cis-Vaccenic acid

Synonym(s):cis-11-Octadecenoic acid;octadec-11(cis)-enoic acid

CAS NO.：506-17-2
Empirical Formula: C18H34O2
Molecular Weight: 282.46
MDL number: MFCD00063187
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-06 18:33:45

What is cis-Vaccenic acid?

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.

The Uses of cis-Vaccenic acid

(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.]

Properties of cis-Vaccenic acid

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 for cis-Vaccenic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.