Retinyl ester (CHEM035553)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:52:46 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035553
Identification
Common NameRetinyl ester
ClassSmall Molecule
DescriptionRetinyl ester, also known as all-E-retinoate, 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. Retinyl ester is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Retinyl ester participates in a number of enzymatic reactions, within cattle. In particular, Retinyl ester can be converted into 11-cis-retinol; which is mediated by the enzyme retinoid isomerohydrolase. In addition, Retinyl ester can be biosynthesized from vitamin a and acetyl-CoA; which is mediated by the enzyme diacylglycerol O-acyltransferase 1. In cattle, retinyl ester is involved in the metabolic pathway called the retinol metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Ester, all-trans-retinylMeSH
all trans Retinyl estersMeSH
Ester, retinylMeSH
all-trans-Retinyl estersMeSH
Retinyl estersMeSH
all trans Retinyl esterMeSH
all-trans-Retinyl esterMeSH
56-Dihydroretinoic acidChEMBL, HMDB
all-e-Retinoic acidChEMBL, HMDB
56-DihydroretinoateGenerator, HMDB
all-e-RetinoateGenerator, HMDB
Chemical FormulaC20H30O2
Average Molecular Mass302.451 g/mol
Monoisotopic Mass302.225 g/mol
CAS Registry NumberNot Available
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethylcyclohexyl)nona-2,4,6,8-tetraenoic acid
Traditional Nameretinyl ester
SMILESCC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O
InChI IdentifierInChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChI KeyWWDMJSSVVPXVSV-YCNIQYBTSA-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
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
logP6.35ALOGPS
logP5.46ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.21 m³·mol⁻¹ChemAxon
Polarizability37.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-3190000000-6350942f5f337f0854aaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-6139000000-103432f8455b3f1da15aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0392000000-fd2bcaee3a8aa8ef1f91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0940000000-d999454a4951b513e106Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-68bb39576638ee359ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0079000000-64d539d74e51ded7a105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-0094000000-9aa61625fad564fa1e56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-2590000000-44b65d0b69f1051e637aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0149000000-a038329babc7de684b42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0393000000-57c7f4184a75a62e820fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4930000000-63ec76ed5f13c9770097Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgr-0973000000-ce5e32df9099194f4779Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yi-3930000000-75c848c7071e888d4488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0103-7900000000-2e43c6610f1ab346d1e6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003598
FooDB IDFDB023204
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6966
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10607936
ChEBI ID545914
PubChem Compound ID5460164
Kegg Compound IDC02075
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zilversmit DB, Morton RE, Hughes LB, Thompson KH: Exchange of retinyl and cholesteryl esters between lipoproteins of rabbit plasma. Biochim Biophys Acta. 1982 Jul 20;712(1):88-93.
2. Kang S, Duell EA, Fisher GJ, Datta SC, Wang ZQ, Reddy AP, Tavakkol A, Yi JY, Griffiths CE, Elder JT, et al.: Application of retinol to human skin in vivo induces epidermal hyperplasia and cellular retinoid binding proteins characteristic of retinoic acid but without measurable retinoic acid levels or irritation. J Invest Dermatol. 1995 Oct;105(4):549-56.
3. Ribaya-Mercado JD, Blanco MC, Fox JG, Russell RM: High concentrations of vitamin A esters circulate primarily as retinyl stearate and are stored primarily as retinyl palmitate in ferret tissues. J Am Coll Nutr. 1994 Feb;13(1):83-6.
4. Stauber PM, Sherry B, VanderJagt DJ, Bhagavan HN, Garry PJ: A longitudinal study of the relationship between vitamin A supplementation and plasma retinol, retinyl esters, and liver enzyme activities in a healthy elderly population. Am J Clin Nutr. 1991 Nov;54(5):878-83.
5. 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.
6. Got L, Gousson T, Delacoux E: Simultaneous determination of retinyl esters and retinol in human livers by reversed-phase high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Jun 23;668(2):233-9.