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CHEBI:17616 - all-trans-retinyl palmitate

ChEBI IDCHEBI:17616
ChEBI Nameall-trans-retinyl palmitate
Stars
ASCII Nameall-trans-retinyl palmitate
DefinitionAn all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.
Secondary ChEBI IDsCHEBI:8819, CHEBI:12784, CHEBI:26542
Last Modified28 July 2021
DownloadsMolfile
FormulaC36H60O2
Net Charge0
Average Mass524.874
Monoisotopic Mass524.45933
SMILESCCCCCCCCCCCCCCCC(=O)OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
InChIInChI=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+
InChIKeyVYGQUTWHTHXGQB-FFHKNEKCSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) blood (UBERON:0000178) PubMed (17009166)
Escherichia coli (ncbitaxon:562) - PubMed (33202630)
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human xenobiotic metabolite  Any human metabolite produced by metabolism of a xenobiotic compound in humans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
fat-soluble vitamin (role)  Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
ChEBI Ontology
Outgoing Relation(s)
all-trans-retinyl palmitate (CHEBI:17616) has functional parent all-trans-retinol (CHEBI:17336)
all-trans-retinyl palmitate (CHEBI:17616) has role Escherichia coli metabolite (CHEBI:76971)
all-trans-retinyl palmitate (CHEBI:17616) has role antioxidant (CHEBI:22586)
all-trans-retinyl palmitate (CHEBI:17616) has role human xenobiotic metabolite (CHEBI:76967)
all-trans-retinyl palmitate (CHEBI:17616) is a all-trans-retinyl ester (CHEBI:63410)
all-trans-retinyl palmitate (CHEBI:17616) is a retinyl palmitate (CHEBI:15040)
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
Synonyms  Source
retinyl palmitateKEGG COMPOUND
vitamin A palmitateKEGG COMPOUND
all-trans-retinyl palmitateKEGG COMPOUND
retinol palmitateKEGG COMPOUND
(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 esterLIPID MAPS
Brand Names  Source
Aquasol AChemIDplus
Optovit-AChemIDplus
ArovitChemIDplus
AfaxinChemIDplus
AlphalinChemIDplus
Chocola AChemIDplus
UniProt Name  Source
all-trans-retinyl hexadecanoateUniProt
Manual XrefsDatabases
C02588KEGG COMPOUND
LMPR01090013LIPID MAPS
HMDB0003648HMDB
D00164KEGG DRUG
CHOCOLA_AMetaCyc
Retinyl_palmitateWikipedia
4197DrugCentral
DBSALT000855DrugBank
FDB030671FooDB
4444162ChemSpider
Registry NumbersSources
Reaxys:1917366Reaxys
CAS:79-81-2ChemIDplus
CAS:79-81-2NIST Chemistry WebBook
Citations