Ximenynic acid

Base Information

• Chemical Name: Ximenynic acid
• CAS No.: 557-58-4
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.435
• European Community (EC) Number: 209-179-1
• NSC Number: 252625
• UNII: IA0Z48P13W
• DSSTox Substance ID: DTXSID501317249
• Nikkaji Number: J6.486F
• Wikipedia: Ximenynic_acid
• Wikidata: Q27280625
• Metabolomics Workbench ID: 970
• ChEMBL ID: CHEMBL1967321
• Mol file: 557-58-4.mol

Synonyms:11-octadecen-9-ynoic acid;santalbic acid;ximenynic acid

Chemical Property of Ximenynic acid

Chemical Property:

• Vapor Pressure: 4.09E-08mmHg at 25°C
• Melting Point: 40-41℃
• Boiling Point: 416.8°Cat760mmHg
• Flash Point: 200°C
• PSA: 37.30000
• Density: 0.936g/cm³
• LogP: 5.33170
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 278.224580195
• Heavy Atom Count: 20
• Complexity: 317

Purity/Quality:

99%, ^*data from raw suppliers

XimeninicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC=CC#CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC/C=C/C#CCCCCCCCC(=O)O
• Uses: Ximeninic Acid is a fatty acid extract in the seed oil of Santalum spicatum, and has been seen to modify the fatty acid composition in mice.

Technology Process of Ximenynic acid

There total 17 articles about Ximenynic 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: 41.0%

11-octadecen-9-ynoic acid (2578-97-4) → trans-ximenynic acid (2578-97-4,136145-04-5,557-58-4)

Guidance literature:

With urea; at 5 ℃; for 4h;

DOI:10.1080/00397911.2011.585443

Reference yield:

12-hydroxyoctadec-9-ynoic acid (925-42-8,84799-85-9,540-13-6) → (11Z)-octadecen-9-ynoic acid (557-58-4,2578-97-4,136145-04-5) + trans-ximenynic acid (2578-97-4,136145-04-5,557-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; thionyl chloride / 3 h / 60 °C

2: potassium hydroxide / ethanol; water / 24 h / Reflux

With pyridine; thionyl chloride; potassium hydroxide; In ethanol; water;

DOI:10.1080/00397911.2011.585443

Reference yield:

12-hydroxyoctadec-9-ynoic acid (925-42-8,84799-85-9,540-13-6) → (11Z)-octadecen-9-ynoic acid (557-58-4,2578-97-4,136145-04-5) + trans-ximenynic acid (2578-97-4,136145-04-5,557-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; thionyl chloride / 3 h / 60 °C

2: potassium hydroxide / ethanol; water / 24 h / Reflux

With pyridine; thionyl chloride; potassium hydroxide; In ethanol; water;

DOI:10.1080/00397911.2011.585443

upstream raw materials:

(Z)-dec-3-en-1-yne

dec-1-yn-4-ol

12-hydroxyoctadec-9-ynoic acid

9,10-dibromo-12-hydroxy-octadecanoic acid

Downstream raw materials:

octadec-11t-en-9-ynoic acid ethyl ester

trans-9,trans-11-octadecadienoic acid

stearic acid

cis-9,trans-11-octadecadienoic acid

Refernces