312:
237:
52:
61:
833:
816:
1079:
497:
823:
retinal, awaiting the arrival of a photon. Once the retinal molecule captures a photon, its configuration change causes it to push against the surrounding opsin protein which may cause the opsin to send a chemical signal to the brain indicating that light has been detected. Retinal is then converted
806:
of light or images by the brain. The absorbance spectrum of the chromophore depends on its interactions with the opsin protein to which it is bound, so that different retinal-opsin complexes will absorb photons of different wavelengths (i.e., different colors of light).
573:
when eaten by an animal. There are many forms of vitamin A, all of which are converted to retinal, which cannot be made without them. The number of different molecules that can be converted to retinal varies from species to species. Retinal was originally called
3633:
Su, Chih-Ying; Luo, Dong-Gen; Terakita, Akihisa; Shichida, Yoshinori; Liao, Hsi-Wen; Kazmi, Manija A.; Sakmar, Thomas P.; Yau, King-Wai (2006). "Parietal-Eye
Phototransduction Components and Their Potential Evolutionary Implications".
2689:"The metabolic pathway of visual pigment chromophore formation in Drosophila melanogaster: All-trans (3S)-3-hydroxyretinal is formed from all-trans retinal via (3R)-3-hydroxyretinal in the dark"
558:
Some microorganisms use retinal to convert light into metabolic energy. In fact, a recent study suggests most living organisms on our planet ~3 billion years ago used retinal, rather than
2492:
Katana, Radoslaw; Guan, Chonglin; Zanini, Damiano; Larsen, Matthew E.; Giraldo, Diego; Geurten, Bart R.H.; Schmidt, Christoph F.; Britt, Steven G.; GΓΆpfert, Martin C. (September 2019).
990:
Although mammals use retinal exclusively as the opsin chromophore, other groups of animals additionally use four chromophores closely related to retinal: 3,4-didehydroretinal (vitamin A
2067:
Hargrave, P. A.; McDowell, J. H.; Curtis, Donna R.; Wang, Janet K.; Juszczak, Elizabeth; Fong, Shao-Ling; Mohana Rao, J. K.; Argos, P. (1983). "The structure of bovine rhodopsin".
510:
3465:
Salom, David; Lodowski, David T.; Stenkamp, Ronald E.; Le Trong, Isolde; Golczak, Marcin; Jastrzebska, Beata; Harris, Tim; Ballesteros, Juan A.; Palczewski, Krzysztof (2006).
174:
3682:; Remington, K; Heidelberg, JF; Halpern, AL; Rusch, D; Eisen, JA; Wu, D; Paulsen, I; et al. (2004). "Environmental Genome Shotgun Sequencing of the Sargasso Sea".
2652:
Seki, Takaharu; Isono, Kunio; Ito, Masayoshi; Katsuta, Yuko (1994). "Flies in the Group
Cyclorrhapha Use (3S)-3-Hydroxyretinal as a Unique Visual Pigment Chromophore".
623:
organisms. No other carotenoids can be converted by animals to retinal. Some carnivores cannot convert any carotenoids at all. The other main forms of vitamin A β
1339:-retinal in the dark state. These proteins are not evolutionarily related to animal opsins and are not GPCRs; the fact that they both use retinal is a result of
2609:
Kumbalasiri T, Rollag MD, Isoldi MC, Castrucci AM, Provencio I (March 2007). "Melanopsin triggers the release of internal calcium stores in response to light".
2897:
Chen, De-Liang; Wang, Guang-yu; Xu, Bing; Hu, Kun-Sheng (2002). "All-trans to 13-cis retinal isomerization in light-adapted bacteriorhodopsin at acidic pH".
2115:
Palczewski K, Kumasaka T, Hori T, Behnke CA, Motoshima H, Fox BA, et al. (August 2000). "Crystal structure of rhodopsin: A G protein-coupled receptor".
351:
691:
948:. Forming the Schiff base linkage involves removing the oxygen atom from retinal and two hydrogen atoms from the free amino group of lysine, giving H
3253:
Kloer, Daniel P.; Ruch, Sandra; Al-Babili, Salim; Beyer, Peter; Schulz, Georg E. (2005). "The
Structure of a Retinal-Forming Carotenoid Oxygenase".
1873:"Mouse Retinal Dehydrogenase 4 (RALDH4), Molecular Cloning, Cellular Expression, and Activity in 9-cis-Retinoic Acid Biosynthesis in Intact Cells"
2687:
Seki, Takaharu; Isono, Kunio; Ozaki, Kaoru; Tsukahara, Yasuo; Shibata-Katsuta, Yuko; Ito, Masayoshi; Irie, Toshiaki; Katagiri, Masanao (1998).
682:
Just as carotenoids are the precursors of retinal, retinal is the precursor of the other forms of vitamin A. Retinal is interconvertible with
3968:
3886:
2552:
Leung, Nicole Y.; Thakur, Dhananjay P.; Gurav, Adishthi S.; Kim, Sang Hoon; Di Pizio, Antonella; Niv, Masha Y.; Montell, Craig (April 2020).
1356:
676:
335:
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
983:
residues. Retinal binds as chromophore at Lys. This lysine is conserved in almost all opsins, only a few opsins have lost it during
698:
326:
3202:
Kawaguchi, Riki; Yu, Jiamei; Honda, Jane; Hu, Jane; Whitelegge, Julian; Ping, Peipei; Wiita, Patrick; Bok, Dean; Sun, Hui (2007).
4343:
1248:
3436:(2006). "Conservation of Distantly Related Membrane Proteins: Photosynthetic Reaction Centers Share a Common Structural Core".
1729:"In Vitro Characterization of a Recombinant Blh Protein from an Uncultured Marine Bacterium as a Ξ²-Carotene 15,15β²-Dioxygenase"
912:. The rods form disks, which contain the rhodopsin molecules in their membranes and which are entirely inside of the cell. The
562:, to convert sunlight into energy. Since retinal absorbs mostly green light and transmits purple light, this gave rise to the
3596:
Send, Robert; Sundholm, Dage (2007). "Stairway to the conical intersection: A computational study of retinal isomerization".
3044:
Barlow, H.B.; Levick, W.R.; Yoon, M. (1971). "Responses to single quanta of light in retinal ganglion cells of the cat".
517:
4348:
269:
3399:"Reconstitution of Purple Membrane Vesicles Catalyzing Light-driven Proton Uptake and Adenosine Triphosphate Formation"
952:
O. Retinylidene is the divalent group formed by removing the oxygen atom from retinal, and so opsins have been called
290:
1260:
968:
960:
889:
3961:
3358:
1324:
964:
1655:"Filling the Gap in Vitamin A Research: Molecular Identification of An Enzyme Cleaving Beta-carotene to Retinal"
1391:
548:
1098:
4333:
1376:
563:
987:. Opsins without the retinal binding lysine are not light sensitive. Such opsins may have other functions.
