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3-Hydroxy-4-methyl-2(5H)-thiophenone Sale

(Synonyms: 头孢氨苄杂质D) 目录号 : GC49819

A degradation product of cefaclor

3-Hydroxy-4-methyl-2(5H)-thiophenone Chemical Structure

Cas No.:34876-35-2

规格 价格 库存 购买数量
5 mg
¥555.00
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10 mg
¥999.00
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25 mg
¥2,221.00
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50 mg
¥3,331.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

3-Hydroxy-4-methyl-2(5H)-thiophenone is a degradation product of the cephalosporin antibiotic cefaclor .1 It is formed from cefaclor under aqueous acidic conditions.

1.Baertschi, S.W., Dorman, D.E., Occolowitz, J.L., et al.Isolation and structure elucidation of the major degradation products of cefaclor formed under aqueous acidic conditionsJ. Pharm. Sci.86(5)526-539(1997)

Chemical Properties

Cas No. 34876-35-2 SDF Download SDF
别名 头孢氨苄杂质D
Canonical SMILES O=C1SCC(C)=C1O
分子式 C5H6O2S 分子量 130.2
溶解度 DMF: 3 mg/ml,DMSO: 5 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): 1 mg/ml 储存条件 -20°C
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1 mg 5 mg 10 mg
1 mM 7.6805 mL 38.4025 mL 76.8049 mL
5 mM 1.5361 mL 7.6805 mL 15.361 mL
10 mM 0.768 mL 3.8402 mL 7.6805 mL
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Research Update

Cephalosporin degradations

J Med Chem 1977 Jul;20(7):963-5.PMID:874972DOI:10.1021/jm00217a022.

The acidic aqueous degradation of the 7alpha-aminophenylglycinamido-containing cephalosporin cephalexin (1a) has been examined. Two major degradation products have been isolated and characterized: 3-formyl-3,6-dihydro-6-phenyl-2.5(1H,4H)-pyrazinedione (5) and 3-Hydroxy-4-methyl-2(5H)-thiophenone (6). By carrying out the reaction in 18O-enriched H2O, the intramolecular nature of the cephalexin degradation has been demonstrated.

Degradation kinetics and mechanism of aminocephalosporins in aqueous solution: cefadroxil

J Pharm Sci 1981 Oct;70(10):1120-8.PMID:7299645DOI:10.1002/jps.2600701008.

The degradation kinetics and mechanism of a new, orally effective cephalosporin derivative, cefadroxil, in aqueous solution were investigated at pH 2.51-11.5 at 35 degrees and ionic strength 0.5. The degradation rates were determined by high=pressure liquid chromatography. At constant pH and temperature, the degradation followed first-order kinetics and a log k-pH profile was presented. The shape of the rate-pH profile resembled that for cephalexin or cephradine under the same conditions. Citrate and phosphate buffers enhanced general acid and base catalysis of the degradation. In aqueous solution, cefadroxil was shown to degrade by three parallel reactions: (a) intramolecular aminolysis by the C-7 side-chain amino group on the beta-lactam moiety, (b) water-catalyzed or spontaneous hydrolysis, and (c) beta-lactam cleavage by the nucleophilic attack of hydroxide ion. In neutral and weak alkaline solutions, the main degradation products were two piperazine-2, 5-diones and 3-Hydroxy-4-methyl-2(5H)-thiophenone, the former being formed from Reaction a, while the latter arose via the degradation pathways of Reaction b and/or c.