Methyl hexadecanoate (CHEM009412)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:04:31 UTC
Update Date2016-11-09 01:13:59 UTC
Accession NumberCHEM009412
Identification
Common NameMethyl hexadecanoate
ClassSmall Molecule
DescriptionMethyl hexadecanoate, also known as methyl palmitate or palmitic acid methyl ester, is a member of the class of compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Thus, methyl hexadecanoate is considered to be a fatty ester lipid molecule. Methyl hexadecanoate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl hexadecanoate is a fatty, oily, and waxy tasting compound found in cloves, which makes methyl hexadecanoate a potential biomarker for the consumption of this food product. Methyl hexadecanoate can be found primarily in saliva.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methyl hexadecanoateGenerator
Methyl palmitateHMDB
Methyl palmitic acidHMDB
Hexadecanoate methyl esterHMDB
Hexadecanoic acid methyl esterHMDB
Palmitic acid methyl esterHMDB
Methyl hexadecanoic acidGenerator
Chemical FormulaC17H34O2
Average Molecular Mass270.451 g/mol
Monoisotopic Mass270.256 g/mol
CAS Registry Number112-39-0
IUPAC Namemethyl hexadecanoate
Traditional Namemethyl hexadecanoate
SMILESCCCCCCCCCCCCCCCC(=O)OC
InChI IdentifierInChI=1S/C17H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-16H2,1-2H3
InChI KeyFLIACVVOZYBSBS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP7.41ALOGPS
logP6.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.85 m³·mol⁻¹ChemAxon
Polarizability36.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9410000000-06e342f68cdd631a32faSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-0090000000-db5787e9b3eaac96f146Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-9100000000-683d8a1de530bbfa7510Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05g3-9000000000-a2b255dd0fdd1efd2edcSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9000000000-baccd6187fe64ba0fb81Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9400000000-6e386a4925d22e506f67Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-5920000000-18adf3ceb15daf1890ffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0090000000-e3f1fb41bc39cf5c3980Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0190000000-837b670351375a88e317Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00di-5980000000-412d3cc4d2d44a828547Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-0uyj-8910000000-abb13bbae38141c27067Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0uej-9600000000-6d6061fa61e38f88acebSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0gbi-1910000000-3309cf3659c2c2662fe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-9000000000-1501685b2e06c466d3b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-000i-9000000000-e103d05527cb34385856Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-9000000000-cad0cc415c906a783cfcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0abc-5900000000-252b278e11ad05aaf4f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-01vt-1900000000-9e5b1071dde4e1224b3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-5900000000-356dc1d8cd57cb9b8810Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-3900000000-8c7e326caeaf4b57bbd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-8d32a33ec60435ad4078Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-6970000000-be7dcb63dde8bf429a3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9610000000-bb567c889e6285679c0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d0e2f55cef37f22099f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1090000000-1b8c8aae3c8b029cfbd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9240000000-4159ba9834de8d7f67c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0090000000-5b7592ccc42ad579e1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1090000000-dbc31b0134593f446482Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-db97441651327b503413Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3290000000-bf26cd76362604fe9bd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9320000000-09573567cce883917735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-0dd6e755d6f048efee33Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061859
FooDB IDFDB003050
Phenol Explorer IDNot Available
KNApSAcK IDC00030755
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID8181
Kegg Compound IDC16995
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fautz E, Rosenfelder G, Grotjahn L: Iso-branched 2- and 3-hydroxy fatty acids as characteristic lipid constituents of some gliding bacteria. J Bacteriol. 1979 Dec;140(3):852-8.
2. Mjabri B, Boucrot P, Aubry J: Hexadecanoic and neuraminic acid incorporations in two rat colon carcinoma cell lipids: selective influence of 1-O-octadecyl 2-O-methyl-3-phosphocholine on glycerolipid and ganglioside biosynthesis. Arch Int Physiol Biochim. 1990 Aug;98(4):163-71.
3. Fagret D, Bontemps L, Apparu M, Keriel C, Mathieu JP, Pernin C, Vidal M, Comet M, Cuchet P: Kinetics of iodomethylated hexadecanoic acid metabolism in the rat myocardium: influence of the number and the position of methyl radicals. Int J Nucl Med Biol. 1985;12(5):363-7.
4. Fagret D, Rocca C, Machecourt J, Wolf JE, Dubois F, Mathieu JP, Comet M: Regional uptake of [123I]-16-iodo3-R,S-methyl hexadecanoic acid in patients with myocardial infarction. Comparison with thallium 201 uptake and wall motion. Am J Card Imaging. 1994 Jan;8(1):1-7.
5. Dharmaratne HR, Nanayakkara NP, Khan IA: (-)-3 beta,4 beta-epoxyvalerenic acid from Valeriana officinalis. Planta Med. 2002 Jul;68(7):661-2.
6. Yuan C, Nan P, Shi S, Zhong Y: Chemical composition of the essential oils of two Chinese endemic Meconopsis species. Z Naturforsch C. 2003 May-Jun;58(5-6):313-5.
7. Goren AC, Bilsel G, Altun M, Satil F, Dirmenci T: Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia. Z Naturforsch C. 2003 Jul-Aug;58(7-8):502-4.
8. HANSEN RP, SHORLAND FB, COOKE NJ: The branched-chain fatty acids of mutton fat. I. The isolation of ( )-14-methyl-hexadecanoic acid. Biochem J. 1952 Oct;52(2):203-7.
9. GERSON T, SHORLAND FB, ADAMS Y, BELL ME: Further studies on the metabolism of the (plus)-anteiso-acids, (plus)-12-methyltetradecanoic acid and (plus)-14-methyl-hexadecanoic acid, in the rat. Biochem J. 1959 Dec;73:594-6.
10. El-Mawla AM, Farag SF, Beuerle T: Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures. Nat Prod Res. 2011 Jan;25(1):45-52. doi: 10.1080/14786419.2010.482937.
11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
12. 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.
13. 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.
14. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
15. The lipid handbook with CD-ROM