Oleic acid

MUFA18:1Ω-9

  Overview

Stats

MUFA
Type
18
Carbons
1
Double bonds
0
Bis-allylic sites
282.5
Weight · g/mol
13.4 °C
Melting point
C18H34O2
Formula

Also known as

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

  At a Glance

Key Points

The most common fatty acid in nature; the main fat of olive and many vegetable oils (name from Latin oleum, 'oil').

Source

Primarily from plant oils, dairy and ruminant fat. Also made by the body.

Type

Long-chain monounsaturated fatty acid with 18 carbons and one cis double bond, an omega-9 fatty acid.

Identification

  Synonyms

Common Name Oleic acid
IUPAC Name (Z)-octadec-9-enoic acid
Traditional Name —
Other Synonyms
  • (9Z)-octadec-9-enoic acid

  External IDs

General References
Wikipedia Oleic_acid
Lipids
Lipid Maps LMFA01030002
Lipid Bank DFA0111
Swiss Lipids 000000418
PlantFA ID —
Food & Nutrition
FooDB FDB012858
INFOODS —
Chemistry / Compounds
PubChem CID 445639
CAS 112-80-1
ChEBI 16196
ChEMBL CHEMBL8659
ChemSpider 393217
InChIKey —
ZINC ID ZINC000006845860
NIKKAJI ID J2.460K
PDBe OLA
UCI (UniChem) —
SureChEMBL 1138
CCDC OLECAC
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0000207
METLIN 190
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS10446
BioCyc/MetaCyc —
MetaNetX ID MNXM306
BiGG ID —
KEGG C00712
KNApSAcK C00001232
Reactome ID —
Drugs & Pharmacology
DrugBank DB04224
DrugCentral 3400
BindingDB 50150484
Guide to Pharm 1054
Probes & Drugs PD011439
Clinical & Medical
SNOMED-CT —
MeSH D019301
NCIt Code C68405
Regulatory
NIH UNII (USA) 2UMI9U37CP
FDA SRS (USA) 2UMI9U37CP
NHPID (Canada) —
DTXSID (USA) DTXSID1025809
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-001-788-274
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

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
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.
Geometric (1)
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.
Positional (4)
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.
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.
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 Oleic acid
Simple Notation 18:1
Notation 18:1(n-9)
IUPAC Name (Z)-octadec-9-enoic acid
Structure:
Molecular C18H34O2
Structure CH3(CH2)7CH=CH(CH2)7COOH
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)O
Cis / Trans cis
E-Z 9Z
Physical:
Weight 282.5 g/mol
Melting Point 13.4 °C
Reactivity
Double Bonds 1
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 118 ATP