Record Information
Version1.0
Creation date2010-04-08 22:14:25 UTC
Update date2015-07-21 06:36:47 UTC
Primary IDFDB019542
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number137-66-6
Structure
Thumb
Synonyms
SynonymSource
6-Hexadecanoyl-L-ascorbic acidbiospider
6-Monopalmitoyl-L-ascorbatebiospider
6-Palmitoyl-L-ascorbic acidbiospider
Ascorbyl palmitate, USANdb_source
Ascorbyl palmitic acidbiospider
Cetyl ascorbatebiospider
E304db_source
L-Ascorbic acid 6-palmitatebiospider
L-Ascorbyl 6-palmitatebiospider
L-ascorbyl monopalmitatebiospider
L-ascorbyl palmitatebiospider
Palmitoyl l-ascorbic acidbiospider
Vitamin c-palmitatebiospider
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
Chemical FormulaC22H38O7
IUPAC name2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecanoate
InChI IdentifierInChI=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 KeyInChIKey=QAQJMLQRFWZOBN-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O
Average Molecular Weight415
Monoisotopic Molecular Weight414
Classification
DescriptionThis compound belongs to the class of chemical entities known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.74%; H 9.24%; O 27.02%DFC
Melting PointMp 107-117°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +22.9 (c, 2 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID10606454
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID54676825
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39883
CRC / DFC (Dictionary of Food Compounds) IDBWR05-S:MBX09-A
EAFUS ID259
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1253371
SuperScent IDNot Available
Wikipedia IDAscorbyl_palmitate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference