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Record Information
Version1.0
Creation Date2014-09-11 05:21:54 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003866
Identification
Common NameRetinol acetate
ClassSmall Molecule
DescriptionRetinol acetate is a dietary supplement, permitted in infant formulas Retinol acetate belongs to the family of Retinoids. These are compounds that is related to vitamin A, especially retinol.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
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
(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
9-cis-Retinyl acetateMeSH
Retinol acetateMeSH
Zuretinol acetic acidGenerator
Chemical FormulaC22H32O2
Average Molecular Mass328.488 g/mol
Monoisotopic Mass328.240 g/mol
CAS Registry Number127-47-9
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
SMILESCC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point57 - 58 °C
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0296-5093000000-8a2656ef2c077328e38fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ou-2796000000-23d5fa3ded24cf2ce558View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-2950000000-dc56b7700cd91e30e27dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-6920000000-2578e6a08463cf407b9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6039000000-618d8d46781b79401e66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9021000000-4cad6dce9bbe94145459View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9130000000-c8a144164e2f0c5636c7View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12112
HMDB IDHMDB0035185
FooDB IDFDB013829
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRetinyl acetate
Chemspider ID8421459
ChEBI ID32095
PubChem Compound ID10245972
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM