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Ricinelaidic Acid Sale

目录号 : GC41189

An LTB4 antagonist

Ricinelaidic Acid Chemical Structure

Cas No.:540-12-5

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25mg
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50mg
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100mg
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250mg
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产品描述

Ricinelaidic acid is a 12-hydroxy fatty acid and an antagonist of leukotriene B4 (LTB4) receptors (Ki = 2 µM in porcine neutrophil membranes). It inhibits chemotaxis and calcium flux induced by LTB4 in isolated human neutrophils (IC50s = 10 and 7 µM, respectively). Ricinelaidic acid (1 mg/kg, i.v.) inhibits bronchoconstriction induced by LTB4 in rats by 46%.

Chemical Properties

Cas No. 540-12-5 SDF
Canonical SMILES O[C@H](CCCCCC)C/C=C/CCCCCCCC(O)=O
分子式 C18H34O3 分子量 298.5
溶解度 DMF: 3 mg/ml,DMSO: 2 mg/ml,Ethanol: miscible,PBS (pH 7.2): 2 mg/ml 储存条件 Store at -20°C
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1 mM 3.3501 mL 16.7504 mL 33.5008 mL
5 mM 0.67 mL 3.3501 mL 6.7002 mL
10 mM 0.335 mL 1.675 mL 3.3501 mL
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Research Update

Insights into the Gelating Abilities of Ricinelaidic Acid and its Ammonium Salts: How do Stereochemistry, Charge, and Chain Lengths Control Gelation of a Long-Chain Alkenoic Acid?

Chemphyschem 2016 Dec 15;17(24):4059-4067.PMID:27862785DOI:10.1002/cphc.201600902.

The gelating abilities of Ricinelaidic Acid (d-REA), the trans-isomer of ricinoleic acid (d-RA), and a series of its alkylammonium and alkane-α,ω-diammonium salts have been examined in a wide range of organic liquids. The gelation efficiency of the trans acid is much better than that of the cis, although neither is as efficient as is the completely saturated molecular gelator analogue, (R)-12-hydroxystearic acid (d-12HSA). The formation of ammonium salts also improves the gelation ability of d-REA in high polarity liquids. The gelating properties are highly dependent upon the chain length of the alkyl group of the alkylammonium salts, but not very dependent on the chain length of the alkane-α,ω-diammonium salts. Structural insights from Fourier transform infrared spectroscopy and powder X-ray diffraction indicate that the absence or presence of unsaturation, the incorporation of (charged) ammonium centers, and the different chain lengths of the alkylammonium salts lead to different packing arrangements and different strengths of H-bonding interactions within the gel assemblies of the d-REA derivatives. Insights into the relationships among the various systematic structural changes to d-REA and the properties of their aggregated structures, including the gel states, are provided.

Ricinoleic acid effect on the electrical activity of the small intestine in rabbits

J Clin Invest 1978 Mar;61(3):640-4.PMID:641145DOI:10.1172/JCI108975.

Using myoelectric recording techniques, we examined the myoelectric effects of castor oil; ricinoleic acid (cis isomer), the active ingredient of castor oil; and Ricinelaidic Acid (trans isomer) in the small intestine of New Zealand white rabbits. Ricinoleic acid, 2 microgram/kg per min (6mM), was perfused into a distal 12-cm ileal loop. An abnormal myoelectric pattern developed that was similar to the alteration in the electrical activity that has previously been reported for cholera enterotoxin. Castor oil, 0.85 ml/kg, had a similar effect. Ricinelaidic Acid, 2 microgram/kg per min, induced no activity. A second preparation consisted of an intraluminal perfusion of ricinoleic acid, 2 microgram/kg per min, into the first section of the duodenum. The abnormal myoelectric pattern was observed in the jejunum and the ileum but not the duodenum. The mean onset time for the development of this altered myoelectric state for all experiments was 3.5 h. These studies suggest that an active motility component in addition to the secretory state exists throughout the small intestine that is exposed to castor oil or ricinoleic acid.

