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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:25:20 UTC
Update Date2018-03-12 21:55:50 UTC
HMDB IDHMDB0039883
Secondary Accession Numbers
  • HMDB39883
Metabolite Identification
Common NameAscorbyl palmitate
DescriptionAntioxidant.Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive (E number E304). Oral supplements of ascorbyl palmitate are less effective, due to the substance breaking down again into its components before being digested. Ascorbyl palmitate is also marketed as "vitamin C ester
Structure
Thumb
Synonyms
ValueSource
6-Hexadecanoyl-L-ascorbic acidHMDB
6-Monopalmitoyl-L-ascorbateHMDB
6-Palmitoyl-L-ascorbic acidHMDB
Ascorbyl palmitate, usanHMDB
Ascorbyl palmitic acidHMDB
Cetyl ascorbateHMDB
e304HMDB
L-Ascorbic acid 6-palmitateHMDB
L-Ascorbyl 6-palmitateHMDB
L-Ascorbyl monopalmitateHMDB
L-Ascorbyl palmitateHMDB
Palmitoyl L-ascorbic acidHMDB
Vitamin c-palmitateHMDB
Ascorbic acid-6-O-palmitateMeSH
6-O-Palmitoylascorbic acidMeSH
Ascorbate 6-palmitateMeSH
6-O-PalmitoylascorbateMeSH
Asc-6-O-palmitateMeSH
Asc6PLMMeSH
Chemical FormulaC22H38O7
Average Molecular Weight414.5329
Monoisotopic Molecular Weight414.26175357
IUPAC Name2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecanoate
Traditional Nameascorbyl palmitate
CAS Registry Number137-66-6
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O
InChI Identifier
InChI=1S/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3
InChI KeyQAQJMLQRFWZOBN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Dihydrofuran
  • Enoate ester
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Enediol
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0062 g/LALOGPS
logP5.23ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.45ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity110.62 m³·mol⁻¹ChemAxon
Polarizability48.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7975000000-817fbadeaf39bf6599f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014r-8651109000-3593ce2b268de2a92097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n1-1549300000-f68a0b35bade79d6d835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2951000000-a83ce14d5111b44f2834View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-4960000000-c812ac147d5f97e36bccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bti-2592200000-3abd8fc115be9a5f3baeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0490000000-b1909900e83191685565View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bti-7690000000-f73051fa0c3da30c41dbView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019542
KNApSAcK IDNot Available
Chemspider ID10606454
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAscorbyl palmitate
METLIN IDNot Available
PubChem Compound54676825
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Let MB, Jacobsen C, Meyer AS: Ascorbyl palmitate, gamma-tocopherol, and EDTA affect lipid oxidation in fish oil enriched salad dressing differently. J Agric Food Chem. 2007 Mar 21;55(6):2369-75. Epub 2007 Feb 24. [PubMed:17319681 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.