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 | n |
| 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. |
Computed Descriptors for cis-Vaccenic acid
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