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Ricinoleic Acid

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Ricinoleic acid (12- hydroxy-9-cis-octadecenoic acid) is a light coloured, unsaturated omega-9 fatty acid that naturally occurs in mature castor plant (Ricinus communis L., Euphorbiaceae) which constitutes for about 90% of the castor oil. 

Production Process:

Ricinoleic acid is obtained from castor oil through hydrolysis, usually carried out under basic conditions. Industrially, ricinoleic acid is manufactured by saponification or fractional distillation of hydrolyzed castor oil. 

Ricinoleic acid serves as an excellent reactant for the synthesis of several different derivatives including Sebacic acid, Undecylenic acid, Methyl ricinoleate, Hydroxy stearic acid(HSA) etc. 

Chemical Properties 

Appearance

Clear Amber Liquid

Boiling Point

416.4 C

CAS Number

141-22-0

Density

0.94 g/mL

EINECS Number

205-470-2

IUPAC Name

(9Z,12R)-12-Hydroxyoctadec-9-Enoic Acid

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/s

InChIKey

WBHHMMIMDMUBKC-QJWNTBNXSA-N

Main Hazards

Irritant

Melting Point

< 10C

Molar Mass

298.46 g/mol

Molecular Formula

C18H34O3

RTECS Number

VJ3150000

Solubility

Slightly Soluble

Synonyms

9-Octadecenoicacid, 12-Hydroxy-, [R-(Z)]-;Ricinoleic Acid (8ci);(R)-12-Hydroxyoleic Acid;12-D-Hydroxy-9-Cis-Octadecenoic Acid;12-Hydroxy-Cis-9-Octadecenoic Acid;12-Hydroxyoctadeca-9-Enoic Acidic 80;Cenwax C;Edenor Ri 90;Nsc 281242;Nouracid Cs 80;Ricinic Acid;Ricinolic Acid

 Applications 

         Primary uses include, coatings, plastics, inks and cosmetics.

         Poly (anhydrides) is hydrolytically degradable polymers which have been used as vehicles for controlled delivery of drugs. A new class of biodegradable polyanhydrides based on ricinoleic acid has been synthesized

         Ricinoleic acid is effective in preventing the growth of numerous species of viruses, bacteria, yeasts, and molds. It's successful as a topical treatment for ringworm, keratoses, skin inflammation, abrasions, fungal-infected finger- and toenails, acne, and chronic pruritus (itching). Generally, for these conditions the affected area is wrapped each night in a castor oil-soaked cloth. Ricinoleic acid is used also as a bactericide. Hence, washing wounds with ricinoleic acid at prescribed dilution levels is sometimes recommended.

          Ricin acts as a blood coagulant

          Macrolactones and polyesters can be derived from ricinoleic acid

         Ricinoleic acid has been used in contraceptive jellies

         Used in soaps, amine compounds, esters in cutting oils, industrial lubricants, emulsifiers, metal working compounds.

         Ricinoleate soaps have been patented as algaecides for aquaculture systems.

         Used in dispersion of pigments and dyes.

         Used in resins, thermosetting acrylics and non-drying plasticizing esters.

         Quaternary ammonium compounds based on ricinoleates and hydroxy stearates have been used in for cosmetics skin and hair care, personal products, germicides and textile processing agents.