petroselinic acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 416953907

| Name = Petroselinic acid

| ImageFile = Petroselinic acid.svg

| ImageSize = 250px

| ImageName = Petroselinic acid

| PIN = (6Z)-Octadec-6-enoic acid

| OtherNames = (6Z)-Octadecenoic acid
(Z)-Octadec-6-enoic acid
cis-6-Octadecenoic acid
cis6-Octadecenoic acid
Petroselinic acid
18:1 cis-6

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 593-39-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3A10DOC461

| EINECS = 209-789-8

| PubChem = 5281125

| ChemSpiderID = 4444569

| RTECS =

| MeSHName =

| ChEBI = 28194

| KEGG = C08363

| 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-

| InChIKey = CNVZJPUDSLNTQU-SEYXRHQNBP

| StdInChI = 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-

| StdInChIKey = CNVZJPUDSLNTQU-SEYXRHQNSA-N

| SMILES = CCCCCCCCCCC\C=C/CCCCC(O)=O

}}

|Section2={{Chembox Properties

| C=18 | H=34 | O=2

| Appearance = White powder

| Density =

| Solubility = Insoluble

| SolubleOther = Soluble

| Solvent = methanol

| BoilingPtC =

| BoilingPt_notes =

| pKa =

| pKb =

| Viscosity =

}}

|Section3={{Chembox Structure

| MolShape =

| Coordination =

| CrystalStruct =

| Dipole =

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.sigmaaldrich.com/catalog/product/sigma/p8750 MSDS from Sigma-Aldrich]

| MainHazards =

| FlashPt =

| GHS_ref={{cite web |title=Petroselinic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/5281125#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=13 December 2021 |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

}}

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherCompounds =

}}

}}

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.[http://www.chemicalbook.com/ChemicalProductProperty_EN_CB5355794.htm ChemicalBook] 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.

Occurrence

Petroselinic was first isolated from parsley seed oil in 1909.{{cite journal |author1=E. Vongerichten |author2=A. Köhler |name-list-style=amp | title = Über Petroselinsäure, eine neue Ölsäure | journal = Berichte der Deutschen Chemischen Gesellschaft| volume = 42 | year = 1909 | pages = 1638–1639 | doi = 10.1002/cber.19090420232 | issue = 2| url = https://zenodo.org/record/1426349 }} Petroselinic acid occurs in high amounts in plants in Apiaceae, Araliaceae,{{cite journal |author1=F. C. Palazzo |author2=A. Tamburello |name-list-style=amp | title = Sopra l'acido iso-oleico dei semi di edera | journal = Atti della Accademia Nazionale die Lincei. Rendiconti. Classe di Science Fisiche, Matematiche e Naturali | volume = 5 | issue = 23 | year = 1914 | pages = 352}} Griselinia (Griseliniaceae){{cite journal |author1=B. Breuer |author2=T. Stuhlfauth |author3=H. Fock |author4=H. Huber | title = Fatty acids of some cornaceae, hydrangeaceae, aquifoliaceae, hamamelidaceae and styracaceae | journal = Phytochemistry | volume = 26 | year = 1987 | pages = 1441–1445 | doi = 10.1016/S0031-9422(00)81830-0 | issue = 5|bibcode=1987PChem..26.1441B }} and in Garryaceae.{{cite journal |author1=R. Kleiman |author2=G. Spencer |name-list-style=amp | title = Search for new industrial oils | journal = Journal of the American Oil Chemists' Society| volume = 59 | year = 1982 | pages = 29–38 | doi = 10.1007/BF02670064|s2cid=83792062 }} In Picramniaceae, petroselinic acid is accompanied by tariric acid.{{cite journal |author1=M. Tsujimoto |author2=H. Koyanagi |name-list-style=amp | title = On Nigaki Oil | journal = Bulletin of the Chemical Society of Japan| volume = 8 | year = 1933 | pages = 161–167 | doi = 10.1246/bcsj.8.161 | issue = 5| doi-access = free }} In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources.{{cite journal | author = Thomas Stuhlfauth | title = Chemosystematische Untersuchungen zur Fettsäurezusammensetzung von Frucht- und Samenölen der Pittosporaceen sowie einiger Arten der Rutales und Araliales, dissertation | journal=Academic Dissertation | publisher = University of Kaiserslautern, Germany | year = 1984 | pages = 52–55}}

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.{{cite journal |author1=T. Stuhlfauth |author2=H. Fock |author3=H. Huber |author4=. K. Klug | title = The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the pittosporaceae, araliaceae, umbelliferae, simaroubaceae and rutaceae | journal = Biochemical Systematics and Ecology | volume = 13 | issue = 4 | year = 1985 | pages = 447–453 | doi = 10.1016/0305-1978(85)90091-2|bibcode=1985BioSE..13..447S }} 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.{{cite journal |author1=B. Breuer, T. Stuhlfauth |author2=H. P. Fock |name-list-style=amp | title = Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography | journal = Journal of Chromatographic Science| volume = 25 | year = 1987 | pages = 302–306 | doi = 10.1093/chromsci/25.7.302 | issue = 7 | pmid=3611285}}

Uses

Petroselinic acid can be used in cosmetics.[http://www.patent-de.com/20100211/DE69927466T3.html Kosmetische Verwendung von Petroselinsäure], Patent DE69927466T3

References