9,12,13-Trihydroxy-10-octadecenoic acid

Base Information

• Chemical Name: 9,12,13-Trihydroxy-10-octadecenoic acid
• CAS No.: 29907-56-0
• Molecular Formula: C₁₈H₃₄O₅
• Molecular Weight: 330.465
• Nikkaji Number: J1.307.754A,J346.162I
• Metabolomics Workbench ID: 2205
• ChEMBL ID: CHEMBL469617
• Mol file: 29907-56-0.mol

Synonyms:9,12,13-TODEA;9,12,13-trihydroxy-10-octadecenoic acid;9,12,13-trihydroxyoctadec-10-enoic acid

Chemical Property of 9,12,13-Trihydroxy-10-octadecenoic acid

Chemical Property:

• Vapor Pressure: 1.62E-13mmHg at 25°C
• Boiling Point: 531.5°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 289.3°C
• Density: 1.074g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 330.24062418
• Heavy Atom Count: 23
• Complexity: 317

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 9,12,13-Trihydroxy-10-octadecenoic acid

There total 10 articles about 9,12,13-Trihydroxy-10-octadecenoic 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:

(E)-(9R,13R)-13-(2,2-Dimethyl-propionyloxy)-9-hydroxy-12-oxo-octadec-10-enoic acid methyl ester (135460-96-7) → (E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid (29907-56-0,95783-98-5,97134-11-7,102735-57-9,102735-58-0,102735-59-1,135214-42-5,135214-43-6,135214-48-1,135214-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

3: 19 mg / KOH / methanol / 28 h / Ambient temperature

With dmap; potassium hydroxide; triethylamine; In methanol; dichloromethane;

Reference yield:

8-{(2R,3S)-3-[(2R,3R)-3-(2,2-Dimethyl-propionyloxy)-2-hydroxy-octyl]-oxiranyl}-octanoic acid methyl ester (135460-95-6) → (E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid (29907-56-0,95783-98-5,97134-11-7,102735-57-9,102735-58-0,102735-59-1,135214-42-5,135214-43-6,135214-48-1,135214-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1: CrO₃*Py₂ / CH₂Cl₂ / 1 h / Ambient temperature

2: SiO₂ / CH₂Cl₂ / 1 h / Ambient temperature

3: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

5: 19 mg / KOH / methanol / 28 h / Ambient temperature

With dmap; potassium hydroxide; silica gel; dipyridine chromium trioxide; triethylamine; In methanol; dichloromethane;

Reference yield:

8-{(2R,3S)-3-[(R)-3-(2,2-Dimethyl-propionyloxy)-2-oxo-octyl]-oxiranyl}-octanoic acid methyl ester → (E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid (29907-56-0,95783-98-5,97134-11-7,102735-57-9,102735-58-0,102735-59-1,135214-42-5,135214-43-6,135214-48-1,135214-49-2)

Guidance literature:

Multi-step reaction with 4 steps

1: SiO₂ / CH₂Cl₂ / 1 h / Ambient temperature

2: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

4: 19 mg / KOH / methanol / 28 h / Ambient temperature

With dmap; potassium hydroxide; silica gel; triethylamine; In methanol; dichloromethane;

upstream raw materials:

(E)-(9R,12R,13R)-9,12,13-Trihydroxy-octadec-10-enoic acid methyl ester

Methyl linoleate

(9Z)-11-[(2RS,3SR)-3-pentyloxyiranyl]undec-9-enoic acid methyl ester

(Z)-11-((4R,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-undec-9-enoic acid methyl ester