232:
3699:
3354:"Retinal Biosynthesis in Fungi: Characterization of the Carotenoid Oxygenase CarX from Fusarium fujikuroi"
2132:
1381:
1360:
3930:
4338:
3940:
3433:
1194:(rhodopsin + hΞ½ β photorhodopsin β bathorhodopsin β lumirhodopsin β metarhodopsin I β metarhodopsin II);
972:
861:
756:
710:
706:
83:
73:
4307:
3954:
3794:
3740:"Dissection of the pathway required for generation of vitamin A and for Drosophila phototransduction"
3691:
3643:
3605:
3478:
3311:
3262:
3215:
2965:
2906:
2851:
2741:
2565:
2505:
2394:
2332:
2228:
2177:
2137:
2124:
2025:
1696:"Oxidative cleavage of carotenoids catalyzed by enzyme models and beta-carotene 15,15'-monooxygenase"
1589:
1546:
1501:
1340:
953:
783:
3704:
1124:
940:, so that the N-terminus head extends outside of the cell. In opsins, retinal binds covalently to a
3924:
1291:
717:
645:
use hydroxylated forms of retinal in their visual systems, which derive from conversion from other
307:
140:
4161:
1431:"Early evolution of purple retinal pigments on Earth and implications for exoplanet biosignatures"
4358:
4328:
3725:
3667:
3286:
3241:
2989:
2634:
2531:
2420:
2252:
2201:
2092:
2049:
1963:
1605:
1519:
1470:
1442:
1267:
1184:
897:
612:
4297:
3116:
Fan, Jie; Woodruff, Michael L; Cilluffo, Marianne C; Crouch, Rosalie K; Fain, Gordon L (2005).
2838:
Oberhauser, Vitus; Voolstra, Olaf; Bangert, Annette; von Lintig, Johannes; Vogt, Klaus (2008).
3900:
3882:
3865:
3822:
3769:
3717:
3659:
3621:
3584:
3549:
3506:
3453:
3420:
3385:
3339:
3278:
3233:
3190:
3147:
3104:
3061:
3032:
2981:
2922:
2879:
2820:
2769:
2710:
2669:
2626:
2591:
2523:
2474:
2412:
2360:
2301:
2244:
2193:
2150:
2084:
2041:
1998:
1955:
1894:
1853:
1801:
1760:
1676:
1632:
1562:
1462:
1386:
1305:
1213:
1087:
779:
552:
2840:"NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide"
1355:
and others had outlined the visual cycle by 1958. For his work, Wald won a share of the 1967
4018:
3855:
3847:
3812:
3802:
3759:
3751:
3709:
3651:
3613:
3574:
3539:
3531:
3496:
3486:
3445:
3410:
3375:
3367:
3329:
3319:
3270:
3223:
3180:
3172:
3137:
3129:
3094:
3086:
3053:
3022:
3014:
2973:
2914:
2869:
2859:
2810:
2800:
2759:
2749:
2700:
2661:
2618:
2581:
2573:
2513:
2464:
2454:
2402:
2350:
2340:
2291:
2283:
2236:
2185:
2142:
2076:
2033:
1990:
1945:
1884:
1843:
1835:
1791:
1750:
1740:
1707:
1666:
1597:
1554:
1509:
1452:
1309:
434:
374:
214:
3935:
2939:
1912:
278:
4353:
937:
767:
760:
416:
798:-retinal configuration. This configuration change pushes against an opsin protein in the
150:
3798:
3695:
3647:
3609:
3482:
3315:
3266:
3219:
2969:
2910:
2855:
2745:
2569:
2509:
2398:
2336:
2232:
2181:
2128:
2029:
1981:
Attwood, T. K.; Findlay, J. B. C. (1994). "Fingerprinting G-protein-coupled receptors".
1593:
1550:
1505:
311:
236:
194:
4101:
4091:
4076:
4013:
4008:
3998:
3860:
3835:
3817:
3782:
3764:
3739:
3501:
3466:
3380:
3353:
3334:
3299:
3204:"A Membrane Receptor for Retinol Binding Protein Mediates Cellular Uptake of Vitamin A"
3185:
3160:
3142:
3117:
3099:
3074:
3027:
3002:
2874:
2839:
2815:
2788:
2764:
2729:
2705:
2688:
2665:
2586:
2553:
2469:
2442:
2296:
2271:
1848:
1823:
1755:
1728:
1142:
1015:
873:
620:
600:
488:
478:
3544:
3519:
3415:
3398:
3352:
Prado-Cabrero, Alfonso; Scherzinger, Daniel; Avalos, Javier; Al-Babili, Salim (2007).
2918:
2728:
Moiseyev, Gennadiy; Chen, Ying; Takahashi, Yusuke; Wu, Bill X.; Ma, Jian-xing (2005).
1950:
1933:
963:(GPCRs). Cattle rhodopsin, the opsin of the rod cells, was the first GPCR to have its
4322:
4239:
4204:
4184:
4171:
4096:
4086:
4023:
4003:
3057:
2535:
2407:
2382:
2355:
2320:
1474:
1364:
1313:
1229:
1199:
1177:
1057:
841:
721:
664:
628:
604:
474:
470:
423:
225:
3671:
3245:
2993:
2638:
2424:
2096:
1967:
1780:"Understanding Retinol Metabolism: Structure and Function of Retinol Dehydrogenases"
832:
815:
657:
Living organisms produce retinal by irreversible oxidative cleavage of carotenoids.
4287:
4267:
4189:
4151:
4141:
4121:
4106:
4033:
3836:"The molecular genetics and evolution of red and green color vision in vertebrates"
3729:
3679:
3535:
3290:
3090:
3001:
Amora, Tabitha L.; Ramos, Lavoisier S.; Galan, Jhenny F.; Birge, Robert R. (2008).
2789:"Role of LRAT on the Retinoid Isomerase Activity and Membrane Association of Rpe65"
2494:"Chromophore-Independent Roles of Opsin Apoproteins in Drosophila Mechanoreceptors"
2256:
2205:
2053:
1871:
Lin, Min; Zhang, Min; Abraham, Michael; Smith, Susan M.; Napoli, Joseph L. (2003).
1609:
1523:
1150:
1073:
1023:
646:
634:
258:
3851:
1580:
MORTON, R. A.; GOODWIN, T. W. (1 April 1944). "Preparation of
Retinene in Vitro".
3561:
Schmidt, Holger; Kurtzer, Robert; Eisenreich, Wolfgang; Schwab, Wilfried (2006).
3133:
3118:"Opsin activation of transduction in the rods of dark-reared Rpe65 knockout mice"
2146:
1558:
4282:
4146:
4126:
4111:
4081:
4063:
4053:
4043:
3896:
2956:
Fernald, Russell D. (2006). "Casting a
Genetic Light on the Evolution of Eyes".
2272:"Studies on rhodopsin. 8. Retinylidenemethylamine, an indicator yellow analogue"
1727:
Kim, Yeong-Su; Kim, Nam-Hee; Yeom, Soo-Jin; Kim, Seon-Won; Oh, Deok-Kun (2009).
1352:
1162:
1043:
945:
893:
616:
559:
540:
51:
2321:"Gain and kinetics of activation in the G-protein cascade of phototransduction"
2270:
Pitt, G. A. J.; Collins, F. D.; Morton, R. A.; Stok, Pauline (1 January 1955).
1839:
4292:
4277:
4272:
4156:
4136:
4116:
3977:
3783:"Leptosphaeria rhodopsin: Bacteriorhodopsin-like proton pump from a eukaryote"
3781:
Waschuk, Stephen A.; Bezerra, Arandi G.; Shi, Lichi; Brown, Leonid S. (2005).
