Ricinolein

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Ricinolein
Triricinolein Structural Formulae V1.svg
Names
Systematic IUPAC name
Propane-1,2,3-triyl tris[(9Z,12R)-12-hydroxyoctadec-9-enoate]
Other names
Glycerin triricinoleate; Glycerol triricinoleate; Glyceryl triricinoleate; Ricinoleic acid triglyceride; Ricinoleic triglyceride; Triricinolein
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.018.016 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-817-0
PubChem CID
UNII
  • InChI=1S/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27-/t51-,52-,53-/m1/s1
  • O=C(CCCCCCC/C=C\C[C@H](O)CCCCCC)OCC(OC(CCCCCCC/C=C\C[C@H](O)CCCCCC)=O)COC(CCCCCCC/C=C\C[C@H](O)CCCCCC)=O
Properties
C57H104O9
Molar mass 933.450 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ricinolein is the chief constituent of castor oil and is the triglyceride of ricinoleic acid. [1] Castor oil, the expressed natural fatty oil of the seeds of Ricinus communis also contains mixtures of the glycerides of isoricinoleic acids and much smaller traces of tristearin and the glyceride of dihydroxysteric acid. Ricinolein is the active principle in the use of castor oil as a purgative and solvent for several medically useful alkaloids.

Related Research Articles

<i>Ricinus</i> Monotypic genus of plant in the family Euphorbiaceae

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 castor and its relation to other species are currently being studied using modern genetic tools. It reproduces with a mixed pollination system which favors selfing by geitonogamy but at the same time can be an out-crosser by anemophily or entomophily.

<span class="mw-page-title-main">Castor oil</span> Vegetable oil obtained by pressing the seeds of the Castor plant

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">Sebacic acid</span> Chemical compound

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula (CH2)8(CO2H)2. 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.

<span class="mw-page-title-main">Alkyd</span> Polyester resin modified by the addition of fatty acids and other components

An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and organic acids. The inclusion of a fatty acid confers a tendency to form flexible coatings. Alkyds are used in paints, varnishes and in moulds for casting. They are the dominant resin or binder in most commercial oil-based coatings. Approximately 200,000 tons of alkyd resins are produced each year. The original alkyds were compounds of glycerol and phthalic acid sold under the name Glyptal. These were sold as substitutes for the darker-colored copal resins, thus creating alkyd varnishes that were much paler in colour. From these, the alkyds that are known today were developed.

Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid functional group. It is a colorless oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Salts and esters of enanthic acid are called enanthates or heptanoates.

Kolliphor EL', formerly known as Cremophor EL, is the registered trademark of BASF Corp. for its version of polyethoxylated castor oil. It is prepared by reacting 35 moles of ethylene oxide with each mole of castor oil. The resulting product is a mixture : the major component is the material in which the hydroxyl groups of the castor oil triglyceride have ethoxylated with ethylene oxide to form polyethylene glycol ethers. Minor components are the polyethyelene glycol esters of ricinoleic acid, polyethyelene glycols and polyethyelene glycol ethers of glycerol. Kolliphor EL is a synthetic, nonionic surfactant used to stabilize emulsions of nonpolar materials in water.

<span class="mw-page-title-main">Polyglycerol polyricinoleate</span> Emulsion used in food production

Polyglycerol polyricinoleate (PGPR), E476, is an emulsifier made from glycerol and fatty acids. In chocolate, compound chocolate and similar coatings, PGPR is mainly used with another substance like lecithin to reduce viscosity. It is used at low levels, and works by decreasing the friction between the solid particles in molten chocolate, reducing the yield stress so that it flows more easily, approaching the behaviour of a Newtonian fluid. It can also be used as an emulsifier in spreads and in salad dressings, or to improve the texture of baked goods. It is made up of a short chain of glycerol molecules connected by ether bonds, with ricinoleic acid side chains connected by ester bonds.

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.

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

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from castor plant seeds and is also found in the sclerotium of ergot. About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

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.

In enzymology, a phosphatidylcholine 12-monooxygenase (EC 1.14.13.26) is an enzyme that catalyzes the chemical reaction

Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.

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

Zinc ricinoleate is the zinc salt of ricinoleic acid, a major fatty acid found in castor oil. It is used in many deodorants as an odor-adsorbing agent. The mechanism of this activity is unclear.

The molecular formula C18H34O3 (molar mass: 298.46 g/mol, exact mass: 298.2508 u) may refer to:

<span class="mw-page-title-main">Diglyceride</span> Type of fat derived from glycerol and two fatty acids

A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. DAGs can act as surfactants and are commonly used as emulsifiers in processed foods. DAG-enriched oil has been investigated extensively as a fat substitute due to its ability to suppress the accumulation of body fat; with total annual sales of approximately USD 200 million in Japan since its introduction in the late 1990s till 2009.

<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.

Hydroxycarboxylic acids are carboxylic acids containing one or more hydroxy (alcohol) functional groups. They are of particular interest because several are bioactive and some are useful precursors to polyesters. The inventory is large.

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. Achaya, K. T.; Saletore, S. A. (1952). "Triricinolein and ricinoleic acid from castor oil". Journal of Scientific & Industrial Research. 11B (11): 471–474.