Ricinoleic acid

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Ricinoleic acid
Ricinoleic acid.svg
Names
Preferred IUPAC name
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names
(R)-12-Hydroxy-9-cis-octadecenoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.974 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1 Yes check.svgY
    Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N Yes check.svgY
  • InChI=1/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1
    Key: WBHHMMIMDMUBKC-QJWNTBNXBT
  • O=C(O)CCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
C18H34O3
Molar mass 298.461 g/mol
Density 0.945 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid [1] and a hydroxy acid. It is a major component of the seed oil obtained from castor plant (Ricinus communis L., Euphorbiaceae) seeds and is also found in the sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

Contents

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil. [2]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888. [3]

Use

Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain nylons, is produced by cleavage of ricinoleic acid. The coproduct is 2-octanol. [4] [5] 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. [6]

The zinc salt is used in personal care products such as deodorants. [7]

See also

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Fatty acid</span> Carboxylic 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, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

<span class="mw-page-title-main">Castor oil</span> Vegetable oil pressed from castor beans

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 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleic acid and linoleic acid are the other significant components.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. It is a major component of the oil from the fruit of oil palms, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty 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-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is part of many oils and thus used in a lot of artificial food, as well as for soap.

<span class="mw-page-title-main">Sebacic acid</span> Chemical compound

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. 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. Sebacic acid is a derivative of castor oil.

The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step. As such, there is no obvious retron for this reaction. The reaction was reported by Nikolai Kischner in 1911 and Ludwig Wolff in 1912.

In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.

Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.

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 skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

Natural oil polyols, also known as NOPs or biopolyols, are polyols derived from vegetable oils by several different techniques. The primary use for these materials is in the production of polyurethanes. Most NOPs qualify as biobased products, as defined by the United States Secretary of Agriculture in the Farm Security and Rural Investment Act of 2002.

Decomposition in animals is a process that begins immediately after death and involves the destruction of soft tissue, leaving behind skeletonized remains. The chemical process of decomposition is complex and involves the breakdown of soft tissue, as the body passes through the sequential stages of decomposition. Autolysis and putrefaction also play major roles in the disintegration of cells and tissues.

<span class="mw-page-title-main">Sodium ricinoleate</span> Chemical compound

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 acids. It is a bactericide. It exhibits several polymorphic structural phases.

<span class="mw-page-title-main">2-Octanol</span> Chemical compound

2-Octanol is an organic compound with the chemical formula CH3CH(OH)(CH2)5CH3. 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 chiral.

11-Aminoundecanoic acid is an organic compound with the formula H2N(CH2)10CO2H. This white solid is classified as an amine and a fatty acid. 11-Aminoundecanoic acid is a precursor to Nylon-11.

Wuhanic acid is a 24-carbon dihydroxy fatty acid with the chemical formula C
24
H
44
O
4
and molecular weight 396.6 g/mol.

References

  1. Frank D. Gunstone; John L. Harwood; Albert J. Dijkstra (2007). The Lipid Handbook. CRC Press. p. 1472. ISBN   978-1420009675.
  2. James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95 (2): 448–52. doi:10.1042/bj0950448. PMC   1214342 . PMID   14340094.
  3. Rider, T. H. (November 1931). "The Purification of Sodium Ricinoleate". Journal of the American Chemical Society . 53 (11): 4130–4133. doi:10.1021/ja01362a031.
  4. Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.
  5. Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.
  6. Diamond, M. J.; Binder, R. G.; Applewhite, T. H. (1965). "Alkaline cleavage of hydroxy unsaturated fatty acids. I. Ricinoleic acid and lesquerolic acid". Journal of the American Oil Chemists' Society. 42 (10): 882–884. doi:10.1007/BF02541184. S2CID   85036911.
  7. Tom's of Maine - About Our Products