506-17-2

Basic information

• Product Name: CIS-11-OCTADECENOIC ACID
• Synonyms: 11-OCTADECENOIC ACID, STANDARD FOR GC;(Z)-11-Octadecenoicacid;11-cis-Vaccenicacid=Vaccenicacid;cis-Vaccenic ac;cis-Vaccenic Acid, Synthetic;(Z)-Octadec-11-enoic acid;cis-11-Vaccenic acid;cis-11-Octad
• CAS NO: 506-17-2
• Molecular Formula: C₁₈H₃₄O₂
• Molecular Weight: 282.46
• Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives
• Mol File: 506-17-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 14-15 °C(lit.)
• Boiling Point: 150 °C0.03 mm Hg(lit.)
• Flash Point: 230 °C
• Appearance: /oil
• Density: 0.887 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.87E-07mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethanol (Soluble), Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• Stability: Light Sensitive, Volatile
• BRN: 1726565
• CAS DataBase Reference: CIS-11-OCTADECENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-11-OCTADECENOIC ACID(506-17-2)
• EPA Substance Registry System: CIS-11-OCTADECENOIC ACID(506-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 506-17-2(Hazardous Substances Data)

Usage

Description

Vaccenic acid is an omega-7 fatty acid. It is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy products such as milk, butter, and yogurt. It is also the predominant fatty acid comprising trans fat in human milk. Its IUPAC name is (E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat. Mammals convert it into rumenic acid, a conjugated linoleic acid, where it shows anticarcinogenic properties. Its stereoisomer, cis-vaccenic acid, also an omega-7 fatty acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil. Its IUPAC name is (Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Uses

(Z)-11-Octadecenoic Acid, is a natural 18:1 ω-7 fatty acid. It is readily incorporated into triglycerides in perfused liver.

Purification Methods

Purify the acid by fractional distillation under high vacuum or crystallisation form its melt in an inert atmosphere away from light. [Beilstein 2 I 198, 2 III 1384, 2 IV 1639.]

InChI:InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7-

Upstream product

• 111-71-7 heptanal 
• 7530-96-3 (11-carboxyundecyl)triphenylphosphonium bromide 
• 2536-38-1 18-bromooctadecanoic acid 
• 60-33-3 linoleic acid 

Downstream Products

• 6198-58-9 methyl (Z)-vaccenate 
• 181875-93-4 C₉₁H₉₁N₃O₂₇ 
• 191482-38-9 C₁₀₇H₁₂₁N₃O₂₇ 
• 1852-04-6 undecanedioic acid 
• 111-71-7 heptanal 
• 693-72-1 trans-Vaccenic acid 
• 95548-26-8 (Z)-octadec-11-enoyl chloride 
• 503-06-0 (11R,12S)-lactobacillic acid 

Relevant articles and documents

Synthesis of trans-vaccenic acid and cis-9-trans-11-conjugated linoleic acid

The preparation of the monounsaturated fatty acid, trans-vaccenic acid 4 (TVA), using both Wittig and one-pot Julia-Kocieński olefination protocol, was achieved in good yield. Similarly a Wittig approach was employed for the stereoselective synthesis of cis-9-trans-11-conjugated linoleic acid 2 from trans-2-nonenal and (8-carboxyoctyl)triphenylphosphonium bromide 12.

Catalytic hydrogenation of linoleic acid on nickel, copper, and palladium

The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas-liquid chromatograph, equipped with a capillary column, and Fourier transform-infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans-9,trans-12; trans-8,cis-12 or cis-9,trans-13; cis-9,trans-12; trans-9,cis-12 and cis-9,cis-12 18:2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double- bond migration during hydrogenation. On Ni and Pd catalysts, the yield of cis-12 and trans-12 monoenoic acids was larger than that of cis-9 and trans-9 monoenoic acids. On the contrary, the yield of cis-9 and trans-9 monoenoic acids was larger than that of cis-12 and trans-12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.