9-Hexadecenoic acid (CHEM010900)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:29:52 UTC
Update Date2016-11-09 01:14:17 UTC
Accession NumberCHEM010900
Identification
Common Name9-Hexadecenoic acid
ClassSmall Molecule
DescriptionA straight-chain, monounsaturated, 16-carbon fatty acid with a trans-double bond at position C-9; the trans-isomer of palmitoleic acid and predominant trans-16:1 isomer in cheeses from goat and ewe milk. Major dietary sources are partly hydrogenated vegetable oils.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(9E)-Hexadecenoic acidChEBI
(e)-9-HexadecenoicacidChEBI
9-trans-Hexadecenoic acidChEBI
t-16:1D9ChEBI
t-9-Hexadecenoic acidChEBI
trans-9-Hexadecenoic acidChEBI
trans-Delta(9)-Hexadecenoic acidChEBI
trans-Palmitoleic acidChEBI
(9E)-HexadecenoateGenerator
9-trans-HexadecenoateGenerator
t-9-HexadecenoateGenerator
trans-9-HexadecenoateGenerator
trans-delta(9)-HexadecenoateGenerator
trans-Δ(9)-hexadecenoateGenerator
trans-Δ(9)-hexadecenoic acidGenerator
trans-PalmitoleateGenerator
PalmitelaidateGenerator
Palmitoleic acidMeSH
Palmitoleic acid, (Z)-isomerMeSH
Palmitoleic acid, sodium salt, (Z)-isomerMeSH
C16:1 trans-9MeSH
PalmitoleateMeSH
Palmitoleic acid, (e)-isomerMeSH
Palmitoleic acid, potassium salt, (Z)-isomerMeSH
(9E)-9-HexadecenoateHMDB
(9E)-9-Hexadecenoic acidHMDB
(e)-9-HexadecenoateHMDB
(e)-9-Hexadecenoic acidHMDB
(e)-Hexadec-9-enoateHMDB
(e)-Hexadec-9-enoic acidHMDB
trans-9-PalmitoleateGenerator
Palmitelaidic acidMeSH
Chemical FormulaC16H30O2
Average Molecular Mass254.408 g/mol
Monoisotopic Mass254.225 g/mol
CAS Registry Number2091-29-4
IUPAC Name(9E)-hexadec-9-enoic acid
Traditional Nametrans-palmitoleic 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-BQYQJAHWSA-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
Polarizability33.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0093020000-3713e3e16e9fc8ff9d4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0090000000-15955555bad036fe5887Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0091010000-7210516a6de9436dfaefSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090000000-dc1afa2b2526cfadca3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-dc1afa2b2526cfadca3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-1590500110-437a071e7d08786be604Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-e0fb9e9cfc066f8f8275Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-1590300110-1fd83ca98726c802644eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03xr-9100000000-753b931fdaad64d31b10Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-9100000000-95d9bf8269a7484bde2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udi-0090000000-ba595d75ac5ffd8e39a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-0090000000-6798051e8e1a3c6902b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03xu-9400000000-97d42bdb3850c52e063bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0190000000-b90e88fd05f27a8c6a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-8890000000-9443f26541262f6a5367Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-48491c01799873ccfd89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-66b803b008379629bb01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1090000000-14c3fbae6fab6e807e87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9320000000-9d124393fa8133067dd9Spectrum
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 IDHMDB0012328
FooDB IDFDB028947
Phenol Explorer IDNot Available
KNApSAcK IDC00052377
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445872
ChEBI ID59265
PubChem Compound ID5282745
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11026624
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=5947520
3. 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.
4. 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.
5. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
6. Mao YY, Bai JQ, Chen JH, Shou ZF, He Q, Wu JY, Chen Y, Cheng YY: A pilot study of GC/MS-based serum metabolic profiling of acute rejection in renal transplantation. Transpl Immunol. 2008 Apr;19(1):74-80. doi: 10.1016/j.trim.2008.01.006. Epub 2008 Feb 22.
7. Hodgson JM, Wahlqvist ML, Boxall JA, Balazs ND: Platelet trans fatty acids in relation to angiographically assessed coronary artery disease. Atherosclerosis. 1996 Feb;120(1-2):147-54.
8. Destaillats F, Wolff RL, Precht D, Molkentin J: Study of individual trans- and cis-16:1 isomers in cow, goat, and ewe cheese fats by gas-liquid chromatography with emphasis on the trans-delta3 isomer. Lipids. 2000 Sep;35(9):1027-32.
9. van Greevenbroek MM, Robertus-Teunissen MG, Erkelens DW, de Bruin TW: Lipoprotein secretion by intestinal Caco-2 cells is affected differently by trans and cis unsaturated fatty acids: effect of carbon chain length and position of the double bond. Am J Clin Nutr. 1998 Sep;68(3):561-7.
10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
11. 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.
12. 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.
13. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
14. The lipid handbook with CD-ROM