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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:59 UTC
Update Date2021-10-13 06:14:37 UTC
HMDB IDHMDB0031264
Secondary Accession Numbers
  • HMDB31264
Metabolite Identification
Common NameMethyl nonanoate
DescriptionMethyl nonanoate, also known as methyl pelargonate or 1-nonanecarboxylate, 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 nonanoate can be obtained from the formal condensation of methanol and nonanoic acid. It is a colourless, oily liquid with a fruity, tropical or pear-like odour, used in perfumes and flavours. It has a waxy, wine-like, green celery flavour. Methyl nonanoate is a very hydrophobic molecule, with a high boiling point of 213 oC. It is practically insoluble in water with a measured water solubility of just 22.5 mgl/L. Outside the human body, methyl nonanoate is found in a number of foods including apples, bananas, blackberries, butter, blue cheese, grapes, hop oil, pineapples, baked potatoes, star fruit, strawberries, tobacco, vanilla and white wine. Methyl nonanoate exhibits nematicidal activity against root-knot and soybean cyst nematodes and was found to be toxic to nematodes at concentrations as low as 0.2 uL a.i./litre (PMID: 19274268 ).
Structure
Data?1563862102
Synonyms
ValueSource
1-Nonanecarboxylic acidChEBI
Methyl ester nonanoic acidChEBI
Methyl N-nonanoateChEBI
Methyl nonylateChEBI
Methyl pelargonateChEBI
Pelargonic acid methyl esterChEBI
1-NonanecarboxylateGenerator
Methyl ester nonanoateGenerator
Methyl N-nonanoic acidGenerator
Methyl nonylic acidGenerator
Methyl pelargonic acidGenerator
Pelargonate methyl esterGenerator
Methyl nonanoic acidGenerator
FEMA 2724HMDB
Nonanoic acid methyl esterHMDB
Methyl nonanoic acid (ester)Generator, HMDB
Chemical FormulaC10H20O2
Average Molecular Weight172.2646
Monoisotopic Molecular Weight172.146329884
IUPAC Namemethyl nonanoate
Traditional Namemethyl nonanoate (ester)
CAS Registry Number1731-84-6
SMILES
CCCCCCCCC(=O)OC
InChI Identifier
InChI=1S/C10H20O2/c1-3-4-5-6-7-8-9-10(11)12-2/h3-9H2,1-2H3
InChI KeyIJXHLVMUNBOGRR-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
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-35 °CNot Available
Boiling Point213.00 to 214.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.023 mg/mL at 25 °CNot Available
LogP4.32Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP10(3.96) g/LALOGPS
logP10(3.29) g/LChemAxon
logS10(-3.6) g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.65 m³·mol⁻¹ChemAxon
Polarizability21.67 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.26631661259
DarkChem[M-H]-140.90931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl nonanoate GC-MS (Non-derivatized)splash10-000i-9300000000-0fea4fadc7a2a00ae4232014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl nonanoate EI-B (Non-derivatized)splash10-00di-9100000000-854ee48fef9dd1f130ae2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl nonanoate EI-B (Non-derivatized)splash10-00di-9000000000-6b14d9620e385334bcce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl nonanoate GC-MS (Non-derivatized)splash10-000i-9300000000-0fea4fadc7a2a00ae4232017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl nonanoate GC-EI-TOF (Non-derivatized)splash10-000i-9500000000-7cc501def8f3d350c53a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl nonanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9200000000-878e9f6c148c07e64d0e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl nonanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl nonanoate 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 - Methyl nonanoate 10V, Positive-QTOFsplash10-00dl-1900000000-4402070c218e203615a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 20V, Positive-QTOFsplash10-00dm-7900000000-61dc588adbedf610479b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 40V, Positive-QTOFsplash10-052f-9000000000-69fc25e19392a49acb152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 10V, Negative-QTOFsplash10-00di-0900000000-ef495fa573b5ca29865c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 20V, Negative-QTOFsplash10-00dr-1900000000-7cc4c16cfe631ca68cc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 40V, Negative-QTOFsplash10-0006-9300000000-bf5aff0797e95e3fefdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 10V, Positive-QTOFsplash10-05fu-9400000000-d9554b08e567c7b7aaea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 20V, Positive-QTOFsplash10-0a4l-9000000000-fb16125acbf705be93f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 40V, Positive-QTOFsplash10-0a4l-9000000000-0f2dc3cf27b3d6ff19df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 10V, Negative-QTOFsplash10-00di-0900000000-a368ddab2a736ce31cd52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 20V, Negative-QTOFsplash10-00di-0900000000-77df2e772271e6b945db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl nonanoate 40V, Negative-QTOFsplash10-0a4l-9100000000-f52e1747abcd8a716bd52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDDB01631
Phenol Explorer Compound IDNot Available
FooDB IDFDB003305
KNApSAcK IDC00049004
Chemspider ID14846
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15606
PDB IDNON
ChEBI ID44499
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Davis EL, Meyers DM, Dullum CJ, Feitelson JS: Nematicidal Activity of Fatty Acid Esters on Soybean Cyst and Root-knot Nematodes. J Nematol. 1997 Dec;29(4S):677-84. [PubMed:19274268 ]
  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.