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gamma-Linolenic acid

Athanor · official

C18H30O2 · 278.4 g/mol

IUPAC name: (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid

Also called GLA, C18:3 omega-6, evening primrose oil

Lipids
Open in Athanor
The structure of gamma-Linolenic acid
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name
(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Synonyms
GLA, C18:3 omega-6, evening primrose oil
+ 38 more

GAMOLENIC ACID, (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid, gamma Linolenic Acid, (Z,Z,Z)-6,9,12-Octadecatrienoic acid, (6,9,12)-linolenic acid, Acido gamolenico, Acide gamolenique, gamoleic acid, Gamolenic-acid, Acidum gamolenicum, gammalinolenic acid, 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-, all-cis-6,9,12-Octadecatrienoic acid, Delta-linolenic acid, Sonova 400, DTXSID7046170, 6Z,9Z,12Z-octadecatrienoic acid, 78YC2MAX4O, (6Z,9Z,12Z)-Octadecatrienoic acid, C18:3 (n-6), 6-cis,9-cis,12-cis-Octadecatrienoic acid, (6z,9z,12z-octadecatrienoic acid, 18:3(N-6), DTXCID5026170, CHEBI:28661, NDI 609, 18:3 (n-6), Gammolin, Gamophase, Kentogam, Unigam, Epogam paed, Acid, Gamolenic, Lin-gam, Gam-o, Efamast 40, Efamast 80, Epogam 40

Molecular formula
C18H30O2
Empirical formula
C9H15O
Molecular weight
278.4 g/mol
Exact mass
278.22458
CAS number
506-26-3
PubChem CID
5280933
Canonical SMILES
CCCCCC=CCC=CCC=CCCCCC(=O)O
Isomeric SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
InChI
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChIKey
VZCCETWTMQHEPK-QNEBEIHSSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
20
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.61
H-bond donors
1
H-bond acceptors
1 computed here · PubChem 2
Rotatable bonds
13
TPSA (Ų)
37.3
Formal charge
0
XLogP3
5.9 PubChem
Complexity
301 PubChem
Stereocenters
None
Double-bond geometry
C6=C7: Z · C9=C10: Z · C12=C13: Z
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C77.65%
  • H10.86%
  • O11.49%

Isotope pattern

100%278.22520%279.2282.3%280.231281.234

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
5.66 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-4.27 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.55 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 278.44
  • log P ≤ 5 (Crippen): 5.66
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 1

Breaks 1 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 43 company reports to ECHA. Source [1].

  • Harmful or irritant
  • H315Causes skin irritation (97.7% of reports)
  • H319Causes serious eye irritation (97.7% of reports)
  • H335May cause respiratory irritation (95.3% of reports)

Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

View all classifications (2)
  • [1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 2.3% (1 of 43) of reports.
  • [1] European Chemicals Agency (ECHA) · 43 reports · WarningH315, H319, H335

Safety data sheets on the supplier’s page: Shenghe Chemical, AbaChemScene, Aladdin Scientific.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  3. [3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  7. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  8. ·Literature on PubChem

Data last updated 2026-10-14.