Retinol (ECMDB21660) (M2MDB002050)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (545)
Record Information
Version2.0
Creation Date2012-08-15 08:51:35 -0600
Update Date2015-09-13 12:56:17 -0600
Secondary Accession Numbers
  • ECMDB21660
Identification
Name:Retinol
DescriptionRetinol 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)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • &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
Chemical Formula:C20H30O
Weight:Average: 286.4516
Monoisotopic: 286.229665582
InChI Key:FPIPGXGPPPQFEQ-OVSJKPMPSA-N
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+
CAS number:68-26-8
IUPAC Name:(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional IUPAC Name:13-cis retinol
SMILES:C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:61-63 °C
Experimental Properties:
PropertyValueSource
LogP:5.68; 5.68 [BIOBYTE (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 m³·mol⁻¹ChemAxon
Polarizability36.28 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Retinol + NAD <> Retinal + NADH + Hydrogen ion
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1190000000-346a3e44c44d46353e80View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7139000000-7242603c3f7f12c824cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0290000000-25c523b646154b291da8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05gj-3900000000-a63c286f931608f650a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9700000000-e627db30469c74bb037fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1490000000-7205fba02aeb80622df8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-3920000000-951836eaf171751b137cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lei-9810000000-b9b76a3e956e61a7d39eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-575d71f5f53354f828c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-c71c47589510cf7c1a0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-3690000000-26f7587a1f34c10cd8f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fe93459d3069e264b77fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-0190000000-f81760535f6050971f92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0960000000-4dbc516b202b90a6c265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-1890000000-fb68e645ac6c84dc722cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-2910000000-aa07b89a9cfe132b8725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dl-5900000000-6de72efc591b252620c9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-052r-2950000000-c24ec8ff8d0ba6c1f23fView in MoNA
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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. Pubmed: 15041701
  • 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. Pubmed: 12221269
  • 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. Pubmed: 15622799
  • 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. Pubmed: 16825693
  • 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. Pubmed: 16507353
  • 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. Pubmed: 12074187
  • 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. Pubmed: 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. Pubmed: 15929633
  • 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. Pubmed: 1414975
  • Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201. Pubmed: 16469975
  • 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. Pubmed: 15531678
  • 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. Pubmed: 15051608
  • 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. Pubmed: 12548314
  • Torma H, Vahlquist A: Vitamin A esterification in human epidermis: a relation to keratinocyte differentiation. J Invest Dermatol. 1990 Jan;94(1):132-8. Pubmed: 2295828
  • 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. Pubmed: 12600856
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID50211
HMDB IDHMDB00305
Pubchem Compound ID445354
Kegg IDC00473
ChemSpider ID393012
WikipediaVitamin A
BioCyc IDRetinols
EcoCyc IDRetinols
Ligand ExpoRTL

Enzymes

Protein Details
1. S-(hydroxymethyl)glutathione dehydrogenase
General function:
Involved in zinc ion binding
Specific function:
Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:
frmA
Uniprot ID:
P25437
Molecular weight:
39359
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Protein Details
2. Alcohol dehydrogenase, propanol-preferring
General function:
Involved in zinc ion binding
Specific function:
Preferred specificity is towards 1-propanol
Gene Name:
adhP
Uniprot ID:
P39451
Molecular weight:
35379
Reactions
An alcohol + NAD(+) = an aldehyde or ketone + NADH.