octadeca-6,9,12-trienoic acid

• ChemBase ID: 104249
• Molecular Formular: C18H30O2
• Molecular Mass: 278.4296
• Monoisotopic Mass: 278.2245802
• SMILES: CCCCC/C=C/C/C=C/C/C=C/CCCCC(=O)O
• Canonical 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)
• InChIKey: VZCCETWTMQHEPK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: octadeca-6,9,12-trienoic acid
• IUPAC Traditional name: 6,9,12-octadecatrienoic acid
• Synonyms: cis,cis,cis-6,9,12-Octadecatrienoic acid; γ-Linolenic acid; 6,9,12-Octadecatrienoic acid; γ-LINOLENIC ACID; Gamma-linolenic acid; gamolenic acid; GLA; Gamma-Linolenic acid; 顺,顺,顺-6,9,12-十八碳三烯酸; γ-亚麻酸

Database IDs

• CAS Number: 506-26-3
• MDL Number: MFCD00065718
• Beilstein Number: 1712253
• PubChem SID: 162091508; 24882200; 24896312
• PubChem CID: 5280933; 5353640
• CHEBI ID: 28661
• ATC CODE: D11AX02
• CHEMBL: 464982
• Chemspider ID: 4444436
• Unique Ingredient Identifier: 78YC2MAX4O
• Wikipedia Title: Gamma-Linolenic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.922493
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.381
• LogD (pH = 7.4): 3.6179216
• Log P: 6.059955
• Molar Refractivity: 89.6354 cm^3
• Polarizability: 33.692265 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Colorless oil; liquid
• Flash Point: 110 °C; 230 °F
• Refractive Index: n20/D 1.471

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (GC); ≥99%; ≥99.0% (GC); 99%
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C18H30O2

DETAILS

MP Biomedicals - 02155244

(6,9,12-Octadecatrienoic acid) Purity: 99% Sealed ampule (liquid).

Sigma Aldrich - L2378

Packaging
10 mg in autosmp vl
Sealed ampule.
Biochem/physiol Actions
γ-Linolenic acid , a polyunsaturated fatty acid, exerts anti-inflammatory effect by decreasing both interleukin (IL) 6 and IL-8 production in the human enterocyte-like cell line Caco-2 and humandendritic cells in vitro 1.
Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds. Gamma-linolenate may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent. Gamma-linolenate, a polyunsaturated fattly acid (PUFA), is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

Sigma Aldrich - 62172

Biochem/physiol Actions
γ-Linolenic acid , a polyunsaturated fatty acid, exerts anti-inflammatory effect by decreasing both interleukin (IL) 6 and IL-8 production in the human enterocyte-like cell line Caco-2 and humandendritic cells in vitro 1.

Sigma Aldrich - 62174

Biochem/physiol Actions
γ-Linolenic acid , a polyunsaturated fatty acid, exerts anti-inflammatory effect by decreasing both interleukin (IL) 6 and IL-8 production in the human enterocyte-like cell line Caco-2 and humandendritic cells in vitro 1.