Stearidonic acid

Base Information

• Chemical Name: Stearidonic acid
• CAS No.: 20290-75-9
• Deprecated CAS: 111174-40-4
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• 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: 20290-75-9.mol

Synonyms:stearidonic acid

Chemical Property of Stearidonic acid

Chemical Property:

• Melting Point: 200℃ (decomposition)
• Refractive Index: 1.4930 (589.3 nm 15℃)
• Boiling Point: 382.5 °C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 279.4 °C
• PSA: 37.30000
• Density: 0.937 g/cm³
• LogP: 5.43650
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly)
• 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:

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

Stearidonic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

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
• Description: Stearidonic acid (SDA) is an ω-3 fatty acid, sometimes called moroctic acid. It is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are the seed oils of hemp, blackcurrant, corn gromwell and echium, and the cyanobacterium Spirulina.
• Uses: Stearidonic Acid onic acid is present in small amounts in seed oils. A 18-carbon, ω-3 fatty acid which is a dietary precursor to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Stearidonic acid is present in small amounts in seed oils.

Technology Process of Stearidonic acid

There total 17 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:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) → stearidonic acid (2091-28-3,20290-75-9,111174-40-4)

Guidance literature:

With Saccharomyces cerevisiae expressing Δ6 fatty acid desaturase; at 30 ℃; for 48h; Microbiological reaction; Enzymatic reaction;

DOI:10.1016/j.bbalip.2010.04.007

upstream raw materials:

(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

(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenal

Downstream raw materials:

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