Record Information
Version1.0
Creation Date2016-05-22 04:30:59 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017654
Identification
Common Name(Z)-Hexadec-9-enoic acid
ClassSmall Molecule
DescriptionA hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(9Z)-Hexadecenoic acidChEBI
(Z)-9-Hexadecenoic acidChEBI
(Z)-Hexadec-9-enoic acidChEBI
16:1DElta9ChEBI
9-cis-Hexadecenoic acidChEBI
cis-9-Hexadecenoic acidChEBI
cis-9-Palmitoleic acidChEBI
cis-delta-9-Hexadecenoic acidChEBI
cis-Delta(9)-Hexadecenoic acidChEBI
cis-Palmitoleic acidChEBI
Oleopalmitic acidChEBI
Palmitolinoleic acidChEBI
Zoomaric acidChEBI
Zoomeric acidChEBI
(9Z)-Hexadec-9-enoateKegg
(9Z)-HexadecenoateGenerator
(Z)-9-HexadecenoateGenerator
(Z)-Hexadec-9-enoateGenerator
9-cis-HexadecenoateGenerator
cis-9-HexadecenoateGenerator
cis-9-PalmitoleateGenerator
cis-delta-9-HexadecenoateGenerator
cis-Δ-9-hexadecenoateGenerator
cis-Δ-9-hexadecenoic acidGenerator
cis-delta(9)-HexadecenoateGenerator
cis-Δ(9)-hexadecenoateGenerator
cis-Δ(9)-hexadecenoic acidGenerator
cis-PalmitoleateGenerator
OleopalmitateGenerator
PalmitolinoleateGenerator
ZoomarateGenerator
ZoomerateGenerator
(9Z)-Hexadec-9-enoic acidGenerator
PalmitoleateGenerator
9-HexadecenoateHMDB
9-Hexadecenoic acidHMDB
HexadecenoateHMDB
Hexadecenoate (N-C16:1)HMDB
Hexadecenoic acidHMDB
Palmitoleic acid, (Z)-isomerHMDB
Palmitoleic acid, (e)-isomerHMDB
C16:1 trans-9HMDB
Palmitelaidic acidHMDB
(9Z)-9-Hexadecenoic acidHMDB
9Z-Hexadecenoic acidHMDB
C16:1HMDB
FA(16:1(9Z))HMDB
FA(16:1n7)HMDB
cis-delta9-Hexadecenoic acidHMDB
cis-Δ9-hexadecenoic acidHMDB
Palmitoleic acidHMDB
Chemical FormulaC16H30O2
Average Molecular Mass254.408 g/mol
Monoisotopic Mass254.225 g/mol
CAS Registry Number373-49-9
IUPAC Name(9Z)-hexadec-9-enoic acid
Traditional Namepalmitoleic acid
SMILESCCCCCC\C=C/CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
InChI KeySECPZKHBENQXJG-FPLPWBNLSA-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 Solubility0.00045 g/LALOGPS
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability32.87 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 (1 TMS)splash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-2900000000-6683cd8579813b4f1ebbSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8910000000-20fcd1fc2d9e095b2c24Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9630000000-7eda678c0ecd65b2e479Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090000000-e72ac58f23bacbf37344Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-d1585cc46cbce84a0506Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0091000000-fd89101236e85a2d9154Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-35027c88ff732ff74b4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-3cac469ac1efde0a3543Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-e5833c7aa4795570bdc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-9090000000-909ebad9120d01bf8e79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-fb5a2e21c48a7d72aac8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0090000000-09c91b61deabc72625f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-e72ac58f23bacbf37344Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-000i-0490000000-472e6cf8ba7a80f708b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0090000000-3c6c13dcd5649fd90845Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-0090000000-e5cccbc8340bb0dce9d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-2490000000-1dbd141e66d6e7a165aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0090000000-202819132f83589a248bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-749f09fec19d95c21683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5005f244d7d1c3502c3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1090000000-cac7fce9a75b0f1abd63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2e782c63ccf72afe9be9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C 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
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 IDDB04257
HMDB IDHMDB0003229
FooDB IDFDB031085
Phenol Explorer IDNot Available
KNApSAcK IDC00001234
BiGG ID246167
BioCyc IDCPD-9245
METLIN ID188
PDB IDNot Available
Wikipedia LinkPalmitoleic acid
Chemspider ID393216
ChEBI ID28716
PubChem Compound ID445638
Kegg Compound IDC08362
YMDB IDYMDB00681
ECMDB IDECMDB21442
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19761868
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24362891
3. Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55.
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. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.
7. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.
8. Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.
9. 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.
10. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.
11. 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
12. Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X
13. 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
14. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en
15. Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55.
16. Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13.
17. Rossner S, Walldius G, Bjorvell H: Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss. Int J Obes. 1989;13(5):603-12.
18. Ho RC, Davy KP, Hickey MS, Summers SA, Melby CL: Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans. Am J Physiol Endocrinol Metab. 2002 Oct;283(4):E799-808.
19. Hori Y, Nakamura K, Yamamoto M, Shimada K, Nakadaira H, Shibuya N, Endoh K, Ogoshi K: Determination of free fatty acids in human bile by high-performance liquid chromatography. Ann Clin Biochem. 1998 Mar;35 ( Pt 2):279-82.
20. Yli-Jama P, Haugen TS, Rebnord HM, Ringstad J, Pedersen JI: Selective mobilisation of fatty acids from human adipose tissue. Eur J Intern Med. 2001 Apr;12(2):107-115.
21. Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78.
22. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
23. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.
24. 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.