2433:
2585:
1812:
484:
314:
1222:
64:
5882:
48:
1217:
38:
1297:
5893:
5913:
1300:
5923:
5872:
5903:
1506:
1302:
1301:
5502:
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1868:
from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe. This process usually gives a yield of around 65%.
1230:
1197:
3295:
Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma L.; Edwards, Jennifer K.; Hutchings, Graham J. (21 November 2014). "Oxidation of Benzyl
Alcohol using in Situ Generated Hydrogen Peroxide".
2083:
3501:
1276:
3476:
EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Consleg-versions do not contain the latest changes in a law)
5665:
2241:
of benzoic acid as a preservative in food are between 0.05 and 0.1%. Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws.
4027:
3981:
1861:
Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation.
1519:
4443:
5630:
5660:
5116:
3340:
5620:
3606:
2329:
Benzoic acid occurs naturally as do its esters in many plant and animal species. Appreciable amounts are found in most berries (around 0.05%). Ripe fruits of several
1303:
2199:
is decreased by 95%. The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food. Benzoic acid, benzoates and their derivatives are used as
4797:
3431:
Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester Bound
Benzoic and Cinnamic Acids of Gum Benzoin Resins by GC-MS HPLC-frit FAB-MS".
1311:
5552:
3862:
3835:
3262:
5805:
5519:
533:
5743:
4060:
3792:
Cosmetic
Ingredient Review Expert Panel Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate".
2916:
2634:
4033:
5581:
3478:
5625:
5487:
4436:
3460:
3376:"Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH"
5595:
5926:
2432:
1325:
3494:
2088:
The temperature required can be lowered to 200 °C by the addition of catalytic amounts of copper(II) salts. The phenol can be converted to
1142:
5439:
5586:
5534:
4741:
4387:
4353:
3569:
3181:
3116:
3091:
3058:
2939:
2716:
1111:
3230:
5789:
5600:
5529:
5454:
5273:
3723:
Juteau, Pierre; Valérie Côté; Marie-France
Duckett; Réjean Beaudet; François Lépine; Richard Villemur; Jean-Guy Bisaillon (January 2005).
3197:
2584:
5777:
5655:
4429:
2453:
2442:
2361:. Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the
4790:
3357:
1318:
3526:
3444:
5794:
5753:
5718:
5703:
5685:
5610:
5389:
2826:
498:
3132:
Shirley, D. A. (1954). "The
Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium".
5799:
5635:
5566:
5561:
1953:
1811:
5738:
5645:
5509:
5424:
5187:
4053:
5767:
5640:
5477:
5444:
4018:
3603:
1178:
3996:
3152:
Huryn, D. M. (1991). "Carbanions of Alkali and
Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". In
5543:
5497:
4933:
4783:
4262:
3725:"Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate"
1865:
1272:
1526:
5772:
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441:
1221:
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5524:
5482:
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4404:
2575:
2188:
462:
5821:
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3269:
2700:
915:
47:
1849:
benzoic acid derivatives. For this reason, benzoic acid for human consumption was obtained by dry distillation of
5957:
5851:
5571:
2879:
2630:
2615:
2554:
1944:
321:
5713:
5074:
5066:
4909:
4038:
1348:
386:
3495:"Indications of the possible formation of benzene from benzoic acid in foods, BfR Expert Opinion No. 013/2006"
2842:
Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide".
2797:
5693:
5605:
5046:
4921:
4746:
4392:
2267:
1905:
947:
5906:
3475:
2667:, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had benzoic acid.
1913:
1216:
392:
309:
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5761:
5681:
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5278:
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1763:
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1244:
1209:
876:
88:
37:
20:
1742:
1656:
Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many
181:
1766:
properties of benzoic acid, which was used for a long time in the preservation of benzoate-containing
251:
5896:
5210:
5039:
4894:
4704:
4363:
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2521:
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76:
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2751:
2697:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2607:
2480:
2283:
2196:
2183:
salt. The mechanism starts with the absorption of benzoic acid into the cell. If the intracellular
2109:
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1437:
479:
147:
5514:
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5293:
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63:
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1005:
3586:
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5384:
5232:
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4452:
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3910:
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3553:
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3345:
3305:
3169:
3165:
3076:
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2704:
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2502:
2491:
2449:
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2156:
1838:
1822:
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1682:
1661:
1579:
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1473:
1025:
964:
656:
556:
450:
5708:
5414:
5376:
5346:
5192:
5125:
4990:
4975:
4899:
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4293:
4215:
4152:
4147:
4023:
3610:
3530:
3482:
3464:
3035:
2972:
2807:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-23)
2637:(IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day.
2567:
2468:
2384:
2379:
2279:
2223:
2148:
2113:
1928:
1850:
1650:
1431:
1417:
355:
3628:"Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE"
3554:
271:
3391:
2108:, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by
1397:
483:
313:
231:
157:
5831:
4995:
4960:
4856:
4752:
4421:
4398:
4177:
4127:
4001:
3915:
3890:
3173:
2546:
2419:
2362:
2215:
1924:
1633:), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –
1497:
1468:
889:
3408:
3375:
3053:(Pearson new international ed.). Harlow: Pearson Education Limited. p. 985.
2875:
5941:
5836:
5356:
5164:
5025:
5005:
4916:
4881:
4302:
4220:
3399:
2899:
2603:
2395:
2245:
2238:
2160:
1893:
can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.
1756:
1060:
645:
635:
302:
3821:
2534:
can be obtained by the reaction of alcohols under acidic water free conditions with
5886:
5846:
5361:
5174:
5144:
5015:
5000:
4846:
4581:
4473:
4460:
4167:
4132:
4080:
3967:
2542:
2535:
2517:
2391:
2291:
2204:
2200:
2089:
1901:
1886:
1846:
1488:
1463:
2351:) contain as much as 0.03–0.13% free benzoic acid. Benzoic acid is also formed in
3604:
Experiment 2: Using Bomb
Calorimetry to Determine the Resonance Energy of Benzene
3231:"Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent"
3162:
Comprehensive
Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1
2777:
5916:
5876:
5462:
5419:
5351:
5331:
5308:
5283:
5087:
5082:
5060:
5053:
5010:
4980:
4950:
4806:
4623:
4469:
4368:
4327:
4312:
4297:
4289:
4240:
4142:
4112:
3938:
Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat".
3765:
3659:
3642:
3153:
3134:
2708:
2611:
2513:
2415:
2298:
2219:
2211:
2207:
2105:
1803:
1734:
1730:
1646:
1629:
group is often abbreviated "Bz" (not to be confused with "Bn" which is used for
1622:
1478:
1375:
1337:
1254:
862:
733:
414:
1755:
determined the composition of benzoic acid. These latter also investigated how
5677:
5429:
5394:
5323:
5110:
4985:
4945:
4814:
4722:
4618:
4599:
4576:
4566:
4558:
4509:
4373:
4337:
4332:
4317:
4235:
4230:
4205:
4187:
4162:
4157:
4107:
3805:
2531:
2317:
In teaching laboratories, benzoic acid is a common standard for calibrating a
2306:
2287:
1767:
1672:
for the industrial synthesis of many other organic substances. The salts and
1011:
858:
840:
822:
786:
756:
722:
701:
584:
262:
3349:
3317:
2985:
2653:. Lethal dose for cats can be as low as 300 mg/kg body weight. The oral
5723:
5434:
5366:
5341:
5303:
5268:
5260:
5242:
5227:
5215:
5159:
5136:
5104:
5099:
4889:
4717:
4688:
4571:
4549:
4541:
4527:
4456:
4322:
4307:
4284:
4182:
4117:
2949:
2571:
2336:
2331:
2302:
2176:
2141:
2125:
1890:
1800:
1483:
985:
844:
3813:
3750:
3709:
2994:
1931:
and virtually all benzyl derivatives are readily oxidized to benzoic acid.
3959:
3924:
3741:
3724:
3668:
3417:
2248:(vitamin C) in some soft drinks, forming small quantities of carcinogenic
2244:
Concern has been expressed that benzoic acid and its salts may react with
1908:. This synthesis offers a convenient exercise for students to carry out a
5698:
5288:
5237:
5093:
5033:
4861:
4831:
4643:
4628:
4545:
4482:
4172:
4122:
2344:
2286:
and Friar's balsam. Such products have a long history of use as topical
2271:
2227:
2168:
1834:
1614:
1324:
1317:
1310:
1283:
1250:
760:
347:
339:
282:
3700:
3683:
3445:
10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;2-Y
2855:
1904:
can be converted to benzoic acid by "carboxylation" of the intermediate
291:
5154:
4871:
4841:
4775:
4710:
4652:
4491:
4225:
4210:
4137:
3951:
2623:
2550:
2249:
2231:
2192:
2180:
1878:
1788:
1626:
1599:
1047:
826:
790:
749:
745:
729:
711:
707:
615:
401:
322:
5871:
3906:
3309:
5298:
5256:
4826:
4633:
4609:
3556:
Wilson and
Gisvold's Textbook of Organic Medicinal and Pharmaceutical
3109:
Introduction to Organic Laboratory Techniques: A Small Scale Approach
2676:
2664:
2399:
2370:
2172:
2120:. These plasticizers, which are used similarly to those derived from
1940:
1796:
1792:
1630:
1033:
741:
737:
242:
1496:
Except where otherwise noted, data are given for materials in their
3338:
Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives".
