4712-34-9

Basic information

• Product Name: petroselinic acid
• Synonyms: octadec-6-enoic acid
• CAS NO: 4712-34-9
• Molecular Formula: C₁₈H₃₄O₂
• Molecular Weight: 282.4614
• Mol File: 4712-34-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 399°Cat760mmHg
• Flash Point: 295.8°C
• Appearance: /
• Density: 0.899g/cm³
• CAS DataBase Reference: petroselinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: petroselinic acid(4712-34-9)
• EPA Substance Registry System: petroselinic acid(4712-34-9)

Safety Data

• Hazardous Substances Data: 4712-34-9(Hazardous Substances Data)

Usage

Definition

ChEBI: An octadecenoic acid having a cis- or trans- double bond at position 6.

Enzyme inhibitor

This unsaturated fatty acid (FWfree-acid = 282.47 g/mol; M.P. = 29.5–30.1°C; CAS 4712-34-9; (Z)-isomer, CAS 593-39-5; (E)-isomer, CAS 593-40-8), also known as petroselinic acid and named systematically (Z)-octadec-6-enoic acid, is found many plants (especially celery, parsley, and caraway seeds). Target(s): chondroitin AC lyase; chondroitin B lyase; DNA polymerase; DNA topoisom\erase I; DNA topoisomerase II; hyaluronate lyase; and linoleate isomerase

Upstream product

• 2462-85-3 linoleic acid methyl ester 

Downstream Products

• 544-74-1 octadec-6-ynoic acid 

Relevant articles and documents

Simple method of preparation of methyl trans-10,cis-12- and cis-9,trans-11-octadecadienoates from methyl linoleate

Pure conjugated isomers of linoleic acid were prepared on a large scale by alkali-isomerization of purified methyl linoleate. The methyl esters of alkali-isomerized linoleic acid contained mainly the methyl cis-9,trans-11- and trans-10,cis-12-octadecadienoates (44 and 47%, respectively). These two isomers were then separated and purified by a series of low-temperature crystallizations from acetone. The isomeric purity obtained for the cis-9,trans-11-octadecadienoate isomer was >90% and that of the trans-10,cis-12-octadecadienoate isomer was 89 to 97%. The isolated yield of the two isomers corresponded to 18 and 25.7%, respectively, of the starting material. The structure of the two isomers was confirmed using partial hydrazine reduction, silver nitrate-thin-layer chromatography of the resulting monoenes and gas chromatography coupled with mass spectrometry of the 4,4-dimethyloxazoline derivatives. Fourier transform infrared spectroscopy of the monoenes gave the confirmation of the geometry of each double bond.