Differential modulation of brain benzodiazepine receptor subtypes by Ricinelaidic Acid in vitro

Biochem Pharmacol 1994 Feb 11;47(4):742-4.PMID:8129750DOI:10.1016/0006-2952(94)90138-4.

The C-18 hydroxy fatty acids Ricinelaidic Acid and ricinoleic acid diminish the oleic acid-stimulated agonist benzodiazepine binding in the rat brain in vitro. The oleic acid-induced enhancement of [3H]diazepam binding was completely abolished in membranes from the cerebellum, but only partially decreased in membranes from the hippocampus, cortex and the whole brain from 7-day-old rat pups. Related hydroxy fatty acids as well as hydroxy fatty acid esters had no effect on the oleic acid-stimulated diazepam receptor binding.

Essential fatty acids are antagonists of the leukotriene B4 receptor

Prostaglandins Leukot Essent Fatty Acids 1995 May;52(5):293-7.PMID:7630916DOI:10.1016/0952-3278(95)90029-2.

A series of essential fatty acids and fatty acid derivatives were evaluated for their ability to inhibit [3H] leukotriene B4 (LTB4) binding to pig neutrophil membranes. The fatty acids varied in chain length, extent of unsaturation, position of unsaturation, and isomerization. Generally, fatty acids with two or more unsaturated sites and chain lengths of 18-22 were potent inhibitors of [3H]LTB4 binding; both n-3 and n-6 fatty acids were inhibitory. The most potent compounds tested were homogammalinolenic acid and Ricinelaidic Acid which gave Ki values of 1 microM and 2 microM in the binding assay. Ricinelaidic Acid was also tested for its ability to inhibit LTB4-mediated chemotaxis (IC50 = 10 microM) and LTB4-induced calcium fluxes (IC50 = 7 microM) in isolated human neutrophils. Ricinelaidic Acid did not show agonist activity in these assays. In an in vivo model of LTB4-induced bronchoconstriction, Ricinelaidic Acid and homogammalinolenic acid gave 46% and 53% inhibition, respectively, at a 1 mg/kg i.v. dose. These results indicate that essential fatty acids are LTB4 receptor antagonists, which may account in part for their reported anti-inflammatory activities.

Monohydroxylation and esterification as determinants of the effects of cis- and trans-9-octadecenoic acids on the permeation of hydrocortisone and 5-fluorouracil across hairless mouse skin in vitro

Int J Pharm 2001 Jan 16;212(2):153-60.PMID:11165072DOI:10.1016/s0378-5173(00)00572-x.

The effects of cis-9-octadecenoic acid (oleic acid) and of a group of chemically related cis- (ricinoleic acid) and trans- (Ricinelaidic Acid) 12-monohydroxylated derivatives and their corresponding ethyl and methyl esters on the skin permeation of model hydrophobic (hydrocortisone, log K=1.61) and hydrophilic (5-fluorouracil, log K=-0.89) drugs was investigated in vitro using excised hairless mouse skin. Drug solutions were prepared in propylene glycol, with and without the addition of a fatty acid to a level of 5%. Whereas the addition of oleic acid markedly enhanced the transdermal flux of both drugs relative to a sample in propylene glycol alone (hydrocortisone approximately 1800-fold; 5-fluorouracil approximately 330-fold), that of a cis- or trans-12-monohydroxylated analog of oleic acid resulted in only a small increase (1.4-2.7-fold for hydrocortisone; 4.4-6.6-fold for 5-fluorouracil). On the other hand, the methyl and ethyl esters of cis- and trans-12-hydroxy-9-octadecenoic acid exerted a much greater enhancing effect (327-720-fold for hydrocortisone, 42-74-fold for 5-fluorouracil) than the corresponding parent fatty acids. Furthermore, whereas the ethyl esters were found to have a greater effect on the skin permeation of hydrocortisone than the methyl esters, the reverse was true with regards to 5-fluorouracil. Additionally, the esters of trans-12-hydroxy-9-octadecenoic acid promoted permeation to an extent comparable to that achieved with their cis-counterparts.