cis-Vaccenic acid Chemical Properties

Melting point:

14-15 °C(lit.)

Boiling point:

150 °C0.03 mm Hg(lit.)

Density 

0.887 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.459(lit.)

Flash point:

230 °C

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Ethanol (Soluble), Methanol (Slightly)

form 

oil

pka

4.78±0.10(Predicted)

BRN 

1726565

Stability:

Light Sensitive, Volatile

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-10

MSDS

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cis-Vaccenic acid Usage And Synthesis

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.

Definition

ChEBI: Cis-vaccenic acid is the cis isomer of vaccenic acid. It is a conjugate acid of a cis-vaccenate(1-).

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.]

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