2917:"Scientists uncover last steps for benzoic acid creation in plants"
1806:. The process uses abundant materials, and proceeds in high yield.
375:
5252:
4904:
4276:
4089:
2821:(8 ed.). New York: W. H. Freeman and Company. pp. AP12.
2660:
for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg.
2650:
2641:
have a significantly lower tolerance against benzoic acid and its
2487:
2476:
2352:
2164:
2093:
1882:
1673:
1043:
425:
222:
180:
170:
3729:
International Journal of Systematic and Evolutionary Microbiology
3500:. German Federal Institute for Risk Assessment. 1 December 2005.
2171:. It is either added directly or created from reactions with its
2387:
contains up to 20% of benzoic acid and 40% benzoic acid esters.
2270:
which is used for the treatment of fungal skin diseases such as
2144:
2117:
1830:
605:
366:
4779:
4425:
4042:
3891:"Studies on the mechanism of the antifungal action of benzoate"
5149:
2646:
2638:
1411:
3643:"Direct Colorimetric Determination of Hippuric Acid in Urine"
2800:
in Linstrom, Peter J.; Mallard, William G. (eds.);
2583:
2431:
2078:{\displaystyle {\ce {C6H5CO2H + 1/2 O2 -> C6H5OH + CO2}}}
1810:
467:
46:
36:
2970:(1832). "Untersuchungen über das Radikal der Benzoesäure".
2184:
1706:
1700:
1691:
1561:
1549:
2802:
1725:
Benzoic acid was discovered in the sixteenth century. The
3997:"Nearly 30% dried, pickled foods fail safety inspections"
3552:
Charles Owens Wilson; Ole Gisvold; John H. Block (2004).
3458:
GSFA Online Food Additive Group Details: Benzoates (2006)
2445:
reaction will take place mainly in 3-position due to the
2071:
2052:
2039:
2023:
1994:
1981:
1968:
1853:. Food-grade benzoic acid is now produced synthetically.
1567:
1295:
3591:
Practical Druggist and Pharmaceutical Review of Reviews
1514:
4028:
Organisation for Economic Co-operation and Development
2934:(6 ed.). Stuttgart: Frankh'sche Verlagshandlung.
2132:
Precursor to sodium benzoate and related preservatives
2003:
1821:
The first industrial process involved the reaction of
1956:
1939:
Benzoic acid is mainly consumed in the production of
1697:
1694:
1570:
1558:
1552:
340:
3764:
Brewster, R. Q.; Williams, B.; Phillips, R. (1955).
3198:"The Grignard Reaction. Preparation of Benzoic Acid"
2479:
are the product of the acid catalysed reaction with
1709:
1688:
1546:
5814:
5752:
5676:
5631:
2024 United Kingdom Shigatoxigenic E. coli outbreak
5453:
5375:
5322:
5251:
5201:
5173:
5135:
5024:
4932:
4880:
4813:
4697:
4679:
4661:
4642:
4608:
4590:
4557:
4540:
4518:
4500:
4481:
4468:
4346:
4275:
4249:
4196:
4098:
4088:
4024:
SIDS Initial Assessment Report for Benzoic Acid
1685:
1555:
3075:
2414:Reactions of benzoic acid can occur at either the
2282:, benzoic acid is also a major ingredient in both
2077:
507:InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
3980:: CS1 maint: DOI inactive as of September 2024 (
3236:. University of Wisconsin-Madison. Archived from
2679: – Organic compound and a form of vitamin B3
517:InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
198:
413:
2779:Solubilities of Inorganic and Organic Compounds
1299:
156:
3560:. Lippincott Williams & Wilkins. pp.
3341:Ullmann's Encyclopedia of Industrial Chemistry
1845:. The product contains significant amounts of
1653:, which was for a long time its only source.
4791:
4437:
4054:
2776:Seidell, Atherton; Linke, William F. (1952).
8:
5806:Spanish Agency for Food Safety and Nutrition
5621:2017–2018 South African listeriosis outbreak
5520:1985 Austrian diethylene glycol wine scandal
3203:. Portland Community College. Archived from
2884:Institute for Occupational Safety and Health
2805:, NIST Standard Reference Database Number 69
1342:121.5 °C (250.7 °F; 394.6 K)
5744:United Kingdom food information regulations
3263:"Experiment 3: Preparation of Benzoic Acid"
2746:
2744:
2742:
2740:
2738:
2736:
2734:
2732:
2730:
2728:
2578:can be achieved by heating the silver salt.
1703:
1564:
4798:
4784:
4776:
4554:
4478:
4444:
4430:
4422:
4095:
4061:
4047:
4039:
3622:
3620:
3618:
3298:Organic Process Research & Development
2635:International Programme on Chemical Safety
1649:carboxylic acid. The name is derived from
482:
312:
270:
25:
5582:2008 United States salmonellosis outbreak
3914:
3740:
3699:
3658:
3407:
3111:. Thomson Brooks/Cole. pp. 312–314.
3082:(3rd ed.). Pergamon Press. pp.
2993:
2626:which is also excreted as hippuric acid.
2570:to benzene may be effected by heating in
2512:Highly reactive acid derivatives such as
2369:) as well as in gland secretions of male
2070:
2065:
2051:
2046:
2038:
2033:
2022:
2017:
1993:
1988:
1980:
1975:
1967:
1962:
1957:
1955:
1783:Benzoic acid is produced commercially by
449:
5626:2018 Australian strawberry contamination
5488:Morinaga Milk arsenic poisoning incident
3995:Chen, Jian; Y.L. Kao (18 January 2010).
3074:D. D. Perrin; W. L. F. Armarego (1988).
2871:
2869:
2867:
2865:
1640:
1636:
1609:
1605:
1589:
1585:
1356:571 °C (1,060 °F; 844 K)
19:"E210" redirects here. For the car, see
5596:2011 United States listeriosis outbreak
4019:International Chemical Safety Card 0103
2895:
2893:
2891:
2688:
2203:for acidic foods and beverages such as
2136:Benzoic acid and its salts are used as
1916:forming reaction in organic chemistry.
538:
503:
478:
391:
290:
5611:2015 Mozambique funeral beer poisoning
5188:Ethylenediaminetetraacetic acid (EDTA)
3973:
3889:Krebs HA, Wiggins D, Stubbs M (1983).
3333:
3331:
3329:
3327:
3031:
3020:
2793:
2791:
2789:
2622:into hippuric acid. Humans metabolize
2394:, benzoate is produced in plants from
2159:. Benzoic acid inhibits the growth of
650:250 °C (482 °F; 523 K)
640:122 °C (252 °F; 395 K)
303:
3869:. Technische Universität Braunschweig
3842:. Technische Universität Braunschweig
2398:. A pathway has been identified from
510:Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N
250:
230:
7:
5902:
5790:Institute for Food Safety and Health
5530:Australian meat substitution scandal
5498:Moroccan oil poisoning disaster 1959
5274:Arsenic contamination of groundwater
3078:Purification of Laboratory Chemicals
2436:benzoic acid aromatic ring reactions
5922:
5778:Food Information and Control Agency
3268:. Towson University. Archived from
2516:are easily obtained by mixing with
2443:Electrophilic aromatic substitution
2092:, which is a starting material for
520:Key: WPYMKLBDIGXBTP-UHFFFAOYAD
404:
374:
3507:from the original on 26 April 2006
3174:10.1016/B978-0-08-052349-1.00002-0
2574:in the presence of copper salts.
1841:is converted to benzoic acid with
14:
5795:International Food Safety Network
5719:International Food Safety Network
5440:Variant Creutzfeldt–Jakob disease
5390:Acid-hydrolyzed vegetable protein
5117:Shigatoxigenic and verotoxigenic
2606:. Benzoic acid is metabolized by
2266:Benzoic acid is a constituent of
2124:ester, represent alternatives to
1762:In 1875 Salkowski discovered the
5921:
5911:
5901:
5892:
5891:
5880:
5870:
5800:Ministry of Food and Drug Safety
5636:Kobayashi red yeast rice scandal
5567:2008 Canada listeriosis outbreak
5562:ICA meat repackaging controversy
3400:10.1128/AEM.57.12.3410-3414.1991
2844:The Journal of Organic Chemistry
2355:after infection with the fungus
2278:. As the principal component of
1864:Benzoic acid can be purified by
1681:
1668:. Benzoic acid is an important
1578:is a white (or colorless) solid
1542:
1504:
1220:
1215:
568:
62:
5739:Quality Assurance International
5646:Food safety incidents in Taiwan
5616:2017 Brazil Operation Weak Meat
5510:1971 Iraq poison grain disaster
5425:Polycyclic aromatic hydrocarbon
2614:, which is then metabolized by
2598:Safety and mammalian metabolism
1825:(trichloromethyl benzene) with
1500:(at 25 °C , 100 kPa).
