15(R)-HYDROXY-9(Z),12(Z)-OCTADECADIENOIC ACID

Base Information

• Chemical Name: 15(R)-HYDROXY-9(Z),12(Z)-OCTADECADIENOIC ACID
• CAS No.: 177931-23-6
• Molecular Formula: C18H32O3
• Molecular Weight: 296.44
• Mol file: 177931-23-6.mol

Synonyms:

Chemical Property of 15(R)-HYDROXY-9(Z),12(Z)-OCTADECADIENOIC ACID

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

99% ^*data from raw suppliers

AvenoleicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Avenoleic acid is a derivative of Linoleic acid (L467495), an anti-inflammatory, acne reductive, and moisture retentive compound when applied topically on the skin. It is popular in the beauty products industry because of its beneficial properties on the skin. Avenoleic acid is an oxygenated fatty acid that is naturally found in cultivated oat seeds.

Technology Process of 15(R)-HYDROXY-9(Z),12(Z)-OCTADECADIENOIC ACID

There total 10 articles about 15(R)-HYDROXY-9(Z),12(Z)-OCTADECADIENOIC 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: 90.0%

methyl (9Z,12Z)-15-hydroxyoctadeca-9,12-dienoate (177746-99-5) → (9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid (177931-23-6)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 0 - 23 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b03054

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) → (12Z,15Z)-9,10-dihydroxyoctadeca-12,15-dienoic acid (955974-89-7) + 12-Hydroxy-octadecadien-(cis-9,cis-15)-saeure, Densipolsaeure (301664-23-3,7121-47-3) + (+/-)-9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid (51146-89-5) + C18H30O4 + 13-hydroxy-9Z,15Z-octadecadienoic acid + (9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid (177931-23-6) + C18H32O3 + C18H30O4 + C18H30O4 + C18H30O4 + 12,13-DiHODE (85416-59-7) + (12Z,15Z)-9-Hydroxy-octadeca-12,15-dienoic acid + 15,16-DiHODE (140129-22-2) + (12Z,15Z)-10-hydroxy-12,15-octadecadienoic acid + (9Z,15Z)-13-hydroxy-12-oxo-9,15-octadecadienoic acid

Guidance literature:

With dihydrogen peroxide; oxygen; at 112 ℃; Mechanism; Flow reactor; Photolysis;

DOI:10.1021/jp508378z

Reference yield:

B 064-034A2 (1262768-92-2) → (9Z,12Z)-15-hydroxyoctadeca-9,12-dienoic acid (177931-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / methanol / 2 h / 0 - 23 °C / Inert atmosphere; Sealed tube

2.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0 - 23 °C / Inert atmosphere; Sealed tube

3.1: caesium carbonate; copper(l) iodide; sodium iodide / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere; Sealed tube

3.2: 0 - 23 °C / Inert atmosphere; Sealed tube

4.1: nickel(II) acetate tetrahydrate; sodium tetrahydroborate; hydrogen; ethylenediamine / ethanol / 0.5 h / 23 °C / Sealed tube

5.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 0 - 23 °C / Inert atmosphere; Sealed tube

With sodium tetrahydroborate; copper(l) iodide; lithium hydroxide monohydrate; carbon tetrabromide; water; hydrogen; nickel(II) acetate tetrahydrate; caesium carbonate; toluene-4-sulfonic acid; ethylenediamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: |Sonogashira Cross-Coupling / 3.2: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.orglett.9b03054

upstream raw materials:

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

B 064-034A₂

8-bromooctanoic acid

10-(trimethylsilyl)dec-9-ynoic acid

Refernces

• 1、 Nah, Theodora,Zhang, Haofei,Worton, David R.,Ruehl, Christopher R.,Kirk, Benjamin B.,Goldstein, Allen H.,Leone, Stephen R.,Wilson, Kevin R.. "Isomeric product detection in the heterogeneous reaction of hydroxyl radicals with aerosol composed of branched and linear unsaturated organic molecules". . p. 11555 - 11571. Retrieved 2015/02/19.