(9E)-12-hydroxyoctadec-9-enoic acid

Base Information

• Chemical Name: (9E)-12-hydroxyoctadec-9-enoic acid
• CAS No.: 7431-95-0
• Molecular Formula: C₁₈H₃₄O₃
• Molecular Weight: 298.466
• European Community (EC) Number: 263-060-9
• NSC Number: 179694
• Nikkaji Number: J452.982K
• Wikidata: Q27158677
• Metabolomics Workbench ID: 2186
• ChEMBL ID: CHEMBL1877670
• Mol file: 7431-95-0.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 (9E)-12-hydroxyoctadec-9-enoic acid

Chemical Property:

• Boiling Point: 416.4 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 219.8 °C
• PSA: 57.53000
• Density: 0.957 g/cm³
• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB
• Canonical SMILES: CCCCCCC(CC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCCCC(C/C=C/CCCCCCCC(=O)O)O

Technology Process of (9E)-12-hydroxyoctadec-9-enoic acid

There total 27 articles about (9E)-12-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: 83.0%

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1080/00397919908086253

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

upstream raw materials:

heptanal

10-undecenoic acid

methyl acetyl ricinoleate

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester

Downstream raw materials:

12-octadecenoic acid

12-oxo-octadec-9-ynoic acid

(Z)-12-hydroxyoctadec-9-enoic acid

ricinoleic acid ethylene glycol methyl ether ester

Refernces

• 1、 Ewonkem, Monique B.,Grinberg, Sarina,Lemcoff, Gabriel,Shaubi, Eleonora,Linder, Charles,Heldman, Eliahu. "Newly synthesized bolaamphiphiles from castor oil and their aggregated morphologies for potential use in drug delivery". . p. 8557 - 8571. Retrieved 2018/04/05.
• 2、 Brinkerhoff, Rafael C.,Tarazona, Hernan F.,De Oliveira, Patrick M.,Flores, Darlene C.,Montes D'Oca, Caroline Da R.,Russowsky, Dennis,Montes D'Oca, Marcelo G.. "Synthesis of β-ketoesters from renewable resources and Meldrum's acid". . p. 49556 - 49559. Retrieved 2014/12/10.