gamma-Linolenic acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for gamma-Linolenic acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the gamma-Linolenic acid?

The molecule gamma-Linolenic acid presents a molecular formula of C18H30O2 and its IUPAC name is (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid.

Gamma-Linolenic acid (GLA) is a polyunsaturated fatty acid that belongs in plant oils. It is a precursor to prostaglandins, which are important for many bodily functions. GLA supplements are sometimes used to treat conditions such as eczema, arthritis, and PMS..

GLA is an omega-6 fatty acid, which means that it is essential for human health but must be obtained from the diet. The body can convert other omega-6 fatty acids into GLA, but this process is inefficient. As a result, GLA supplements are sometimes used to increase levels of this important fatty acid..

GLA belongs in plant oils, such as borage oil and evening primrose oil. It is also found in some animal foods, such as grass-fed beef and eggs. GLA supplements are available in capsule, tablet, and liquid form..

GLA supplements are sometimes used to treat conditions such as eczema, arthritis, and PMS. GLA has anti-inflammatory properties and may help to reduce the symptoms of these conditions. GLA supplements are generally safe, but they can cause side effects such as upset stomach, diarrhea, and headache..

If you are considering taking GLA supplements, talk to your healthcare provider to see if they are right for you..

3D structure

Cartesian coordinates

Geometry of gamma-Linolenic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

gamma-Linolenic acid VZCCETWTMQHEPK-QNEBEIHSSA-N chemical compound 2D structure molecule svg
gamma-Linolenic acid

 

Molecule descriptors

 
IUPAC name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
InChI codeInChI=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-
InChI KeyVZCCETWTMQHEPK-QNEBEIHSSA-N
SMILESCCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (6,9,12)-linolenic acid
  • (6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid
  • (6Z,9Z,12Z)-Octadecatrienoate
  • (6Z,9Z,12Z)-Octadecatrienoic acid
  • (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
  • (6z,9z,12z-octadecatrienoic acid
  • (Z,Z,Z)-6,9,12-Octadecatrienoate
  • (Z,Z,Z)-6,9,12-Octadecatrienoic acid
  • .gamma.-Linolenic Acid
  • 18:3 (n-6)
  • 18:3(N-6)
  • 506-26-3
  • 506L263
  • 6(Z),9(Z),12(Z)-Octadecatrienoate
  • 6(Z),9(Z),12(Z)-Octadecatrienoic acid
  • 6,9,12-Octadecatrienoate
  • 6,9,12-Octadecatrienoic acid
  • 6,9,12-Octadecatrienoic acid, (Z,Z,Z)-
  • 6,9,12-all-cis-Octadecatrienoate
  • 6,9,12-all-cis-Octadecatrienoic acid
  • 6-cis,9-cis,12-cis-Octadecatrienoic acid
  • 6Z,9Z,12Z-octadecatrienoate
  • 6Z,9Z,12Z-octadecatrienoic acid
  • 78YC2MAX4O
  • A871498
  • AC-33785
  • Acide gamolenique
  • Acido gamolenico
  • Acidum gamolenicum
  • BDBM50269532
  • BML3-B06
  • BSPBio_001338
  • C06426
  • C18:3 (n-6)
  • C18:3, n-6,9,12 all-cis
  • C18:3,n-6
  • C18:3n-6,9,12
  • C18H30O2 (cis,cis,cis-octadeca-6,9,12-trienoic acid)
  • CCRIS 7668
  • CS-W012291
  • D07213
  • D58CCA4A-7FFA-4E8B-A758-EAA7D073B343
  • DB-029858
  • DB13854
  • DS-10685
  • DSSTox_CID_26170
  • DSSTox_GSID_46170
  • DSSTox_RID_81401
  • Delta-linolenic acid
  • Efamast
  • Epogam
  • GAMMA-LINOLENIC ACID (18:3 n-6)
  • GAMOLENIC ACID
  • GLA
  • GTPL4710
  • Gamma Linoleic Acid
  • Gamma-linoleic acid
  • Gammolenic acid
  • Gamolenic acid (INN)
  • Gamolenic-acid
  • HMS1361C20
  • HMS1791C20
  • HMS1989C20
  • HMS2230A18
  • HMS3402C20
  • HMS3649H09
  • HY-N7140
  • IDI1_033808
  • L0152
  • LMFA01030141
  • Ligla
  • MFCD00065718
  • MLS001333661
  • MLS001333662
  • NCGC00160469-01
  • NCGC00160469-02
  • NCGC00160469-03
  • NCGC00160469-04
  • NDI 609
  • Octadeca-6,9,12-triensaeure
  • Octadecatrienoic acid, 6,9,12-(Z,Z,Z)-
  • Q415885
  • SMR000058609
  • SR-01000838334
  • SR-01000838334-2
  • Sonova 400
  • all-cis-6,9,12-Octadecatrienoic acid
  • all-cis-6,9,12-octadecatrienoate
  • cis,cis,cis,6,9,12-Octa-decatrienoic acid-18:3 n6 lithium salt
  • cis,cis,cis-6,9,12-Octadecatrienoic acid
  • cis-6, cis-9, cis-12-octadecatrienoic acid
  • cis-6,cis-9,cis-12-Octadecatrienoic acid
  • cis-Delta(6,9,12)-octadecatrienoate
  • cis-Delta(6,9,12)-octadecatrienoic acid
  • gamma Linolenic Acid
  • gamma-Linolenic acid
  • gamma-Linolensaeure
  • gamma-Llnolenic acid
  • gamma-linolenic-acid
  • gammalinolenic acid
  • gamoleic acid
  • s5743
  • y-Linolenic acid
  • z,z,z-6,9,12-Octadecatrienoic acid
  • z,z,z-octadeca-6,9,12-trienoic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3777423
  • CAS-506-26-3
  • UNII-78YC2MAX4O
  • AKOS022175367
  • BRD-K18059238-001-02-1
  • DTXSID7046170
  • CHEMBL464982
  • CHEBI:28661
  • Tox21_111835
  • SCHEMBL19418

Physico-Chemical properties

IUPAC name(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
Molecular formulaC18H30O2
Molecular weight278.43
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity88.99
LogP5.7
Topological polar surface area37.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.