3467:"Crystal structure of a photoactivated deprotonated intermediate of rhodopsin"
2622:
2577:
2518:
2493:
1994:
1457:
1430:
1114:
1094:-retinal. For example, the visual cycle of mammalian rod cells is as follows:
1048:
1035:
980:
917:
913:
877:
845:
803:
596:
592:
445:
399:
205:
60:
17:
2016:
Bownds, Deric (December 1967). "Site of
Attachment of Retinal in Rhodopsin".
1671:
1654:
1466:
1042:)-enantiomer is to be expected if 3-hydroxyretinal is produced directly from
4302:
4262:
4214:
3807:
3713:
3655:
3491:
3449:
3324:
3274:
3228:
3203:
2977:
2864:
2754:
1745:
1712:
1695:
1301:
1154:
984:
921:
909:
837:
582:
570:
3869:
3826:
3773:
3721:
3663:
3625:
3588:
3579:
3562:
3553:
3510:
3457:
3389:
3343:
3282:
3237:
3194:
3151:
3036:
2985:
2926:
2883:
2824:
2805:
2773:
2630:
2595:
2527:
2478:
2305:
2248:
2197:
2154:
1898:
1889:
1872:
1857:
1805:
1796:
1779:
1764:
1680:
1636:
3755:
3424:
3065:
2714:
2673:
2459:
2416:
2364:
2345:
2168:
Murakami M, Kouyama T (May 2008). "Crystal structure of squid rhodopsin".
2088:
2045:
2002:
1959:
1566:
1078:
104:)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
4254:
4199:
4048:
4038:
4028:
3985:
3176:
3108:
1623:
BALL, S; GOODWIN, TW; MORTON, RA (1946). "Retinene1-vitamin A aldehyde".
1317:
1256:
905:
608:
585:
576:
3371:
2189:
770:, is an important signaling molecule and hormone in vertebrate animals.
595:
animals ingest retinal directly from meat, or they produce retinal from
4244:
2080:
1321:
1019:
683:
624:
537:
466:
245:
31:
3617:
3018:
2287:
2037:
880:
blue. Anchoring of transducin to the membrane has been drawn in black.
4209:
4131:
2240:
1601:
1514:
1489:
1173:
1166:
1027:
976:
941:
933:
929:
925:
901:
799:
791:
638:
38:
916:
head of the molecule extends into the interior of the disk, and the
487:
Except where otherwise noted, data are given for materials in their
37:
This article is about the molecule. For the anatomical feature, see
2383:"Rhodopsin and bacteriorhodopsin: structure-function relationships"
1537:
Wald, G (11 October 1968). "Molecular basis of visual excitation".
1447:
4194:
3563:"The Carotenase AtCCD1 from Arabidopsis thaliana Is a Dioxygenase"
2787:
Jin, Minghao; Yuan, Quan; Li, Songhua; Travis, Gabriel H. (2007).
1824:"Retinoic Acid Synthesis and Signaling during Early Organogenesis"
1270:
with beta-carotene monooxygenases; the homologous ninaB enzyme in
1118:
1077:
1014:). Many fish and amphibians use 3,4-didehydroretinal, also called
885:
831:
814:
720:
or, more often, simply vitamin A. Retinal can also be oxidized to
642:
544:
185:
173:
163:
1090:, which is the front-end of phototransduction. It regenerates 11-
828:
configuration by ATP phosphorylation, and the cycle begins again.
802:, which triggers a chemical signaling cascade, which results in
3950:
2219:
Collins, F. D. (March 1953). "Rhodopsin and
Indicator Yellow".
1274:
has both retinal-forming carotenoid-oxygenase activity and all-
920:
tail extends into the cytoplasm of the cell. The opsins in the
759:
also known as retinaldehyde dehydrogenases (RALDHs) as well as
3946:
3159:
Hecht, Selig; Shlaer, Simon; Pirenne, Maurice Henri (1942).
2730:"RPE65 is the isomerohydrolase in the retinoid visual cycle"
892:(GPCRs). Opsins, like other GPCRs, have seven transmembrane
295:
3518:
SchΓ€fer, GΓΌnter; Engelhard, Martin; MΓΌller, Volker (1999).
2443:"The Gluopsins: Opsins without the Retinal Binding Lysine"
619:. These carotenoids must be obtained from plants or other
3901:"Nobel Lecture: The Molecular Basis of Visual Excitation"
428:
61 to 64 Β°C (142 to 147 Β°F; 334 to 337 K)
794:
of the correct wavelength β straightens out into an all-
936:. The cones form incomplete disks that are part of the
505:
1429:
DasSarma, Shiladitya; Schwieterman, Edward W. (2018).
2899:
1934:"G protein involvement in receptor-effector coupling"
4253:
4223:
4170:
4062:
3984:
3877:Briggs, Winslow R.; Spudich, John L., eds. (2005).
2376:
2374:
3834:Yokoyama, Shozo; Radlwimmer, F. Bernhard (2001).
2110:
2108:
2106:
790:-retinal configuration, which β upon capturing a
732:O β retinoic acid + NADH + H (catalyzed by RALDH)
3738:Wang, Tao; Jiao, Yuchen; Montell, Craig (2007).
3298:Luo, Dong-Gen; Xue, Tian; Yau, King-Wai (2008).
580:, and was renamed after it was discovered to be
257:
3787:Proceedings of the National Academy of Sciences
3471:Proceedings of the National Academy of Sciences
3304:Proceedings of the National Academy of Sciences
2844:Proceedings of the National Academy of Sciences
2734:Proceedings of the National Academy of Sciences
2436:
2434:
2325:Proceedings of the National Academy of Sciences
1490:"Carotenoids and the Vitamin A Cycle in Vision"
686:, the transport and storage form of vitamin A:
149:
896:connected by six loops. They are found in the
359:CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
3962:
3397:Racker, Efraim; Stoeckenius, Walther (1974).
3075:"Responses of retinal rods to single photons"
944:in the seventh transmembrane helix through a
569:Retinal itself is considered to be a form of
8:
2547:
2545:
2441:GΓΌhmann M, Porter ML, Bok MJ (August 2022).
1648:
1646:
1327:. In these molecules, light causes the all-
819:An opsin protein surrounds a molecule of 11-
3003:"Spectral Tuning of Deep Red Cone Pigments"
1300:-retinal is also an essential component of
3969:
3955:
3947:
3931:Vision and Light-Induced Molecular Changes
3524:Microbiology and Molecular Biology Reviews
2940:Nobel Prize in Physiology or Medicine 1967
1817:
1815:
1653:von Lintig, Johannes; Vogt, Klaus (2000).
766:Retinoic acid, sometimes called vitamin A
310:
235:
213:
43:
3859:
3816:
3806:
3763:
3703:
3578:
3543:
3500:
3490:
3414:
3379:
3333:
3323:
3227:
3184:
3141:
3098:
3073:Baylor, D A; Lamb, T D; Yau, K W (1979).
3026:
2873:
2863:
2814:
2804:
2763:
2753:
2704:
2585:
2554:"Functions of Opsins in Drosophila Taste"
2517:
2468:
2458:
2406:
2354:
2344:
2295:
2136:
1983:Protein Engineering, Design and Selection
1949:
1932:Casey, P J; Gilman, A G (February 1988).