5768:European Food Safety Authority
5641:Food safety incidents in China
5478:1858 Bradford sweets poisoning
5445:Water fluoridation controversy
3954:(inactive 11 September 2024).
3684:"Phenylpropanoid Biosynthesis"
2819:Quantitative Chemical Analysis
2701:The Royal Society of Chemistry
2610:into an intermediate product,
2026:
1795:. The process is catalyzed by
1179:Occupational safety and health
574:
562:
1:
4263:3-(p-Fluorobenzoyloxy)tropane
4250:ArCO2- (not para-amino or Ph)
3374:A D Warth (1 December 1991).
2234:) and other acidified foods.
1920:Oxidation of benzyl compounds
1676:of benzoic acid are known as
5773:Food and Drug Administration
5455:Food contamination incidents
3641:Tomokuni K, Ogata M (1972).
2588:benzoic acid group reactions
2471:apply also to benzoic acid.
2297:Benzoic acid was used as an
1759:is related to benzoic acid.
1664:of benzoic acid are used as
811:g/100 g (19.2 °C)
600:Colorless crystalline solid
5827:Food and drink prohibitions
5601:Bihar school meal poisoning
5525:United Kingdom BSE outbreak
5483:1900 English beer poisoning
4837:Antibiotic use in livestock
3863:"glycine N-acyltransferase"
2709:10.1039/9781849733069-00648
2576:Hunsdiecker decarboxylation
2377:) or Asian bull elephants (
2309:in the early 20th century.
2187:changes to 5 or lower, the
1364:or concentration (LD, LC):
871:g/100 g (25 °C)
853:g/100 g (25 °C)
835:g/100 g (20 °C)
817:g/100 g (23 °C)
799:g/100 g (−18 °C)
781:g/100 g (23 °C)
775:g/100 g (−13 °C)
769:g/100 g (−18 °C)
32:
16:Organic compound (C6H5COOH)
5981:
5822:Curing (food preservation)
4895:Monosodium glutamate (MSG)
4354:Anesthetic/vasoconstrictor
3780:, vol. 3, p. 337
3585:Lillard, Benjamin (1919).
2919:. Purdue Agriculture News.
2906:. Retrieved on 2014-05-23.
2490:are usually prepared from
2325:Biology and health effects
2254:
805:g/100 g (15 °C)
18:
5865:
5852:Genetically modified food
5704:Food labeling regulations
5572:2008 Chinese milk scandal
4736:
4382:
4259:(3,4,5-Trimethoxybenzoyl)
3806:10.1080/10915810152630729
3766:"3,5-Dinitrobenzoic Acid"
3660:10.1093/clinchem/18.4.349
3587:"Troches of Benzoic Acid"
3463:26 September 2007 at the
2880:GESTIS Substance Database
2631:World Health Organization
2313:Niche and laboratory uses
2100:Precursor to plasticizers
1945:oxidative decarboxylation
1494:
1403:
1360:
1196:
1176:
1171:
1053:
998:
549:
529:
494:
140:
99:
87:
75:
70:
61:
31:
5714:Food safety in Australia
4910:High-fructose corn syrup
3350:10.1002/14356007.a03_555
3107:Donald L. Pavia (2004).
2986:10.1002/jlac.18320030302
1912:, an important class of
1263:Precautionary statements
5694:Acceptable daily intake
5606:2013 horse meat scandal
5047:Clostridium perfringens
4313:Cinchocaine (Dibucaine)
4075:sodium channel blockers
3344:. Weinheim: Wiley-VCH.
3049:Wade, Leroy G. (2014).
2817:Harris, Daniel (2010).
2452:; i.e. benzoic acid is
2116:with the corresponding
1906:phenylmagnesium bromide
1779:Industrial preparations
1733:was first described by
948:Magnetic susceptibility
5762:Centre for Food Safety
5577:2008 Irish pork crisis
5279:Benzene in soft drinks
3380:Appl Environ Microbiol
2930:Neumüller O-A (1988).
2803:NIST Chemistry WebBook
2589:
2467:Reactions typical for
2437:
2257:Benzene in soft drinks
2189:anaerobic fermentation
2079:
1816:
1306:
93:Benzenecarboxylic acid
52:
42:
5784:Food Standards Agency
5734:Organic certification
5729:Nutrition facts label
5473:Esing Bakery incident
5261:environment pollution
4359:Bupivacaine/meloxicam
3836:"butyrate-CoA ligase"
3742:10.1099/ijs.0.02914-0
3481:19 April 2003 at the
2932:Römpps Chemie-Lexikon
2703:. 2014. p. 745.
2587:
2435:
2214:), sparkling drinks (
2140:, represented by the
2080:
1897:From Grignard reagent
1814:
1658:secondary metabolites
1645:. It is the simplest
1305:
610:Faint, pleasant odor
117:Phenylcarboxylic acid
89:Systematic IUPAC name
50:
40:
21:Toyota Corolla (E210)
5553:2006 North American
5211:Acesulfame potassium
5040:Campylobacter jejuni
4934:Intestinal parasites
4807:Consumer food safety
4646:-containing products
4612:-containing products
4485:-containing products
4364:Lidocaine/prilocaine
4173:Procaine (Novocaine)
3609:9 March 2012 at the
3527:"Whitfield Ointment"
3243:on 23 September 2015
3011:Berl Klin Wochenschr
3009:Salkowski E (1875).
2522:phosphorus chlorides
2507:phosphorus pentoxide
2447:electron-withdrawing
2341:V. vitis macrocarpon
2268:Whitfield's ointment
1954:
1947:at 300−400 °C:
1857:Laboratory synthesis
1739:Alexius Pedemontanus
1737:(1556), and then by
1438:Hydroxybenzoic acids
1288:(fire diamond)
980:1.504 (132 °C)
114:Phenylmethanoic acid
77:Preferred IUPAC name
51:Ball-and-stick model
5857:Conspiracy theories
5410:Heterocyclic amines
5314:Shellfish poisoning
3800:(Suppl. 3): 23–50.
3392:1991ApEnM..57.3410W
3210:on 26 February 2015
2856:10.1021/jo01304a033
2608:butyrate-CoA ligase
2284:tincture of benzoin
2197:phosphofructokinase
2110:transesterification
2073:
2054:
2041:
2025:
1996:
1983:
1970:
978:1.5397 (20 °C)
657:Solubility in water
630:g/cm (130 °C)
592: g/mol
212:Beilstein Reference
129:Hydrogenphenic acid
28:
5963:E-number additives
5515:Toxic oil syndrome
5468:Swill milk scandal
5294:Diethylstilbestrol
4966:Diphyllobothriasis
4763:Never to phase III
4409:Never to phase III
3952:10.1136/vr.90.3.53
3168:. pp. 49–75.
2973:Annalen der Chemie
2602:It is excreted as
2590:
2562:sodium borohydride
2549:is possible using
2438:
2138:food preservatives
2075:
2061:
2042:
2029:
2013:
2012:
1984:
1971:
1958:
1914:carbon–carbon bond
1817:
1743:Blaise de Vigenère
1666:food preservatives
1527:Infobox references
1447:Nitrobenzoic acids
1442:Aminobenzoic acids
1423:Potassium benzoate
1404:Related compounds
1386:mg/kg (rat, oral)
1307:
994:mPa (130 °C)
910:kPa (200 °C)
696:g/L (100 °C)
53:
43:
26:
5935:
5934:
5842:Food preservation
5651:Foodborne illness
5203:Sugar substitutes
4956:Cryptosporidiosis
4938:parasitic disease
4852:HGH controversies
4819:food contaminants
4773:
4772:
4732:
4731:
4536:
4535:
4453:Ectoparasiticides
4419:
4418:
4271:
4270:
4070:Local anesthetics
3907:10.1042/bj2140657
3879:Substrate/Product
3852:Substrate/Product
3778:Collected Volumes
3771:Organic Syntheses
3701:10.1093/mp/ssp106
3682:Vogt, T. (2010).
3571:978-0-7817-3481-3
3533:on 9 October 2007
3310:10.1021/op500195e
3304:(11): 1455–1460.
3183:978-0-08-052349-1
3118:978-0-534-40833-6
3093:978-0-08-034715-8
3060:978-1-292-02165-2
3051:Organic Chemistry
3030:Missing or empty
2941:978-3-440-04516-9
2900:Sigma-Aldrich Co.
2850:(16): 3299–3305.
