Vernolic acid

Base Information

• Chemical Name: Vernolic acid
• CAS No.: 503-07-1
• Molecular Formula: C₁₈H₃₂O₃
• Molecular Weight: 296.45
• Hs Code.: 2918990090
• UNII: 4S5JF40ZOQ,FR42854EPW
• DSSTox Substance ID: DTXSID40895851
• Nikkaji Number: J9.572I
• Wikipedia: Vernolic_acid
• Wikidata: Q28530676
• Metabolomics Workbench ID: 2318,201063
• Mol file: 503-07-1.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:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1C(O1)CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCC[C@@H]1[C@@H](O1)C/C=C\CCCCCCCC(=O)O

Technology Process of Vernolic acid

There total 2 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:

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate (2733-91-7) → cis-12,13-epoxyoctadeca-cis-9-enoic acid (503-07-1,16833-57-1,7576-35-4)

Guidance literature:

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate; With sodium hydroxide; In tetrahydrofuran; water; at 23 ℃; for 6h;

With hydrogenchloride; In tetrahydrofuran; water; pH=4.5;

DOI:10.1016/S0040-4039(01)00694-3

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-12,13-epoxyoctadeca-cis-9-enoic acid (503-07-1,16833-57-1,7576-35-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cytochrome P₄₅₀BM₃, wild type; NADPH; K₂CO₃ / various solvent(s) / 0.25 h / 20 °C / pH 7.4

1.2: 45 percent / diethyl ether; methanol

2.1: NaOH / tetrahydrofuran; H₂O / 6 h / 23 °C

2.2: HCl / tetrahydrofuran; H₂O / pH 4.5

With sodium hydroxide; cytochrome P₄₅₀BM₃; wild type; potassium carbonate; NADPH; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(01)00694-3

Reference yield:

cis-12,13-epoxyoctadeca-cis-9-enoic acid (503-07-1,16833-57-1,7576-35-4) → D-erythro-12,13-dihydroxy-octadec-9c-enoic acid ethyl ester (112271-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; diethyl ether; acetic acid anhydride / beim Erwaermen des Reaktionsprodukts mit Silberacetat und wasserhaltiger Essigsaeure und Behandeln des danach isolierten Reaktionsprodukts mit aethanol. Kalilauge

With diethyl ether; hydrogen bromide; acetic anhydride;

DOI:10.1039/jr9560001611

upstream raw materials:

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate

linoleic acid

Downstream raw materials:

(+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid

L_g-threo-12,13-dihydroxy-octadecanoic acid

D-erythro-12,13-dihydroxy-octadec-9c-enoic acid ethyl ester

D-erythro-12,13-dihydroxy-octadecanoic acid

Refernces