| Identification | More | [Name]
RICINOLEIC ACID | [CAS]
141-22-0 | [Synonyms]
12-HYDROXY-9-OCTADECENOIC ACID
(+)-12-HYDROXYOLEIC ACID
12-HYDROXYOLEIC ACID
DELTA 9 CIS 12 HYDROXY OCTADECENOIC ACID
[R]-12-HYDROXY-CIS-9-OCTADECANOIC ACID
[R]-12-HYDROXY-CIS-9-OCTADECENOIC ACID
RICINOLEIC ACID
RICINOLIC ACID
(9Z)-12-Hydroxy-9-octadecenoic acid
(r-(z))-9-octadecenoicaci
[r-(z)]-12-hydroxy-9-octadecenoicacid
[theta-(z)]-9-octadecenoicaci
12-hydroxy-,[R-(Z)]-9-Octadecenoicacid
12-Hydroxy-cis-9-octadecenoic acid
12-hydroxy-cis-9-octadecenoicacid
12-hydroxy-oleicaci
9-Octadecenoic acid, 12-hydroxy-, [R-(Z)]-
9-Octadecenoic acid,12-hydroxy-,(Z)-
9-octadecenoicacid,12-hydroxy-(cis)
9-octadecenoicacid,12-hydroxy-,[R]- | [EINECS(EC#)]
205-470-2 | [Molecular Formula]
C18H34O3 | [MDL Number]
MFCD00084840 | [Molecular Weight]
298.46 | [MOL File]
141-22-0.mol |
| Chemical Properties | Back Directory | [Definition]
A C1
8
unsaturated fatty acid that comprises 80% of
the fatty acid content of castor oil.
| [Appearance]
yellow viscous liquid | [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℃) | [Fp ]
248°C | [storage temp. ]
2-8°C
| [solubility ]
Ethanol | [form ]
Liquid | [pka]
4.78±0.10(Predicted) | [color ]
Colorless to Red to Green | [Specific Gravity]
0.943 (20/4℃) | [optical activity]
[α]/D 6.5±1.5°, c = 2 in acetone | [Merck ]
8211 | [BRN ]
1727813 | [Stability:]
Light Sensitive | [InChIKey]
WBHHMMIMDMUBKC-GKUQOKNUSA-N | [LogP]
5.607 (est) | [Uses]
- 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).
- surface coating: it is used as an efficient pigment/dye dispersants in inks, coatings, plastics, cosmetics, etc.
- textiles: Ricinoleic acid provides polarity, surface wetting and lubricity.
- rubber: the sodium/potassium soaps of Ricinoleic acid are emulsifiers and foam stabilizers.
- vinyl polymers: it's sodium soap is useful as emulsifier, stabilizer and defoamer for emulsion polymerization of resins such as PVC & PVAc
- food additives: it's used in the production of PGPR (polyglycerol polyricinoleate) for use in chocolate.
| [CAS DataBase Reference]
141-22-0(CAS DataBase Reference) | [EPA Substance Registry System]
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)- (141-22-0) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
VJ3150000
| [HS Code ]
29181990 | [Hazardous Substances Data]
141-22-0(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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 | [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. | [storage]
Store at -20°C | [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.] |
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