octadeca-9,12,15-trienoic acid

• ChemBase ID: 102569
• Molecular Formular: C18H30O2
• Molecular Mass: 278.4296
• Monoisotopic Mass: 278.2245802
• SMILES: CC/C=C/C/C=C/C/C=C/CCCCCCCC(=O)O
• Canonical SMILES: CC/C=C/C/C=C/C/C=C/CCCCCCCC(=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/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)
• InChIKey: DTOSIQBPPRVQHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: octadeca-9,12,15-trienoic acid; (9E,12E,15E)-octadeca-9,12,15-trienoic acid
• IUPAC Traditional name: octadeca-9,12,15-trienoic acid; elaidolinoleic acid
• Synonyms: 9,12,15-Octadecatrienoic Acid; LINOLENIC ACID; (9E,12E,15E)-octadeca-9,12,15-trienoic acid; ALA; Linolenic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; (9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid; Industrene 120; Alpha-Linolenic acid; α-Lnn; cis,cis,cis-9,12,15-Octadecatrienoic acid; Linolenic acid; 顺,顺,顺-9,12,15-十八碳三烯酸; 亚麻酸

Database IDs

• CAS Number: 463-40-1
• EC Number: 207-334-8
• MDL Number: MFCD00065720
• Beilstein Number: 1727693
• PubChem SID: 162088144; 24896311; 24882199; 24882198
• PubChem CID: 5282822; 5280934
• CHEBI ID: 27432
• CHEMBL: 8739
• Chemspider ID: 4444437
• DrugBank ID: DB00132
• Unique Ingredient Identifier: 0RBV727H71
• Wikipedia Title: Alpha-Linolenic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.9881673
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4320216
• LogD (pH = 7.4): 3.6783652
• 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

• Melting Point: -11 °C(lit.); -11.3 °C (11.7 °F)
• Boiling Point: 230-232 °C (446-449.6 °F) at 1 mmHg; 230-232 °C/1 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 0.914 g/mL at 25 °C(lit.); 0.916 at 20 °C (water = 1)
• Refractive Index: n20/D 1.477; n20/D 1.480; n20/D 1.480(lit.)
• Vapor Pressure: Very low, 0.05 mm Hg (7 Pa) at 125 °C (257 °F)

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~70% (GC); ≥97.0% (GC); ≥98.5% (GC); ≥99%
• Grade: analytical standard
• Impurities: ~25% linoleic acid; ~5% oleic acid
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH3(CH2CH=CH)3(CH2)7CO2H
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02102188

A 45-65% concentrate of linolenic acid.
Storage:0°C

Sigma Aldrich - 62170

Biochem/physiol Actions
An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.1

Sigma Aldrich - L2376

Biochem/physiol Actions
An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.1
Packaging
Sealed ampule

Sigma Aldrich - 62160

Biochem/physiol Actions
An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.1

Sigma Aldrich - 62159

Biochem/physiol Actions
An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.1
Other Notes
Review: Essential fatty acid requirements of different species2; The balance between α-linolenic and linoleic acid3; Dietary linolenic acid in man4