2.0 2012-08-15 08:51:35 -0600 2015-09-13 12:56:17 -0600 ECMDB21660 M2MDB002050 Retinol Retinol is also known as Vitamin A. In E. coli, retinol can be oxidized to retinal in a reversible reaction catalyzed by alcohol dehydrogenases (EC 1.1.1.1) such as those encoded by E. coli genes frmA and adhP. This reaction also reduces NAD+ to NADH. (KEGG) &alpha (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol A-Mulsal A-Sol A-Vi-Pel A-Vitan Acon Afaxin Agiolan Agoncal Alcovit A All trans-Retinol All-trans-Retinol All-trans-Retinyl alcohol All-trans-Vitamin A All-trans-Vitamin A alcohol All-trans-Vitamin A1 All-trans-Vitamin A1 alcohol Alphalin Alphasterol Anatola Anatola A Anti-Infective Vitamin Antixerophthalmic vitamin Aoral Apexol Apostavit Aquasol A Aquasynth Atars Atav Avibon Avita Avitol Axerol Axerophthol B-Retinol Bentavit A Beta-Retinol Biosterol Chocola A Del-VI-A Disatabs Tabs Dofsol Dohyfral A Epiteliol Hi-A-Vita Homagenets Aoral Lard Factor Lin Myvpack Nio-A-Let Oleovitamin A Ophthalamin Plivit A Prepalin Retin-11,12-t2-ol (9CI) Retinol Retinol (ACD/Name 4.0) Retinyl A Retrovitamin A Ro-a-vit Sehkraft A Solu-A Sterol Super A Tegosphere VitA Testavol Testavol S Thalasphere Trans-Retinol Trans-Vitamin A alcohol Vaflol Vafol Veroftal Vi-&alpha Vi-a Vi-alpha Vi-Dom-A Vi-α Vio-A Vitamin a Vitamin A (Feed) Vitamin A alcohol Vitamin A alcohol (VAN) Vitamin A cryst Vitamin A oil Vitamin A Palmitate Vitamin A Palmitic acid Vitamin A Solubilized Vitamin a1 Vitamin A1 alcohol Vitavel A Vitpex Vogan Vogan-Neu [11,12-3H]-Retinol β-Retinol C20H30O 286.4516 286.229665582 (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol 13-cis retinol 68-26-8 C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ FPIPGXGPPPQFEQ-OVSJKPMPSA-N Solid Membrane logp 6.38 ALOGPS logs -4.58 ALOGPS solubility 7.58e-03 g/l ALOGPS melting_point 61-63 oC logp 4.69 ChemAxon pka_strongest_acidic 16.44 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol ChemAxon average_mass 286.4516 ChemAxon mono_mass 286.229665582 ChemAxon smiles C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C20H30O ChemAxon inchi InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+ ChemAxon inchikey FPIPGXGPPPQFEQ-OVSJKPMPSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 97.92 ChemAxon polarizability 36.28 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21999 Specdb::CMs 38969 Specdb::CMs 174214 Specdb::EiMs 1998 Specdb::MsMs 314854 Specdb::MsMs 314855 Specdb::MsMs 314856 Specdb::MsMs 360676 Specdb::MsMs 360677 Specdb::MsMs 360678 Specdb::MsMs 1218230 Specdb::MsMs 1218231 Specdb::MsMs 1218232 Specdb::MsMs 2702691 Specdb::MsMs 2702692 Specdb::MsMs 2702693 Specdb::MsMs 3002209 Specdb::MsMs 3002210 Specdb::MsMs 3002211 Specdb::NmrTwoD 2027 HMDB00305 445354 393012 C00473 50211 Retinols RTL Vitamin A Norum KR, Blomhoff R: McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage. Am J Clin Nutr. 1992 Oct;56(4):735-44. 1414975 Graham-Maar RC, Schall JI, Stettler N, Zemel BS, Stallings VA: Elevated vitamin A intake and serum retinol in preadolescent children with cystic fibrosis. Am J Clin Nutr. 2006 Jul;84(1):174-82. 16825693 Sorenson AW, Delhumeau C, Bernstein MS, Costanza MC, Morabia A: Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000. Eur J Clin Nutr. 2003 Jan;57(1):177-85. 12548314 Alberts D, Ranger-Moore J, Einspahr J, Saboda K, Bozzo P, Liu Y, Xu XC, Lotan R, Warneke J, Salasche S, Stratton S, Levine N, Goldman R, Islas M, Duckett L, Thompson D, Bartels P, Foote J: Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin. Clin Cancer Res. 2004 Mar 15;10(6):1875-80. 15041701 Wieringa FT, Dijkhuizen MA, West CE, Thurnham DI, Muhilal, Van der Meer JW: Redistribution of vitamin A after iron supplementation in Indonesian infants. Am J Clin Nutr. 2003 Mar;77(3):651-7. 12600856 Egeland GM, Berti P, Soueida R, Arbour LT, Receveur O, Kuhnlein HV: Age differences in vitamin A intake among Canadian Inuit. Can J Public Health. 2004 Nov-Dec;95(6):465-9. 15622799 Ribaya-Mercado JD, Solon FS, Fermin LS, Perfecto CS, Solon JA, Dolnikowski GG, Russell RM: Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements. Am J Clin Nutr. 2004 Apr;79(4):633-41. 15051608 Kieu NT, Yurie K, Hung NT, Yamamoto S, Chuyen NV: Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes. Asia Pac J Clin Nutr. 2002;11(2):92-7. 12074187 Torma H, Vahlquist A: Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J Invest Dermatol. 1990 Jan;94(1):132-8. 2295828 Allen LH, Haskell M: Estimating the potential for vitamin A toxicity in women and young children. J Nutr. 2002 Sep;132(9 Suppl):2907S-2919S. 12221269 Ribaya-Mercado JD, Solomons NW, Medrano Y, Bulux J, Dolnikowski GG, Russell RM, Wallace CB: Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A. Am J Clin Nutr. 2004 Nov;80(5):1291-8. 15531678 Marquez M, Yepez CE, Sutil-Naranjo R, Rincon M: [Basic aspects and measurement of the antioxidant vitamins A and E] Invest Clin. 2002 Sep;43(3):191-204. 12229281 Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32. 15929633 Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201. 16469975 Jumpsen JA, Brown NE, Thomson AB, Paul Man SF, Goh YK, Ma D, Clandinin MT: Fatty acids in blood and intestine following docosahexaenoic acid supplementation in adults with cystic fibrosis. J Cyst Fibros. 2006 May;5(2):77-84. Epub 2006 Feb 28. 16507353 http://hmdb.ca/system/metabolites/msds/000/000/224/original/HMDB00305.pdf?1358896186 S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml Alcohol dehydrogenase, propanol-preferring P39451 ADHP_ECOLI adhP http://ecmdb.ca/proteins/P39451.xml Retinol + NAD <> Retinal + NADH + Hydrogen ion R02124