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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000305
Secondary Accession Numbers
  • HMDB00305
Metabolite Identification
Common NameVitamin A
DescriptionVitamin A (retinol) is a yellow fat-soluble, antioxidant vitamin important in vision and bone growth. It belongs to the family of chemical compounds known as retinoids. Retinol is ingested in a precursor form; animal sources (milk and eggs) contain retinyl esters, whereas plants (carrots, spinach) contain pro-vitamin A carotenoids. Hydrolysis of retinyl esters results in retinol while pro-vitamin A carotenoids can be cleaved to produce retinal. Retinal, also known as retinaldehyde, can be reversibly reduced to produce retinol or it can be irreversibly oxidized to produce retinoic acid. Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.
Structure
Data?1582752122
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-olChEBI
all-trans-Retinyl alcoholChEBI
all-trans-Vitamin a alcoholChEBI
AlphalinChEBI
Chocola aChEBI
RetinolChEBI
Vitamin a1ChEBI
Aquasol aKegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-olHMDB
all-trans-RetinolHMDB
b-RetinolHMDB
beta-RetinolHMDB
trans-RetinolHMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomerHMDB
all trans RetinolHMDB
11-cis-RetinolHMDB
Vitamin aChEBI
Chemical FormulaC20H30O
Average Molecular Weight286.4516
Monoisotopic Molecular Weight286.229665582
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
Traditional Nameα-sol
CAS Registry Number68-26-8
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
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+
InChI KeyFPIPGXGPPPQFEQ-OVSJKPMPSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP5.68BIOBYTE (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability36.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.59731661259
DarkChem[M-H]-174.04931661259
DarkChem[M+H]+177.59731661259
DarkChem[M-H]-174.04931661259
AllCCS[M+H]+174.32932859911
AllCCS[M-H]-179.66432859911
DeepCCS[M+H]+185.87130932474
DeepCCS[M-H]-183.51330932474
DeepCCS[M-2H]-217.15630932474
DeepCCS[M+Na]+192.38330932474
AllCCS[M+H]+174.332859911
AllCCS[M+H-H2O]+171.132859911
AllCCS[M+NH4]+177.332859911
AllCCS[M+Na]+178.232859911
AllCCS[M-H]-179.732859911
AllCCS[M+Na-2H]-180.432859911
AllCCS[M+HCOO]-181.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vitamin AC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C3108.0Standard polar33892256
Vitamin AC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C2431.2Standard non polar33892256
Vitamin AC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C2417.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vitamin A,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CCC12597.7Semi standard non polar33892256
Vitamin A,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC12794.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1190000000-7c2230ee88e04e8f37412017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin A GC-MS (1 TMS) - 70eV, Positivesplash10-0006-7139000000-7242603c3f7f12c824cd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vitamin A GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052r-2950000000-c24ec8ff8d0ba6c1f23f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vitamin A Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0290000000-25c523b646154b291da82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vitamin A Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-05gj-3900000000-a63c286f931608f650a32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vitamin A Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05mo-9700000000-e627db30469c74bb037f2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 10V, Positive-QTOFsplash10-00kr-0490000000-97ed49d705440e4d32e72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 20V, Positive-QTOFsplash10-00ks-3930000000-7c5bfbd8b838b97dc2aa2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 40V, Positive-QTOFsplash10-0fri-9820000000-6a49bab0c891ffe1e5b22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 10V, Negative-QTOFsplash10-000i-0090000000-d0ff1cdc72141d0daa0e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 20V, Negative-QTOFsplash10-0a4r-0090000000-c0a067ff8ed271b809452017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 40V, Negative-QTOFsplash10-00ku-4590000000-cfc35aba420e707075f72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 10V, Negative-QTOFsplash10-0a4i-0090000000-fe93459d3069e264b77f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 20V, Negative-QTOFsplash10-05mx-0190000000-f81760535f6050971f922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 40V, Negative-QTOFsplash10-00li-0960000000-4dbc516b202b90a6c2652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 10V, Positive-QTOFsplash10-015i-1890000000-fb68e645ac6c84dc722c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 20V, Positive-QTOFsplash10-05a9-2910000000-aa07b89a9cfe132b87252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vitamin A 40V, Positive-QTOFsplash10-06dl-5900000000-6de72efc591b252620c92021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Placenta
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.78 +/- 0.33 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.84 +/- 0.46 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.76 +/- 0.44 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.02 (0.34-2.1) uMAdolescent (13-18 years old)BothNormal details
BloodDetected and Quantified0.530-2.100 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0-2 uMInfant (0-1 year old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified1-2 uMChildren (1-13 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified1-2 uMAdolescent (13-18 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified1-2 uMAdult (>18 years old)Both
Normal
    • CALIPER Paediatri...
