Petroselinic acid

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Petroselinic acid
Petroselinic acid
Names
IUPAC name
(6Z)-Octadec-6-enoic acid
Other names
(6Z)-Octadecenoic acid
(Z)-Octadec-6-enoic acid
cis-6-Octadecenoic acid
cis-Δ6-Octadecenoic acid
Petroselinic acid
18:1 cis-6
Identifiers
593-39-5 YesY
ChEBI CHEBI:28194
ChemSpider 4444569
EC Number 209-789-8
Jmol 3D model Interactive image
KEGG C08363
PubChem 5281125
  • InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)/b13-12-
    Key: CNVZJPUDSLNTQU-SEYXRHQNSA-N
  • InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)/b13-12-
    Key: CNVZJPUDSLNTQU-SEYXRHQNBP
  • CCCCCCCCCCC\C=C/CCCCC(O)=O
Properties
C18H34O2
Molar mass 282.47 g·mol−1
Appearance White powder
Insoluble
Solubility in methanol Soluble
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Petroselinic acid is a fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available.[1] In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated with a lipid number of 18:1 cis-6. It has the formula CH3(CH2)10CH=CH(CH2)4COOH. The term "petroselinic" means related to, or derived from, oil of Petroselinum, parsley. Petroselinic acid is an positional isomer of oleic acid.

Occurrence

Petroselinic was first isolated from parsley seed oil in 1909.[2] Petroselinic acid occurs in high amounts in plants in Apiaceae, Araliaceae,[3] Griselinia (Griseliniaceae)[4] and in Garryaceae.[5] In Picramniaceae, petroselinic acid is accompanied by tariric acid.[6] In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources.[7]

The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales.[8] Besides petroselinic acid, oleic acid has been shown to be present in all cases examined.

Production and chemical behavior

Fatty acids mostly occur as their esters, commonly the triglycerides, which are the greasy materials in many natural oils. Via the process of saponification, the fatty acids can be obtained.

The trans isomer of petroselinic acid is called petroselaidic acid.

In chemical analysis, petroselinic acid can be separated from other fatty acids by gas chromatography of methyl esters; additionally, a separation of unsaturated isomers is possible by argentation thin-layer chromatography.[9]

Uses

Petroselinic acid can be used in cosmetics.[10]

References

  1. ↑ ChemicalBook [1]
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Kosmetische Verwendung von Petroselinsäure, Patent DE69927466T3
Retrieved from "https://infogalactic.com/w/index.php?title=Petroselinic_acid&oldid=688712851"