Rumenic acid

PUFA18:2Ω-7 Trans CLA

  Overview

Stats

PUFA
Type
18
Carbons
2
Double bonds
0
Bis-allylic sites
280.4
Weight · g/mol
—
Melting point
C18H32O2
Formula

Also known as

IUPAC (9Z,11E)-octadeca-9,11-dienoic acid
Traditional Bovinic acid

  At a Glance

Key Points

The main natural conjugated linoleic acid (CLA) — 85–90% of the CLA in dairy fat; also called bovinic acid.

Source

Primarily from dairy; also in ruminant fat.

Type

Long-chain polyunsaturated fatty acid with 18 carbons and two trans double bonds (conjugated), an omega-7 fatty acid.

Identification

  Synonyms

Common Name Rumenic acid
IUPAC Name (9Z,11E)-octadeca-9,11-dienoic acid
Traditional Name Bovinic acid
Other Synonyms No other synonyms recorded.

  External IDs

General References
Wikipedia Rumenic_acid
Lipids
Lipid Maps LMFA01030118
Lipid Bank DFA0184
Swiss Lipids 000001204
PlantFA ID —
Food & Nutrition
FooDB FDB093753
INFOODS —
Chemistry / Compounds
PubChem CID 5280644
CAS 2540-56-9
ChEBI 32798
ChEMBL CHEMBL4303722
ChemSpider 4444245
InChIKey —
ZINC ID ZINC000008219019
NIKKAJI ID J604.211B
PDBe —
UCI (UniChem) 1070816
SureChEMBL 1270204
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0003797
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1693
BioCyc/MetaCyc —
MetaNetX ID MNXM3889
BiGG ID —
KEGG C04056
KNApSAcK C00052217
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD020555
Clinical & Medical
SNOMED-CT —
MeSH C046938
NCIt Code —
Regulatory
NIH UNII (USA) 46JZW3MR59
FDA SRS (USA) 46JZW3MR59
NHPID (Canada) —
DTXSID (USA) DTXSID1041003
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-018-862
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:2 (7)

Other fatty acids sharing the 18:2 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Rumenic acid
(9Z,11E)-octadeca-9,11-dienoic acid
 9Z,11E Trans
5280644
Category —
Conjugation Type Conjugated
SMILES CCCCCC\C=C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
Geometric (1)
9E,11E-CLA
(9E,11E)-octadeca-9,11-dienoic acid
 9E,11E Trans
5460677
Category Conjugated trans-trans Fatty Acid
Conjugation Type Conjugated
SMILES CCCCCC/C=C/C=C/CCCCCCCC(=O)O
Description The fully conjugated di-trans isomer, possessing the highest melting point of the 18:2 series due to its straight linear structural stacking capabilities.
Origin Details
Origin Source Type Details
Severe Thermal Conversion Cooking Formed through the rigorous thermal degradation or extreme catalytic processing of standard conjugated linoleic acids.
Positional (5)
Linoleic acid
(9Z,12Z)-octadeca-9,12-dienoic acid
 9Z,12Z —
5280450
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
(10E,12Z)-Octadecadienoic acid
(10E,12Z)-octadeca-10,12-dienoic acid
 10E,12Z Trans
5282800
Category —
Conjugation Type Conjugated
SMILES CCCCC/C=C\C=C\CCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Linoelaidic acid
(9E,12E)-octadeca-9,12-dienoic acid
 9E,12E Trans
5282457
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C\C/C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
9Z,12E-Octadecadienoic Acid
(9Z,12E)-octadeca-9,12-dienoic acid
 9Z,12E Trans
Category Isolated mono-trans Fatty Acid
Conjugation Type Isolated
SMILES CCCCC/C=C/C\C=C/CCCCCCCC(=O)O
Description A mono-trans geometric isomer where only the delta-12 double bond has been flipped into the E configuration.
Origin Details
Origin Source Type Details
Thermal/Refining Degradation Cooking Formed during high-temperature industrial deodorization, chemical refining processes, or extended deep-frying of seed oils.
9E,12Z-Octadecadienoic Acid
(9E,12Z)-octadeca-9,12-dienoic acid
 9E,12Z Trans
6442998
Category Isolated mono-trans Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C/C=C/CCCCCCCC(=O)O
Description A mono-trans geometric isomer where only the delta-9 double bond has been converted to the E conformation.
Origin Details
Origin Source Type Details
Thermal/Refining Degradation Cooking Generated via free radical-mediated isomerization during the severe thermal stress or commercial processing of plant lipid matrices.

Chemical Properties

Name(s):
Common Name Rumenic acid
Simple Notation 18:2
Notation 18:2(n-7)
IUPAC Name (9Z,11E)-octadeca-9,11-dienoic acid
Traditional Name Bovinic acid
Structure:
Molecular C18H32O2
SMILES CCCCCC\C=C\C=C/CCCCCCCC(O)=O
Cis / Trans trans
E-Z 9Z,11E
Physical:
Weight 280.4 g/mol
Reactivity
Double Bonds 2
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 117 ATP