details
BloodDetected and Quantified2.3 (1.2-3.5) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.0600 +/- 0.620 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.220 +/- 0.590 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.580 +/- 0.710 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.720 +/- 0.790 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified1.770 +/- 0.740 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified2.390 +/- 0.800 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified2.310 +/- 0.960 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.470 +/- 0.770 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.831 +/- 0.499 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.0736 +/- 0.485 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.220 +/- 0.496 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.580 +/- 0.360 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.0841 +/- 0.499 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.182 +/- 0.499 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.200 +/- 0.634 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.740 +/- 0.540 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.790 +/- 0.530 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.790 +/- 0.540 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.800 +/- 0.500 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.810 +/- 0.550 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.820 +/- 0.510 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.820 +/- 0.560 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.840 +/- 0.530 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.850 +/- 0.530 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.860 +/- 0.450 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.870 +/- 0.510 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.880 +/- 0.430 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.880 +/- 0.470 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.880 +/- 0.480 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.890 +/- 0.420 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.950 +/- 0.470 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.951 +/- 0.520 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.732 +/- 2.217 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified6.113 +/- 2.594 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified6.249 +/- 1.850 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.42 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.63 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.993 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.18 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.445 +/- 0.384 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.910 +/- 0.430 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.950 +/- 0.610 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.970 +/- 0.650 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.391 +/- 0.782 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2.700 +/- 1.100 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified5.781 +/- 2.356 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified5.861 +/- 2.726 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified1.99 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.18 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.47 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified1.980 +/- 0.540 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.0800 +/- 0.620 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.130 +/- 0.380 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified2.400 +/- 0.900 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified5.666 +/- 2.0387 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified6.553 +/- 2.315 uMAdult (>18 years old)MaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.015 +/- 0.010 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
BloodDetected and Quantified2.50 +/- 0.86 uMAdult (>18 years old)BothHemodialysis details
BloodDetected and Quantified0.45 uMAdult (>18 years old)Male
Abetalipoproteinemia
details
BloodDetected and Quantified2.0 (1.2-2.5) uMAdult (>18 years old)FemaleEndometrial cancer details
BloodDetected and Quantified1.466 +/- 0.349 uMAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. Cabral PC, Diniz Ada S, de Arruda IK: Vitamin A and zinc status in patients on maintenance haemodialysis. Nephrology (Carlton). 2005 Oct;10(5):459-63. [PubMed:16221095 ]
Endometrial cancer
  1. Jeong NH, Song ES, Lee JM, Lee KB, Kim MK, Yun YM, Lee JK, Son SK, Lee JP, Kim JH, Hur SY, Kwon YI: Preoperative levels of plasma micronutrients are related to endometrial cancer risk. Acta Obstet Gynecol Scand. 2009;88(4):434-9. doi: 10.1080/00016340902767187. [PubMed:19235557 ]
Pregnancy
  1. Mikkelsen TB, Osler M, Olsen SF: Validity of protein, retinol, folic acid and n-3 fatty acid intakes estimated from the food-frequency questionnaire used in the Danish National Birth Cohort. Public Health Nutr. 2006 Sep;9(6):771-8. [PubMed:16925883 ]
Abetalipoproteinemia
  1. Lazaro RP, Dentinger MP, Rodichok LD, Barron KD, Satya-Murti S: Muscle pathology in Bassen-Kornzweig syndrome and vitamin E deficiency. Am J Clin Pathol. 1986 Sep;86(3):378-87. [PubMed:2944375 ]
Associated OMIM IDs
DrugBank IDDB00162
Phenol Explorer Compound IDNot Available
FooDB IDFDB023841
KNApSAcK IDC00031437
Chemspider IDNot Available
KEGG Compound IDC17276
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVitamin_A
METLIN IDNot Available
PubChem Compound445354
PDB IDNot Available
ChEBI ID17336
Food Biomarker OntologyNot Available
VMH IDRETINOL
MarkerDB IDMDB00000141
Good Scents IDNot Available
References
Synthesis ReferenceIsler, O.; Ronco, A.; Guex, W.; Hindley, N. C.; Huber, W.; Dialer, K.; Kofler, M. Esters and ethers of synthetic vitamin A. Helvetica Chimica Acta (1949), 32 489-505.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Enzymes

General function:
Involved in diacylglycerol O-acyltransferase activity
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:
DGAT1
Uniprot ID:
O75907
Molecular weight:
55277.735
Reactions
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl esterdetails
Acyl-CoA + Vitamin A → Coenzyme A + Retinyl esterdetails
Palmityl-CoA + Vitamin A → Coenzyme A + Retinyl palmitatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-retinol and 13-cis-retinol, but not all-trans-retinol. Active in the presence of NAD as cofactor but not in the presence of NADP.
Gene Name:
RDH5
Uniprot ID:
Q92781
Molecular weight:
34978.425
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular weight:
39867.27
Reactions
Vitamin A + NAD → Retinal + NADH + Hydrogen Iondetails
General function:
Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:
LRAT
Uniprot ID:
O95237
Molecular weight:
25702.635
Reactions
Phosphatidylcholine + Vitamin A → 2-Acyl-sn-glycero-3-phosphocholine + Retinyl esterdetails

Only showing the first 10 proteins. There are 20 proteins in total.