Ricinelaidic acid

Base Information

• Chemical Name: Ricinelaidic acid
• CAS No.: 540-12-5
• Molecular Formula: C18H34O3
• Molecular Weight: 298.466
• Hs Code.: 2918199090
• UNII: 9O64E391KI
• DSSTox Substance ID: DTXSID801316395
• Nikkaji Number: J6.386J,J712.022B
• Wikipedia: Ricinelaidic_acid
• Wikidata: Q7331160
• Metabolomics Workbench ID: 2248
• ChEMBL ID: CHEMBL1235634
• Mol file: 540-12-5.mol

Synonyms:12-D-hydroxy-9-trans-octadecenoic acid;12-hydroxy-9-octadecenic acid;12-hydroxy-9-octadecenoic acid;12-hydroxyoctadec-cis-9-enoic acid;9-octadecenoic acid, 12-hydroxy-, (9E,12R)-;ricinelaidic acid;ricinoleic acid;ricinoleic acid, (R-(E))-isomer

Chemical Property of Ricinelaidic acid

Chemical Property:

• PSA: 57.53000
• LogP: 5.07930
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 298.25079494
• Heavy Atom Count: 21
• Complexity: 261

Purity/Quality:

98%min ^*data from raw suppliers

Ricinelaidic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(CC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCCC[C@H](C/C=C/CCCCCCCC(=O)O)O

Technology Process of Ricinelaidic acid

There total 7 articles about Ricinelaidic 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: 78.0%

methyl (12R)-hydroxyoctadec-(9E)-enoate (7706-01-6) → ricinelaidic acid (540-12-5,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.8b00734

Reference yield: 49.0%

Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) → ricinelaidic acid (540-12-5,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With diphenyldisulfane; In hexane; for 3h; UV-irradiation;

DOI:10.15227/orgsyn.063.0192

Reference yield:

heptanal (111-71-7) + 10-undecenoic acid (112-38-9) → Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) + ricinelaidic acid (540-12-5,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With ethylaluminum dichloride; In dichloromethane; at 0 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00152a011

upstream raw materials:

Ricinoleic acid

heptanal

10-undecenoic acid

methyl (12R)-hydroxyoctadec-(9E)-enoate

Downstream raw materials:

(E)-12-Oxooctadec-9-enoic Acid

trans-9,trans-11-octadecadienoic acid

oenanthic acid

stearic acid

Refernces

• 1、 Negelmann, Lars,Pisch, Sandra,Bornscheuer, Uwe,Schmid, Rolf D.. "Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom". . p. 117 - 134. Retrieved 2007/10/03.
• 2、 Thalmann, Adolf,Oertle, Konrad,Gerlach, Hans. "Ricinelaidic acid lactone". . p. 192 - 192. Retrieved 2017/05/23.