1888:
1847:
1795:
1754:
1744:
1711:
1670:
1513:
1456:
1446:
277:
27:Vitamin A aldehyde, a polyene chromophore
3734:The oceans are full of type 1 rhodopsin.
1913:"KEGG ENZYME: 1.2.3.11 retinal oxidase"
1409:
1407:
1403:
1335:retinal, which then cycles back to all-
1046:carotenoids. Cyclorrhaphans, including
679:or a beta-carotene 15,15'-dioxygenase.
356:
331:
306:
2381:Ovchinnikov, Yu.A. (8 November 1982).
226:
3936:Retinal Anatomy and Visual Capacities
2069:Biophysics of Structure and Mechanism
1441:(3) (published 2018-10-11): 241β250.
1435:International Journal of Astrobiology
1357:Nobel Prize in Physiology or Medicine
876:terminus of rhodopsin is red and the
631:β may both be produced from retinal.
481:; 3-hydroxyretinal; 4-hydroxyretinal
338:Key: NCYCYZXNIZJOKI-OVSJKPMPSA-N
193:
7:
904:of eye. The opsin in the vertebrate
543:. Retinal, bound to proteins called
248:
3879:Handbook of Photosensory Receptors
3432:Sadekar, Sumedha; Raymond, Jason;
2706:10.1046/j.1432-1327.1998.2570522.x
2666:10.1111/j.1432-1033.1994.tb20097.x
1026:(the so-called higher flies), all
1002:)-3-hydroxyretinal (both vitamin A
677:beta-carotene 15,15'-monooxygenase
25:
1249:lecithin retinol acyltransferases
2693:European Journal of Biochemistry
2654:European Journal of Biochemistry
844:(heads red and tails blue) with
840:(rainbow-colored) embedded in a
495:
386:
59:
50:
3598:Journal of Physical Chemistry A
3567:Journal of Biological Chemistry
3438:Molecular Biology and Evolution
3403:Journal of Biological Chemistry
3300:"How vision begins: An odyssey"
2793:Journal of Biological Chemistry
2611:Photochemistry and Photobiology
1938:Journal of Biological Chemistry
1877:Journal of Biological Chemistry
1784:Journal of Biological Chemistry
1733:Journal of Biological Chemistry
1659:Journal of Biological Chemistry
1086:The visual cycle is a circular
751:(catalyzed by retinal oxidase),
551:, the light-detection stage of
491:(at 25 Β°C , 100 kPa).
3536:10.1128/MMBR.63.3.570-620.1999
3520:"Bioenergetics of the Archaea"
3091:10.1113/jphysiol.1979.sp012716
1778:LidΓ©n, M; Eriksson, U (2006).
1255:Steps 3, 4, 5, and 6 occur in
872:(black) in the rhodopsin. The
392:
380:
1:
3416:10.1016/S0021-9258(19)43080-9
3165:Journal of General Physiology
2919:10.1016/S1011-1344(02)00245-2
1951:10.1016/s0021-9258(18)69103-3
1822:Duester, G (September 2008).
1488:Wald, George (14 July 1934).
1259:; Steps 1, 2, and 7 occur in
1010:)-4-hydroxyretinal (vitamin A
627:and a partially active form,
3943:, Imperial College v-chemlib
3161:"Energy, Quanta, and Vision"
3134:10.1113/jphysiol.2005.091942
3058:10.1016/0042-6989(71)90033-2
2408:10.1016/0014-5793(82)80805-3
2147:10.1126/science.289.5480.739
1559:10.1126/science.162.3850.230
1266:RPE65 isomerohydrolases are
1239:-retinol + fatty acid β all-
1018:. With the exception of the
716:Retinol is called vitamin A
611:. They also produce it from
3852:10.1093/genetics/158.4.1697
961:G protein-coupled receptors
890:G protein-coupled receptors
860:Ξ³ yellow. There is a bound
547:, is the chemical basis of
4375:
1840:10.1016/j.cell.2008.09.002
1700:Pure and Applied Chemistry
1289:
1261:retinal pigment epithelium
1071:
1038:of 3-hydroxyretinal. The (
786:, retinal begins in an 11-
36:
29:
2623:10.1562/2006-07-11-RA-964
2578:10.1016/j.cub.2020.01.068
2519:10.1016/j.cub.2019.07.036
1458:10.1017/S1473550418000423
1325:anoxygenic photosynthesis
1316:, which are important in
1060:have been found to use (4
485:
455:
367:
347:
322:
133:
110:
82:
72:
67:
58:
49:
3927:- National Health Museum
3052:(Supplement 3): 87β101.
1694:Woggon, Wolf-D. (2002).
1672:10.1074/jbc.275.16.11915
1392:Visual phototransduction
1351:The American biochemist
1139:-retinol dehydrogenases;
1135:-retinal + NADH + H; 11-
959:Opsins are prototypical
549:visual phototransduction
30:Not to be confused with
4344:Photosynthetic pigments
3808:10.1073/pnas.0409659102
3744:Journal of Cell Biology
3714:10.1126/science.1093857
3656:10.1126/science.1123802
3492:10.1073/pnas.0608022103
3348:Good historical review.
3325:10.1073/pnas.0708405105
3275:10.1126/science.1108965
3229:10.1126/science.1136244
2978:10.1126/science.1127889
2865:10.1073/pnas.0807805105
2755:10.1073/pnas.0503460102
1995:10.1093/protein/7.2.195
1746:10.1074/jbc.M109.002618
1713:10.1351/pac200274081397
1625:The Biochemical Journal
1377:Purple Earth hypothesis
1257:rod cell outer segments
1206:O β aporhodopsin + all-
979:rhodopsin contains 348
564:Purple Earth Hypothesis
4224:Vitamin A retinoids (C
3580:10.1074/jbc.M511668200
3434:Blankenship, Robert E.
2806:10.1074/jbc.M701432200
1890:10.1074/jbc.M211417200
1797:10.1074/jbc.R500027200
1382:Sensory nervous system
1361:Haldan Keffer Hartline
1331:-retinal to become 13-
1083:
998:)-3-hydroxyretinal, (3
881:
868:Ξ±-subunit and a bound
829:
780:conjugated chromophore
757:retinal dehydrogenases
711:alcohol dehydrogenases
707:retinol dehydrogenases
3925:First Steps of Vision
3756:10.1083/jcb.200610081
3450:10.1093/molbev/msl079
3122:Journal of Physiology
3079:Journal of Physiology
2460:10.3390/cells11152441
2346:10.1073/pnas.93.2.566
1224:-retinol + NADP; all-
1081:
973:X-ray crystallography
954:retinylidene proteins
835:
818:
743:O β retinoic acid + H
701:β retinal + NADH + H,
415:Orange crystals from
84:Systematic IUPAC name
3177:10.1085/jgp.25.6.819
2504:(17): 2961β2969.e4.
1341:convergent evolution
1286:Microbial rhodopsins
1282:isomerase activity.
1064:)-4-hydroxyretinal.
1056:)-3-hydroxyretinal.
884:Retinal is bound to
694:+ H β retinol + NADP
653:Vitamin A metabolism
607:β both of which are
4349:Signal transduction
3799:2005PNAS..102.6879W
3696:2004Sci...304...66V
3648:2006Sci...311.1617S
3642:(5767): 1617β1621.