2718:978-0-85404-182-4
2499:benzoic anhydride
2404:4-hydroxybenzoate
2358:Nectria galligena
2122:terephthalic acid
2064:
2057:
2045:
2032:
2016:
2011:
1999:
1987:
1974:
1961:
1910:Grignard reaction
1866:recrystallization
1843:hydrochloric acid
1833:or iron salts as
1827:calcium hydroxide
1815:toluene oxidation
1785:partial oxidation
1768:cloudberry fruits
1749:Justus von Liebig
1582:with the formula
1535:Chemical compound
1533:
1532:
1459:Related compounds
1452:Phenylacetic acid
1392:Safety data sheet
1245:Hazard statements
1006:Crystal structure
904:kPa (100 °C)
624:g/cm (15 °C)
463:CompTox Dashboard
182:Interactive image
57:
56:
5970:
5958:Phenyl compounds
5925:
5924:
5915:
5905:
5904:
5895:
5894:
5887:Drink portal
5885:
5884:
5883:
5875:
5874:
5786:(United Kingdom)
5535:Jack in the Box
5506:
5493:Minamata disease
5405:Food irradiation
5385:4-Hydroxynonenal
5233:Sodium cyclamate
5076:Escherichia coli
5068:Escherichia coli
4800:
4793:
4786:
4777:
4592:Chloride channel
4555:
4502:Chloride channel
4479:
4446:
4439:
4432:
4423:
4096:
4078:
4063:
4056:
4049:
4040:
4007:
4006:
3992:
3986:
3985:
3979:
3971:
3935:
3929:
3928:
3918:
3886:
3880:
3878:
3876:
3874:
3859:
3853:
3851:
3849:
3847:
3832:
3826:
3825:
3789:
3783:
3781:
3774:
3761:
3755:
3754:
3744:
3720:
3714:
3713:
3703:
3679:
3673:
3672:
3662:
3638:
3632:
3631:
3624:
3613:
3601:
3595:
3594:
3582:
3576:
3575:
3559:
3549:
3543:
3542:
3540:
3538:
3529:. Archived from
3523:
3517:
3516:
3514:
3512:
3506:
3499:
3491:
3485:
3473:
3467:
3455:
3449:
3448:
3428:
3422:
3421:
3411:
3371:
3365:
3363:
3335:
3322:
3321:
3292:
3286:
3284:
3282:
3280:
3275:on 13 April 2015
3274:
3267:
3259:
3253:
3252:
3250:
3248:
3242:
3235:
3227:
3221:
3219:
3217:
3215:
3209:
3202:
3194:
3188:
3187:
3166:Elsevier Science
3149:
3143:
3142:
3129:
3123:
3122:
3104:
3098:
3097:
3081:
3071:
3065:
3064:
3046:
3040:
3039:
3033:
3028:
3026:
3018:
3006:
3000:
2999:
2997:
2960:
2954:
2953:
2927:
2921:
2920:
2913:
2907:
2897:
2886:
2873:
2860:
2859:
2839:
2833:
2832:
2814:
2808:
2795:
2784:
2783:
2773:
2767:
2766:
2764:
2762:
2748:
2723:
2722:
2693:
2629:For humans, the
2620:-acyltransferase
2526:thionyl chloride
2503:acetic anhydride
2501:is induced with
2492:benzoyl chloride
2469:carboxylic acids
2450:carboxylic group
2390:In terms of its
2375:Ovibos moschatus
2319:bomb calorimeter
2084:
2082:
2081:
2076:
2074:
2072:
2069:
2062:
2055:
2053:
2050:
2043:
2040:
2037:
2030:
2024:
2021:
2014:
2004:
1997:
1995:
1992:
1985:
1982:
1979:
1972:
1969:
1966:
1959:
1839:calcium benzoate
1837:. The resulting
1829:in water, using
1823:benzotrichloride
1753:Friedrich Wöhler
1727:dry distillation
1716:
1715:
1712:
1711:
1708:
1705:
1702:
1699:
1696:
1693:
1690:
1687:
1644:
1620:
1612:
1593:
1580:organic compound
1577:
1576:
1573:
1572:
1569:
1566:
1563:
1560:
1557:
1554:
1551:
1548:
1517:
1511:
1508:
1507:
1474:Benzoyl chloride
1432:carboxylic acids
1385:
1327:
1320:
1313:
1298:
1278:
1274:
1270:
1256:
1252:
1224:
1219:
1166:
1159:
1135:
1128:
1104:
1097:
1076:
1069:
1054:Thermochemistry
1042:
993:
965:Refractive index
957:
909:
903:
897:
870:
852:
834:
816:
810:
804:
798:
780:
774:
768:
695:
690:g/L (75 °C)
689:
684:g/L (40 °C)
683:
678:g/L (25 °C)
677:
672:g/L (18 °C)
671:
665:
629:
623:
591:
576:
570:
564:
557:Chemical formula
487:
486:
471:
469:
453:
417:
406:
395:
378:
356:Gmelin Reference
342:
324:
316:
305:
294:
274:
254:
234:
202:
184:
160:
66:
41:Skeletal formula
33:
29:
5980:
5979:
5973:
5972:
5971:
5969:
5968:
5967:
5938:
5937:
5936:
5931:
5881:
5879:
5877:Food portal
5869:
5861:
5810:
5748:
5709:Food libel laws
5672:
5500:
5449:
5415:Modified starch
5377:Food processing
5371:
5318:
5247:
5197:
5193:Sodium benzoate
5169:
5131:
5126:Vibrio cholerae
5020:
4991:Gnathostomiasis
4976:Fasciolopsiasis
4928:
4876:
4867:Mercury in fish
4809:
4804:
4774:
4769:
4768:
4753:Clinical trials
4728:
4698:Other/ungrouped
4693:
4681:Organophosphate
4675:
4671:Benzyl benzoate
4657:
4638:
4604:
4586:
4532:
4520:Organophosphate
4514:
4496:
4464:
4450:
4420:
4415:
4414:
4399:Clinical trials
4378:
4342:
4294:Levobupivacaine
4267:
4245:
4216:Cyclomethycaine
4192:
4153:Metabutoxycaine
4148:Metabutethamine
4084:
4072:
4067:
4015:
4010:
3994:
3993:
3989:
3972:
3937:
3936:
3932:
3888:
3887:
3883:
3872:
3870:
3861:
3860:
3856:
3845:
3843:
3834:
3833:
3829:
3791:
3790:
3786:
3776:
3763:
3762:
3758:
3722:
3721:
3717:
3688:Molecular Plant
3681:
3680:
3676:
3640:
3639:
3635:
3626:
3625:
3616:
3611:Wayback Machine
3602:
3598:
3584:
3583:
3579:
3572:
3551:
3550:
3546:
3536:
3534:
3525:
3524:
3520:
3510:
3508:
3504:
3497:
3493:
3492:
3488:
3483:Wayback Machine
3474:
3470:
3465:Wayback Machine
3456:
3452:
3430:
3429:
3425:
3373:
3372:
3368:
3360:
3337:
3336:
3325:
3294:
3293:
3289:
3278:
3276:
3272:
3265:
3261:
3260:
3256:
3246:
3244:
3240:
3233:
3229:
3228:
3224:
3213:
3211:
3207:
3200:
3196:
3195:
3191:
3184:
3151:
3150:
3146:
3131:
3130:
3126:
3119:
3106:
3105:
3101:
3094:
3073:
3072:
3068:
3061:
3048:
3047:
3043:
3029:
3019:
3008:
3007:
3003:
2995:2027/hvd.hxdg3f
2962:
2961:
2957:
2942:
2929:
2928:
2924:
2915:
2914:
2910:
2898:
2889:
2874:
2863:
2841:
2840:
2836:
2829:
2816:
2815:
2811:
2796:
2787:
2782:. Van Nostrand.
2775:
2774:
2770:
2760:
2758:
2750:
2749:
2726:
2719:
2695:
2694:
2690:
2686:
2673:
2658:
2600:
2594:
2568:Decarboxylation
2558:
2497:Dehydration to
2465:
2428:
2412:
2380:Elephas maximus
2335:species (e.g.,
2327:
2315:
2264:
2259:
2224:phosphoric acid
2134:
2114:methyl benzoate
2102:
1952:
1951:
1937:
1929:benzyl chloride
1922:
1899:
1875:
1859:
1781:
1776:
1723:
1684:
1680:
1642:
1638:
1634:
1618:
1611:
1607:
1603:
1591:
1587:
1583:
1545:
1541:
1536:
1529:
1524:
1523:
1522: ?)
