Methyl 13-hydroxy-9,11-octadecadienoate

Base Information

• Chemical Name: Methyl 13-hydroxy-9,11-octadecadienoate
• CAS No.: 23324-72-3
• Molecular Formula: C₁₉H₃₄O₃
• Molecular Weight: 310.477
• Hs Code.: 2918199090
• Nikkaji Number: J42.503F,J2.069.985J
• Mol file: 23324-72-3.mol

Synonyms:Methyl 13-hydroxy-9,11-octadecadienoate;23324-72-3;9,11-OCTADECADIENOIC ACID, 13-HYDROXY-, METHYL ESTER;SCHEMBL677201;LS-97650;(9E,11E)-13-Hydroxy-9,11-octadecadienoic acid methyl ester

Chemical Property of Methyl 13-hydroxy-9,11-octadecadienoate

Chemical Property:

• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.4200 (estimate)
• Boiling Point: 417.5°Cat760mmHg
• PKA: 14.75±0.20(Predicted)
• Flash Point: 158.3°C
• PSA: 46.53000
• Density: 0.938g/cm³
• LogP: 4.94370
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 310.25079494
• Heavy Atom Count: 22
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

METHYLHYDROXYOCTADECADIENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCCCCCCCC(=O)OC)O
• Isomeric SMILES: CCCCCC(/C=C/C=C/CCCCCCCC(=O)OC)O

Technology Process of Methyl 13-hydroxy-9,11-octadecadienoate

There total 28 articles about Methyl 13-hydroxy-9,11-octadecadienoate 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: 86.0%

13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester (79790-32-2) → 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:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0009-3084(03)00087-2

Reference yield:

methyl 9-iodononanoate (75452-47-0) → 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:

Multi-step reaction with 3 steps

1: 97 percent / acetonitrile / 36 h / Heating

2: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 5 min

3: 70 percent / sodium borohydride / methanol / 0.08 h / 0 °C

With sodium tetrahydroborate; potassium tert-butylate; In methanol; acetonitrile;

Reference yield:

1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine (6542-05-8) → methyl 9-hydroxy-trans-10,trans-12-octadecadienoate (6157-02-4) + 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) + methyl 13-hydroxyoctadeca-trans-9,trans-11-dienoate (28392-55-4) + (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid methyl ester (10075-07-7)

Guidance literature:

1,2-Dilinoleoyl-sn-glycerol-3-phosphorylcholine; With sodium salt of choleic acid; ΔNt-NspLOX; at 20 ℃; for 0.5h; pH=7.5;

With tin(ll) chloride; In methanol;

With sodium methylate; at 20 ℃; for 0.333333h; Further stages.;

DOI:10.1016/j.phytochem.2008.03.002

upstream raw materials:

diazomethane

12-13-monoepoxy-9-octadecenoic acid

linoleic acid

(R,S)-coriolic acid

Downstream raw materials:

Benzoic acid (2E,4Z)-(R)-12-methoxycarbonyl-1-pentyl-dodeca-2,4-dienyl ester

methyl 13(S)-(benzoyloxy)octadeca-9(Z),11(E)-dienoate

(13R)-hydroxylinoleic acid methyl ester

benzoate of 13-hydroxy-(Z)-9-(E)-11-octadecadienonic acid methylester

Refernces

• 1、 Morales, Arturo,Dobarganes, Carmen,Marquez-Ruiz, Gloria,Velasco, Joaquin. "Quantitation of hydroperoxy-, keto- and hydroxy-dienes during oxidation of FAMEs from high-linoleic and high-oleic sunflower oils". experimental part. p. 1271 - 1279. Retrieved 2011/08/21.
• 2、 Okada, Youji,Tanaka, Kaoru,Sato, Eisuke,Okajima, Haruo. "Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L.". experimental part. p. 1097 - 1102. Retrieved 2009/02/05.