3610:2007JPCA..111.8766S
3483:2006PNAS..10316123S
3477:(44): 16123β16128.
3372:10.1128/EC.00392-06
3316:2008PNAS..105.9855L
3267:2005Sci...308..267K
3220:2007Sci...315..820K
2970:2006Sci...313.1914F
2964:(5795): 1914β1918.
2911:2002JPPB...66..188C
2856:2008PNAS..10519000O
2799:(29): 20915β20924.
2746:2005PNAS..10212413M
2740:(35): 12413β12418.
2570:2020CBio...30E1367L
2564:(8): 1367β1379.e6.
2510:2019CBio...29E2961K
2399:1982FEBSL.148..179O
2337:1996PNAS...93..566L
2276:Biochemical Journal
2233:1953Natur.171..469C
2190:10.1038/nature06925
2182:2008Natur.453..363M
2129:2000Sci...289..739P
2030:1967Natur.216.1178B
2024:(5121): 1178β1181.
1665:(16): 11915β11920.
1594:1944Natur.153..405M
1551:1968Sci...162..230W
1506:1934Natur.134...65W
1292:Microbial rhodopsin
965:amino acid sequence
898:photoreceptor cells
852:Ξ± is colored red, G
435:Solubility in water
407: gΒ·mol
46:
2319:Lamb, T D (1996).
2081:10.1007/BF00535659
1243:-retinyl ester + H
1220:+ NADPH + H β all-
1121:isomerohydrolases;
1084:
1030:examined use the (
882:
830:
518:Infobox references
456:Related compounds
122:Vitamin A aldehyde
45:All-trans-retinal
44:
4316:
4315:
4308:Zuretinol acetate
3888:978-3-527-31019-7
3793:(19): 6879β6883.
3618:10.1021/jp073908l
3604:(36): 8766β8773.
3573:(15): 9845β9851.
3444:(11): 2001β2007.
3310:(29): 9855β9862.
3261:(5719): 267β269.
3214:(5813): 820β825.
3019:10.1021/bi702069d
2288:10.1042/bj0590122
2227:(4350): 469β471.
2038:10.1038/2161178a0
1883:(11): 9856β9861.
1588:(3883): 405β406.
1387:Visual perception
1306:bacteriorhodopsin
1088:enzymatic pathway
864:molecule in the G
728:retinal + NAD + H
553:visual perception
526:Chemical compound
524:
523:
462:Related compounds
440:Nearly insoluble
291:CompTox Dashboard
175:Interactive image
16:(Redirected from
4366:
3971:
3964:
3957:
3948:
3913:
3911:
3910:
3905:
3892:
3873:
3863:
3846:(4): 1697β1710.
3830:
3820:
3810:
3777:
3767:
3733:
3707:
3680:Venter, J. Craig
3675:
3629:
3592:
3582:
3557:
3547:
3514:
3504:
3494:
3461:
3428:
3418:
3393:
3383:
3347:
3337:
3327:
3294:
3249:
3231:
3198:
3188:
3155:
3145:
3112:
3102:
3069:
3040:
3030:
2997:
2942:
2937:
2931:
2930:
2894:
2888:
2887:
2877:
2867:
2835:
2829:
2828:
2818:
2808:
2784:
2778:
2777:
2767:
2757:
2725:
2719:
2718:
2708:
2684:
2678:
2677:
2649:
2643:
2642:
2606:
2600:
2599:
2589:
2549:
2540:
2539:
2521:
2489:
2483:
2482:
2472:
2462:
2438:
2429:
2428:
2410:
2378:
2369:
2368:
2358:
2348:
2316:
2310:
2309:
2299:
2267:
2261:
2260:
2241:10.1038/171469a0
2216:
2210:
2209:
2165:
2159:
2158:
2140:
2138:10.1.1.1012.2275
2123:(5480): 739β45.
2112:
2101:
2100:
2064:
2058:
2057:
2013:
2007:
2006:
1978:
1972:
1971:
1953:
1944:(6): 2577β2580.
1929:
1923:
1922:
1920:
1919:
1909:
1903:
1902:
1892:
1868:
1862:
1861:
1851:
1819:
1810:
1809:
1799:
1790:(19): 13001β04.
1775:
1769:
1768:
1758:
1748:
1739:(23): 15781β93.
1724:
1718:
1717:
1715:
1706:(8): 1397β1408.
1691:
1685:
1684:
1674:
1650:
1641:
1640:
1620:
1614:
1613:
1602:10.1038/153405a0
1577:
1571:
1570:
1534:
1528:
1527:
1517:
1515:10.1038/134065a0
1485:
1479:
1478:
1460:
1450:
1426:
1420:
1416:, 13th Edition,
1411:
1310:channelrhodopsin
761:retinal oxidases
508:
502:
499:
498:
406:
394:
388:
382:
375:Chemical formula
315:
314:
299:
297:
281:
261:
250:
239:
228:
217:
197:
177:
153:
63:
54:
47:
21:
4374:
4373:
4369:
4368:
4367:
4365:
4364:
4363:
4319:
4318:
4317:
4312:
4249:
4227:
4219:
4177:
4166:
4069:
4058:
3991:
3980:
3975:
3921:
3916:
3908:
3906:
3903:
3895:
3889:
3876:
3833:
3780:
3737:
3705:10.1.1.124.1840
3690:(5667): 66β74.
3678:
3632:
3595:
3560:
3517:
3464:
3431:
3396:
3359:Eukaryotic Cell
3351:
3297:
3252:
3201:
3158:
3115:
3072:
3046:Vision Research
3043:
3013:(16): 4614β20.
3000:
2955:
2951:
2949:Further reading
2946:
2945:
2938:
2934:
2896:
2895:
2891:
2850:(48): 19000β5.
2837:
2836:
2832:
2786:
2785:
2781:
2727:
2726:
2722:
2686:
2685:
2681:
2651:
2650:
2646:
2608:
2607:
2603:
2558:Current Biology
2551:
2550:
2543:
2498:Current Biology
2491:
2490:
2486:
2440:
2439:
2432:
2380:
2379:
2372:
2318:
2317:
2313:
2269:
2268:
2264:
2218:
2217:
2213:
2176:(7193): 363β7.
2167:
2166:
2162:
2114:
2113:
2104:
2066:
2065:
2061:
2015:
2014:
2010:
1980:
1979:
1975:
1931:
1930:
1926:
1917:
1915:
1911:
1910:
1906:
1870:
1869:
1865:
1821:
1820:
1813:
1777:
1776:
1772:
1726:
1725:
1721:
1693:
1692:
1688:
1652:
1651:
1644:
1622:
1621:
1617:
1579:
1578:
1574:
1545:(3850): 230β9.
1536:
1535:
1531:
1487:
1486:
1482:
1428:
1427:
1423:
1412:
1405:
1400:
1373:
1349:
1304:opsins such as
1294:
1288:
1246:
1205:
1185:photoisomerizes
1160:
1108:
1076:
1070:
1013:
1005:
993:
975:) determined.
