Ricinoleic acid

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Ricinoleic acid
Names
IUPAC name
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names
(R)-12-Hydroxy-9-cis-octadecenoic acid
12-Hydroxy-9-cis-octadecenoic acid
Ricinelaidic acid
Ricinic acid
Properties
C18H34O3
Molar mass 298.461 g/mol
Appearance Colorless oily liquid
Odor Odorless
Density 0.945 g/cm3 (20 °C)[1]
Melting point 5.5 °C (41.9 °F; 278.6 K) [3]
Boiling point 242 °C (468 °F; 515 K) [2]
0.346 g/100 ml (at 25 °C)
Solubility Miscible with benzene, chloroform, diethyl ether
Vapor pressure 4.49·10-3 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 224 °C (435.2 °F; 497 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ricinoleic acid, is an unsaturated omega-9 hydroxy fatty acid. It is a major component of the seed oil obtained from mature castor plant seeds (Ricinus communis L., Euphorbiaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid. The compound is chiral and occurs naturally as the dextro isomer.

Properties

Chemical

The compounds can be hydrolyzed to various long chain alcohols.

Physical

Ricinoleic acid is a colorless viscous liquid, immiscible with water but miscible with many organic solvents.

Availability

Ricinoleic acid is sold by chemical suppliers.

Can be easily obtained from castor oil.

Preparation

Ricinoleic acid can be easily made by saponification of castor oil. For better purification, fractional distillation can be employed.

Projects

  • Make deodorant
  • Make sodium ricinoleate
  • Make zinc ricinoleate
  • Make methyl ricinoleate

Handling

Safety

Ricinoleic acid has low toxicity, though like it's parent oil it's a powerful laxative if ingested.

Since ricin, the toxic protein from the castor beans, is insoluble in castor oil and most organic solvents, there is no risk of poisoning, if you're exposed to crude castor oil or ricinoleic acid.

Storage

Ricinoleic acid is best kept in closed plastic or glass bottles.

Disposal

No special disposal is required. Can be burned or poured down the drain.

References

  1. Straus; Heinze; Salzmann; Chemische Berichte; vol. 66; (1933); p. 638
  2. Narasimhan; Kothawade; Pharande; Mourya; Dhake; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 11; (2003); p. 2828 - 2834
  3. Ibrahim, Sarah A.; Li, S. Kevin; Pharmaceutical Research; vol. 27; nb. 1; (2010); p. 115 - 125

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