Petroselinic acid

Base Information

• Chemical Name: Petroselinic acid
• CAS No.: 593-39-5
• Molecular Formula: C18H34 O2
• Molecular Weight: 282.467
• Hs Code.: 2916190090
• European Community (EC) Number: 209-789-8
• UNII: 3A10DOC461
• ChEMBL ID: CHEMBL3139878
• DSSTox Substance ID: DTXSID301026575
• Metabolomics Workbench ID: 500
• NCI Thesaurus Code: C68414
• Nikkaji Number: J13.804E
• Wikidata: Q2080732
• Wikipedia: Petroselinic_acid
• Mol file: 593-39-5.mol

Synonyms:petroselenic acid;petroselinic acid;petroselinic acid, (E)-isomer;petroselinic acid, (Z)-isomer;petroselinic acid, sodium salt, (Z)-isomer

Chemical Property of Petroselinic acid

Chemical Property:

• Vapor Pressure: 1.76E-07mmHg at 25°C
• Melting Point: 29.5-30.1°
• Refractive Index: nD40 1.4533
• Boiling Point: 399°Cat760mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 295.8°C
• PSA: 37.30000
• Density: 0.899g/cm³
• LogP: 6.10850
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly)
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 282.255880323
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

98%,99%, ^*data from raw suppliers

(6Z)-6-OctadecenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC=CCCCCC(=O)O
• Isomeric SMILES: CCCCCCCCCCC/C=C\CCCCC(=O)O
• Uses: (6Z)-6-Octadecenoic Acid, is a monounsaturated fatty acid and isomer of oleic acid, that is a component of plant lipids. Arachidonic acid levels decrease, while linoleic acid levels increase, in the heart, liver, and blood of rats fed a diet containing petroselinic acid.

Technology Process of Petroselinic acid

There total 19 articles about Petroselinic 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: 45.0%

(6Z)-6-octadecen-1-ol (2774-87-0) → Petroselinic acid (593-39-5)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1007/s11745-017-4262-1

Reference yield:

12-deoxyphorbol-13-(6Z)-octadecenoate → Petroselinic acid (593-39-5)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 24h;

DOI:10.1080/14786419.2019.1616728

Reference yield:

6-octadecyn-1-ol (2861-50-9) → Petroselinic acid (593-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen; quinoline / hexane / 20 °C

2: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With quinoline; dipyridinium dichromate; palladium 10% on activated carbon; hydrogen; In hexane; N,N-dimethyl-formamide;

DOI:10.1007/s11745-017-4262-1

upstream raw materials:

octadec-6-ynoic acid

erythro-6,7-Dihydroxyoctadecanoic acid

ethanol

6,7-dibromo-octadecanoic acid

Downstream raw materials:

methyl petroselinate

cis-Petroselinsaeure-propylester

Petroselaidic acid

erythro-6,7-Dihydroxy-stearinsaeure

Refernces

• 1、 Carballeira, Néstor M.,Montano, Nashbly,Morales, Christian,Mooney, Joseph,Torres, Xiomara,Díaz, Dakeishla,Sanabria-Rios, David J.. "2-Methoxylated FA Display Unusual Antibacterial Activity Towards Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (CIMRSA) and Escherichia coli". . p. 535 - 548. Retrieved 2017/06/07.