Ricinoleic acid

Last updated
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
AppearanceYellow viscous liquid
Density 0.945 g/cm3
Melting point 5 °C (41 °F; 278 K)
Boiling point 245 °C (473 °F; 518 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point 228 °C (442 °F; 501 K)
Safety data sheet (SDS) Fisher Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 the seeds of castor plant (Ricinus communis L., Euphorbiaceae), the plant that produces ricin. It is also found in the sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the ricinolein.

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 often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. 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">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound 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">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<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">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 ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, 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.

<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 due to the presence of impurities. 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 a common component of oils, and thus occurs in many types of food, as well as in soap.

<span class="mw-page-title-main">Allyl group</span> Chemical group (–CH₂–CH=CH₂)

In organic chemistry, an allyl group is a substituent with the structural formula −CH2−HC=CH2. It consists of a methylene bridge attached to a vinyl group. The name is derived from the scientific name for garlic, Allium sativum. In 1844, Theodor Wertheim isolated an allyl derivative from garlic oil and named it "Schwefelallyl". The term allyl applies to many compounds related to H2C=CH−CH2, some of which are of practical or of everyday importance, for example, allyl chloride.

<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.

In organic chemistry, a homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series. A homologous series is a group of compounds that differ by a constant unit, generally a methylene group. The reactants undergo a homologation when the number of a repeated structural unit in the molecules is increased. The most common homologation reactions increase the number of methylene units in saturated chain within the molecule. For example, the reaction of aldehydes or ketones with diazomethane or methoxymethylenetriphenylphosphine to give the next homologue in the series.

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   978-1-4200-0967-5.
  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. ISBN   3-527-30673-0.
  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