9-Tetradecenoic acid, (9Z)- (CHEM012732)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:00:58 UTC
Update Date2016-11-09 01:14:38 UTC
Accession NumberCHEM012732
Identification
Common Name9-Tetradecenoic acid, (9Z)-
ClassSmall Molecule
DescriptionA tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration. Myristoleic acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • OECD HPV Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(9Z)-Tetradecenoic acidChEBI
(Z)-Tetradec-9-enoic acidChEBI
9-Tetradecenoic acidChEBI
9Z-Tetradecenoic acidChEBI
cis-9-Tetradecenoic acidChEBI
cis-Delta(9)-Tetradecenoic acidChEBI
cis-Tetradec-9-enoic acidChEBI
(9Z)-TetradecenoateGenerator
(Z)-Tetradec-9-enoateGenerator
9-TetradecenoateGenerator
9Z-TetradecenoateGenerator
cis-9-TetradecenoateGenerator
cis-delta(9)-TetradecenoateGenerator
cis-Δ(9)-tetradecenoateGenerator
cis-Δ(9)-tetradecenoic acidGenerator
cis-Tetradec-9-enoateGenerator
MyristoleateGenerator
(9Z)-Tetradec-9-enoateHMDB
(9Z)-Tetradec-9-enoic acidHMDB
(9Z)-9-Tetradecenoic acidHMDB
(Z)-9-Tetradecenoic acidHMDB
9(Z)-Tetradecenoic acidHMDB
9-cis-Tetradecenoic acidHMDB
FA(14:1(9Z))HMDB
FA(14:1n5)HMDB
Myristoleic acidHMDB
Myristolenic acidHMDB
Oleomyristic acidHMDB
cis-delta9-Tetradecenoic acidHMDB
cis-Δ9-Tetradecenoic acidHMDB
Chemical FormulaC14H26O2
Average Molecular Mass226.355 g/mol
Monoisotopic Mass226.193 g/mol
CAS Registry Number544-64-9
IUPAC Name(9Z)-tetradec-9-enoic acid
Traditional Namemyristoleic acid
SMILESCCCC\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChI KeyYWWVWXASSLXJHU-WAYWQWQTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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
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 Solubility0.0022 g/LALOGPS
logP5.69ALOGPS
logP5.01ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability28.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9800000000-71fb52f9fefd5cb3790eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00a9-9520000000-b85c6ba98a1ce24c3518Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-57b079c6d11a9714cb51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-4fcda40660e1f5947eb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9120000000-50121015a2477be41becSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0595-9000000000-98c3d58fb9e1e7c41c90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004i-0090000000-e588f40ae851251aee81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0390000000-6a2bf4ff780562d5fdd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-6930000000-bd53c7ac25c8930728e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-cd017bd3efd7fa06ee6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-c6a068748e37ad83d1d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1590000000-999dd13c5871dbb32a3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-97121a85c8e202172ecfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-6c6d923a7644bf907b73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1090000000-bf30a380076470239567Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b037435cdbd96f2e828dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7j-9330000000-790a04dc9533b3b6607bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o1-9000000000-fa6bdbb819001b908171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-aaba2dc5fc19c49556c2Spectrum
MSMass Spectrum (Electron Ionization)splash10-0aou-9100000000-1823acbf402fe87fba5bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0002000
FooDB IDFDB012633
Phenol Explorer IDNot Available
KNApSAcK IDC00001229
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6424
PDB IDNot Available
Wikipedia LinkMyristoleic_acid
Chemspider ID4444564
ChEBI ID27781
PubChem Compound ID5281119
Kegg Compound IDC08322
YMDB IDYMDB00680
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304730
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11380153
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19761868
4. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.
5. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.
6. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.
7. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.
8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
9. M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021
10. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
11. Mamalakis G, Kafatos A, Board S: Type A behavior and adipose tissue linoleic acid: implications for stress management. J Am Coll Nutr. 1994 Jun;13(3):292-7.
12. Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7.
13. Iguchi K, Okumura N, Usui S, Sajiki H, Hirota K, Hirano K: Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate. 2001 Apr;47(1):59-65.
14. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.