951:
938:plasma membrane
867:
859:
855:
851:
824:back to its 11-
813:
784:Vertebrate eyes
776:
750:
746:
742:
738:
731:
675:catalyzed by a
670:
655:
613:Ξ²-cryptoxanthin
532:(also known as
527:
520:
515:
514:
513: ?)
504:
500:
496:
492:
463:
437:
417:petroleum ether
404:
391:
385:
377:
363:
360:
355:
354:
343:
340:
339:
336:
330:
329:
318:
300:
293:
284:
264:
251:
220:
200:
180:
167:
156:
143:
129:
128:
106:
105:
78:
42:
35:
28:
23:
22:
15:
12:
11:
5:
4372:
4370:
4362:
4361:
4356:
4351:
4346:
4341:
4336:
4334:Apocarotenoids
4331:
4321:
4320:
4314:
4313:
4311:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4259:
4257:
4255:Retinoid drugs
4251:
4250:
4248:
4247:
4242:
4237:
4231:
4229:
4225:
4221:
4220:
4218:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4181:
4179:
4175:
4172:Apocarotenoids
4168:
4167:
4165:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4104:
4102:Diadinoxanthin
4099:
4094:
4092:Citranaxanthin
4089:
4084:
4079:
4077:Antheraxanthin
4073:
4071:
4067:
4060:
4059:
4057:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3995:
3993:
3989:
3982:
3981:
3976:
3974:
3973:
3966:
3959:
3951:
3945:
3944:
3938:
3933:
3928:
3920:
3919:External links
3917:
3915:
3914:
3893:
3887:
3874:
3831:
3778:
3750:(2): 305β316.
3735:
3676:
3630:
3593:
3558:
3530:(3): 570β620.
3515:
3462:
3429:
3409:(2): 662β663.
3394:
3366:(4): 650β657.
3349:
3295:
3250:
3199:
3171:(6): 819β840.
3156:
3113:
3070:
3041:
2998:
2952:
2950:
2947:
2944:
2943:
2932:
2905:(3): 188β194.
2889:
2830:
2779:
2720:
2699:(2): 522β527.
2679:
2660:(2): 691β696.
2644:
2617:(2): 273β279.
2601:
2541:
2484:
2430:
2393:(2): 179β191.
2370:
2331:(2): 566β570.
2311:
2282:(1): 122β128.
2262:
2211:
2160:
2102:
2075:(4): 235β244.
2059:
2008:
1989:(2): 195β203.
1973:
1924:
1904:
1863:
1811:
1770:
1719:
1686:
1642:
1615:
1572:
1529:
1480:
1421:
1402:
1401:
1399:
1396:
1395:
1394:
1389:
1384:
1379:
1372:
1369:
1348:
1345:
1290:Main article:
1287:
1284:
1253:
1252:
1244:
1233:
1230:dehydrogenases
1211:
1203:
1197:
1196:
1195:
1170:
1158:
1140:
1122:
1106:
1103:-retinyl ester
1072:Main article:
1069:
1066:
1016:dehydroretinal
1011:
1003:
991:
949:
865:
857:
853:
849:
812:
809:
775:
772:
753:
752:
748:
744:
740:
736:
733:
729:
703:
702:
695:
673:
672:
668:
654:
651:
621:photosynthetic
599:β either from
525:
522:
521:
516:
494:
493:
489:standard state
486:
483:
482:
479:dehydroretinal
464:
461:
458:
457:
453:
452:
449:
442:
441:
438:
433:
430:
429:
426:
420:
419:
413:
409:
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402:
396:
395:
389:
383:
378:
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369:
365:
364:
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316:
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301:
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117:
113:
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108:
107:
87:
86:
80:
79:
76:
70:
69:
65:
64:
56:
55:
26:
24:
18:11-cis retinal
14:
13:
10:
9:
6:
4:
3:
2:
4371:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4326:
4324:
4309:
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4266:
4264:
4261:
4260:
4258:
4256:
4252:
4246:
4243:
4241:
4240:Retinoic acid
4238:
4236:
4233:
4232:
4230:
4222:
4216:
4213:
4211:
4208:
4206:
4205:Food orange 7
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4185:Abscisic acid
4183:
4182:
4180:
4173:
4169:
4163:
4160:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4103:
4100:
4098:
4097:Cryptoxanthin
4095:
4093:
4090:
4088:
4087:Canthaxanthin
4085:
4083:
4080:
4078:
4075:
4074:
4072:
4065:
4061:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3996:
3994:
3987:
3983:
3979:
3972:
3967:
3965:
3960:
3958:
3953:
3952:
3949:
3942:
3939:
3937:
3934:
3932:
3929:
3926:
3923:
3922:
3918:
3902:
3898:
3894:
3890:
3884:
3880:
3875:
3871:
3867:
3862:
3857:
3853:
3849:
3845:
3841:
3837:
3832:
3828:
3824:
3819:
3814:
3809:
3804:
3800:
3796:
3792:
3788:
3784:
3779:
3775:
3771:
3766:
3761:
3757:
3753:
3749:
3745:
3741:
3736:
3731:
3727:
3723:
3719:
3715:
3711:
3706:
3701:
3697:
3693:
3689:
3685:
3681:
3677:
3673:
3669:
3665:
3661:
3657:
3653:
3649:
3645:
3641:
3637:
3631:
3627:
3623:
3619:
3615:
3611:
3607:
3603:
3599:
3594:
3590:
3586:
3581:
3576:
3572:
3568:
3564:
3559:
3555:
3551:
3546:
3541:
3537:
3533:
3529:
3525:
3521:
3516:
3512:
3508:
3503:
3498:
3493:
3488:
3484:
3480:
3476:
3472:
3468:
3463:
3459:
3455:
3451:
3447:
3443:
3439:
3435:
3430:
3426:
3422:
3417:
3412:
3408:
3404:
3400:
3395:
3391:
3387:
3382:
3377:
3373:
3369:
3365:
3361:
3360:
3355:
3350:
3345:
3341:
3336:
3331:
3326:
3321:
3317:
3313:
3309:
3305:
3301:
3296:
3292:
3288:
3284:
3280:
3276:
3272:
3268:
3264:
3260:
3256:
3251:
3247:
3243:
3239:
3235:
3230:
3225:
3221:
3217:
3213:
3209:
3205:
3200:
3196:
3192:
3187:
3182:
3178:
3174:
3170:
3166:
3162:
3157:
3153:
3149:
3144:
3139:
3135:
3131:
3127:
3123:
3119:
3114:
3110:
3106:
3101:
3096:
3092:
3088:
3084:
3080:
3076:
3071:
3067:
3063:
3059:
3055:
3051:
3047:
3042:
3038:
3034:
3029:
3024:
3020:
3016:
3012:
3008:
3004:
2999:
2995:
2991:
2987:
2983:
2979:
2975:
2971:
2967:
2963:
2959:
2954:
2953:
2948:
2941:
2936:
2933:
2928:
2924:
2920:
2916:
2912:
2908:
2904:
2900:
2893:
2890:
2885:
2881:
2876:
2871:
2866:
2861:
2857:
2853:
2849:
2845:
2841:
2834:
2831:
2826:
2822:
2817:
2812:
2807:
2802:
2798:
2794:
2790:
2783:
2780:
2775:
2771:
2766:
2761:
2756:
2751:
2747:
2743:
2739:
2735:
2731:
2724:
2721:
2716:
2712:
2707:
2702:
2698:
2694:
2690:
2683:
2680:
2675:
2671:
2667:
2663:
2659:
2655:
2648:
2645:
2640:
2636:
2632:
2628:
2624:
2620:
2616:
2612:
2605:
2602:
2597:
2593:
2588:
2583:
2579:
2575:
2571:
2567:
2563:
2559:
2555:
2548:
2546:
2542:
2537:
2533:
2529:
2525:
2520:
2515:
2511:
2507:
2503:
2499:
2495:
2488:
2485:
2480:
2476:
2471:
2466:
2461:
2456:
2452:
2448:
2444:
2437:
2435:
2431:
2426:
2422:
2418:
2414:
2409:
2404:
2400:
2396:
2392:
2388:
2384:
2377:
2375:
2371:
2366:
2362:
2357:
2352:
2347:
2342:
2338:
2334:
2330:
2326:
2322:
2315:
2312:
2307:
2303:
2298:
2293:
2289:
2285:
2281:
2277:
2273:
2266:
2263:
2258:
2254:
2250:
2246:
2242:
2238:
2234:
2230:
2226:
2222:
2215:
2212:
2207:
2203:
2199:
2195:
2191:
2187:
2183:
2179:
2175:
2171:
2164:
2161:
2156:
2152:
2148:
2144:
2139:
2134:
2130:
2126:
2122:
2118:
2111:
2109:
2107:
2103:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2063:
2060:
2055:
2051:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2012:
2009:
2004:
2000:
1996:
1992:
1988:
1984:
1977:
1974:
1969:
1965:
1961:
1957:
1952:
1947:
1943:
1939:
1935:
1928:
1925:
1914:
1908:
1905:
1900:
1896:
1891:
1886:
1882:
1878:
1874:
1867:
1864:
1859:
1855:
1850:
1845:
1841:
1837:
1834:(6): 921β31.
