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)
[Wiki en表示]
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 Y |
ChEBI |
CHEBI:28592 Y |
ChemSpider |
558800 Y |
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 Y
Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N Y
-
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 Y |
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)
|
Y verify (what is: Y/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] 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.
Contents
- 1 Production
- 2 Biological activities
- 3 See also
- 4 References
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]
See also
- Castor oil
- Ricinelaidic acid, the trans isomer of ricinoleic acid
- Ricinolein, the triglyceride of ricinoleic acid
- Sodium ricinoleate, the sodium salt of ricinoleic acid
- Polyglycerol polyricinoleate, a polymer of glycerol with ricinoleic acid side chains, used as an emulsifier in chocolate
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
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
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
![File:Ricinoleic Acid Structural Formulae](https://1mg.info/0/b/5/0152.jpg)
![200px-Ricinoleic_acid.svg.png](https://1mg.info/0/b/5/0153.jpg)
![Description Ricinoleic-acid.png](https://1mg.info/0/b/5/0154.jpg)
![ricinoleic acid results in 3 moles of the](https://1mg.info/0/b/5/0155.jpg)
![Ricinoleic acid Mass Spectrum](https://1mg.info/0/b/5/0156.jpg)