Record Information
Version1.0
Creation date2010-04-08 22:10:56 UTC
Update date2018-05-29 01:08:04 UTC
Primary IDFDB013828
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRetinol
DescriptionConstituent of many fish-liver oils, milk, egg-yolk, etc. Nutrient, dietary supplement [DFC] Retinol is one of the animal forms of vitamin A. It is a diterpenoid and an alcohol. It is convertible to other forms of vitamin A, and the retinyl ester derivative of the alcohol serves as the storage form of the vitamin in animals. [Wikipedia]. Retinol is found in many foods, some of which are beer, common wheat, scrapple, and catfish.
CAS Number68-26-8
Structure
Thumb
Synonyms
SynonymSource
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-olChEBI
(9cis)-RetinolChEBI
9-cis RetinolHMDB
(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-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-olHMDB
Afaxindb_source
Agiolanbiospider
Agoncalbiospider
all-trans-Retinolmanual
all-trans-Retinyl alcoholbiospider
all-trans-Vitamin Abiospider
all-trans-Vitamin A alcoholbiospider
all-trans-Vitamin A1biospider
AlphalinChEBI
Alphasterolbiospider
Antixerophthalmic vitaminbiospider
Avibonbiospider
Avitolbiospider
Axeroldb_source
Axerophtholdb_source
b-Retinolbiospider
beta-Retinolbiospider
Biosterolbiospider
Epiteliolbiospider
Gadoldb_source
Ophthalaminbiospider
Prepalindb_source
Retrovitamin abiospider
Sehkraft abiospider
trans-Retinolbiospider
trans-Vitamin A alcoholbiospider
Vitamin Adb_source
Vitamin A alcoholdb_source
Vitamin a1ChEBI
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
Polarizability35.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30O
IUPAC name(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
InChI IdentifierInChI=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-MKOSUFFBSA-N
Isomeric SMILESC\C(=C/CO)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C
Average Molecular Weight286.4516
Monoisotopic Molecular Weight286.229665582
Classification
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.86%; H 10.56%; O 5.59%DFC
Melting PointMp 63-64°DFC
Boiling PointBp0.000001 137-138°DFC
Experimental Water SolubilityNot Available
Experimental logP5.68BIOBYTE (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 328 (E1%/1cm 1780) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0490000000-97ed49d705440e4d32e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-3930000000-7c5bfbd8b838b97dc2aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-9820000000-6a49bab0c891ffe1e5b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-d0ff1cdc72141d0daa0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-c0a067ff8ed271b80945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-4590000000-cfc35aba420e707075f7View in MoNA
ChemSpider ID393012
ChEMBL IDCHEMBL986
KEGG Compound IDC17276
Pubchem Compound ID445354
Pubchem Substance IDNot Available
ChEBI ID17336
Phenol-Explorer IDNot Available
DrugBank IDDB00162
HMDB IDHMDB00305
CRC / DFC (Dictionary of Food Compounds) IDJHQ00-R:JHQ00-R
EAFUS ID3860
Dr. Duke IDVITAMIN-A|VIT-A
BIGG ID35081
KNApSAcK IDC00031437
HET IDRTL
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRetinol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Diacylglycerol O-acyltransferase 1DGAT1O75907
Diacylglycerol O-acyltransferase 2DGAT2Q96PD7
Lecithin retinol acyltransferaseLRATO95237
Acyl-CoA wax alcohol acyltransferase 2AWAT2Q6E213
Acyl-CoA wax alcohol acyltransferase 1AWAT1Q58HT5
Retinol dehydrogenase 8RDH8Q9NYR8
Retinol dehydrogenase 11RDH11Q8TC12
Retinol dehydrogenase 10RDH10Q8IZV5
Short-chain dehydrogenase/reductase 3DHRS3O75911
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074 map00830
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.