Pinolenic acidPnA

PUFA18:3Ω-6

  Overview

Stats

PUFA
Type
18
Carbons
3
Double bonds
1
Bis-allylic sites
278.4
Weight · g/mol
—
Melting point
C18H30O2
Formula

Also known as

IUPAC (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Synonyms

  At a Glance

Key Points

The fatty acid characteristic of pine nuts, richest in Siberian pine.

Source

Primarily from plants.

Type

Long-chain polyunsaturated fatty acid with 18 carbons and three cis double bonds, an omega-6 fatty acid.

Identification

  Synonyms

Common Name Pinolenic acid
IUPAC Name (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Traditional Name —
Other Synonyms
  • all-cis-5,9,12-octadecatrienoic acid

  External IDs

General References
Wikipedia Pinolenic_acid
Lipids
Lipid Maps LMFA01030344
Lipid Bank —
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5312495
CAS 16833-54-8
ChEBI 86136
ChEMBL —
ChemSpider —
InChIKey —
ZINC ID ZINC000027646178
NIKKAJI ID —
PDBe —
UCI (UniChem) 23315529
SureChEMBL 1021463
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB —
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS2406
BioCyc/MetaCyc CPD-14869
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD019867
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) B810C93MD7
FDA SRS (USA) B810C93MD7
NHPID (Canada) —
DTXSID (USA) DTXSID00895852
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-009-019-192
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:3 (11)

Other fatty acids sharing the 18:3 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Pinolenic acid
(5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
 5Z,9Z,12Z —
5312495
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\CC\C=C/CCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (1)
Columbinic Acid
(5E,9Z,12Z)-octadeca-5,9,12-trienoic acid
 5E,9Z,12Z Trans
5312485
Category Non-Methylene-Interrupted Omega-6 Polyunsaturated Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CC/C=C/CCCC(=O)O
Description A non-methylene-interrupted Δ5-trans omega-6 polyunsaturated fatty acid found in Aquilegia (columbine) and Thalictrum seed oils, capable of reversing essential fatty-acid deficiency symptoms without serving as a prostaglandin precursor.
Origin Details
Origin Source Type Details
Ranunculaceae Seed Oils Natural Concentrated in seeds of Aquilegia vulgaris (columbine), Thalictrum, and related Ranunculaceae species.
Positional (9)
α-Linolenic acid
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
 9Z,12Z,15Z —
5280934
Category —
Conjugation Type Isolated
SMILES CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
γ-Linolenic acid
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
 6Z,9Z,12Z —
5280933
Category —
Conjugation Type Isolated
SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Punicic acid
(9Z,11E,13Z)-octadeca-9,11,13-trienoic acid
 9Z,11E,13Z Trans
5281126
Category —
Conjugation Type Conjugated
SMILES CCCC/C=C\C=C\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
alpha-Eleostearic acid
(9Z,11E,13E)-octadeca-9,11,13-trienoic acid
 9Z,11E,13E Trans
5281115
Category —
Conjugation Type Conjugated
SMILES CCCC\C=C\C=C\C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
beta-Eleostearic acid
(9E,11E,13E)-octadeca-9,11,13-trienoic acid
 9E,11E,13E Trans
5282820
Category —
Conjugation Type Conjugated
SMILES CCCC\C=C\C=C\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Catalpic acid
(9E,11E,13Z)-octadeca-9,11,13-trienoic acid
 9E,11E,13Z Trans
5385589
Category —
Conjugation Type Conjugated
SMILES CCCC/C=C\C=C\C=C\CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Calendic acid
(8E,10E,12Z)-octadeca-8,10,12-trienoic acid
 8E,10E,12Z Trans
5282818
Category —
Conjugation Type Conjugated
SMILES CCCCC/C=C\C=C\C=C\CCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Jacaric Acid
(8Z,10E,12Z)-octadeca-8,10,12-trienoic acid
 8Z,10E,12Z Trans
5282817
Category Conjugated Linolenic Acid (CLnA, n-6)
Conjugation Type Conjugated
SMILES CCCCC\C=C/C=C/C=C\CCCCCCC(=O)O
Description A conjugated linolenic acid isomer found in Jacaranda mimosifolia seed oil, investigated for pro-apoptotic activity in leukemia cell lines.
Origin Details
Origin Source Type Details
Jacaranda Seed Oil Natural Comprises approximately 37% of seed oil fatty acids of Jacaranda mimosifolia (Bignoniaceae).
Rumelenic Acid
(9Z,11E,15Z)-octadeca-9,11,15-trienoic acid
 9Z,11E,15Z Trans
5280644
Category Ruminant Conjugated Linolenic Acid (CLnA, n-3)
Conjugation Type Conjugated
SMILES CC\C=C/CC/C=C/C=C\CCCCCCCC(=O)O
Description A partially conjugated omega-3 fatty acid (9,11-conjugated with isolated 15-DB) produced as a biohydrogenation intermediate of alpha-linolenic acid in ruminant rumen and present in dairy fat.
Origin Details
Origin Source Type Details
Rumen Biohydrogenation Natural Produced in cattle and sheep rumen by linoleate isomerase action on alpha-linolenic acid as an intermediate in microbial biohydrogenation to vaccenic and stearic acids.

Chemical Properties

Name(s):
Common Name Pinolenic acid
Abbreviation PnA
Simple Notation 18:3
Notation 18:3(n-6) NMI Δ5,9,12
IUPAC Name (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Structure:
Molecular C18H30O2
SMILES CCCCC/C=C\C/C=C\CC\C=C/CCCC(=O)O
Cis / Trans cis
E-Z 5Z,9Z,12Z
Physical:
Weight 278.4 g/mol
Reactivity
Double Bonds 3
Bis-Allylic Carbons 1 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 115.5 ATP