2420-56-6

Basic information

• Product Name: Conjugated linoleic acid
• Synonyms: 10E,Z12-CLA;(10E,12Z)-10,12-OCTADECADIENOIC ACID;10E,12Z-CLA;10(E),12(Z)-OCTADECADIENOIC ACID;10TR-12C-OCTADECADIENOIC ACID;10-TRANS, 12-CIS CLA;LINOLEIC ACID (10-TRANS, 12-CIS);DELTA 10 TRANS DELTA 12 CIS OCTADECADIENOIC ACID
• CAS NO: 2420-56-6
• Molecular Formula: C₁₈H₃₂O₂
• Molecular Weight: 280.45
• EINECS: 1308068-626-2
• Mol File: 2420-56-6.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 381.6 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: /
• Density: 0.911 g/cm³
• Vapor Pressure: 9.54E-07mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: −20°C
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: Conjugated linoleic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Conjugated linoleic acid(2420-56-6)
• EPA Substance Registry System: Conjugated linoleic acid(2420-56-6)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• RIDADR: UN 1170 3/PG 2 -Ethanol,solution
• Hazardous Substances Data: 2420-56-6(Hazardous Substances Data)

Usage

Description

Conjugated linoleic acid (CLA) is a group of 8 geometric isomers of linoleic acid, characterized by two contiguous double bonds. It is primarily found in meat and dairy products, with the predominant isomer in animal tissue being 9Z,11E, and smaller amounts of 10E,12Z also present. CLA has been associated with various health benefits, including antioxidant and antitumor activities, which are believed to be due to competitive inhibition of Δ6-desaturase and/or PPARγ activation.

Uses

Used in the Beauty Products Industry:
Conjugated linoleic acid is used as an ingredient in beauty products for its anti-inflammatory, acne reductive, and moisture-retentive properties when applied topically on the skin. It is particularly popular for its beneficial effects on skin health.
Used in the Pharmaceutical Industry:
Conjugated linoleic acid is used as a potential therapeutic agent due to its various antioxidant and antitumor activities. These activities have been attributed to its ability to inhibit Δ6-desaturase and/or activate PPARγ, which may contribute to the reported health benefits of dietary supplementation with CLA.
Used in the Nutritional Supplements Industry:
As a dietary supplement, CLA is used to provide the reported health benefits associated with its consumption, such as improved immune function, reduced body fat, and enhanced muscle growth. It is often marketed as a weight management and sports performance supplement.

InChI:InChI=1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)

Upstream product

• 2462-85-3 linoleic acid methyl ester 
• 56-23-5 tetrachloromethane 
• 60-33-3 linoleic acid 
• 111-46-6 diethylene glycol 
• 112-53-8 1-dodecyl alcohol 
• 141-22-0 Ricinoleic acid 
• 112-63-0 Methyl linoleate 
• 119-61-9 benzophenone 
• 8001-23-8 safflower oil 
• 330214-87-4 t10,c12 conjugated linoleic acid ethyl ester 
• 71-36-3 butan-1-ol 

Downstream Products

• 65410-38-0 12-oxo-(10E)-dodecan-10-oic acid 
• 5578-80-3 ω-oxydecanocarboxylic acid 
• 54232-59-6 9‐oxo‐10E,12Z‐octadecanoic acid 
• 1002-79-5 (10E,12Z)-10,12-octadecadienoic acid methyl ester 
• 822-10-6 (9Z,11E)-methyl octadeca-9,11-dienoate 
• 1311271-89-2 (Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl (10E,12Z)-linoleate 
• 1311271-87-0 (Z)-2-(3-chlorobenzylidene)-3-oxo-2,3-dihydrobenzofuran-5-yl (10E,12Z)-linoleate 
• 1311271-85-8 (Z)-2-(4-fluorobenzylidene)-3-oxo-2,3-dihydrobenzofuran-5-yl (10E,12Z)-linoleate 
• 1311271-83-6 (Z)-2-(3-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-5-yl (10E,12Z)-linoleate 
• 1311271-91-6 3-(4-methoxybenzyl)-4-oxo-4H-chromen-7-yl (10E,12Z)-linoleate 

Relevant articles and documents

Investigation of Micellization and Vesiculation of Conjugated Linoleic Acid by Means of Self-Assembling and Self-Crosslinking

Bioactive and biocompatible conjugated linoleic acid (CLA) has been only considered as a food or medicine ingredient due to its rare natural occurrence. In this work, the surface activities and pH-induced self-assembling behaviors of the semi-synthetic CLA molecules into micelles or vesicles were systematically investigated. First, the self-assembling of CLA was studied in detail, and it was found that aside from temperature and ionic strength, pH is the prominent factor affecting the self-assembling of CLA. Moreover, stable CLA ufasomes (unsaturated fatty acid liposomes) in uniform size were obtained by self-crosslinking of the CLA ufasomes, and the morphologies of the crosslinked CLA assemblies were recorded by transmission electron microscopy, which made known the pH-induced formation of the CLA ufasomes or the CLA micelles. The crosslinked CLA assemblies presented improved properties such as a higher calcium stability, a lower lime soap dispersing requirement and a better solubilization ability than that of the CLA molecules themselves or the pre-crosslinked linoleic acids. These investigations could be helpful for comprehensively understanding effects of environment factors on self-assembling behaviors of conjugated fatty acids and responsive polymerization of polymerizable surfactants.

Synthesis of phosphatidylcholine with conjugated linoleic acid and studies on its cytotoxic activity

Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82%) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87% yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

Sustainable and efficient methodology for CLA synthesis and identification

Microwave-assisted organic synthesis and continuous-flow techniques have been successfully employed for the preparation of conjugated linoleic acids (CLA), compounds with high health beneficial effects. A good production rate of CLA was obtained. A sustainable methodology for the differentiation of both positional and geometrical CLA isomers (diene), based on the analysis by NMR spectroscopy of the resulting Diels-Alder cycloadducts with an appropriate dienophile, was developed.