Petroselinic acid is a

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

that occurs naturally in several

animal Animals are multicellular, eukaryotic organisms in the Kingdom (biology), biological kingdom Animalia. With few exceptions, animals Heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, are Motilit ...

and

vegetable fats and oils Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fat ...

. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a

monounsaturated In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple est ...

omega-12 fatty acid, abbreviated with a

lipid number In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

of 18:1

cis Cis or cis- may refer to: Places * Cis, Trentino, in Italy * In Poland: ** Cis, Świętokrzyskie Voivodeship, south-central ** Cis, Warmian-Masurian Voivodeship, north Math, science and biology * cis (mathematics) (cis(''θ'')), a trigonome ...

-6. It has the formula CH₃(CH₂)₁₀CH=CH(CH₂)₄COOH. The term "petroselinic" means related to, or derived from,

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...

of ''

Petroselinum ''Petroselinum'' (parsley) is a genus of two species of flowering plants in the family Apiaceae, native to western and southern Europe and northern Africa.The Euro+Med Plantbase Project''Petroselinum''/ref> They are bright green hairless biennial ...

'',

parsley Parsley, or garden parsley (''Petroselinum crispum'') is a species of flowering plant in the family Apiaceae that is native to the central and eastern Mediterranean region (Sardinia, Lebanon, Israel, Cyprus, Turkey, southern Italy, Greece, Por ...

. Despite its name, petroselinic acid does not contain any

selenium Selenium is a chemical element with the symbol Se and atomic number 34. It is a nonmetal (more rarely considered a metalloid) with properties that are intermediate between the elements above and below in the periodic table, sulfur and tellurium, ...

. Petroselinic acid is a positional

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega ...

Occurrence

Petroselinic was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in

Apiaceae Apiaceae or Umbelliferae is a family of mostly aromatic flowering plants named after the type genus ''Apium'' and commonly known as the celery, carrot or parsley family, or simply as umbellifers. It is the 16th-largest family of flowering plants ...

Araliaceae The Araliaceae are a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants. The morphology of Araliaceae varies widely, but it is predominantly distinguisha ...

Griselinia ''Griselinia'' is a genus of seven species of shrubs and trees, with a highly disjunct distribution native to New Zealand and South America. It is a classic example of the Antarctic flora. It is the sole genus in the family Griseliniaceae; in th ...

(Griseliniaceae) and in

Garryaceae Garryaceae is a small family of plants known commonly as the silktassels.Garryaceae.
Flora o ...

. In

Picramniaceae Picramniaceae is a small, mainly neotropical family of four genera '' Aenigmanu'', ''Alvaradoa'', '' Nothotalisia'' and '' Picramnia''. The family is the only member of the order Picramniales. Members of the family were formerly placed in the fa ...

, petroselinic acid is accompanied by tariric acid. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. 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 The Apiales are an order of flowering plants. The families are those recognized in the APG III system. This is typical of the newer classifications, though there is some slight variation and in particular, the Torriceliaceae may also be divide ...

as well as within the

Garryales The Garryales are a small order of dicotyledons, including only two families and three genera. Description Garryales are woody plants that are either hairless or have very fine hairs. Members of the family Garryaceae are evergreen, whereas thos ...

. 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

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s, commonly the

triglyceride A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as w ...

s, which are the greasy materials in many natural oils. Via the process of

saponification Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...

, 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 Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for separating and analyzing compounds that can be vaporized without decomposition. Typical uses of GC include testing the purity of a particular substance, ...

of methyl esters; additionally, a separation of unsaturated isomers is possible by argentation thin-layer chromatography.

Uses

Petroselinic acid can be used in cosmetics.Kosmetische Verwendung von Petroselinsäure
Patent DE69927466T3

References

{{Fatty acids Fatty acids Alkenoic acids