 2094: 2085: 2076:10665/371090 2066: 2057: 2033: 2027: 2003: 1996: 1977: 1972: 1940:(1): 49–57. 1937: 1933: 1910:10 September 1908:. Retrieved 1854: 1850: 1840: 1830:10 September 1828:. Retrieved 1789: 1765: 1702: 1658:derivatives 1652: 1646:utilized by 1633: 1597: 1586:Biosynthesis 1572: 1567: 1563: 1536: 1532: 1528: 1524: 1520: 1513:double bonds 1506: 1500: 1498: 1458: 1439: 1404:chylomicrons 1397: 1386: 1377: 1366: 1362: 1330:Osteoporosis 1197: 1181: 1164:cathelicidin 1140: 1104: 1091:Glycoprotein 1089: 1080:color vision 1049: 1044: 1040: 1036: 1032: 1028: 1024: 1012: 1004: 980: 965:visual cycle 962: 959:Visual cycle 935: 917: 904: 895: 889: 883: 877: 873: 865:osteoporosis 862: 858: 846:Xavier Mertz 839: 836: 825: 816:Side effects 807: 788: 781: 778:Medical uses 761: 738: 694: 690: 689: 254: 250: 246: 242: 201:Legal status 195:Legal status 81:License data 25: 5341:Trifarotene 5296:Fenretinide 5109:Fenretinide 4973:Rubixanthin 4953:Fucoxanthin 4938:Dinoxanthin 4908:Astaxanthin 4880:Lycopersene 4870:Phytofluene 4804:Carotenoids 4746:from market 4557:Niacinamide 4514:Octotiamine 4335:Tocotrienol 3766:Tetrahedron 3521:18 February 3279:: 105–131. 2905:(11): 746. 2202:10665/44053 1824:"Vitamin A" 1777:chromophore 1769:George Wald 1757:Paul Karrer 1556:Schiff base 1541:chromophore 1519:chain. The 1373:carotenoids 1200:nutritional 1127:macrophages 1123:neutrophils 1107:lymphocytes 971:within the 921:rhombomeres 869:carotenosis 583: g·mol 535:100.000.621 437:CHEBI:17336 225:Identifiers 5646:Diterpenes 5625:Categories 5440:Bexarotene 5356:BMS-195614 5331:Tazarotene 5291:Etretinate 5179:modulators 5124:Temarotene 5119:Tazarotene 5104:Etretinate 5099:Bexarotene 4983:Zeaxanthin 4963:Neoxanthin 4943:Echinenone 4850:ζ-Carotene 4845:ε-Carotene 4840:δ-Carotene 4835:γ-Carotene 4830:β-Carotene 4825:α-Carotene 4635:Folic acid 4595:Pyridoxine 4580:Pantethine 4537:Riboflavin 4410:Various (K 4308:Tocopherol 4283:Tacalcitol 4191:Ergosterol 4157:β-Carotene 4152:α-Carotene 3739:US 2609396 3720:US 2917524 3256:7 November 3056:(2): 302. 2673:Pediatrics 2130:14 January 2105:14 January 1795:References 1725:biochemist 1600:β-carotene 1549:vertebrate 1453:See also: 1422:Deficiency 1400:intestines 1352:fortified 1223:Solubility 1168:microbiome 1072:cone cells 1009:isomerizes 926:mesenchyme 914:Embryology 820:See also: 812:patients. 588:3D model ( 576:Molar mass 468:PDB ligand 397:81G40H8B0T 389:G2SH0XKK91 360:ChemSpider 320:IUPHAR/BPS 284:11103-57-4 267:CAS Number 234:IUPAC name 129:Drug class 5515:LG-100754 5489:vitamin A 5475:LG-100754 5470:LG-101506 5465:LG-100268 5414:Agonists: 5391:Liarozole 5320:vitamin A 5232:Adapalene 5227:Acitretin 5217:AC-261066 5200:Agonists: 5129:Tretinoin 5089:Acitretin 5041:Peridinin 4812:Carotenes 4756:Phase III 4744:Withdrawn 4609:Pyritinol 4489:analogues 4167:Tretinoin 4060:Vitamin A 3701:DE 954247 3679:. Wiley. 3106:10 August 3050:Nutrients 2899:Nutrients 1873:1083-6160 1767:In 1967, 1737:butterfat 1703:In 1912, 1581:Synthesis 1545:rhodopsin 1495:Chemistry 1320:Hair loss 1210:Nutrition 1068:rhodopsin 1060:vitamin A 1056:vitamin A 1011:into all- 890:increased 854:Antarctic 832:lactation 798:margarine 749:pregnancy 706:vitamin A 695:vitamin A 457:ChEMBL986 111:Routes of 73:Monograph 67:Drugs.com 5656:Vitamins 5615:Medicine 5582:See also 5525:UVI-3003 5495:SR-11237 5381:MM-11253 5371:ER-50891 5222:AC-55649 5026:Crocetin 4875:Torulene 4865:Phytoene 4855:Lycopene 4478:Thiamine 4122:Vitamins 4034:11070368 3991:Archived 3965:20256189 3916:27157783 3908:21015124 3865:10203551 3824:27542506 3816:23183288 3647:24592582 3596:18 April 3572:24852372 3497:24852372 3448:38769419 3439:11239848 3399:15325918 3364:15572756 3293:34115520 3251:InterPro 3192:16140154 3151:11348076 3143:14738139 3082:33494277 3024:17569825 2987:17 March 2931:27879662 2856:18805086 2804:18805086 2752:39133222 2743:11318670 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