Petroselinic acid

MUFA18:1Ω-12

  Overview

Stats

MUFA
Type
18
Carbons
1
Double bonds
0
Bis-allylic sites
282.5
Weight · g/mol
—
Melting point
C18H34O2
Formula

Also known as

IUPAC (6Z)-octadec-6-enoic acid

  At a Glance

Source

Primarily from plants.

Type

Long-chain monounsaturated fatty acid with 18 carbons and one cis double bond, an omega-12 fatty acid.

Identification

  Synonyms

Common Name Petroselinic acid
IUPAC Name (6Z)-octadec-6-enoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030066
Lipid Bank DFA0105
Swiss Lipids 000001201
PlantFA ID —
Food & Nutrition
FooDB FDB012765
INFOODS —
Chemistry / Compounds
PubChem CID 5281125
CAS 593-39-5
ChEBI 28194
ChEMBL CHEMBL3139878
ChemSpider —
InChIKey —
ZINC ID ZINC000008221028
NIKKAJI ID J13.804E
PDBe 4I1
UCI (UniChem) —
SureChEMBL SCHEMBL93332
CCDC VOXFUJ
NMRShiftDB 60019886
Metabolites & Pathways
HMDB HMDB0002080
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1115
BioCyc/MetaCyc —
MetaNetX ID MNXM20401
BiGG ID —
KEGG C08363
KNApSAcK C00001235
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD053695
Clinical & Medical
SNOMED-CT —
MeSH C008820
NCIt Code C68414
Regulatory
NIH UNII (USA) 3A10DOC461
FDA SRS (USA) 3A10DOC461
NHPID (Canada) —
DTXSID (USA) DTXSID301026575
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-003-959-363
eMolecules 593862
Mcule —
ChemicalBook CB5355794
MedChemExpress HY-113362

Isomers of 18:1 (6)

Other fatty acids sharing the 18:1 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Petroselinic acid
(6Z)-octadec-6-enoic acid
 6Z —
5281125
Category —
Conjugation Type —
SMILES CCCCCCCCCCC/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Positional (5)
Oleic acid
(Z)-octadec-9-enoic acid
 9Z —
445639
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
cis-Vaccenic acid
(11Z)-octadec-11-enoic acid
 11Z —
5282761
Category —
Conjugation Type —
SMILES CCCCCC\C=C/CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Elaidic acid
(E)-octadec-9-enoic acid
 9E Trans
637517
Category —
Conjugation Type —
SMILES CCCCCCCC\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
trans-Vaccenic acid
(E)-octadec-11-enoic acid
 11E Trans
5281127
Category —
Conjugation Type —
SMILES CCCCCC\C=C\CCCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Isooleic acid
(E)-octadec-10-enoic acid
 10E —
5282760
Category —
Conjugation Type —
SMILES CCCCCCC/C=C/CCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.

Chemical Properties

Name(s):
Common Name Petroselinic acid
Simple Notation 18:1
Notation 18:1(n-12)
IUPAC Name (6Z)-octadec-6-enoic acid
Structure:
Molecular C18H34O2
SMILES CCCCCCCCCCC/C=C\CCCCC(=O)O
Cis / Trans cis
E-Z 6Z
Physical:
Weight 282.5 g/mol
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 118.5 ATP