Record Information
Version1.0
Creation date2010-04-08 22:06:03 UTC
Update date2020-09-17 15:29:59 UTC
Primary IDFDB004036
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHexadecenoic acid
DescriptionPalmitoleic acid, also known as palmitoleate or zoomaric acid or C16:1, is an omega-7 monounsaturated fatty acid that is found in plants (PMID: 11308350) such as cannabis plants (PMID:6991645) and marine sources (PMID: 19382347). It 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. Palmitoleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Palmitoleic acid exists in all living species, ranging from bacteria to humans. Macadamia nuts and buckthorn seed oil contain the cis isomer of palmitoleic acid. Palmitoleic acid is also found in mung beans, java plums, napa cabbages, cucurbita (gourd), and kiwis. It is also a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Palmitoleic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and cirrhosis; palmitoleic acid has also been linked to the inborn metabolic disorder isovaleric acidemia. Palmitoleic acid has been reported to have beneficial effects on insulin sensitivity, cholesterol metabolism, and hemostasis. Other positive effects reported include lowering LDL cholesterol and increasing high-density lipoprotein cholesterol (HDL)(https://doi.org/10.1016/B978-1-78242-247-1.00004-1).
CAS Number373-49-9
Structure
Thumb
Synonyms
SynonymSource
trans-Hexa-dec-2-enoateGenerator
(2E)-Hexadecenoic acidChEBI
(e)-2-Hexadecenoic acidChEBI
2-Palmitoleic acidChEBI
2-trans-Hexadecenoic acidChEBI
Gaidic acidChEBI
t-16:1D2ChEBI
t-2-Hexadecenoic acidChEBI
trans-2-Hexadecenoic acidChEBI
trans-Delta(2)-Hexadecenoic acidChEBI
trans-Hexadec-2-enoic acidChEBI
(2E)-HexadecenoateGenerator
(e)-2-HexadecenoateGenerator
2-PalmitoleateGenerator
2-trans-HexadecenoateGenerator
GaidateGenerator
t-2-HexadecenoateGenerator
trans-2-HexadecenoateGenerator
trans-delta(2)-HexadecenoateGenerator
trans-δ(2)-hexadecenoateGenerator
trans-δ(2)-hexadecenoic acidGenerator
trans-Hexadec-2-enoateGenerator
Hexadecenoic acid, (e)-isomerMeSH, HMDB
cis-Hexadecenoic acidMeSH, HMDB
Hexadecenoic acidMeSH, HMDB
Hexadecenoic acid, (Z)-isomerMeSH, HMDB
trans-Hexadecenoic acidMeSH, HMDB
Predicted Properties
PropertyValueSource
logP6.25ChemAxon
pKa (Strongest Acidic)5.03ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.18 m³·mol⁻¹ChemAxon
Polarizability33.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H30O2
IUPAC name(2E)-hexadec-2-enoic acid
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
Isomeric SMILESCCCCCC\C=C/CCCCCCCC(O)=O
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHexadecenic acid, 1 TMS, GC-MS Spectrumsplash10-017j-5900000000-58442a5c08ea8c4926d0Spectrum
GC-MSHexadecenic acid, non-derivatized, GC-MS Spectrumsplash10-017j-5900000000-58442a5c08ea8c4926d0Spectrum
Predicted GC-MSHexadecenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p6-9820000000-ca98f4a0dd8ff557bc6cSpectrum
Predicted GC-MSHexadecenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-022i-9551000000-39e4b8ad34555c61b4adSpectrum
Predicted GC-MSHexadecenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0190000000-1228a4503bc27bed1ebf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-3960000000-1370ead704dcac4cec1f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9700000000-85e6708e40be2971ffc92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-bb3d892e7f48a711d0ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0090000000-6a46dea6de3429b733742016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9440000000-668a65146f3042b031de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-37cfc189faecac3c95772021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-b570c7cdc86145fba0212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-1960000000-8371cc75a9113569270b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-4490000000-61560c3648170efe92742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9520000000-26416932e2aa677515762021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9100000000-9eed9d946622d4a4c83c2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDHEXADECENOIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).