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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:02 UTC
Update Date2019-07-23 07:17:20 UTC
HMDB IDHMDB0061859
Secondary Accession Numbers
  • HMDB61859
Metabolite Identification
Common NameMethyl hexadecanoic acid
DescriptionMethyl hexadecanoic acid, also known as methyl palmitate or hexadecanoate methyl ester, 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. Methyl hexadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866240
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 Weight270.4507
Monoisotopic Molecular Weight270.255880332
IUPAC Namemethyl hexadecanoate
Traditional Namemethyl hexadecanoate
CAS Registry Number112-39-0
SMILES
CCCCCCCCCCCCCCCC(=O)OC
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP10(7.41) g/LALOGPS
logP10(6.4) g/LChemAxon
logS10(-6.6) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.77331661259
DarkChem[M-H]-171.37731661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid GC-MS (Non-derivatized)splash10-000i-9410000000-06e342f68cdd631a32fa2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid CI-B (Non-derivatized)splash10-00di-0090000000-db5787e9b3eaac96f1462017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid EI-B (Non-derivatized)splash10-00dr-9100000000-683d8a1de530bbfa75102017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid EI-B (Non-derivatized)splash10-05g3-9000000000-a2b255dd0fdd1efd2edc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid EI-B (Non-derivatized)splash10-05fr-9000000000-baccd6187fe64ba0fb812017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl hexadecanoic acid GC-EI-TOF (Non-derivatized)splash10-000i-9400000000-6e386a4925d22e506f672017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl hexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-5920000000-18adf3ceb15daf1890ff2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl hexadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid Orbitrap 4V, positive-QTOFsplash10-00di-0090000000-e3f1fb41bc39cf5c39802020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid Orbitrap 7V, positive-QTOFsplash10-00di-0190000000-837b670351375a88e3172020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid Orbitrap 9V, positive-QTOFsplash10-00di-5980000000-412d3cc4d2d44a8285472020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid Orbitrap 12V, positive-QTOFsplash10-0uyj-8910000000-abb13bbae38141c270672020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid Orbitrap 15V, positive-QTOFsplash10-0uej-9600000000-6d6061fa61e38f88aceb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-0gbi-1910000000-3309cf3659c2c2662fe62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-00di-9000000000-1501685b2e06c466d3b72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-000i-9000000000-e103d05527cb343858562020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-0a4i-9000000000-cad0cc415c906a783cfc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-0abc-5900000000-252b278e11ad05aaf4f52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-01vt-1900000000-9e5b1071dde4e1224b3e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-0a4i-5900000000-356dc1d8cd57cb9b88102020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl hexadecanoic acid n/a 18V, positive-QTOFsplash10-00di-3900000000-8c7e326caeaf4b57bbd02020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 10V, Positive-QTOFsplash10-00dr-0190000000-8d32a33ec60435ad40782016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 20V, Positive-QTOFsplash10-00ds-6970000000-be7dcb63dde8bf429a3d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 40V, Positive-QTOFsplash10-052f-9610000000-bb567c889e6285679c0d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-d0e2f55cef37f22099f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 20V, Negative-QTOFsplash10-014r-1090000000-1b8c8aae3c8b029cfbd42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 40V, Negative-QTOFsplash10-052f-9240000000-4159ba9834de8d7f67c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 10V, Negative-QTOFsplash10-00kr-0090000000-5b7592ccc42ad579e1ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 20V, Negative-QTOFsplash10-014r-1090000000-dbc31b0134593f4464822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-db97441651327b5034132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 10V, Positive-QTOFsplash10-00di-3290000000-bf26cd76362604fe9bd72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 20V, Positive-QTOFsplash10-0ab9-9320000000-09573567cce8839177352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl hexadecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-0dd6e755d6f048efee332021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003050
KNApSAcK IDC00030755
Chemspider IDNot Available
KEGG Compound IDC16995
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8181
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:118159 ]
  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. [PubMed:1707612 ]
  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. [PubMed:3833822 ]
  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. [PubMed:8130610 ]
  5. Dharmaratne HR, Nanayakkara NP, Khan IA: (-)-3 beta,4 beta-epoxyvalerenic acid from Valeriana officinalis. Planta Med. 2002 Jul;68(7):661-2. [PubMed:12143008 ]
  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. [PubMed:12872920 ]
  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. [PubMed:12939035 ]
  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. [PubMed:13018208 ]
  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. [PubMed:13827622 ]
  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. [PubMed:21240761 ]
  11. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  15. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.