all-trans-retinyl palmitate (PAMDB120531)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120531
Identification
Name: all-trans-retinyl palmitate
Description:An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • all-trans-retinyl hexadecanoate
  • all-trans-Retinyl palmitate
  • Retinol palmitate
  • Retinyl palmitate
  • Vitamin A palmitate
Chemical Formula: C36H60O2
Average Molecular Weight: 524.869
Monoisotopic Molecular Weight: 524.45935
InChI Key: VYGQUTWHTHXGQB-FFHKNEKCSA-N
InChI:InChI=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+
CAS number: 79-81-2
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
Traditional IUPAC Name: vitamin a palmitate
SMILES:CCCCCCCCCCCCCCCC(OCC=C(C=CC=C(C=CC1(C(CCCC=1C)(C)C))C)C)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acid esters
Direct Parent Wax 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 Framework Aliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 28.5 °C
Experimental Properties:
PropertyValueReference
Melting Point28.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.07e-05 mg/mLALOGPS
logP10.12ALOGPS
logP11.62ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity171.51 m3·mol-1ChemAxon
Polarizability70.5 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
all-trans-retinyl palmitate + Water → Retinols + palmitate + Hydrogen ion
all-trans-retinyl palmitate + Water → Retinol + palmitate + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Surman SL, Jones BG, Sealy RE, Rudraraju R, Hurwitz JL (2014)Oral retinyl palmitate or retinoic acid corrects mucosal IgA responses toward an intranasal influenza virus vaccine in vitamin A deficient mice. Vaccine 32, Pubmed: 24657715
  • Carvalho O, Gonçalves C (2014)Retinol and retinyl palmitate in fetal mice liver: sexual dimorphism. Journal of pediatric endocrinology & metabolism : JPEM 27, Pubmed: 23945125
  • Viñas P, Bravo-Bravo M, López-García I, Hernández-Córdoba M (2013)Quantification of ß-carotene, retinol, retinyl acetate and retinyl palmitate in enriched fruit juices using dispersive liquid-liquid microextraction coupled to liquid chromatography with fluorescence detection and atmospheric pressure chemical ionization-mass spectrometry. Journal of chromatography. A 1275, Pubmed: 23290361
  • Shimada J, Taniguchi J, Mori M, Sato Y, Takuwa H, Ito H, Kuwabara S (2013)Retinol palmitate prevents ischemia-induced cell changes in hippocampal neurons through the Notch1 signaling pathway in mice. Experimental neurology 247, Pubmed: 23651513
  • da Cunha MS, Siqueira EM, Trindade LS, Arruda SF (2014)Vitamin A deficiency modulates iron metabolism via ineffective erythropoiesis. The Journal of nutritional biochemistry 25, Pubmed: 24998947
Synthesis Reference: Ajima, Ayako; Takahashi, Katsunobu; Matsushima, Ayako; Saito, Yuji; Inada, Yuji. Retinyl esters synthesis by polyethylene glycol-modified lipase in benzene. Biotechnology Letters (1986), 8(8), 547-52.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
HMDBHMDB03648
LIPID_MAPSLMPR01090013
CHEMSPIDER4444162
PUBCHEM5280531
CHEBI17616
LIGAND-CPDC02588
CAS79-81-2