Vernolic acid

Base Information

• Chemical Name: Vernolic acid
• CAS No.: 17966-13-1
• Molecular Formula: C18H32 O3
• Molecular Weight: 296.45
• UNII: 4S5JF40ZOQ,FR42854EPW
• DSSTox Substance ID: DTXSID40895851
• Nikkaji Number: J9.572I
• Wikipedia: Vernolic_acid
• Wikidata: Q28530676
• Metabolomics Workbench ID: 2318,201063
• Mol file: 17966-13-1.mol

Synonyms:cis-12-epoxyoctadeca-cis-9-enoate;cis-12-epoxyoctadeca-cis-9-enoic acid;vernoleate;vernolic acid

Chemical Property of Vernolic acid

Chemical Property:

• Vapor Pressure: 2.29E-07mmHg at 25°C
• Boiling Point: 395.8°Cat760mmHg
• Flash Point: 130°C
• PSA: 49.83000
• Density: 0.969g/cm³
• LogP: 5.09570
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 296.23514488
• Heavy Atom Count: 21
• Complexity: 299

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1C(O1)CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCC[C@@H]1[C@@H](O1)C/C=C\CCCCCCCC(=O)O
• Uses: (±)-cis-12,13-Epoxy-9(Z)-octadecenoic Acid, an isomer of (-)-Vernolic Acid (V128710). a fatty acid that is monounsaturated and contains an epoxide. It is It is the cis epoxide derived from the C12–C13 alkene of linoleic acid, and an isomer of coronaric acid. Vernolic acid is the key component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.

Technology Process of Vernolic acid

There total 5 articles about Vernolic 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:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → (+/-)-cis-9,10-epoxy-12(Z)-octadecenoic acid (16833-56-0,61949-82-4,65167-83-1,110658-06-5,113972-57-9,126639-25-6,132201-82-2,135094-09-6,146987-78-2) + (+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid (17966-13-1,16833-57-1,7576-35-4)

Guidance literature:

With peroxygenase from tomato yeast extract; dihydrogen peroxide; In aq. acetate buffer; at 30 ℃; for 1h; pH=6; Enzymatic reaction;

DOI:10.1016/j.phytochem.2013.02.020

Reference yield:

→ (+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid (17966-13-1,16833-57-1,7576-35-4)

Guidance literature:

With quinoline; Lindlar's catalyst; Petroleum ether; Hydrogenation;

DOI:10.1039/jr9610005270

Reference yield:

→ (+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid (17966-13-1,16833-57-1,7576-35-4)

Guidance literature:

upstream raw materials:

cis-12,13-epoxyoctadeca-cis-9-enoic acid

(-)-vernolic acid

linoleic acid

Downstream raw materials:

(+/-)-threo-12,13-Dihydroxy-octadecansaeure

(+/-)-erythro-12,13-Dihydroxy-octadecansaeure

12-Aminododecanoic acid

12-oxododecanoic acid

Refernces