1833:
1829:
1825:
1818:
1816:
1812:
1807:
1803:
1798:
1793:
1789:
1785:
1781:
1774:
1771:
1766:
1762:
1757:
1752:
1747:
1742:
1738:
1734:
1730:
1723:
1720:
1714:
1709:
1705:
1701:
1697:
1690:
1687:
1682:
1678:
1673:
1668:
1664:
1660:
1656:
1649:
1647:
1643:
1638:
1634:
1630:
1626:
1619:
1616:
1611:
1607:
1603:
1599:
1595:
1591:
1587:
1583:
1576:
1573:
1568:
1564:
1560:
1556:
1552:
1548:
1544:
1540:
1533:
1530:
1525:
1521:
1516:
1511:
1507:
1503:
1499:
1495:
1491:
1484:
1481:
1476:
1472:
1468:
1464:
1459:
1454:
1449:
1444:
1440:
1436:
1432:
1425:
1422:
1419:
1415:
1410:
1408:
1404:
1397:
1393:
1390:
1388:
1385:
1383:
1380:
1378:
1375:
1374:
1370:
1368:
1366:
1365:Ragnar Granit
1362:
1358:
1354:
1346:
1344:
1342:
1338:
1334:
1330:
1326:
1323:
1319:
1315:
1314:halorhodopsin
1311:
1307:
1303:
1299:
1293:
1285:
1283:
1281:
1277:
1273:
1269:
1264:
1263:(RPE) cells.
1262:
1258:
1250:
1242:
1238:
1234:
1231:
1227:
1223:
1219:
1217:
1212:
1209:
1201:
1200:metarhodopsin
1198:
1193:
1192:
1190:
1186:
1183:
1180:II (i.e., 11-
1179:
1178:metarhodopsin
1175:
1171:
1168:
1164:
1156:
1152:
1148:
1146:
1141:
1138:
1134:
1130:
1128:
1123:
1120:
1116:
1112:
1104:
1102:
1097:
1096:
1095:
1093:
1089:
1080:
1075:
1067:
1065:
1063:
1059:
1058:Firefly squid
1055:
1051:
1050:
1045:
1041:
1037:
1033:
1029:
1025:
1021:
1017:
1009:
1001:
997:
988:
986:
982:
978:
974:
970:
966:
962:
957:
955:
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
903:
899:
895:
894:alpha-helices
891:
887:
879:
875:
871:
863:
856:Ξ² blue, and G
847:
843:
842:lipid bilayer
839:
834:
827:
822:
817:
810:
808:
805:
801:
797:
793:
789:
785:
781:
778:Retinal is a
773:
771:
769:
764:
762:
758:
755:catalyzed by
734:
727:
726:
725:
723:
722:retinoic acid
719:
714:
712:
708:
705:catalyzed by
700:
696:
693:
689:
688:
687:
685:
680:
678:
666:
665:beta-carotene
663:
662:
661:
660:For example:
658:
652:
650:
648:
644:
640:
636:
635:Invertebrates
632:
630:
629:retinoic acid
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
588:
587:
584:
579:
578:
572:
567:
565:
561:
556:
554:
550:
546:
542:
539:
535:
534:retinaldehyde
531:
519:
512:
507:
490:
484:
480:
476:
475:beta-carotene
472:
471:retinoic acid
468:
465:
460:
459:
454:
450:
447:
444:
443:
439:
436:
432:
431:
427:
425:
424:Melting point
422:
421:
418:
414:
411:
410:
403:
401:
398:
397:
379:
376:
372:
371:
366:
357:
353:
346:
332:
328:
321:
313:
309:
308:DTXSID5025998
305:
304:
302:
292:
288:
287:
280:
276:
275:
273:
271:
268:
267:
260:
256:
255:
253:
247:
243:
242:
238:
234:
231:
229:
227:ECHA InfoCard
224:
223:
216:
212:
211:
209:
207:
204:
203:
196:
192:
191:
189:
187:
184:
183:
176:
172:
171:
169:
165:
160:
159:
152:
148:
147:
145:
142:
138:
137:
132:
124:
121:
119:Retinaldehyde
118:
115:
114:
109:
103:
99:
95:
91:
85:
81:
75:
71:
66:
62:
57:
53:
48:
40:
33:
19:
4339:Cyclohexenes
4288:Isotretinoin
4268:Alitretinoin
4234:
4190:Apocarotenal
4162:Zeinoxanthin
4152:Violaxanthin
4142:Rhodoxanthin
4122:Flavoxanthin
4107:Diatoxanthin
4064:Xanthophylls
4034:Neurosporene
3907:. Retrieved
3897:Wald, George
3878:
3843:
3839:
3790:
3786:
3747:
3743:
3687:
3683:
3639:
3635:
3601:
3597:
3570:
3566:
3527:
3523:
3474:
3470:
3441:
3437:
3406:
3402:
3363:
3357:
3307:
3303:
3258:
3254:
3211:
3207:
3168:
3164:
3128:(1): 83β95.
3125:
3121:
3082:
3078:
3049:
3045:
3010:
3007:Biochemistry
3006:
2961:
2957:
2935:
2902:
2898:
2892:
2847:
2843:
2833:
2796:
2792:
2782:
2737:
2733:
2723:
2696:
2692:
2682:
2657:
2653:
2647:
2614:
2610:
2604:
2561:
2557:
2501:
2497:
2487:
2453:(15): 2441.
