Palmitoleic acid

MUFA16:1Ω-7

  Overview

Stats

MUFA
Type
16
Carbons
1
Double bonds
0
Bis-allylic sites
254.41
Weight · g/mol
-0.1 °C
Melting point
C16H30O2
Formula

Also known as

IUPAC (Z)-hexadec-9-enoic acid
Synonyms

  At a Glance

Key Points

An omega-7 fatty acid; a rare fat component, found in highest concentration in the liver.

Source

Primarily from fish & seafood and plants; also in dairy. Also made by the body.

Type

Long-chain monounsaturated fatty acid with 16 carbons and one cis double bond, an omega-7 fatty acid.

Identification

  Synonyms

Common Name Palmitoleic acid
IUPAC Name (Z)-hexadec-9-enoic acid
Traditional Name —
Other Synonyms
  • (9Z)-hexadecenoic acid
  • (Z)-9-hexadecenoic acid
  • 9-cis-hexadecenoic acid
  • cis-9-Hexadecenoic acid
  • zoomaric acid

  External IDs

General References
Lipids
Lipid Maps LMFA01030056
Lipid Bank DFA0095
Swiss Lipids 000000411
PlantFA ID —
Food & Nutrition
FooDB FDB031085
INFOODS —
Chemistry / Compounds
PubChem CID 445638
CAS 373-49-9
ChEBI 28716
ChEMBL CHEMBL453509
ChemSpider 393216
InChIKey —
ZINC ID ZINC000008221009
NIKKAJI ID J12.503B
PDBe PAM
UCI (UniChem) —
SureChEMBL 33310
CCDC —
NMRShiftDB 60018902
Metabolites & Pathways
HMDB HMDB0003229
METLIN 188
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1033
BioCyc/MetaCyc —
MetaNetX ID MNXM162245
BiGG ID 246167
KEGG C08362
KNApSAcK C00001234, C00029354
Reactome ID —
Drugs & Pharmacology
DrugBank DB04257
DrugCentral —
BindingDB 50269531
Guide to Pharm 5547
Probes & Drugs PD019634
Clinical & Medical
SNOMED-CT —
MeSH C008757
NCIt Code C68408
Regulatory
NIH UNII (USA) 209B6YPZ4I
FDA SRS (USA) 209B6YPZ4I
NHPID (Canada) —
DTXSID (USA) DTXSID0041197
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-001-740-137
eMolecules 530342
Mcule —
ChemicalBook CB1384985
MedChemExpress HY-W011873

Isomers of 16:1 (4)

Other fatty acids sharing the 16:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Palmitoleic acid
(Z)-hexadec-9-enoic acid
 9Z —
445638
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
Palmitelaidic acid
(9E)-hexadec-9-enoic acid
 9E Trans
5282745
Category —
Conjugation Type —
SMILES CCCCCC\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (2)
Hypogeic acid
(Z)-hexadec-7-enoic acid
 7Z —
5318393
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Sapienic acid
(Z)-hexadec-6-enoic acid
 6Z —
5312419
Category —
Conjugation Type —
SMILES CCCCCCCCC/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Palmitoleic acid
Simple Notation 16:1
Notation 16:1(n-7)
IUPAC Name (Z)-hexadec-9-enoic acid
Structure:
Molecular C16H30O2
Structure CH3(CH2)5CH=CH(CH2)7COOH
SMILES CCCCCC\C=C/CCCCCCCC(=O)O
Cis / Trans cis
E-Z 9Z
Physical:
Weight 254.41 g/mol
Melting Point -0.1 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 7
ATP Yield (Net) 104.5 ATP