1513:
1509:
1505:
1501:
1487:
1482:
1477:
1472:
1467:
1460:
1450:
1445:
1440:
1434:
1421:
1418:Sodium benzoate
1414:
1383:
1379:
1373:
1353:
1350:
1332:
1331:
1330:
1329:
1322:
1315:
1308:
1304:
1296:
1265:
1247:
1233:
1212:
1189:
1164:
1160:
1157:
1151:
1147:
1144:
1143:Std enthalpy of
1133:
1129:
1126:
1120:
1116:
1113:
1112:Std enthalpy of
1102:
1098:
1095:
1088:
1085:
1074:
1070:
1063:
1040:
1036:
1022:
1020:Molecular shape
1008:
991:
979:
975:
973:
955:
951:
941:
934:
924:
907:
905:
901:
899:
898:Pa (25 °C)
895:
868:
850:
832:
814:
812:
808:
806:
802:
800:
796:
778:
776:
772:
770:
766:
726:
719:
693:
691:
687:
685:
681:
679:
675:
673:
669:
667:
666:g/L (0 °C)
663:
659:
627:
625:
621:
589:
579:
573:
567:
559:
545:
542:
537:
536:
525:
522:
521:
518:
512:
511:
508:
502:
501:
490:
472:
465:
456:
436:
420:
407:
381:
358:
348:(preservatives)
334:
297:
277:
257:
237:
214:
205:
187:
174:
163:
150:
136:
135:
126:Carboxylbenzene
120:Benzoyl alcohol
95:
94:
83:
82:
24:
17:
12:
11:
5:
5978:
5977:
5974:
5966:
5965:
5960:
5955:
5950:
5940:
5939:
5933:
5932:
5930:
5929:
5919:
5909:
5899:
5889:
5866:
5863:
5862:
5860:
5859:
5854:
5849:
5844:
5839:
5834:
5832:Food marketing
5829:
5824:
5818:
5816:
5815:Related topics
5812:
5811:
5809:
5808:
5803:
5797:
5792:
5787:
5781:
5775:
5770:
5765:
5758:
5756:
5750:
5749:
5747:
5746:
5741:
5736:
5731:
5726:
5721:
5716:
5711:
5706:
5701:
5696:
5690:
5688:
5674:
5673:
5671:
5670:
5669:
5668:
5663:
5658:
5648:
5643:
5638:
5633:
5628:
5623:
5618:
5613:
5608:
5603:
5598:
5593:
5584:
5579:
5574:
5569:
5564:
5559:
5550:
5541:
5532:
5527:
5522:
5517:
5512:
5507:
5495:
5490:
5485:
5480:
5475:
5470:
5465:
5459:
5457:
5451:
5450:
5448:
5447:
5442:
5437:
5432:
5427:
5422:
5417:
5412:
5407:
5402:
5400:Food additives
5397:
5392:
5387:
5381:
5379:
5373:
5372:
5370:
5369:
5364:
5359:
5354:
5349:
5344:
5339:
5334:
5328:
5326:
5320:
5319:
5317:
5316:
5311:
5306:
5301:
5296:
5291:
5286:
5281:
5276:
5271:
5265:
5263:
5249:
5248:
5246:
5245:
5240:
5235:
5230:
5225:
5224:
5223:
5213:
5207:
5205:
5199:
5198:
5196:
5195:
5190:
5185:
5179:
5177:
5171:
5170:
5168:
5167:
5162:
5157:
5152:
5147:
5141:
5139:
5133:
5132:
5130:
5129:
5122:
5114:
5107:
5102:
5097:
5090:
5085:
5080:
5072:
5064:
5057:
5050:
5043:
5036:
5030:
5028:
5026:Microorganisms
5022:
5021:
5019:
5018:
5013:
5008:
5003:
4998:
4996:Paragonimiasis
4993:
4988:
4983:
4978:
4973:
4968:
4963:
4961:Cyclosporiasis
4958:
4953:
4948:
4942:
4940:
4930:
4929:
4927:
4926:
4925:
4924:
4914:
4913:
4912:
4902:
4897:
4892:
4886:
4884:
4882:Food additives
4878:
4877:
4875:
4874:
4869:
4864:
4859:
4857:Lead poisoning
4854:
4849:
4844:
4839:
4834:
4829:
4823:
4821:
4811:
4810:
4805:
4803:
4802:
4795:
4788:
4780:
4771:
4770:
4767:
4766:
4765:
4764:
4761:
4750:
4744:
4738:
4737:
4734:
4733:
4730:
4729:
4727:
4726:
4714:
4707:
4701:
4699:
4695:
4694:
4692:
4691:
4685:
4683:
4677:
4676:
4674:
4673:
4667:
4665:
4659:
4658:
4656:
4655:
4649:
4647:
4640:
4639:
4637:
4636:
4631:
4626:
4621:
4615:
4613:
4606:
4605:
4603:
4602:
4596:
4594:
4588:
4587:
4585:
4584:
4579:
4574:
4569:
4563:
4561:
4552:
4538:
4537:
4534:
4533:
4531:
4530:
4524:
4522:
4516:
4515:
4513:
4512:
4506:
4504:
4498:
4497:
4495:
4494:
4488:
4486:
4476:
4466:
4465:
4451:
4449:
4448:
4441:
4434:
4426:
4417:
4416:
4413:
4412:
4411:
4410:
4407:
4396:
4390:
4384:
4383:
4380:
4379:
4377:
4376:
4371:
4366:
4361:
4356:
4350:
4348:
4344:
4343:
4341:
4340:
4335:
4330:
4325:
4320:
4315:
4310:
4305:
4300:
4287:
4281:
4279:
4273:
4272:
4269:
4268:
4266:
4265:
4260:
4253:
4251:
4247:
4246:
4244:
4243:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4202:
4200:
4194:
4193:
4191:
4190:
4185:
4180:
4178:Proxymetacaine
4175:
4170:
4165:
4160:
4155:
4150:
4145:
4140:
4135:
4130:
4128:Chloroprocaine
4125:
4120:
4115:
4110:
4104:
4102:
4093:
4086:
4085:
4068:
4066:
4065:
4058:
4051:
4043:
4037:
4036:
4031:
4021:
4014:
4013:External links
4011:
4009:
4008:
4002:The China Post
3987:
3930:
3901:(3): 657–663.
3881:
3854:
3827:
3784:
3756:
3735:(1): 245–250.
3715:
3674:
3653:(4): 349–351.
3633:
3614:
3596:
3577:
3570:
3544:
3518:
3486:
3468:
3450:
3433:Phytochem Anal
3423:
3386:(12): 3410–4.
3366:
3359:978-3527306732
3358:
3323:
3287:
3254:
3222:
3189:
3182:
3144:
3124:
3117:
3099:
3092:
3066:
3059:
3041:
3001:
2980:(3): 249–282.
2955:
2940:
2922:
2908:
2887:
2861:
2834:
2827:
2809:
2785:
2768:
2752:"benzoic acid"
2724:
2717:
2687:
2685:
2682:
2681:
2680:
2672:
2669:
2656:
2599:
2596:
2592:
2591:
2580:
2579:
2565:
2556:
2547:benzyl alcohol
2539:
2529:
2510:
2495:
2484:
2464:
2463:Carboxyl group
2461:
2440:
2439:
2427:
2424:
2420:carboxyl group
2411:
2408:
2363:rock ptarmigan
2326:
2323:
2314:
2311:
2276:athlete's foot
2263:
2260:
2239:concentrations
2216:carbon dioxide
2133:
2130:
2101:
2098:
2086:
2085:
2068:
2060:
2049:
2036:
2028:
2020:
2010:
2007:
2002:
1991:
1978:
1965:
1936:
1933:
1925:Benzyl alcohol
1921:
1918:
1898:
1895:
1874:
1871:
1858:
1855:
1819:
1818:
1780:
1777:
1775:
1772:
1722:
1719:
1598:consists of a
1534:
1531:
1530:
1525:
1503:
1502:
1498:standard state
1495:
1492:
1491:
1469:Benzyl alcohol
1461:
1458:
1455:
1454:
1435:
1429:
1426:
1425:
1415:
1409:
1406:
1405:
1401:
1400:
1395:
1388:
1387:
1380:
1371:
1369:
1366:
1365:
1358:
1357:
1354:
1347:
1344:
1343:
1340:
1334:
1333:
1323:
1316:
1309:
1294:
1293:
1292:
1291:
1289:
1280:
1279:
1277:P305+P351+P338
1266:
1261:
1258:
1257:
1248:
1243:
1240:
1239:
1234:
1229:
1226:
1225:
1213:
1208:
1205:
1204:
1194:
1193:
1190:
1187:
1184:
1183:
1174:
1173:
1169:
1168:
1161:
1155:
1149:
1141:
1138:
1137:
1130:
1124:
1118:
1110:
1107:
1106:
1099:
1093:
1082:
1079:
1078:
1071:
1059:
1056:
1055:
1051:
1050:
1037:
1032:
1029:
1028:
1023:
1018:
1015:
1014:
1009:
1004:
1001:
1000:
996:
995:
988:
982:
981:
976:
971:
963:
960:
959:
952:
946:
943:
942:
940:
939:
936:
932:
928:
926:
922:
912:
911:
892:
890:Vapor pressure
886:
885:
882:
873:
872:
865:
855:
854:
847:
837:
836:
829:
819:
818:
793:
783:
782:
763:
753:
752:
724:
717:
704:
698:
697:
660:
655:
652:
651:
648:
642:
641:
638:
632:
631:
618:
612:
611:
608:
602:
601:
598:
594:
593:
587:
581:
580:
577:
571:
565:
560:
555:
552:
551:
547:
546:
544:
543:
541:O=C(O)c1ccccc1
540:
532:
531:
530:
527:
526:
524:
523:
519:
516:
515:
513:
509:
506:
505:
497:
496:
495:
492:
491:
489:
488:
475:
473:
461:
458:
457:
455:
454:
446:
444:
438:
437:
435:
434:
430:
428:
422:
421:
419:
418:
410:
408:
400:
397:
396:
389:
383:
382:
380:
379:
371:
369:
363:
362:
359:
354:
351:
350:
344:
336:
335:
333:
332:
328:
326:
318:
317:
307:
299:
298:
296:
295:
287:
285:
279:
278:
276:
275:
267:
265:
259:
258:
256:
255:
247:
245:
239:
238:
236:
235:
227:
225:
219:
218:
215:
210:
207:
206:
204:
203:
195:
193:
189:
188:
186:
185:
177:
175:
168:
165:
164:
162:
161:
153:
151:
146:
143:
142:
138:
137:
134:
133:
130:
127:
124:
123:Benzoylic acid
121:
118:
115:
112:
109:
106:
105:Carboxybenzene
102:
101:
97:
96:
92:
91:
85:
84:
80:
79:
73:
72:
68:
67:
59:
58:
55:
54:
44:
15:
13:
10:
9:
6:
4:
3:
2:
5976:
5975:
5964:
5961:
5959:
5956:
5954:
5951:
5949:
5948:Benzoic acids
5946:
5945:
5943:
5928:
5920:
5918:
5914:
5910:
5908:
5900:
5898:
5890:
5888:
5878:
5873:
5868:
5867:
5864:
5858:
5855:
5853:
5850:
5848:
5845:
5843:
5840:
5838:
5837:Food politics
5835:
5833:
5830:
5828:
5825:
5823:
5820:
5819:
5817:
5813:
5807:
5804:
5802:(South Korea)
5801:
5798:
5796:
5793:
5791:
5788:
5785:
5782:
5779:
5776:
5774:
5771:
5769:
5766:
5763:
5760:
5759:
5757:
5755:
5751:
5745:
5742:
5740:
5737:
5735:
5732:
5730:
5727:
5725:
5722:
5720:
5717:
5715:
5712:
5710:
5707:
5705:
5702:
5700:
5697:
5695:
5692:
5691:
5689:
5687:
5683:
5679:
5675:
5667:
5666:United States
5664:
5662:
5659:
5657:
5654:
5653:
5652:
5649:
5647:
5644:
5642:
5639:
5637:
5634:
5632:
5629:
5627:
5624:
5622:
5619:
5617:
5614:
5612:
5609:
5607:
5604:
5602:
5599:
5597:
5594:
5592:
5590:
5587:2011 Germany
5585:
5583:
5580:
5578:
5575:
5573:
5570:
5568:
5565:
5563:
5560:
5558:
5556:
5551:
5549:
5547:
5544:1996 Odwalla
5542:
5540:
5538:
5533:
5531:
5528:
5526:
5523:
5521:
5518:
5516:
5513:
5511:
5508:
5504:
5499:
5496:
5494:
5491:
5489:
5486:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5460:
5458:
5456:
5452:
5446:
5443:
5441:
5438:
5436:
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5416:
5413:
5411:
5408:
5406:
5403:
5401:
5398:
5396:
5393:
5391:
5388:
5386:
5383:
5382:
5380:
5378:
5374:
5368:
5365:
5363:
5360:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5329:
5327:
5325:
5321:
5315:
5312:
5310:
5307:
5305:
5302:
5300:
5297:
5295:
5292:
5290:
5287:
5285:
5282:
5280:
5277:
5275:
5272:
5270:
5267:
5266:
5264:
5262:
5258:
5254:
5250:
5244:
5241:
5239:
5236:
5234:
5231:
5229:
5226:
5222:
5219:
5218:
5217:
5214:
5212:
5209:
5208:
5206:
5204:
5200:
5194:
5191:
5189:
5186:
5184:
5181:
5180:
5178:
5176:
5175:Preservatives
5172:
5166:
5165:Methamidophos
5163:
5161:
5158:
5156:
5153:
5151:
5148:
5146:
5143:
5142:
5140:
5138:
5134:
5128:
5127:
5123:
5121:
5120:
5115:
5113:
5112:
5108:
5106:
5103:
5101:
5098:
5096:
5095:
5091:
5089:
5086:
5084:
5081:
5079:
5077:
5073:
5071:
5069:
5065:
5063:
5062:
5058:
5056:
5055:
5051:
5049:
5048:
5044:
5042:
5041:
5037:
5035:
5032:
5031:
5029:
5027:
5023:
5017:
5014:
5012:
5009:
5007:
5006:Toxoplasmosis
5004:
5002:
4999:
4997:
4994:
4992:
4989:
4987:
4984:
4982:
4979:
4977:
4974:
4972:
4969:
4967:
4964:
4962:
4959:
4957:
4954:
4952:
4949:
4947:
4944:
4943:
4941:
4939:
4935:
4931:
4923:
4920:
4919:
4918:
4917:Vegetable oil
4915:
4911:
4908:
4907:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4887:
4885:
4883:
4879:
4873:
4870:
4868:
4865:
4863:
4860:
4858:
4855:
4853:
4850:
4848:
4845:
4843:
4840:
4838:
4835:
4833:
4830:
4828:
4825:
4824:
4822:
4820:
4816:
4812:
4808:
4801:
4796:
4794:
4789:
4787:
4782:
4781:
4778:
4762:
4760:
4757:
4756:
4754:
4751:
4748:
4745:
4743:
4740:
4739:
4735:
4724:
4720:
4719:
4715:
4713:
4712:
4708:
4706:
4703:
4702:
4700:
4696:
4690:
4687:
4686:
4684:
4682:
4678:
4672:
4669:
4668:
4666:
4664:
4660:
4654:
4651:
4650:
4648:
4645:
4641:
4635:
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4616:
4614:
4611:
4607:
4601:
4598:
4597:
4595:
4593:
4589:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4564:
4562:
4560:
4556:
4553:
4551:
4547:
4543:
4539:
4529:
4526:
4525:
4523:
4521:
4517:
4511:
4508:
4507:
4505:
4503:
4499:
4493:
4490:
4489:
4487:
4484:
4480:
4477:
4475:
4471:
4467:
4462:
4458:
4454:
4447:
4442:
4440:
4435:
4433:
4428:
4427:
4424:
4408:
4406:
4403:
4402:
4400:
4397:
4394:
4391:
4389:
4386:
4385:
4381:
4375:
4372:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4351:
4349:
4345:
4339:
4336:
4334:
4331:
4329:
4326:
4324:
4321:
4319:
4316:
4314:
4311:
4309:
4306:
4304:
4303:Butanilicaine
4301:
4299:
4295:
4291:
4288:
4286:
4283:
4282:
4280:
4278:
4274:
4264:
4261:
4258:
4255:
4254:
4252:
4248:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4203:
4201:
4199:
4195:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4105:
4103:
4101:
4097:
4094:
4091:
4087:
4082:
4076:
4071:
4064:
4059:
4057:
4052:
4050:
4045:
4044:
4041:
4035:
4032:
4029:
4025:
4022:
4020:
4017:
4016:
4012:
4004:
4003:
3998:
3991:
3988:
3983:
3977:
3969:
3965:
3961:
3957:
3953:
3949:
3945:
3941:
3934:
3931:
3926:
3922:
3917:
3912:
3908:
3904:
3900:
3896:
3892:
3885:
3882:
3868:
3864:
3858:
3855:
3841:
3837:
3831:
3828:
3823:
3819:
3815:
3811:
3807:
3803:
3799:
3795:
3788:
3785:
3779:
3773:
3772:
3767:
3760:
3757:
3752:
3748:
3743:
3738:
3734:
3730:
3726:
3719:
3716:
3711:
3707:
3702:
3697:
3693:
3689:
3685:
3678:
3675:
3670:
3666:
3661:
3656:
3652:
3648:
3644:
3637:
3634:
3629:
3623:
3621:
3619:
3615:
3612:
3608:
3605:
3600:
3597:
3592:
3588:
3581:
3578:
3573:
3567:
3563:
3558:
3557:
3548:
3545:
3532:
3528:
3522:
3519:
3503:
3496:
3490:
3487:
3484:
