(13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid

Base Information

• Chemical Name: (13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid
• CAS No.: 87984-82-5
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.434
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID80708279
• Mol file: 87984-82-5.mol

Synonyms:DTXSID80708279;13(s)-hydroxy-9,11,15-octadecatrienoic acid;(13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid

Chemical Property of (13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.63130
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 294.21949481
• Heavy Atom Count: 21
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

13(S)-HOTrE ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCC=CC[C@@H](C=CC=CCCCCCCCC(=O)O)O
• Description: 13(S)-HOTrE is the 15-lipoxygenase (15-LO) product of linolenic acid. It has been detected in cell membranes and as the cholesteryl ester associated with the lesions of atherosclerosis, and in the biomembranes of soybeans exposed to 15-LO.

Technology Process of (13S)-13-Hydroxyoctadeca-9,11,15-trienoic acid

There total 15 articles about (13S)-13-Hydroxyoctadeca-9,11,15-trienoic 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: 73.0%

(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester (90080-97-0) → (+)-(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (87984-82-5)

Guidance literature:

With potassium carbonate; In methanol; water; Ambient temperature;

DOI:10.1016/S0040-4020(01)80454-3

Reference yield: 53.0%

(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid (67597-26-6) → (+)-(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (87984-82-5)

Guidance literature:

With phosphorous acid trimethyl ester; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(02)00231-4

Reference yield: 23.0%

(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) → (+)-(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (87984-82-5)

Guidance literature:

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid; With soybean lipoxygenase; oxygen;

With sodium tetrahydroborate; Further stages.;

DOI:10.1039/b710284d

upstream raw materials:

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

(9Z,11E,13S,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid methyl ester

(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid

dec-9-ynoic acid

Refernces

• 1、 An, Jung-Ung,Hong, Seung-Hye,Oh, Deok-Kun. "Regiospecificity of a novel bacterial lipoxygenase from Myxococcus xanthus for polyunsaturated fatty acids". . p. 823 - 833. Retrieved 2018/05/14.
• 2、 Schulz, Stefan,Yildizhan, Selma,Stritzke, Katja,Estrada, Catalina,Gilbert, Lawrence E.. "Macrolides from the scent glands of the tropical butterflies Heliconius cydno and Heliconius pachinus". . p. 3434 - 3441. Retrieved 2008/09/19.