Ricinoleic acid Chemical Properties

Melting point:

22.5-24.5℃

alpha 

D22 +6.67°; D26 +7.15° (c = 5 in acetone)

Boiling point:

bp10 245°

Density 

0.940 g/mL at 20 °C(lit.)

refractive index 

1.4740 (589.3 nm, 25℃)

Flash point:

248°C

storage temp. 

-20°C

solubility 

Ethanol

pka

4.78±0.10(Predicted)

form 

Liquid

Specific Gravity

0.943 (20/4℃)

color 

Colorless to Red to Green

optical activity

[α]/D 6.5±1.5°, c = 2 in acetone

Merck 

14,8211

BRN 

1727813

Stability:

Light Sensitive

InChIKey

WBHHMMIMDMUBKC-GKUQOKNUSA-N

LogP

5.607 (est)

CAS DataBase Reference

141-22-0(CAS DataBase Reference)

EPA Substance Registry System

9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)- (141-22-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

VJ3150000

HS Code 

29181990

Hazardous Substances Data

141-22-0(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Ricinoleic acid Usage And Synthesis

Description

Ricinoleic acid is an unsaturated omega-9 fatty acid and is an important component of the seed oil obtained from mature castor plants seeds. The compound is produced for industries by fractional distillation or saponification of hydrolysed castor oil. It is normally used in manufacturing personal care products such as deodorants. Much of ricinoleic acid characteristics and effects can be associated with castor oil.

Chemical Properties

Colorless to yellow, viscous liquid.Soluble in most organic solvents; insoluble in water. Com- bustible.

Chemical Properties

Ricinoleic acid (synonym castor oil fatty acid) is an unsaturated fatty acid prepared from castor oil. When Ricinoleic acid is pyrolyzed (heated in the absence of air), it breaks down in undecylenic acid and n-heptaldehyde.
appearance yellowish, clear, viscous liquid
specific gravity (at 25°C) 0.938 - 0.944
refractive index (at 25°C) 1.4695 - 1.4700
acid value mg KOH/g min.175
iodine value 82 - 90
saponification value mg KOH/g 180 - 190
hydroxyl value 150 - 160
unsaponifiable matter max. 1
colour Gardner max. 7

Uses

1. soaps: Ricinoleic acid can be reacted with various bases (caustic, ammonia, ethanolamines, etc.) to produce soaps having the desired characteristics (solubility, physical characteristics, polarity, etc.) depending on the final application. Some of them are: cutting oils, industrial lubricants, emulsifiers and metal working fluids. Transparent bar soaps & high solids liquids soaps are made possible by using Ricinoleic acid. The same for industrial germicides, disinfectants and heavy duty detergents (solubilization of phenolic and cresylic bodies).
2. surface coating: it is used as an efficient pigment/dye dispersants in inks, coatings, plastics, cosmetics, etc.
3. textiles: Ricinoleic acid provides polarity, surface wetting and lubricity.
4. rubber: the sodium/potassium soaps of Ricinoleic acid are emulsifiers and foam stabilizers.
5. vinyl polymers: it's sodium soap is useful as emulsifier, stabilizer and defoamer for emulsion polymerization of resins such as PVC & PVAc
6. food additives: it's used in the production of PGPR (polyglycerol polyricinoleate) for use in chocolate.

Uses

Soaps, Turkey red oil, textile finishing, source of sebacic acid and heptanol, ricinoleate salts, 12- hydroxystearic acid.

Uses

Ricinolic Acid is a metabolite of linoleic acid from Lactobacilli and has antifungal activity in bread. Ricinolic Acid is also a metabolite of castor oil and has shown to activate intestinal and uterine smooth-muscle cells through EP3 prostanoid receptors inducing diarrhea and labor in pregnant females.

Definition

ChEBI: Ricinoleic acid is a (9Z)-12-hydroxyoctadec-9-enoic acid in which the 12-hydroxy group has R-configuration. It is a conjugate acid of a ricinoleate. It is a C18 unsaturated fatty acid that comprises 80% of the fatty acid content of castor oil.

Carcinogenicity

Four rabbits given intermittent subcutaneous injections of 3120 mg/kg ricinoleic acid for 52 weeks developed subcutaneous neoplasms. The tumorigenic potential of ricinoleic acid injected intravaginally in groups of 20 mice was also studied. No tumors attributable to ricinoleic acid treatment were observed in three studies after 18–20 months.

Purification Methods

Purify it as the methyl acetylricinoleate [Rider J Am Chem Soc 53 4130 1931], fractionally distilling it at 180-185o/0.3mm, then 87g of this ester is hydrolysed by refluxing with KOH (56g), water (25mL), and MeOH (250mL) for 10minutes. The free acid is separated on acidification and extracted into Et2O, dried (Na2SO4), filtered, evaporated and the residue is crystallised from acetone at -50o, and distilled in small batches, b 180o/0.005mm. The R-enantiomer has m +5.5o, b 245o/10mm and [] 26D +7.2o (c 5, Me2CO). [Bailey et al. J Chem Soc 3027 1957, Beilstein 3 IV 1026, 1207.]

Ricinoleic acid(141-22-0)Related Product Information

• RICINOLEIC ACID
• Methyl 12-hydroxyoleate, Ricinoleic acid methyl ester, (R)-12-Hydroxy-cis-9-octadecenoic acid methyl ester,RICINOLEIC ACID METHYL ESTER
• RICINOLEIC ACID CETYL ESTER,RICINOLEIC ACID N-HEXADECYL ESTER,Ricinoleic Acid Hexadecyl Ester
• RICINOLEIC ACID 2-HYDROXYETHYL ESTER
• Sodium ricinolate
• RICINOLEIC ACID ETHYL ESTER,Ricinoleic acid ethyl ester, (R)-12-Hydroxy-cis-9-octadecenoic acid ethyl ester
• RICINOLEIC ACID CALCIUM SALT
• MAGNESIUM RICINOLEATE
• PROPYLENE GLYCOL MONORICINOLEATE
• Ricinoleic acid
• POLYGLYCERYL-3 POLYRICINOLEATE
• Ricinoleic acid isopropyl ester
• [R-(Z)]-3-[(12-hydroxy-1-oxo-9-octadecenyl)amino]propyltrimethylammonium methyl sulphate
• 12-HYDROXYSTEARIC ACID
• RICINOLEIC ACID BUTYL ESTER,RICINOLEIC ACID N-BUTYL ESTER
• GLYCEROL TRIACETYLRICINOLEATE
• Ricinoleamide DEA
• POLYGLYCERYL-6 RICINOLEATE