3480:
3477:
3472:
3469:
3466:
3462:
3459:
3454:
3451:
3446:
3442:
3438:
3434:
3427:
3424:
3419:
3415:
3410:
3405:
3401:
3397:
3393:
3389:
3385:
3381:
3377:
3370:
3367:
3361:
3355:
3351:
3347:
3343:
3342:
3334:
3332:
3330:
3328:
3324:
3319:
3315:
3311:
3307:
3303:
3299:
3291:
3288:
3271:
3264:
3258:
3255:
3239:
3232:
3226:
3223:
3206:
3199:
3193:
3190:
3185:
3179:
3175:
3171:
3167:
3163:
3159:
3155:
3148:
3145:
3140:
3137:
3136:
3128:
3125:
3120:
3114:
3110:
3103:
3100:
3095:
3089:
3085:
3080:
3079:
3070:
3067:
3062:
3056:
3052:
3045:
3042:
3037:
3024:
3016:
3012:
3005:
3002:
2996:
2991:
2987:
2983:
2979:
2975:
2974:
2969:
2965:
2959:
2956:
2951:
2947:
2943:
2937:
2933:
2926:
2923:
2918:
2912:
2909:
2905:
2901:
2896:
2894:
2892:
2888:
2885:
2881:
2877:
2872:
2870:
2868:
2866:
2862:
2857:
2853:
2849:
2845:
2838:
2835:
2830:
2828:9781429254366
2824:
2820:
2813:
2810:
2806:
2804:
2799:
2794:
2792:
2790:
2786:
2781:
2780:
2772:
2769:
2757:
2753:
2747:
2745:
2743:
2741:
2739:
2737:
2735:
2733:
2731:
2729:
2725:
2720:
2714:
2710:
2706:
2702:
2699:. Cambridge:
2698:
2692:
2689:
2683:
2678:
2675:
2674:
2670:
2668:
2666:
2661:
2659:
2652:
2648:
2644:
2640:
2636:
2632:
2627:
2625:
2621:
2619:
2613:
2609:
2605:
2604:hippuric acid
2597:
2595:
2586:
2582:
2581:
2577:
2573:
2569:
2566:
2563:
2559:
2552:
2548:
2544:
2541:Reduction to
2540:
2537:
2533:
2530:
2527:
2523:
2519:
2515:
2511:
2508:
2504:
2500:
2496:
2493:
2489:
2486:Benzoic acid
2485:
2482:
2478:
2474:
2473:
2472:
2470:
2462:
2460:
2458:
2456:
2451:
2448:
2444:
2434:
2430:
2429:
2426:Aromatic ring
2425:
2423:
2421:
2417:
2416:aromatic ring
2409:
2407:
2405:
2401:
2397:
2396:cinnamic acid
2393:
2388:
2386:
2382:
2381:
2376:
2372:
2368:
2364:
2360:
2359:
2354:
2350:
2346:
2342:
2338:
2334:
2333:
2324:
2322:
2320:
2312:
2310:
2308:
2304:
2300:
2295:
2293:
2292:decongestants
2290:and inhalant
2289:
2285:
2281:
2277:
2273:
2269:
2261:
2258:
2253:
2251:
2247:
2246:ascorbic acid
2242:
2240:
2235:
2233:
2229:
2225:
2221:
2217:
2213:
2209:
2206:
2202:
2201:preservatives
2198:
2194:
2190:
2186:
2182:
2178:
2174:
2170:
2166:
2162:
2158:
2154:
2150:
2146:
2143:
2139:
2131:
2129:
2127:
2123:
2119:
2115:
2111:
2107:
2099:
2097:
2095:
2091:
2066:
2058:
2047:
2034:
2018:
2008:
2005:
2000:
1989:
1976:
1963:
1950:
1949:
1948:
1946:
1942:
1934:
1932:
1930:
1926:
1919:
1917:
1915:
1911:
1907:
1903:
1896:
1894:
1892:
1888:
1884:
1880:
1873:By hydrolysis
1872:
1870:
1867:
1862:
1856:
1854:
1852:
1848:
1844:
1840:
1836:
1832:
1828:
1824:
1813:
1809:
1808:
1807:
1805:
1802:
1798:
1794:
1790:
1786:
1778:
1773:
1771:
1769:
1765:
1760:
1758:
1757:hippuric acid
1754:
1750:
1746:
1744:
1740:
1736:
1732:
1728:
1720:
1718:
1714:
1679:
1675:
1671:
1667:
1663:
1659:
1654:
1652:
1648:
1632:
1628:
1624:
1616:
1601:
1597:
1581:
1575:
1540:
1528:
1521:
1516:
1499:
1493:
1490:
1485:
1480:
1475:
1470:
1465:
1462:
1457:
1456:
1453:
1448:
1443:
1439:
1436:
1433:
1428:
1427:
1424:
1419:
1416:
1413:
1408:
1407:
1402:
1399:
1396:
1393:
1390:
1389:
1381:
1377:
1368:
1367:
1363:
1359:
1355:
1352:
1346:
1345:
1341:
1339:
1336:
1335:
1328:
1321:
1314:
1290:
1287:
1286:
1282:
1281:
1267:
1264:
1260:
1259:
1249:
1246:
1242:
1241:
1238:
1235:
1232:
1228:
1227:
1223:
1218:
1214:
1211:
1207:
1206:
1202:
1200:
1195:
1191:
1186:
1185:
1181:
1180:
1175:
1170:
1162:
1154:
1146:
1140:
1139:
1131:
1123:
1115:
1109:
1108:
1100:
1092:
1087:
1081:
1080:
1072:
1067:
1062:
1061:Heat capacity
1058:
1057:
1052:
1049:
1045:
1038:
1035:
1034:Dipole moment
1031:
1030:
1027:
1024:
1021:
1017:
1016:
1013:
1010:
1007:
1003:
1002:
997:
989:
987:
984:
983:
977:
970:
966:
962:
961:
953:
949:
945:
944:
937:
930:
929:
927:
921:
917:
914:
913:
893:
891:
888:
887:
883:
881:
880:
875:
874:
866:
864:
860:
857:
856:
848:
846:
842:
839:
838:
830:
828:
824:
821:
820:
794:
792:
788:
785:
784:
764:
762:
758:
755:
754:
751:
747:
743:
739:
735:
731:
727:
720:
713:
709:
705:
703:
700:
699:
661:
658:
654:
653:
649:
647:
646:Boiling point
644:
643:
639:
637:
636:Melting point
634:
633:
619:
617:
614:
613:
609:
607:
604:
603:
599:
596:
595:
588:
586:
583:
582:
561:
558:
554:
553:
548:
539:
535:
528:
514:
504:
500:
493:
485:
481:
480:DTXSID6020143
477:
476:
474:
464:
460:
459:
452:
448:
447:
445:
443:
440:
439:
432:
431:
429:
427:
424:
423:
416:
412:
411:
409:
403:
399:
398:
394:
390:
388:
385:
384:
377:
373:
372:
370:
368:
365:
364:
360:
357:
353:
352:
349:
345:
343:
338:
337:
330:
329:
327:
325:
320:
319:
315:
311:
308:
306:
304:ECHA InfoCard
301:
300:
293:
289:
288:
286:
284:
281:
280:
273:
269:
268:
266:
264:
261:
260:
253:
249:
248:
246:
244:
241:
240:
233:
229:
228:
226:
224:
221:
220:
216:
213:
209:
208:
201:
197:
196:
194:
191:
190:
183:
179:
178:
176:
172:
167:
166:
159:
155:
154:
152:
149:
145:
144:
139:
131:
128:
125:
122:
119:
116:
113:
111:Dracylic acid
110:
107:
104:
103:
98:
90:
86:
78:
74:
69:
65:
60:
49:
45:
39:
35:
34:
30:
27:Benzoic acid
22:
5847:Food quality
5754:Institutions
5588:
5554:
5545:
5536:
5420:Nitrosamines
5183:Benzoic acid
5182:
5145:Chlorpyrifos
5124:
5118:
5109:
5092:
5075:
5067:
5059:
5052:
5045:
5038:
5016:Trichuriasis
5001:Toxocariasis
4971:Enterobiasis
4847:Formaldehyde
4716:
4709:
4662:
4582:Bioallethrin
4474:pediculicide
4347:Combinations
4197:
4168:Propoxycaine
4133:Dimethocaine
4100:Aminobenzoic
4034:ChemicalLand
4000:
3990:
3976:cite journal
3946:(3): 53–58.
3943:
3939:
3933:
3898:
3894:
3884:
3871:. Retrieved
3866:
3857:
3844:. Retrieved
3839:
3830:
3797:
3793:
3787:
3777:
3769:
3759:
3732:
3728:
3718:
3691:
3687:
3677:
3650:
3646:
3636:
3599:
3590:
3580:
3555:
3547:
3535:. Retrieved
3531:the original
3521:
3509:. Retrieved
3489:
3471:
3453:
3439:(2): 63–73.
3436:
3432:
3426:
3383:
3379:
3369:
3339:
3301:
3297:
3290:
3277:. Retrieved
3270:the original
3257:
3245:. Retrieved
3238:the original
3225:
3212:. Retrieved
3205:the original
3192:
3161:
3154:Trost, B. M.
