Petroselinic acid

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. Despite its name, petroselinic acid does not contain any selenium. Petroselinic acid is a positional isomer of oleic 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-Δ^6-Octadecenoic acid Petroselinic acid 18:1 cis-6
Identifiers
CAS Number	593-39-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28194
ChemSpider	4444569
ECHA InfoCard	100.008.901
EC Number	209-789-8
KEGG	C08363
PubChem CID	5281125
UNII	3A10DOC461
InChI 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
SMILES CCCCCCCCCCC\C=C/CCCCC(O)=O
Properties
Chemical formula	C18H34O2
Molar mass	282.468 g·mol^−1
Appearance	White powder
Solubility in water	Insoluble
Solubility in methanol	Soluble
Hazards
Safety data sheet	MSDS from Sigma-Aldrich
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26-S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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
2. E. Vongerichten & A. Köhler (1909). "Über Petroselinsäure, eine neue Ölsäure". Berichte der Deutschen Chemischen Gesellschaft. 42 (2): 1638–1639. doi:10.1002/cber.19090420232.
3. F. C. Palazzo & A. Tamburello (1914). "Sopra l'acido iso-oleico dei semi di edera". Atti della Accademia Nazionale die Lincei. Rendiconti. Classe di Science Fisiche, Matematiche e Naturali. 5 (23): 352.
4. B. Breuer; T. Stuhlfauth; H. Fock; H. Huber (1987). "Fatty acids of some cornaceae, hydrangeaceae, aquifoliaceae, hamamelidaceae and styracaceae". Phytochemistry. 26 (5): 1441–1445. doi:10.1016/S0031-9422(00)81830-0.
5. R. Kleiman & G. Spencer (1982). "Search for new industrial oils". Journal of the American Oil Chemists' Society. 59: 29–38. doi:10.1007/BF02670064. S2CID 83792062.
6. M. Tsujimoto & H. Koyanagi (1933). "On Nigaki Oil". Bulletin of the Chemical Society of Japan. 8 (5): 161–167. doi:10.1246/bcsj.8.161.
7. Thomas Stuhlfauth (1984). "Chemosystematische Untersuchungen zur Fettsäurezusammensetzung von Frucht- und Samenölen der Pittosporaceen sowie einiger Arten der Rutales und Araliales, dissertation". University of Kaiserslautern, Germany: 52–55. Cite journal requires |journal= (help)
8. T. Stuhlfauth; H. Fock; H. Huber; . K. Klug (1985). "The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the pittosporaceae, araliaceae, umbelliferae, simaroubaceae and rutaceae". Biochemical Systematics and Ecology. 13 (4): 447–453. doi:10.1016/0305-1978(85)90091-2.
9. B. Breuer, T. Stuhlfauth & H. P. Fock (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography". Journal of Chromatographic Science. 25 (7): 302–306. doi:10.1093/chromsci/25.7.302. PMID 3611285.
10. Kosmetische Verwendung von Petroselinsäure, Patent DE69927466T3