Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic 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 ...
. 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 fat ...
and a
hydroxy acid. It is a major component of the seed oil obtained from mature
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 a genus in the family. Most spurges, such as ''Euphorbia paralias'', are herbs, but some, e ...
) seeds or in sclerotium 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 ca ...
(''Claviceps purpurea'' Tul.,
Clavicipitaceae
The Clavicipitaceae are a family of fungi within the order Hypocreales. A 2008 estimate placed 43 genera in the family, but recent work has increased this number to 97.
Phylogeny
Molecular phylogenetic analysis of multigene DNA sequence data ...
). About 90% of the fatty acid content in
castor oil
Castor oil is a vegetable oil pressed from castor beans.
It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about ...
is the
triglyceride formed from ricinoleic acid.
Production
Ricinoleic acid is manufactured for industries by
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. ...
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 to ...
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 hydrolysis ...
castor oil.
The first attempts to prepare ricinoleic acid were made by
Friedrich Krafft
Friedrich Krafft (February 21, 1852 in Bonn – June 3, 1923 in Heidelberg) was a German chemist. He studied with Friedrich August Kekulé von Stradonitz, Rudolf Clausius and Gerhard vom Rath.
In colloidal chemistry, the Krafft temperature ...
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. ...
((CH
2)
8(CO
2H)
2), which is used in preparing certain
nylon
Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic.
Nylon is a silk-like thermoplastic, generally made from petro ...
s, is produced by cleavage of ricinoleic acid. The coproduct is
2-octanol.
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 due to bacterial breakdown of perspiration or vaginal secretions, for example in the armpits, groin, or feet. A subclass of deodorants, called antiperspirants, prevents s ...
s.
Biological activities
Ricinoleic acid exerts
analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
and
anti-inflammatory
Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as o ...
effects.
Ricinoleic acid specifically activates the
EP3 prostanoid receptor for
prostaglandin E2
Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin with oxytocic properties that is used as a medication. Dinoprostone is used in labor induction, bleeding after delivery, termination of pregnancy, and ...
.
Ricinoleic acid acts as a specific algicide for the control of cyanobacteria (formerly called blue-green algae).
See also
*
Castor oil
Castor oil is a vegetable oil pressed from castor beans.
It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about ...
*
Lesquerolic acid
Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in ''Paysonia lasiocarpa'' and other '' Paysonia'' and ''Physaria'' species. This compound has the ''R'' configuration at the alcohol-bearing stereocenter, and it is of the ''Z'' ...
, a similar chemical, which could be described as ricinoleic acid with -CH
2-CH
2- group inserted between carboxyl group and the double bound.
*
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 substa ...
, a
polymer
A polymer (; Greek '' poly-'', "many" + ''-mer'', "part")
is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
of
glycerol
Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
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. Altho ...
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:
Arts, entertainment, and media
* Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom
* ''Trans'' (film ...
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 mu ...
, 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 ...
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 with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantitie ...
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
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...
of ricinoleic acid
References
{{Prostanoid signaling modulators
Fatty acids
Hydroxy acids
Castor oil plant