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Record Information
StatusDetected and Quantified
Creation Date2009-06-03 20:33:59 UTC
Update Date2020-02-26 21:37:22 UTC
Secondary Accession Numbers
  • HMDB12328
Metabolite Identification
Common NamePalmitelaidic acid
DescriptionPalmitelaidic acid is a trans fatty acid (the trans isomer of palmitoleic acid). Trans fatty acids are known to cause changes in plasma lipids and lipoprotein phenotypes, but the mechanisms involved are unknown. The major dietary sources of trans fatty acids are partly hydrogenated vegetable oils, mainly elaidic acid (t-18:1D9). Additional sources are animal and dairy fats [palmitelaidic acid (t-16:1D9) and t-vaccenic acid (t-18:1D11)] and partly hydrogenated fish oils. (very-long-chain trans fatty acids, ie, >C22) (PMID: 9734731 ). Palmitelaidic acid has been reported as the predominant trans-16:1 isomer in cheeses made with goat and ewe milks (PMID: 11026624 ).
(9E)-Hexadecenoic acidChEBI
9-trans-Hexadecenoic acidChEBI
t-9-Hexadecenoic acidChEBI
trans-9-Hexadecenoic acidChEBI
trans-Delta(9)-Hexadecenoic acidChEBI
trans-Palmitoleic acidChEBI
trans-Δ(9)-hexadecenoic acidGenerator
(9E)-9-Hexadecenoic acidHMDB
(e)-9-Hexadecenoic acidHMDB
(e)-Hexadec-9-enoic acidHMDB
Palmitoleic acid, (e)-isomerHMDB
Palmitoleic acid, (Z)-isomerHMDB
Palmitoleic acid, sodium salt, (Z)-isomerHMDB
C16:1 trans-9HMDB
Palmitoleic acidHMDB
Palmitoleic acid, potassium salt, (Z)-isomerHMDB
Palmitelaidic acidMeSH
Chemical FormulaC16H30O2
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
IUPAC Name(9E)-hexadec-9-enoic acid
Traditional Nametrans-palmitoleic acid
CAS Registry Number10030-73-6
InChI Identifier
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
  • 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

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00045 g/LALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified1.97 +/- 1.4 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
    • Zerihun T. Dame, ...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028947
KNApSAcK IDNot Available
Chemspider ID4445872
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282745
PDB IDNot Available
ChEBI ID59265
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:18346641 ]
  2. 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. [PubMed:8645355 ]
  3. 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. [PubMed:11026624 ]
  4. 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. [PubMed:9734731 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.