Stearidonic acid

Base Information

• Chemical Name: Stearidonic acid
• CAS No.: 111174-40-4
• Deprecated CAS: 111174-40-4
• Molecular Weight: 276.41372
• European Community (EC) Number: 606-502-1
• UNII: P4CEK3495O
• DSSTox Substance ID: DTXSID20920493
• Wikipedia: Stearidonic_acid
• Wikidata: Q2739877
• Metabolomics Workbench ID: 774
• ChEMBL ID: CHEMBL484430
• Mol file: 111174-40-4.mol

Synonyms:stearidonic acid

Chemical Property of Stearidonic acid

Chemical Property:

• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 276.208930132
• Heavy Atom Count: 20
• Complexity: 335

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCC=CCC=CCC=CCC=CCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O

Technology Process of Stearidonic acid

There total 18 articles about Stearidonic 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: 62.0%

6,9,12,15-cis-octadecanetetraenoic acid methyl ester (73097-00-4) → stearidonic acid (2091-28-3,20290-75-9,111174-40-4)

Guidance literature:

With lithium hydroxide; In methanol; water; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1007/s10600-015-1485-3

Reference yield: 56.0%

(all-Z)-Octadeca-6,9,12,15-tetraenal → stearidonic acid (2091-28-3,20290-75-9,111174-40-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; In water; acetonitrile; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.009

Reference yield:

γ-linolenic acid (C18:3) (34615-07-1) → 6,9,12,15-n-octadecatetraenoic acid (2091-28-3,111174-40-4)

Guidance literature:

With Saccharomyces cerevisiae IFO10150 expressing Saccharomyces kluyveri ω3 fatty acid desaturase Sk-FAD3; In water; at 30 ℃;

DOI:10.1271/bbb.80361

upstream raw materials:

γ-linolenic acid (C18:3)

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

Methyl (all-Z)-5,6-epoxyicosa-8,11,14,17-tetraenoate

(3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraenal

Downstream raw materials:

6,9,12,15-cis-octadecanetetraenoic acid methyl ester

C₁₉H₃₀O₂

Refernces

• 1、 Jakobsen, Martin Gjerde,Vik, Anders,Hansen, Trond Vidar. "Concise syntheses of three ω-3 polyunsaturated fatty acids". . p. 5837 - 5839. Retrieved 2012.
• 2、 Oura, Takahiro,Kajiwara, Susumu. "Substrate specificity and regioselectivity of Δ12 and ω3 fatty acid desaturases from Saccharomyces kluyveri". experimental part. p. 3174 - 3179. Retrieved 2009/04/07.