Ricinoleic Acid
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Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic acid, is a
fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
. It is an unsaturated
omega-9 fatty acid Omega−9 fatty acids (ω−9 fatty acids or ''n''−9 fatty acids) are a family of unsaturated fatty acids which have in common a final carbon–carbon double bond in the omega−9 position; that is, the ninth bond from the methyl end of the f ...
and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of
castor plant ''Ricinus communis'', the castor bean or castor oil plant, is a species of perennial flowering plant in the spurge family, Euphorbiaceae. It is the sole species in the monotypic genus, ''Ricinus'', and subtribe, Ricininae. The evolution of ca ...
(''Ricinus communis'' L.,
Euphorbiaceae Euphorbiaceae (), the spurge family, is a large family of flowering plants. In English, they are also commonly called euphorbias, which is also the name of Euphorbia, the type genus of the family. Most spurges, such as ''Euphorbia paralias'', ar ...
), the plant that produces
ricin Ricin ( ) is a lectin (a carbohydrate-binding protein) and a highly potent toxin produced in the seeds of the castor oil plant, ''Ricinus communis''. The median lethal dose (LD50) of ricin for mice is around 22 micrograms per kilogram of body ...
. It is also found in the
sclerotium A sclerotium (; : sclerotia () is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant u ...
of
ergot Ergot ( ) or ergot fungi refers to a group of fungi of the genus ''Claviceps''. The most prominent member of this group is '' Claviceps purpurea'' ("rye ergot fungus"). This fungus grows on rye and related plants, and produces alkaloids that c ...
(''Claviceps purpurea'' Tul.,
Clavicipitaceae The Clavicipitaceae are a family (biology), family of fungi within the order Hypocreales. A 2008 estimate placed 43 genus, genera in the family, but a study in 2020 has increased this number to 50. Phylogeny Molecular phylogeny, phylogenetic ana ...
). About 90% of the fatty acid content in
castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...
is the
ricinolein Ricinolein is the chief constituent of castor oil and is the triglyceride of ricinoleic acid. Castor oil, the expressed natural fatty oil of the seeds of ''Ricinus communis'' also contains mixtures of the glycerides of isoricinoleic acids and much ...
.


Production

Ricinoleic acid is manufactured for industries by
saponification Saponification is a process of cleaving esters into carboxylate salts and Alcohol (chemistry), alcohols by the action of aqueous alkali. Typically aqueous sodium hydroxide solutions are used. It is an important type of alkaline hydrolysis. When the ...
or
fractional distillation Fractional distillation is the separation of a mixture into its component parts, or fractions. Chemical compounds are separated by heating them to a temperature at which one or more fractions of the mixture will vaporize. It uses distillation ...
of
hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
castor oil. The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.


Use

Sebacic acid Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula . It is a white flake or powdered solid. ''Sebaceus'' is Latin for tallow candle, ''sebum'' is Latin for tallow, and refers to its use in the manufacture of candles. ...
((CH2)8(CO2H)2), which is used in preparing certain
nylon Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieti ...
s, is produced by cleavage of ricinoleic acid. The coproduct is
2-octanol 2-Octanol (octan-2-ol, 2-OH) is an organic compound with the chemical formula . It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is ...
. The mechanism of the base-induced cleavage is proposed to proceed by initial dehydrogenation of the secondary alcohol, affording the ketone. The resulting α,β-unsaturated ketone undergoes retroaldol reaction, resulting in lysis of the C-C bond. The zinc salt is used in personal care products such as
deodorant A deodorant is a substance applied to the body to prevent or mask body odor caused by bacterial breakdown of perspiration, for example in the armpits, groin, or feet. A subclass of deodorants, called antiperspirants, prevents sweating itself, t ...
s.Tom's of Maine – About Our Products
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See also

*
Castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...
*
Lesquerolic acid Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in '' Paysonia lasiocarpa'' and other '' Paysonia'' and ''Physaria'' species. The acid is typically found together with other hydroxylated fatty acids, such as densipolic, auric ...
, a similar chemical, which could be described as ricinoleic acid with -CH2-CH2- group inserted between carboxyl group and the double bond. *
Polyglycerol polyricinoleate Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids (usually from castor bean, but also from soybean oil). In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another subst ...
, a
polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
of
glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
with ricinoleic acid side chains, used as an
emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...
in chocolate *
Ricinelaidic acid Ricinelaidic acid or (+)-(''R'')-ricinelaidic acid is an unsaturated omega-9 trans fatty acid. It is the trans-isomer of the fatty acid ricinoleic acid. External links Information about ricinelaidic acidin ''Organic Syntheses ''Organic Syn ...
, the
trans isomer Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Sociology * Trans, a sociological term which may refer to: ** Transgender, people who identify themselves with a gender that dif ...
of ricinoleic acid *
Ricinolein Ricinolein is the chief constituent of castor oil and is the triglyceride of ricinoleic acid. Castor oil, the expressed natural fatty oil of the seeds of ''Ricinus communis'' also contains mixtures of the glycerides of isoricinoleic acids and much ...
, the
triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...
of ricinoleic acid *
Sodium ricinoleate Sodium ricinoleate is the sodium salt of ricinoleic acid, the principal fatty acid derived from castor oil. It is used in making soap, where its molecular structure causes it to lather more easily than comparable sodium soaps derived from fatty a ...
, the
sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
of ricinoleic acid *
Undecylenic acid Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the s ...
, a product of
pyrolysis Pyrolysis is a process involving the Bond cleavage, separation of covalent bonds in organic matter by thermal decomposition within an Chemically inert, inert environment without oxygen. Etymology The word ''pyrolysis'' is coined from the Gree ...
of ricinoleic acid


References

{{Prostanoid signaling modulators Fatty acids Hydroxy acids Castor oil plant