2450:
2446:
2390:
2387:FEBS Letters
2386:
2328:
2324:
2314:
2279:
2275:
2265:
2224:
2220:
2214:
2173:
2169:
2163:
2120:
2116:
2072:
2068:
2062:
2021:
2017:
2011:
1986:
1982:
1976:
1941:
1937:
1927:
1916:. Retrieved
1907:
1880:
1876:
1866:
1831:
1827:
1787:
1783:
1773:
1736:
1732:
1722:
1703:
1699:
1689:
1662:
1658:
1631:(5β6): lix.
1628:
1624:
1618:
1585:
1581:
1575:
1542:
1538:
1532:
1500:(3376): 65.
1497:
1493:
1483:
1438:
1434:
1424:
1417:
1413:
1350:
1336:
1332:
1328:
1297:
1295:
1279:
1275:
1271:
1265:
1254:
1240:
1236:
1225:
1221:
1215:
1207:
1188:
1181:
1172:rhodopsin +
1151:aporhodopsin
1144:
1136:
1132:
1126:
1110:
1100:
1091:
1085:
1082:Visual cycle
1074:Visual cycle
1068:Visual cycle
1061:
1053:
1047:
1039:
1031:
1024:Cyclorrhapha
1007:
999:
995:
989:
969:3D-structure
958:
888:, which are
883:
869:
836:Animal GPCR
825:
820:
795:
787:
777:
765:
754:
715:
704:
681:
674:
671:β 2 retinal,
659:
656:
647:xanthophylls
633:
615:, a type of
591:
581:
575:
568:
557:
533:
529:
528:
134:Identifiers
111:Other names
101:
97:
93:
89:
4283:Fenretinide
4147:Rubixanthin
4127:Fucoxanthin
4112:Dinoxanthin
4082:Astaxanthin
4054:Lycopersene
4044:Phytofluene
3978:Carotenoids
3085:: 613β634.
1414:Merck Index
1353:George Wald
1165:linkage to
1163:Schiff base
1131:+ NAD β 11-
1113:-retinol +
1044:xanthophyll
946:Schiff base
848:below it. G
735:retinal + O
709:(RDHs) and
617:xanthophyll
597:carotenoids
560:chlorophyll
541:chromophore
412:Appearance
368:Properties
233:100.003.760
195:CHEBI:17898
4323:Categories
4298:Temarotene
4293:Tazarotene
4278:Etretinate
4273:Bexarotene
4157:Zeaxanthin
4137:Neoxanthin
4117:Echinenone
4024:ΞΆ-Carotene
4019:Ξ΅-Carotene
4014:Ξ΄-Carotene
4009:Ξ³-Carotene
4004:Ξ²-Carotene
3999:Ξ±-Carotene
3909:2009-02-23
1918:2009-03-10
1448:1810.05150
1398:References
1272:Drosophila
1268:homologous
1169:, -CH=NH-;
1115:fatty acid
1049:Drosophila
1036:enantiomer
981:amino acid
922:cone cells
918:C-terminus
914:N-terminus
878:C-terminus
874:N-terminus
846:transducin
804:perception
697:retinol +
690:retinal +
605:Ξ²-carotene
601:Ξ±-carotene
593:Vertebrate
555:(vision).
446:Solubility
400:Molar mass
279:RR725D715M
206:ChemSpider
162:3D model (
141:CAS Number
74:IUPAC name
4359:Vitamin A
4329:Aldehydes
4303:Tretinoin
4263:Acitretin
4215:Peridinin
3986:Carotenes
3881:. Wiley.
3700:CiteSeerX
2536:201420079
2133:CiteSeerX
1475:119341330
1467:1473-5504
1318:bacterial
1302:microbial
1228:-retinol
1210:-retinal;
1161:O; forms
1155:rhodopsin
1022:suborder
1006:), and (4
985:evolution
910:rhodopsin
906:rod cells
838:rhodopsin
782:. In the
609:carotenes
583:vitamin A
571:vitamin A
4200:Crocetin
4049:Torulene
4039:Phytoene
4029:Lycopene
3899:(1967).
3870:11545071
3840:Genetics
3827:15860584
3774:17452532
3722:15001713
3672:28604455
3664:16543463
3626:17713894
3589:16459333
3554:10477309
3511:17060607
3458:16887904
3390:17293483
3344:18632568
3283:15821095
3246:25258551
3238:17255476
3195:19873316
3152:15994181
3037:18370404
2994:84439732
2986:17008522
2927:11960728
2884:19020100
2825:17504753
2774:16116091
2639:23060331
2631:16961436
2596:32243853
2528:31447373
2479:35954284
2425:85819100
2306:14351151
2249:13046517
2198:18480818
2155:10926528
2097:20407577
1968:38970721
1899:12519776
1858:18805086
1806:16428379
1765:19366683
1681:10766819
1637:20341217
1371:See also
1322:archaeal
1251:(LRATs).
1218:-retinal
1147:-retinal
1129:-retinol
1052:, use (3
1020:dipteran
713:(ADHs).
637:such as
586:aldehyde
577:retinene
451:Soluble
151:116-31-4
116:Retinene
4245:Retinol
4235:Retinal
4210:Ionones
3941:Retinal
3861:1461741
3818:1100770
3795:Bibcode
3765:2064138
3730:1454587
3692:Bibcode
3684:Science
3644:Bibcode
3636:Science
3606:Bibcode
3502:1637547
3479:Bibcode
3425:4272126
3381:1865656
3335:2481352
3312:Bibcode
3291:6318853
3263:Bibcode
3255:Science
3216:Bibcode
3208:Science
3186:2142545
3143:1474752
3100:1281447
3066:5293890
3028:2492582
2966:Bibcode
2958:Science
2907:Bibcode
2875:2596218
2852:Bibcode
2816:2747659
2765:1194921
2742:Bibcode
2715:9826202
2674:8001586
2587:7252503
2566:Bibcode
2506:Bibcode
2470:9368030
2417:6759163
2395:Bibcode
2365:8570596
2333:Bibcode
2297:1216098
2257:4152360
2229:Bibcode
2206:4339970
2178:Bibcode
2125:Bibcode
2117:Science
2089:6342691
2054:1657759
2046:4294735
2026:Bibcode
2003:8170923
1960:2830256
1849:2632951
1756:2708875
1610:4111460
1590:Bibcode
1567:4877437
1547:Bibcode
1539:Science
1524:4022911
1502:Bibcode
1347:History
1187:to all-
1109:O β 11-
1028:insects
900:in the
870:retinal
718:alcohol
684:retinol
639:insects
625:retinol
538:polyene
536:) is a
530:Retinal
511:what is
509: (
467:retinol
448:in fat
405:284.443
246:PubChem
77:Retinal
32:Retinol
4354:Vision
4176:<40
4132:Lutein
3885:
3868:
3858:
3825:
3815:
3772:
3762:
3728:
3720:
3702:
3670:
3662:
3624:
3587:
3552:
3545:103747
3542:
3509:
3499:
3456:
3423:
3388:
3378:
3342:
3332:
3289:
3281:
3244:
3236:
3193:
3183:
3150:
3140:
3109:112243
3107:
3097:
3064:
3035:
3025:
2992:
2984:
2925:
2882:
2872:
2823:
2813:
2772:
2762:
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