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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:25:20 UTC
Update Date2021-10-13 08:23:03 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
Data?1563863453
Synonyms
ValueSource
Ascorbyl palmitic acidGenerator
6-Hexadecanoyl-L-ascorbic acidHMDB
6-Monopalmitoyl-L-ascorbateHMDB
6-Palmitoyl-L-ascorbic acidHMDB
Ascorbyl palmitate, usanHMDB
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, HMDB
6-O-Palmitoylascorbic acidMeSH, HMDB
Ascorbate 6-palmitateMeSH, HMDB
6-O-PalmitoylascorbateMeSH, HMDB
Asc-6-O-palmitateMeSH, HMDB
Asc6PLMMeSH, HMDB
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point107 - 117 °CNot Available
Boiling Point546.00 to 547.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP6.868 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0062 g/LALOGPS
logP10(5.23) g/LALOGPS
logP10(5.01) g/LChemAxon
logS10(-4.8) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ascorbyl palmitateCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O4548.2Standard polar33892256
Ascorbyl palmitateCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O2906.4Standard non polar33892256
Ascorbyl palmitateCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O3001.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ascorbyl palmitate,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C)C1OC(=O)C(O)=C1O3188.6Semi standard non polar33892256
Ascorbyl palmitate,1TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O[Si](C)(C)C)=C1O3196.0Semi standard non polar33892256
Ascorbyl palmitate,1TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O[Si](C)(C)C3220.8Semi standard non polar33892256
Ascorbyl palmitate,2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C)C1OC(=O)C(O[Si](C)(C)C)=C1O3234.4Semi standard non polar33892256
Ascorbyl palmitate,2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C)C1OC(=O)C(O)=C1O[Si](C)(C)C3249.7Semi standard non polar33892256
Ascorbyl palmitate,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C3262.2Semi standard non polar33892256
Ascorbyl palmitate,3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C)C1OC(=O)C(O[Si](C)(C)C)=C1O[Si](C)(C)C3315.2Semi standard non polar33892256
Ascorbyl palmitate,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C(C)(C)C)C1OC(=O)C(O)=C1O3449.1Semi standard non polar33892256
Ascorbyl palmitate,1TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O3478.7Semi standard non polar33892256
Ascorbyl palmitate,1TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O[Si](C)(C)C(C)(C)C3504.0Semi standard non polar33892256
Ascorbyl palmitate,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C(C)(C)C)C1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O3744.1Semi standard non polar33892256
Ascorbyl palmitate,2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C(C)(C)C)C1OC(=O)C(O)=C1O[Si](C)(C)C(C)(C)C3766.9Semi standard non polar33892256
Ascorbyl palmitate,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3770.6Semi standard non polar33892256
Ascorbyl palmitate,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(O[Si](C)(C)C(C)(C)C)C1OC(=O)C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4017.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ascorbyl palmitate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7975000000-817fbadeaf39bf6599f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ascorbyl palmitate GC-MS (3 TMS) - 70eV, Positivesplash10-014r-8651109000-3593ce2b268de2a920972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ascorbyl palmitate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 10V, Positive-QTOFsplash10-05n1-1549300000-f68a0b35bade79d6d8352016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 20V, Positive-QTOFsplash10-0a4i-2951000000-a83ce14d5111b44f28342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 40V, Positive-QTOFsplash10-000b-4960000000-c812ac147d5f97e36bcc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 10V, Negative-QTOFsplash10-0bti-2592200000-3abd8fc115be9a5f3bae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 20V, Negative-QTOFsplash10-0a4r-0490000000-b1909900e831916855652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 40V, Negative-QTOFsplash10-0bti-7690000000-f73051fa0c3da30c41db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 10V, Negative-QTOFsplash10-03di-0211900000-3578bcc2055e27c49a272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 20V, Negative-QTOFsplash10-0a4l-9440100000-8c881797694162ee55f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 40V, Negative-QTOFsplash10-0a4i-9270000000-4d2a7fac6e682060cba02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 10V, Positive-QTOFsplash10-014i-2931600000-cc6fb503f57d0f40bf6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 20V, Positive-QTOFsplash10-014j-9751100000-3ccf2b13170e49462a1e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ascorbyl palmitate 40V, Positive-QTOFsplash10-052f-9100000000-57c541fcd7c3368173132021-09-22Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1253371
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.