Record Information
Version1.0
Creation date2015-05-07 19:45:31 UTC
Update date2019-11-26 03:21:51 UTC
Primary IDFDB030671
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameall-trans-retinyl palmitate
DescriptionRetinyl palmitate, also known as vitamin a palmitate or aquasol a, is a member of the class of compounds known as wax monoesters. Wax monoesters are waxes bearing an ester group at exactly one position. Thus, retinyl palmitate is considered to be an isoprenoid lipid molecule. Retinyl palmitate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Retinyl palmitate can be found in a number of food items such as rocket salad (sspecies), black elderberry, common grape, and vaccinium (blueberry, cranberry, huckleberry), which makes retinyl palmitate a potential biomarker for the consumption of these food products. Retinyl palmitate can be found primarily in blood, as well as throughout most human tissues. In humans, retinyl palmitate is involved in the retinol metabolism. Retinyl palmitate is also involved in vitamin A deficiency, which is a metabolic disorder. An alternate spelling, retinol palmitate, which violates the -yl organic chemical naming convention for esters, is also frequently seen .
CAS Number79-81-2
Structure
Thumb
Synonyms
SynonymSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoateChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoic acid esterChEBI
AfaxinChEBI
all-trans-Retinol palmitateChEBI
all-trans-Retinyl hexadecanoateChEBI
AlphalinChEBI
Aquasol aChEBI
ArovitChEBI
Chocola aChEBI
O(15)-HexadecanoylretinolChEBI
Optovit-aChEBI
Retinol hexadecanoateChEBI
Retinol palmitateChEBI
Retinyl hexadecanoateChEBI
trans-Retinol palmitateChEBI
trans-Retinyl palmitateChEBI
Vitamin a palmitateChEBI
all-trans-Retinyl palmitateKegg
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoic acidGenerator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoate esterGenerator
all-trans-Retinol palmitic acidGenerator
all-trans-Retinyl hexadecanoic acidGenerator
Retinol hexadecanoic acidGenerator
Retinol palmitic acidGenerator
Retinyl hexadecanoic acidGenerator
trans-Retinol palmitic acidGenerator
trans-Retinyl palmitic acidGenerator
Vitamin a palmitic acidGenerator
all-trans-Retinyl palmitic acidGenerator
Retinyl palmitic acidGenerator
all-trans-Vitamin a palmitateHMDB
AquapalmHMDB
Axerophthol palmitateHMDB
Dispatabs tabsHMDB
Ester found in fish liver oilsHMDB
Lutavit a 500 plusHMDB
MyvakHMDB
MyvaxHMDB
Optovit aHMDB
Testavol SHMDB
Vitazyme aHMDB
Predicted Properties
PropertyValueSource
Water Solubility8.1e-05 g/LALOGPS
logP10.12ALOGPS
logP11.62ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity171.51 m³·mol⁻¹ChemAxon
Polarizability70.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC36H60O2
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-yl hexadecanoate
InChI IdentifierInChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
InChI KeyVYGQUTWHTHXGQB-FFHKNEKCSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Average Molecular Weight524.8604
Monoisotopic Molecular Weight524.459331164
Classification
Description Belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentWax monoesters
Alternative Parents
Substituents
  • Wax monoester skeleton
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSall-trans-retinyl palmitate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-07vr-6590330000-c4a001ec8772bbd8b673Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00n0-0391040000-4bcb419b1aa363c5a184Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3890000000-13b63fb441c04d797a5aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-4910200000-ec9d8c6e06e67e406eaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0090050000-063ec803b899247ff625Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-ceacddaa1af7bfe01b93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-2090000000-010cffd7fdb5e0c0ae62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-0970350000-ae98e4da36c7fef49b01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1960010000-e463420790c3679b3761Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-3930000000-2209374e0a45d158da93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0060090000-71bf924b1d2a2be5b8a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090010000-5bffb18764c70498c127Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9870000000-8e1a1ac617c6db688b0bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference