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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:28:53 UTC
Update Date2021-10-13 06:34:55 UTC
HMDB IDHMDB0033724
Secondary Accession Numbers
  • HMDB33724
Metabolite Identification
Common NameUndecylenic acid
DescriptionUndecylenic acid, also known as 10-undecylenate or omega-undecenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecylenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecylenic acid is found in black elderberry. Undecylenic acid is a flavouring ingredient and is a sweet and woody-tasting compound. Undecylenic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID:31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. Undecylenic acid is used in the production of the bioplastic Nylon-11, in the treatment of fungal infections in the skin, and as a precursor in the manufacture of a wide assortment of pharmaceuticals, cosmetics, perfumes, and personal hygiene products.
Structure
Data?1580854635
Synonyms
ValueSource
10-Hendecenoic acidChEBI
10-UndecensaeureChEBI
10-Undecylenic acidChEBI
Acide 10-undecanoiqueChEBI
Acide 10-undecyliqueChEBI
Acido 10-undecenoicoChEBI
Omega-hendecenoic acidChEBI
Omega-undecenoic acidChEBI
Undecelinic acidChEBI
Undecen-10-acid-1ChEBI
Undecen-10-saeureChEBI
Undecenoic acidChEBI
CruexKegg
10-HendecenoateGenerator
10-UndecylenateGenerator
Omega-hendecenoateGenerator
Omega-undecenoateGenerator
UndecelinateGenerator
UndecenoateGenerator
UndecylenateGenerator
10-Undecenoic acidMeSH
MycodermineMeSH
10-HendecenoicHMDB
10-Henedecenoic acidHMDB
9-Undecenoic acidHMDB
9-Undecylenic acidHMDB
DeclidHMDB
DesenexHMDB
FEMA 3247HMDB
N-Undecylenic acidHMDB
N-UNDECYLENIC ACID (10-1)HMDB
RenselinHMDB
SevinonHMDB
Undec-10-enoic acidHMDB
Undecyl-10-enic acidHMDB
Undecylenenic acidHMDB
Undecylenic acid, usanHMDB
Undecylenic acidsHMDB
Zinc undecylenate (undecylenic acid)HMDB
10-UndecenoateHMDB
Undecylenic acidHMDB
ω-Hendecenoic acidHMDB
ω-Undecenoic acidHMDB
Chemical FormulaC11H20O2
Average Molecular Weight184.2753
Monoisotopic Molecular Weight184.146329884
IUPAC Nameundec-10-enoic acid
Traditional Namedesenex
CAS Registry Number112-38-9
SMILES
OC(=O)CCCCCCCCC=C
InChI Identifier
InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
InChI KeyFRPZMMHWLSIFAZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point24.5 °CNot Available
Boiling Point137.00 °C. @ 2.00 mm HgThe Good Scents Company Information System
Water Solubility0.074 mg/mL at 30 °CNot Available
LogP3.86Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP10(3.84) g/LALOGPS
logP10(3.73) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity54.12 m³·mol⁻¹ChemAxon
Polarizability22.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.64631661259
DarkChem[M-H]-145.03231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Undecylenic acidOC(=O)CCCCCCCCC=C2341.6Standard polar33892256
Undecylenic acidOC(=O)CCCCCCCCC=C1396.6Standard non polar33892256
Undecylenic acidOC(=O)CCCCCCCCC=C1480.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Undecylenic acid,1TMS,isomer #1C=CCCCCCCCCC(=O)O[Si](C)(C)C1544.8Semi standard non polar33892256
Undecylenic acid,1TBDMS,isomer #1C=CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C1787.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-0a6u-9100000000-50cef3280113666a9e232017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-0a7l-9000000000-830e35fcbdcb4ba9b5742017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-056u-9200000000-5b8c18292287532e1deb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-00ls-9600000000-b0c6c3ec0da35153ca5d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-0a6u-9100000000-50cef3280113666a9e232018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-0a7l-9000000000-830e35fcbdcb4ba9b5742018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-056u-9200000000-5b8c18292287532e1deb2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Undecylenic acid EI-B (Non-derivatized)splash10-00ls-9600000000-b0c6c3ec0da35153ca5d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecylenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mx-9300000000-c83d63d3e351f1befd832017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecylenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9210000000-1ea20b56f43f28dc11722017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Undecylenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0apl-9100000000-c392a15a3cd57ccae1482014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Undecylenic acid LC-ESI-IT , negative-QTOFsplash10-001i-0900000000-b90f772663028aa6c2732017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 10V, Positive-QTOFsplash10-014r-0900000000-d8a5d703a9d2aebb6b992015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 20V, Positive-QTOFsplash10-00kr-4900000000-270e01bbabb57dca4ec22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 40V, Positive-QTOFsplash10-05nf-9100000000-aa66183f7300eea3b4b42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 10V, Negative-QTOFsplash10-001i-0900000000-e0832ba35c6a39bb8de02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 20V, Negative-QTOFsplash10-00m0-1900000000-7c7091c9da9db8d3bd822015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 40V, Negative-QTOFsplash10-0a4l-9300000000-bb79df7af5aab06986f02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 10V, Positive-QTOFsplash10-001j-9500000000-c5d68ca2d338cff02df92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 20V, Positive-QTOFsplash10-067i-9000000000-02a41b4e4b35021d18e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 40V, Positive-QTOFsplash10-0aou-9000000000-459198bd399044a1297f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 10V, Negative-QTOFsplash10-001i-0900000000-d44a0375430320d81c4d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 20V, Negative-QTOFsplash10-0159-1900000000-397d0040ec861d2e84032021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Undecylenic acid 40V, Negative-QTOFsplash10-0pvl-9300000000-7b2ba3000e5fbafc4a582021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDBSALT001514
Phenol Explorer Compound IDNot Available
FooDB IDFDB011844
KNApSAcK IDNot Available
Chemspider ID10771160
KEGG Compound IDC13910
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUndecylenic_acid
METLIN IDNot Available
PubChem Compound5634
PDB IDNot Available
ChEBI ID35045
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1035691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]
  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.