CIS-8,11,14-EICOSATRIENOIC ACID

Base Information

• Chemical Name: CIS-8,11,14-EICOSATRIENOIC ACID
• CAS No.: 1783-84-2
• Deprecated CAS: 135625-06-8
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.489
• European Community (EC) Number: 217-233-0
• UNII: FC398RK06S
• ChEMBL ID: CHEMBL465183
• DSSTox Substance ID: DTXSID00912351
• Metabolomics Workbench ID: 588
• NCI Thesaurus Code: C68343
• Nikkaji Number: J110.768B
• Wikidata: Q415398
• Wikipedia: Dihomo-%CE%B3-linolenic_acid
• Mol file: 1783-84-2.mol

Synonyms:8,11,14-Eicosatrienoicacid, (Z,Z,Z)- (8CI);(Z,Z,Z)-8,11,14-Eicosatrienoic acid;8,11,14-Eicosatrienoic acid;8,11,14-all-cis-Eicosatrienoic acid;8Z,11Z,14Z-Eicosatrienoic acid;Bishomo-g-linolenic acid;DGLA;Dihomo-g-linolenic acid;Ro 12-1989;all-cis-8,11,14-Eicosatrienoic acid;cis-8,11,14-Eicosatrienoic acid;cis-8,cis-11,cis-14-Eicosatrienoic acid;g-Homolinolenic acid;

Chemical Property of CIS-8,11,14-EICOSATRIENOIC ACID

Chemical Property:

• Vapor Pressure: 8.09E-08mmHg at 25°C
• Refractive Index: n20/D 1.478(lit.)
• Boiling Point: 408.5°C at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 144 °F
• PSA: 37.30000
• Density: 0.917g/cm³
• LogP: 6.44070
• Storage Temp.: −20°C
• Solubility.: chloroform: 50 mg/mL, clear, colorless
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 306.255880323
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

98%,99%, ^*data from raw suppliers

cis-8,11,14-Eicosatrienoic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O
• Recent ClinicalTrials: Efficacy and Safety of Orally Administered DS107 in Adult Patients With Moderate to Severe Atopic Dermatitis
• Recent EU Clinical Trials: A Randomised, Double-blind, Placebo-controlled Study to Assess the Efficacy and Safety of Orally Administered DS107 in Adult Patients with Moderate to Severe Atopic Dermatitis
• Description: Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω?6 fatty acid. In physiological literature, it is given the name 20:3 (ω?6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid (GLA; 18:3, ω?6). GLA, in turn, is a desaturation product of linoleic acid (18:2, ω?6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.
• Uses: cis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action. cis-8,11,14-Eicosatrienoic acid may be used as an analytical reference standard for the determination of the analyte in plant species and biological matrices by chromatography-based techniques.

Technology Process of CIS-8,11,14-EICOSATRIENOIC ACID

There total 11 articles about CIS-8,11,14-EICOSATRIENOIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-iodo-(6Z,9Z,12Z)-6,9,12-octadecatriene (24149-06-2) + t-butyl lithioacetate (150942-98-6) → cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2)

Guidance literature:

toluene-4-sulfonic acid; Yield given. Multistep reaction; 1.) HMPT, -78 deg C to -35 deg C, 1 h, 2.) toluene, 100 deg C, 2 h;

Reference yield:

all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) → cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2)

Guidance literature:

With lithium hydroxide; In methanol; for 2h; Yield given; Ambient temperature;

Reference yield:

→ cis-8,11,14-eicosatrienoic acid (7324-41-6,68820-40-6,133939-47-6,133939-49-8,1783-84-2)

Guidance literature:

upstream raw materials:

1-iodo-(6Z,9Z,12Z)-6,9,12-octadecatriene

t-butyl lithioacetate

all-cis-8,11,14-eicosatrienoic acid methyl ester

1-Heptyne

Downstream raw materials:

15-hydroxyeicosa-8,11,13-trienoic acid

N-dihomo-γlinolenoyl ethanolamide

HETrE

15(S)-hydroxyeicosatrienoic acid

Refernces

• 1、 Xue, Gang,Liu, Fengxia,Wang, Ying,Huang, Kaixun. "Optimization of synthetic conditions for the preparation of dihomo-γ-linolenic acid from γ-linolenic acid". experimental part. p. 77 - 82. Retrieved 2010/03/31.
• 2、 -. "Desaturase genes and uses thereof". . . Retrieved 2008/06/13.