ricinoleic acid

Ricinoleic acid
Names
	IUPAC name (9Z,12R)-12-Hydroxyoctadec-9-enoic acid
	Other names R12-Hydroxy-9-cis-octadecenoic acid
Identifiers
CAS Registry Number	141-22-0
ChEBI	CHEBI:28592
ChemSpider	558800
	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 ; Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N ; 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 ;
Jmol-3D images	Image
PubChem	643684
	SMILES O=C(O)CCCCCCC\C=C/C[C@H](O)CCCCCC ;
UNII	I2D0F69854
Properties
Chemical formula	C18H34O3
Molar mass	298.461 g/mol
Density	0.945 g/cm3
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/09 02:51:56」(JST)

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[Wiki en表示]

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid.^[1] It is a major component of the seed oil obtained from mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.^[2] The zinc salt is used in personal care products,^[3] such as deodorants.^[4]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.^[5]

Biological activities

Ricinoleic acid exerts analgesic and anti-inflammatory effects.^[6]

Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.^[7]

Ricinoleic acid acts as a specific algicide for the control of blue-green algae.^[8]

References

^ Frank D. Gunstone, John L. Harwood, Albert J. Dijkstra (2007). The Lipid Handbook. 10: CRC Press. p. 1472. ISBN 1420009672.
^ James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95: 448–52. PMC 1214342. PMID 14340094.
^ "zinc ricinoleate". Environmental Working Group.
^ Tom's of Maine - About Our Products
^ Rider, T.H. (November 1931). "The purification of sodium ricinoleate ". Journal of the American Chemical Society 53: 4130–4133. doi:10.1021/ja01362a031. Retrieved 5 February 2013.
^ Vieira C, Evangelista S, Cirillo R, Lippi A, Maggi CA, Manzini S (2000). "Effect of ricinoleic acid in acute and subchronic experimental models of inflammation". Mediators Inflamm. 9 (5): 223–8. doi:10.1080/09629350020025737. PMC 1781768. PMID 11200362.
^ Tunaru S, Althoff TF, Nüsing RM, Diener M, Offermanns S (2012). "Castor oil induces laxation and uterus contraction via ricinoleic acid activating prostaglandin EP3 receptors". Proc Natl Acad Sci USA 109 (23): 9179–9184. doi:10.1073/pnas.1201627109. PMC 3384204. PMID 22615395.
^ US 4398937, "Selective algaecides for control of cyanochloronta", published 1983

UpToDate Contents

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English Journal

Fast determination of multiple-reaction intermediates for long-chain dicarboxylic Acid biotransformation by gas chromatography-flame ionization detector.

Cho YH1, Lee HJ1, Lee JE1, Kim SJ2, Park K3, Lee do Y1, Park YC1.
Journal of microbiology and biotechnology.J Microbiol Biotechnol.2015 May 28;25(5):704-8.
For the analysis of multiple-reaction intermediates for long-chain dicarboxylic acid biotransformation, simple and reproducible methods of extraction and derivatization were developed on the basis of gas chromatography with flame ionization detector (GC-FID) instead of mass spectrometry. In the deri
PMID 25737121

Expression levels of chaperones influence biotransformation activity of recombinant Escherichia coli expressing Micrococcus luteus alcohol dehydrogenase and Pseudomonas putida Baeyer-Villiger monooxygenase.

Baek AH1, Jeon EY, Lee SM, Park JB.
Biotechnology and bioengineering.Biotechnol Bioeng.2015 May;112(5):889-95. doi: 10.1002/bit.25521. Epub 2015 Mar 13.
We demonstrated for the first time that the archaeal chaperones (i.e., γ-prefoldin and thermosome) can stabilize enzyme activity in vivo. Ricinoleic acid biotransformation activity of recombinant Escherichia coli expressing Micrococcus luteus alcohol dehydrogenase and the Pseudomonas putida KT2440
PMID 25545273

Whole Cell Bioconversion of Ricinoleic Acid to 12-Ketooleic Acid by Recombinant Corynebacterium glutamicum-Based Biocatalyst.

Lee BH1, Lee SB1, Kim HS1, Jeong KJ2, Park JY3, Park KM4, Lee JW1.
Journal of microbiology and biotechnology.J Microbiol Biotechnol.2015 Apr 28;25(4):452-8.
The biocatalytic efficiency of recombinant Corynebacterium glutamicum ATCC 13032 expressing the secondary alcohol dehydrogenase of Micrococcus luteus NCTC2665 was studied. Recombinant C. glutamicum converts ricinoleic acid to a product, identified by gas chromatography/mass spectrometry as 12-ketool
PMID 25639721

Japanese Journal

Green Synthesis of Isopropyl Ricinoleate

Khan Nishat R.,Pratap Amit P.
Journal of Oleo Science 62(3), 153-158, 2013-03-00
NAID 40019582137

Effects of TAK-480, a Novel Tachykinin NK_2-Receptor Antagonist, on Visceral Hypersensitivity in Rabbits and Ricinoleic Acid-Induced Defecation in Guinea Pigs

Tanaka Takahiro,Tanaka Akiko,Nakamura Akihiro [他],MATSUSHITA Kozo,IMANISHI Akio,MATSUMOTO OKANO Shiho,INATOMI Nobuhiro,MIURA Kasei,TOYODA Masao,MIZOJIRI Gaku,TSUKIMI Yasuhiro
Journal of pharmacological sciences 120(1), 15-25, 2012-09-20
… In addition, TAK-480 suppressed ricinoleic acid<I>–</I>induced defecation without affecting spontaneous defecation in guinea pigs, whereas alosetron suppressed both. …
NAID 10031071815

Related Pictures

[1] Frank D. Gunstone, John L. Harwood, Albert J. Dijkstra (2007). The Lipid Handbook. 10: CRC Press. p. 1472. ISBN 1420009672.

[2] James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95: 448–52. PMC 1214342. PMID 14340094.

[3] "zinc ricinoleate". Environmental Working Group.

[4] Tom's of Maine - About Our Products

[5] Rider, T.H. (November 1931). "The purification of sodium ricinoleate ". Journal of the American Chemical Society 53: 4130–4133. doi:10.1021/ja01362a031. Retrieved 5 February 2013.

[6] Vieira C, Evangelista S, Cirillo R, Lippi A, Maggi CA, Manzini S (2000). "Effect of ricinoleic acid in acute and subchronic experimental models of inflammation". Mediators Inflamm. 9 (5): 223–8. doi:10.1080/09629350020025737. PMC 1781768. PMID 11200362.

[7] Tunaru S, Althoff TF, Nüsing RM, Diener M, Offermanns S (2012). "Castor oil induces laxation and uterus contraction via ricinoleic acid activating prostaglandin EP3 receptors". Proc Natl Acad Sci USA 109 (23): 9179–9184. doi:10.1073/pnas.1201627109. PMC 3384204. PMID 22615395.

[8] US 4398937, "Selective algaecides for control of cyanochloronta", published 1983

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