(9E)-11-hydroxyoctadec-9-enoic acid

Base Information

• Chemical Name: (9E)-11-hydroxyoctadec-9-enoic acid
• CAS No.: 110567-68-5
• Molecular Formula: C₁₈H₃₄O₃
• Molecular Weight: 298.466
• Mol file: 110567-68-5.mol

Synonyms:

Chemical Property of (9E)-11-hydroxyoctadec-9-enoic acid

Chemical Property:

• Vapor Pressure: 1.48E-08mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9E)-11-hydroxyoctadec-9-enoic acid

There total 10 articles about (9E)-11-hydroxyoctadec-9-enoic 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: 35.0%

Elaidic acid (112-79-8,2027-47-6) → trans-9,10-epoxystearic acid + 11-hydroxy-9(E)-octadecenoic acid (110567-68-5) + (E)-8-hydroxyoctadec-9-enoic acid (148409-56-7)

Guidance literature:

With cytochrome P₄₅₀ from Thermus thermophilus HB₂₇; dihydrogen peroxide; In aq. buffer; at 45 ℃; for 1h; pH=7.5; regioselective reaction; Kinetics; Enzymatic reaction;

DOI:10.1021/bi300514j

Reference yield: 34.0%

C26H39BrO4 → 11-hydroxy-9(E)-octadecenoic acid (110567-68-5)

Guidance literature:

With sodium hydroxide; In methanol; Reflux;

DOI:10.1016/j.fitote.2020.104639

Reference yield:

oleic acid-(4-bromo-phenacyl ester) (61393-53-1) → 11-hydroxy-9(E)-octadecenoic acid (110567-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane; decane / 72 h / 20 °C

2: sodium hydroxide / methanol / Reflux

With tert.-butylhydroperoxide; selenium(IV) oxide; sodium hydroxide; In methanol; decane; dichloromethane;

DOI:10.1016/j.fitote.2020.104639

upstream raw materials:

trans-9-hydroperoxyoctadec-10-enoic acid

cis-Octadecenoic acid

Elaidic acid

oleic acid-(4-bromo-phenacyl ester)

Refernces

• 1、 Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava. "Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27". . p. 7880 - 7890. Retrieved 2013/01/15.
• 2、 Porter, Ned A.,Wujek, Jacqueline Sullivan. "Allylic Hydroperoxide Rearrangement: β-Scission or Concerted Pathway?". . p. 5085 - 5089. Retrieved 2007/10/02.