Record Information
Version1.0
Creation date2010-04-08 22:09:46 UTC
Update date2018-05-29 18:27:48 UTC
Primary IDFDB011675
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePalmitoleic acid
DescriptionPalmitoleic acid, or (Z)-9-hexadecenoic acid, is an omega-7 monounsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues, but generally found in higher concentrations in the liver. It is biosynthesized from palmitic acid by the action of the enzyme delta-9 desaturase. Macadamia oil (Macadamia integrifolia) and Sea Buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively (Wikipedia).
CAS Number373-49-9
Structure
Thumb
Synonyms
SynonymSource
(Z)-9-Hexadecenoic acidChEBI
(Z)-Hexadec-9-enoic acidChEBI
16:1DElta9ChEBI
9-cis-Hexadecenoic acidChEBI
cis-9-Hexadecenoic acidChEBI
cis-Delta(9)-Hexadecenoic acidChEBI
Palmitolinoleic acidChEBI
Zoomaric acidChEBI
(9Z)-Hexadec-9-enoateKegg
(Z)-9-HexadecenoateGenerator
(Z)-Hexadec-9-enoateGenerator
9-cis-HexadecenoateGenerator
cis-9-HexadecenoateGenerator
cis-delta(9)-HexadecenoateGenerator
cis-Δ(9)-hexadecenoateGenerator
cis-Δ(9)-hexadecenoic acidGenerator
PalmitolinoleateGenerator
ZoomarateGenerator
(9Z)-Hexadec-9-enoic acidGenerator
PalmitoleateGenerator
(9Z)-Hexadecenoic acidHMDB
(9Z)-HexadecenoateHMDB
9-HexadecenoateHMDB
9-Hexadecenoic acidHMDB
cis-9-Palmitoleic acidHMDB
cis-delta-9-HexadecenoateHMDB
cis-delta-9-Hexadecenoic acidHMDB
cis-PalmitoleateHMDB
cis-Palmitoleic acidHMDB
HexadecenoateHMDB
Hexadecenoate (N-C16:1)HMDB
Hexadecenoic acidHMDB
OleopalmitateHMDB
Oleopalmitic acidHMDB
ZoomerateHMDB
Zoomeric acidHMDB
Palmitoleic acid, (Z)-isomerHMDB
Palmitoleic acid, sodium salt, (Z)-isomerHMDB
Palmitoleic acid, (e)-isomerHMDB
Palmitoleic acid, potassium salt, (Z)-isomerHMDB
C16:1 trans-9HMDB
Palmitelaidic acidHMDB
(z)-palmitoleic acidbiospider
16:1Delta9ChEBI
16:1δ9Generator
9-Hexadecenoic acid, (9Z)-biospider
9-Hexadecenoic acid, (Z)-biospider
cis-δ(9)-hexadecenoateGenerator
cis-δ(9)-hexadecenoic acidGenerator
PALMITOLEateGenerator
Palmitoleic aciddb_source
Physetoleic aciddb_source
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H30O2
IUPAC name(9Z)-hexadec-9-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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 75.54%; H 11.89%; O 12.58%DFC
Melting PointMp 0.5°DFC
Boiling PointBp0.6 162°DFC
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 Indexn20D 1.4582DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-2900000000-6683cd8579813b4f1ebbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8910000000-20fcd1fc2d9e095b2c24View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9630000000-7eda678c0ecd65b2e479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090000000-e72ac58f23bacbf37344View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-d1585cc46cbce84a0506View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0091000000-fd89101236e85a2d9154View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-35027c88ff732ff74b4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-3cac469ac1efde0a3543View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-e5833c7aa4795570bdc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-9090000000-909ebad9120d01bf8e79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-fb5a2e21c48a7d72aac8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0090000000-09c91b61deabc72625f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-993c95f96e1ca69a41c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-e72ac58f23bacbf37344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0090000000-202819132f83589a248bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-749f09fec19d95c21683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5005f244d7d1c3502c3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1090000000-cac7fce9a75b0f1abd63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2e782c63ccf72afe9be9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID393216
ChEMBL IDCHEMBL453509
KEGG Compound IDC08362
Pubchem Compound ID445638
Pubchem Substance IDNot Available
ChEBI ID28716
Phenol-Explorer IDNot Available
DrugBank IDDB04257
HMDB IDHMDB03229
CRC / DFC (Dictionary of Food Compounds) IDCQD88-W:GXX07-I
EAFUS IDNot Available
Dr. Duke IDPHYSETOLEIC-ACID|PALMITOLEIC-ACID
BIGG ID246167
KNApSAcK IDC00029354
HET IDPAM
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPalmitoleic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
soapDUKE
Enzymes
NameGene NameUniProt ID
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.