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Ricinoleic acid information


Ricinoleic acid
Names
Preferred IUPAC name
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names
(R)-12-Hydroxy-9-cis-octadecenoic acid
Identifiers
CAS Number
  • 141-22-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28592 checkY
ChemSpider
  • 558800 checkY
ECHA InfoCard 100.004.974 Edit this at Wikidata
KEGG
  • C08365 ☒N
PubChem CID
  • 643684
UNII
  • I2D0F69854 checkY
CompTox Dashboard (EPA)
  • DTXSID0041567 Edit this at Wikidata
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 checkY
    Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N checkY
  • InChI=1/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
    Key: WBHHMMIMDMUBKC-QJWNTBNXBT
SMILES
  • O=C(O)CCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
Chemical formula
C18H34O3
Molar mass 298.461 g/mol
Appearance Yellow viscous liquid
Density 0.945 g/cm3
Melting point 5 °C (41 °F; 278 K)
Boiling point 245 °C (473 °F; 518 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point 228 °C (442 °F; 501 K)
Safety data sheet (SDS) Fisher Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid[1] and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of castor plant (Ricinus communis L., Euphorbiaceae), the plant that produces ricin. It is also found in the sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the ricinolein.

  1. ^ Frank D. Gunstone; John L. Harwood; Albert J. Dijkstra (2007). The Lipid Handbook. CRC Press. p. 1472. ISBN 978-1420009675.

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Ricinoleic acid

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Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is...

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Castor oil

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is well known as a source of ricinoleic acid, a monounsaturated, 18-carbon fatty acid. Among fatty acids, ricinoleic acid is unusual in that it has a hydroxyl...

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Dicarboxylic acid

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rancidity. It was first obtained by oxidation of castor oil (ricinoleic acid) with nitric acid. It is now produced industrially by oxidation of cyclohexanol...

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Enanthic acid

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"blossom." The methyl ester of ricinoleic acid, obtained from castor bean oil, is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl...

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Polyglycerol polyricinoleate

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fatty acids are separately heated to above 200 °C, to create interesterified ricinoleic fatty acids. The polyglycerol and the interesterified ricinoleic fatty...

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Nylon 11

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process of creating Nylon 11 begins with ricinoleic acid which makes up 85-90% of castor oil. Ricinoleic acid is first transesterified with methanol creating...

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Salicylic acid

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Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or, white), bitter-tasting solid, it is a precursor to and a metabolite...

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Undecylenic acid

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Salts and esters of undecylenic acid are known as undecylenates. Undecylenic acid is prepared by pyrolysis of ricinoleic acid, which is derived from castor...

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Laxative

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Castor oil is a glyceride that is hydrolyzed by pancreatic lipase to ricinoleic acid, which produces laxative action by an unknown mechanism. Properties...

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Hydroxycarboxylic acid

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aspirin Ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid)), a major component of the seed oil obtained from castor plant Common amino acids: Serine...

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Zinc ricinoleate

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Zinc ricinoleate is the zinc salt of ricinoleic acid, a major fatty acid found in castor oil. It is used in many deodorants as an odor-adsorbing agent...

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Linoleic acid

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Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups (−CH=CH−) are cis. It is a fatty acid sometimes...

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Ricinolein

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is the chief constituent of castor oil and is the triglyceride of ricinoleic acid. Castor oil, the expressed natural fatty oil of the seeds of Ricinus...

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Tiaprofenic acid is a nonsteroidal anti-inflammatory drug (NSAID) of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain...

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Sebacic acid

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properties of lubricating oils on metals. Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. Octanol...

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Phenylacetylrinvanil

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amide of vanillylamine and ricinoleic acid, with the hydroxyl group on ricinoleic acid esterified with phenylacetic acid. It is used to study the function...

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Ricinus

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component of many cosmetics. As an anti-microbial. The high percentage of ricinoleic acid residues in castor oil and its derivatives, inhibits many microbes...

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Fenamic acid

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including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid. These drugs are commonly referred to as "anthranilic acid derivatives" or...

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Lesquerolic acid

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Lesquerolic acid is chemically similar to ricinoleic acid, but with two additional carbons at the carboxyl end of the carbon chain. Lesquerolic acid, with other...

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Sodium ricinoleate

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Sodium ricinoleate is the sodium salt of ricinoleic acid, the principal fatty acid derived from castor oil. It is used in making soap, where its molecular...

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Arachidonic acid

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Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is formed by biosynthesis from linoleic acid in...

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Kolliphor EL

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Paclitaxel (Taxol), anti-cancer[citation needed] Aci-Jel (acetic acid / oxyquinoline / ricinoleic acid - vaginal)[citation needed] Sandimmune (cyclosporine injection...

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Latanoprost

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acid reaches the circulation, it is quickly metabolised in the liver by fatty acid beta oxidation to 1,2-dinor- and 1,2,3,4-tetranor-latanoprost acid;...

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Thromboxane

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Thromboxane-A synthase, an enzyme found in platelets, converts the arachidonic acid derivative prostaglandin H2 to thromboxane. People with asthma tend to have...

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