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Record Information
Version2.0
Created at2020-11-23 19:39:48 UTC
Updated at2021-08-19 23:59:20 UTC
NP-MRD IDNP0002763
Secondary Accession NumbersNone
Natural Product Identification
Common NameRetinyl palmitate
Provided ByBMRBBMRB logo
DescriptionRetinyl palmitate, also known as aquasol a or vitamin a palmitate, belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position. Retinyl palmitate is a drug. In humans, retinyl palmitate is involved in the retinol metabolism pathway. Retinyl palmitate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1988 (PMID: 3349096). Based on a literature review a significant number of articles have been published on Retinyl palmitate (PMID: 17984079) (PMID: 15045249) (PMID: 11448569) (PMID: 10404832).
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC36H60O2
Average Mass524.8604 Da
Monoisotopic Mass524.45933 Da
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 Namevitamin a palmitate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
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+
InChI KeyVYGQUTWHTHXGQB-FFHKNEKCSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.8e-11 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0003648
DrugBank IDDBSALT000855
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030671
KNApSAcK IDNot Available
Chemspider ID4444162
KEGG Compound IDC02588
BioCyc IDCHOCOLA_A
BiGG IDNot Available
Wikipedia LinkRetinyl_palmitate
METLIN IDNot Available
PubChem Compound5280531
PDB IDNot Available
ChEBI ID17616
Good Scents IDrw1302861
References
General References
  1. Thomas JB, Kline MC, Schiller SB, Ellerbe PM, Sniegoski LT, Duewer DL, Sharpless KE: Certification of fat-soluble vitamins, carotenoids, and cholesterol in human serum: Standard Reference Material 968b. Anal Bioanal Chem. 1996 Aug;356(1):1-9. doi: 10.1007/s0021663560001. [PubMed:15045249 ]
  2. Fernandez-Miranda C, Cancelas P, Sanz M, Porres A, Gamez Gerique J: Influence of apolipoprotein-E phenotypes on postprandial lipoprotein metabolism after three different fat loads. Nutrition. 2001 Jul-Aug;17(7-8):529-33. doi: 10.1016/s0899-9007(01)00552-4. [PubMed:11448569 ]
  3. Weintraub M, Grosskopf I, Trostanesky Y, Charach G, Rubinstein A, Stern N: Thyroxine replacement therapy enhances clearance of chylomicron remnants in patients with hypothyroidism. J Clin Endocrinol Metab. 1999 Jul;84(7):2532-6. doi: 10.1210/jcem.84.7.5812. [PubMed:10404832 ]
  4. Lindstrom MB, Sternby B, Borgstrom B: Concerted action of human carboxyl ester lipase and pancreatic lipase during lipid digestion in vitro: importance of the physicochemical state of the substrate. Biochim Biophys Acta. 1988 Mar 25;959(2):178-84. doi: 10.1016/0005-2760(88)90029-x. [PubMed:3349096 ]