4158-12-7

Basic information

• Product Name: Octadecanoic acid, 10-oxo-
• Synonyms: Octadecanoic acid, 10-oxo-
• CAS NO: 4158-12-7
• Molecular Formula: C₁₈H₃₄O₃
• Molecular Weight: 298.4608
• Mol File: 4158-12-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 77 °C
• Boiling Point: 444.1°Cat760mmHg
• Flash Point: 236.5°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 3.99E-09mmHg at 25°C
• Refractive Index: 1.46
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: Octadecanoic acid, 10-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecanoic acid, 10-oxo-(4158-12-7)
• EPA Substance Registry System: Octadecanoic acid, 10-oxo-(4158-12-7)

Safety Data

• Hazardous Substances Data: 4158-12-7(Hazardous Substances Data)

Usage

General Description

Octadecanoic acid, 10-oxo- is a fatty acid containing 18 carbon atoms with a ketone group at the 10th position. It is also known as 10-oxostearic acid and is a chemical compound commonly found in nature, particularly in animal fats and vegetable oils. Octadecanoic acid, 10-oxo- is used in various industrial applications, including as a precursor for the synthesis of various esters and waxes. It is also utilized in the production of cosmetics, lubricants, and pharmaceuticals. Additionally, this chemical compound is studied for its potential biological activities and therapeutic uses, particularly in the fields of dermatology and medicine. Overall, octadecanoic acid, 10-oxo- is a versatile and important chemical with various practical and scientific applications.

InChI:InChI=1/C18H34O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h2-16H2,1H3,(H,20,21)

Upstream product

• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 111-20-6 1,10-decanedioic acid 
• 111-86-4 n-Octylamine 
• 112-05-0 nonanoic acid 
• 638-26-6 10-hydroxystearic acid 

Relevant articles and documents

Conversion of oleic acid to 10-ketostearic acid by Sphingobacterium sp. strain O22

The conversion of oleic acid by a bacterium, tentatively identified as Sphingobacterium thalpophilum strain O22, was investigated. The microorganism was isolated as a stable culture from compost that was enriched with soybean oil outdoors and subsequently with oleic acid in the laboratory. Strain O22 converted oleic acid to products identified as 10-ketostearic acid (95% of the total conversion product) and 10-hydroxystearic acid (5%). This is in contrast to S. thalpophilum strain B-14797, which produces solely 10-hydroxystearic acid. Maximal conversion was reached in about 36 h after the addition of oleic acid to the fermentation broth. The yield of 10-ketostearic acid was approximately 75% from 0.26 g of oleic acid in 30 mL fermentation broth at 28 °C and 200 rpm for 48 h. This is the first report on the major production of 10-ketostearic acid by a microorganism in the genus Sphingobacterium.

PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES

The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

Biotransformation of Oleic Acid to Optically Active γ-Dodecalactone

We contemplated the formation of γ-dodecalactone through microbial conversion consisting of two steps, the first for oxidizing oleic acid into 10-hydroxystearic acid and the second for the formation of γ-dodecalactone from the hydroxy acid.Microorganisms were screened for production of 10-hydroxystearic acid from oleic acid.A bacterium which could produce the hydroxy acid with a transformation yield of 61.5percent at a concentration of 5percent oleic acid was isolated.The hydroxy acid was found to be biotransformed to γ-dodecalactone by baker's yeast.The enantiomeric composition of the biosynthetic γ-dodecalactone was estimated to be the (R)- configuration and the optical purity of the lactone was estimated to be 87.6percent e.e.The biotransformation yield from oleic acid to γ-dodecalactone was 22.5percent.