3147:
3138:
3133:
3127:
3108:
3102:
3077:
3069:
3050:
3044:
3032:|title=
3023:cite journal
3014:
3010:
3004:
2977:
2971:
2958:
2931:
2925:
2911:
2904:Benzoic acid
2847:
2843:
2837:
2818:
2812:
2801:
2798:Benzoic acid
2778:
2771:
2759:. Retrieved
2756:chemister.ru
2755:
2696:
2691:
2662:
2628:
2617:
2601:
2593:
2543:benzaldehyde
2536:benzonitrile
2520:agents like
2518:halogenation
2514:acid halides
2466:
2454:
2441:
2413:
2392:biosynthesis
2389:
2378:
2374:
2367:Lagopus muta
2366:
2356:
2349:V. myrtillus
2348:
2340:
2330:
2328:
2316:
2296:
2265:
2243:
2236:
2205:citrus fruit
2135:
2106:plasticizers
2103:
2090:cyclohexanol
2087:
1938:
1923:
1902:Bromobenzene
1900:
1887:benzonitrile
1876:
1863:
1860:
1820:
1804:naphthenates
1782:
1761:
1747:
1724:
1677:
1655:
1539:Benzoic acid
1538:
1537:
1489:Benzonitrile
1464:Benzaldehyde
1361:
1349:Autoignition
1284:
1236:
1198:
1188:Main hazards
1177:
1152:
1121:
1090:
1065:
968:
938:11.02 (DMSO)
919:
878:
426:RTECS number
393:benzoic+acid
141:Identifiers
132:Phenoic acid
100:Other names
81:Benzoic acid
5927:WikiProject
5764:(Hong Kong)
5501: [
5463:Devon colic
5337:Breast milk
5309:Nonylphenol
5284:Bisphenol A
5221:controversy
5088:Hepatitis E
5083:Hepatitis A
5061:Enterovirus
5054:Cronobacter
5011:Trichinosis
4981:Fasciolosis
4951:Anisakiasis
4922:controversy
4815:Adulterants
4749:from market
4705:Dimethicone
4624:Dixanthogen
4559:Pyrethrines
4470:Insecticide
4395:from market
4328:Mepivacaine
4298:Ropivacaine
4290:Bupivacaine
4241:Piperocaine
4143:Meprylcaine
4113:Benzonatate
4073:(primarily
3158:Fleming, I.
3135:Org. React.
2612:benzoyl-CoA
2532:Orthoesters
2385:Gum benzoin
2299:expectorant
2288:antiseptics
2280:gum benzoin
2220:soft drinks
2212:citric acid
2096:synthesis.
1877:Like other
1851:gum benzoin
1847:chlorinated
1741:(1560) and
1735:Nostradamus
1731:gum benzoin
1651:gum benzoin
1623:substituent
1479:Benzylamine
1376:median dose
1362:Lethal dose
1351:temperature
1338:Flash point
1231:Signal word
1182:(OHS/OSH):
863:1,4-dioxane
734:ethyl ether
706:Soluble in
597:Appearance
550:Properties
310:100.000.562
232:CHEBI:30746
5953:Excipients
5942:Categories
5678:Regulation
5661:death toll
5430:Shortening
5395:Acrylamide
5324:Food fraud
5304:Mycotoxins
5137:Pesticides
5111:Salmonella
4986:Giardiasis
4946:Amoebiasis
4890:Flavorings
4723:Crotamiton
4619:Disulfiram
4600:Ivermectin
4577:Phenothrin
4567:Permethrin
4510:Ivermectin
4374:Iontocaine
4338:Trimecaine
4333:Prilocaine
4318:Etidocaine
4308:Carticaine
4236:Isobucaine
4231:Hexylcaine
4206:Amylocaine
4188:Tetracaine
4163:Orthocaine
4158:Nitracaine
4108:Benzocaine
3537:15 October
3017:: 297–298.
2761:24 October
2684:References
2418:or at the
2307:antiseptic
2255:See also:
2126:phthalates
1774:Production
1764:antifungal
1210:Pictograms
1145:combustion
1012:Monoclinic
999:Structure
859:Solubility
841:Solubility
823:Solubility
787:Solubility
757:Solubility
702:Solubility
585:Molar mass
451:8SKN0B0MIM
263:ChemSpider
169:3D model (
148:CAS Number
5724:ISO 22000
5686:watchdogs
5682:standards
5656:outbreaks
5557:outbreaks
5435:Trans fat
5347:Olive oil
5269:Aflatoxin
5243:Sucralose
5228:Saccharin
5216:Aspartame
5160:Malathion
5105:Rotavirus
5100:Norovirus
4759:Phase III
4747:Withdrawn
4718:toluidine
4689:Malathion
4572:Pyrethrum
4550:scabicide
4542:Acaricide
4528:Malathion
4457:arthropod
4405:Phase III
4393:Withdrawn
4323:Lidocaine
4285:Articaine
4257:Amoproxan
4226:β-Eucaine
4221:α-Eucaine
4183:Risocaine
4118:Butacaine
4026:from the
3895:Biochem J
3794:Int J Tox
3647:Clin Chem
3318:1083-6160
2572:quinoline
2475:Benzoate
2457:directing
2410:Reactions
2337:cranberry
2332:Vaccinium
2303:analgesic
2262:Medicinal
2177:potassium
2167:and some
2142:E numbers
2104:Benzoate
2027:⟶
1891:benzamide
1801:manganese
1678:benzoates
1670:precursor
1613:) with a
1596:structure
1484:Benzamide
1201:labelling
1192:Irritant
1114:formation
1084:Std molar
986:Viscosity
954:−70.28·10
845:olive oil
744:, liquid
433:DG0875000
331:200-618-2
323:EC Number
252:ChEMBL541
5917:Cookbook
5897:Category
5699:E number
5591:outbreak
5548:outbreak
5539:outbreak
5289:Dieldrin
5238:Sorbitol
5094:Listeria
5034:Botulism
4862:Melamine
4832:Aldicarb
4663:Benzoate
4644:Chlorine
4629:Mesulfen
4546:miticide
4483:Chlorine
4123:Butamben
3822:13639993
3814:11766131
3751:15653882
3710:20035037
3694:: 2–20.
3607:Archived
3511:30 March
3502:Archived
3479:Archived
3461:Archived
3279:12 March
3247:12 March
3214:12 March
3160:(eds.).
3141:: 28–58.
2968:Wöhler F
2964:Liebig J
2950:50969944
2671:See also
2616:glycine
2481:alcohols
2371:muskoxen
2345:bilberry
2272:ringworm
2237:Typical
2195:through
2169:bacteria
1879:nitriles
1835:catalyst
1745:(1596).
1647:aromatic
1619:−C(=O)OH
1615:carboxyl
1594:, whose
1430:Related
1398:JT Baker
1285:NFPA 704
1172:Hazards
1105:J/mol·K
1077:J/mol·K
950:(χ)
931:4.202 (H
761:methanol
750:acetates
341:E number
283:DrugBank
5907:Commons
5780:(Spain)
5589:E. coli
5555:E. coli
5546:E. coli
5537:E. coli
5357:Seafood
5257:poisons
5155:Lindane
5119:E. coli
5078:O157:H7
5070:O104:H4
4872:Sudan I
4842:Cyanide
4711:Quassia
4653:Lindane
4492:Lindane
4211:Cocaine
4198:Benzoic
4138:Lucaine
4092:by acid
3968:2553612
3960:4672555
3940:Vet Rec
3925:6226283
3916:1152300
3669:5012256
3418:1785916
3388:Bibcode
2882:of the
2878:in the
2876:Record
2624:toluene
2551:DIBAL-H
2250:benzene
2232:vinegar
2228:pickles
2193:glucose
2181:calcium
1789:toluene
1721:History
1627:benzoyl
1600:benzene
1520:what is
1518: (
1412:cations
1167:kJ/mol
1136:kJ/mol
1086:entropy
1048:dioxane
958:cm/mol
916:Acidity
827:acetone
791:ethanol
746:ammonia
742:phenyls
730:alcohol
712:benzene
708:acetone
616:Density
590:122.123
402:PubChem
292:DB03793
217:636131
158:65-85-0
5362:Shrimp
5299:Dioxin
5253:Toxins
4827:3-MCPD
4742:WHO-EM
4634:Thiram
4610:Sulfur
4388:WHO-EM
4277:Amides
4090:Esters
4030:(OECD)
3966:
3958:
3923:
3913:
3867:BRENDA
3840:BRENDA
3820:
3812:
3749:
3708:
3667:
3568:
3416:
3409:183988
3406:
3356:
3316:
3180:
3115:
3090:
3057:
2948:
2938:
2825:
2715:
2677:Niacin
2665:Taipei
2488:amides
2477:esters
2400:phenol
2353:apples
2305:, and
2208:juices
2173:sodium
2155:, and
1941:phenol
1883:amides
1797:cobalt
1793:oxygen
1674:esters
1631:benzyl
1625:. The
1602:ring (
1515:verify
1512:
1410:Other
1394:(SDS)
1384:
1237:Danger
1165:
1134:
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