(+/-)-13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID, CHOLESTERYL ESTER

Base Information

• Chemical Name: (+/-)-13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID, CHOLESTERYL ESTER
• CAS No.: 167354-91-8
• Molecular Formula: C₄₅H₇₆O₃
• Molecular Weight: 665.097
• Mol file: 167354-91-8.mol

Synonyms:Cholest-5-en-3-ol(3b)-,13-hydroxy-9,11-octadecadienoate, [3(9Z,11E)]-

Chemical Property of (+/-)-13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID, CHOLESTERYL ESTER

Chemical Property:

• PSA: 46.53000
• LogP: 12.72390

Purity/Quality:

98%min ^*data from raw suppliers

(+/-)13-HODEcholesterylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (±)13-HODE cholesteryl ester was originally extracted from atherosclerotic lesions and shown to be produced by Cu2+-catalyzed oxidation of LDL. Later studies determined that 15-LO from rabbit reticulocytes and human monocytes were able to metabolize cholesteryl linoleate, a major component of LDL, to 13-HODE cholesteryl ester.[Cayman Chemical] (+/-)13-HODE cholesteryl ester is an oxidative product from LDL found in atherosclerotic lesions.

Technology Process of (+/-)-13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID, CHOLESTERYL ESTER

There total 2 articles about (+/-)-13-HYDROXY-9Z,11E-OCTADECADIENOIC ACID, CHOLESTERYL ESTER 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:

cholesterol linoleate (604-33-1) → (8E,12Z)-10-Hydroxy-octadeca-8,12-dienoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester + cholesteryl 13-hydroxyoctadeca-cis-9,trans-11-dienoate (167354-91-8) + cholesteryl 9-hydroxyoctadeca-trans-10,cis-12-dienoate (33783-76-5,143442-54-0,330800-93-6) + (9Z,13E)-12-Hydroxy-octadeca-9,13-dienoic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Guidance literature:

cholesterol linoleate; With oxygen; methylene blue; In hexane; isopropyl alcohol; at 4 ℃; for 5h; Irradiation;

With potassium iodide; In ethanol; at 20 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1016/S0009-3084(99)00049-3

Reference yield:

cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate (167354-92-9) → cholesteryl 13-hydroxyoctadeca-cis-9,trans-11-dienoate (167354-91-8)

Guidance literature:

With triphenylphosphine; In diethyl ether;

DOI:10.1021/tx9600098

Reference yield:

sodium methylate (124-41-4) + cholesteryl 13-hydroxyoctadeca-cis-9,trans-11-dienoate (167354-91-8) → methyl coriolate (6410-93-1,10075-08-8,10219-70-2,23324-72-3,24058-13-7,26474-38-4,28392-55-4,57884-99-8,96393-37-2,114297-07-3,109837-85-6)

Guidance literature:

In methanol;

DOI:10.1021/tx9600098

upstream raw materials:

cholesterol linoleate

cholesterol 13-hydroperoxy-cis-9,trans-11-octadecadienoate

Downstream raw materials:

methyl coriolate

Refernces

• 1、 Kenar, James A.,Havrilla, Christine M.,Porter, Ned A.,Guyton, John R.,Brown, Spencer A.,Klemp, Keith F.,Selinger, Elizabeth. "Identification and quantification of the regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low density lipoprotein and high density lipoprotein". . p. 737 - 744. Retrieved 2007/10/03.