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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:08:02 UTC
Update Date2019-07-23 06:17:59 UTC
HMDB IDHMDB0035185
Secondary Accession Numbers
  • HMDB35185
Metabolite Identification
Common NameRetinol acetate
DescriptionRetinol acetate, also known as vitamin a acetate or dagravit a forte, 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. Retinol acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Retinol acetate is a potentially toxic compound.
Structure
Data?1563862679
Synonyms
ValueSource
Retinol acetic acidGenerator
13-cis-Retinyl acetateHMDB
Acetateall-trans-retinolHMDB
Acetic acid, retinyl esterHMDB
all-trans-Retinol acetateHMDB
all-trans-Retinyl acetateHMDB
all-trans-RetinylacetateHMDB
all-trans-Vitamin a acetateHMDB
CrystaletsHMDB
Davitan a 650HMDB
MyvakHMDB
MyvaxHMDB
O(15)-AcetylretinolHMDB
O~15~-acetyl-retinolHMDB
O~15~-acetylretinolHMDB
Retinol acetate (JP15)HMDB
RETINOL acetATE (see retinoidprojects 1 and 3)HMDB
Retinol, acetateHMDB
Retinol, acetate, all-trans- (8ci)HMDB
Retinol, acetate, labeled with tritiumHMDB
Retinyl acetateHMDB
trans-Retinyl acetateHMDB
trans-Vitamin a acetateHMDB
Vitamin a acetateHMDB
Vitamin a acetate (tritiated)HMDB
Vitamin a alcohol acetateHMDB
Vitamin a esterHMDB
Vitamin a, acetateHMDB
Vitamin a1 acetateHMDB
Dagravit a forteHMDB
RetiNitHMDB
Retinol acetate, (9,13-cis)-isomerHMDB
Vitamin a dispersaHMDB
Dif vitamin a masivoHMDB
Vitamin-a-saarHMDB
9-cis-Retinyl acetateMeSH
(2E,4E,6Z)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetic acidGenerator
Retinol acetateMeSH
Chemical FormulaC22H32O2
Average Molecular Weight328.4883
Monoisotopic Molecular Weight328.240230268
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-yl acetate
Traditional Name(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate
CAS Registry Number127-47-9
SMILES
CC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9-,18-14+
InChI KeyQGNJRVVDBSJHIZ-AQDFTDIISA-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 ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point57 - 58 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP6.56ALOGPS
logP5.14ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.07 m³·mol⁻¹ChemAxon
Polarizability40.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-5093000000-8a2656ef2c077328e38fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ou-2796000000-23d5fa3ded24cf2ce558Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2950000000-dc56b7700cd91e30e27dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-6920000000-2578e6a08463cf407b9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6039000000-618d8d46781b79401e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9021000000-4cad6dce9bbe94145459Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-c8a144164e2f0c5636c7Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12112
Phenol Explorer Compound IDNot Available
FooDB IDFDB013829
KNApSAcK IDNot Available
Chemspider ID8421459
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRetinyl acetate
METLIN IDNot Available
PubChem Compound10245972
PDB IDNot Available
ChEBI ID32095
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.