RICINOLEIC ACID
- Iupac Name：(Z,12R)-12-hydroxyoctadec-9-enoic acid
- CAS No.: 141-22-0
- Molecular Weight：298.46076
- Modify Date.: 2022-11-05 05:14
- Introduction: 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.Ricinoleic acid is normally used in manufacturing personal care products such as deodorants. Much of ricinoleic acid characteristics and effects can be associated with castor oil.
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1. Names and Identifiers
- 1.1 Name
- RICINOLEIC ACID
- 1.2 Synonyms
(9Z,12R)-12-Hydroxy-9-octadecenoic acid (9Z,12R)-12-Hydroxyoctadec-9-enoic acid (R)-12-Hydroxyoleic acid (R)-Ricinoleic acid 12-D-Hydroxy-9-cis-octadecenoic acid 12-Hydroxy-cis-9-octadecenoic acid 12-Hydroxyoctadeca-9-enoic acid 9-Nonadecenoic acid, 12-hydroxy-, (9Z,12R)- 9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)- 9-Octadecenoic acid, 12-hydroxy-, [R-(Z)]- Cenwax C CS 80 Edenor Ri 90 H 1657 kyselina12-hydroxy-9-oktadecenova kyselinaricinolova l'acide ricinoleique Nouracid CS 80 Nouracid CZ 80 NSC 281242 Oleic acid, 12-hydroxy- P -10 acid Ricinic acid ricinicacid Ricinolic Acid
- 1.3 CAS No.
- 141-22-0
- 1.4 CID
- 643684
- 1.5 EINECS(EC#)
- 205-470-2
- 1.6 Molecular Formula
- C18H34O3 (isomer)
- 1.7 Inchi
- 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/s1
- 1.8 InChkey
- WBHHMMIMDMUBKC-QJWNTBNXSA-N
- 1.9 Canonical Smiles
- CCCCCCC(CC=CCCCCCCCC(=O)O)O
- 1.10 Isomers Smiles
- CCCCCC[C@H](C/C=C\CCCCCCCC(=O)O)O
2. Properties
- 2.1 Density
- 0.940 g/mL at 20 °C(lit.)
- 2.1 Melting point
- 〈10 oC
- 2.1 Boiling point
- 416.4 °C at 760 mmHg
- 2.1 Refractive index
- 1.479
- 2.1 Flash Point
- 219.8 °C
- 2.1 Precise Quality
- 298.25100
- 2.1 PSA
- 57.53000
- 2.1 logP
- 5.07930
- 2.1 Solubility
- 几乎不溶 (0.03 g/L) (25 oC),
- 2.2 Viscosity
- 400 cSt at 25 °C
- 2.3 Appearance
- Clear amber liquid with some foots
- 2.4 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 liquidspecific gravity (at 25°C) 0.938 - 0.944refractive index (at 25°C) 1.4695 - 1.4700acid value mg KOH/g min.175iodine value 82 - 90saponification value mg KOH/g 180 - 190hydroxyl value 150 - 160unsaponifiable matter max. 1colour Gardner max. 7
- 2.5 Color/Form
- COLORLESS TO YELLOW VISCOUS LIQUID
- 2.6 pKa
- 4.78±0.10(Predicted)
- 2.7 Water Solubility
- Very slightly soluble in water
- 2.8 Spectral Properties
- SPECIFIC OPTICAL ROTATION: +6.67 DEG @ 22 DEG C/D; +7.15 DEG @ 26 DEG C/D (C= 5 IN ACETONE); INDEX OF REFRACTION: 1.4716 @ 20 DEG C/D
MAX ABSORPTION LESS THAN 210 NM
IR: 21992 (Sadtler Research Laboratories Prism Collection)
NMR: 9779 (Sadtler Research Laboratories Spectral Collection)
- 2.9 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- A C18unsaturated fatty acid that comprises 80% ofthe fatty acid content of castor oil.
- 3.2 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 Preparation Products And Raw materials Preparation Products
- 3.3 Usage
- Soaps, Turkey red oil, textile finishing, sourceof sebacic acid and heptanol, ricinoleate salts, 12-hydroxystearic acid.
4. Safety and Handling
- 4.1 Symbol
- GHS07;
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- 26-36
- 4.1 Hazard Declaration
- H315; H319; H335
- 4.1 Caution Statement
- P261; P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- VJ3150000
- 4.1 Safety
- Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
141-22-0Total: 5 Synthesis Route
9. Computational chemical data
- Molecular Weight: 298.46076g/mol
- Molecular Formula: C18H34O3
- Compound Is Canonicalized: True
- XLogP3-AA: 5.7
- Exact Mass: 298.25079494
- Monoisotopic Mass: 298.25079494
- Complexity: 261
- Rotatable Bond Count: 15
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 57.5
- Heavy Atom Count: 21
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAICCAAAAgCIACDSCAAAAAAgAAAICAEAAAgAEBIAAQAAQAAEwAAIAAOIyKCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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