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4-Epioxytetracycline

4-Epioxytetracycline Structure
CAS No.
14206-58-7
Chemical Name:
4-Epioxytetracycline
Synonyms
4-EPIOXYTETRACYCLINE;Oxytetracycline IMpurity A;[4R-(4α,4aβ,5β,5aβ,6α,12aβ]-;Oxytetracycline EP Impurity A;4-Epi-Oxytetracycline, EvoPure;Oxytetracycline Hydrochloride EP Impurity A;4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY ST;Oxytetracycline EP Impurity A/4-epi-Oxytetracycline;Oxytetracycline Impurity 1(Oxytetracycline EP Impurity A);4-Epioxytetracycline,97%,'can be used as secondary standard'
CBNumber:
CB4500795
Molecular Formula:
C22H24N2O9
Molecular Weight:
460.43
MOL File:
14206-58-7.mol
MSDS File:
SDS
Modify Date:
2024/7/18 18:48:51

4-Epioxytetracycline Properties

Melting point 168°C
Boiling point 839.6±65.0 °C(Predicted)
Density 1.71±0.1 g/cm3(Predicted)
storage temp. Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility DMSO: slightly soluble; Methanol: slightly, heated
pka 4.50±1.00(Predicted)
form Powder
color Greenish-beige to brownish
Stability Hygroscopic, Light Sensitive, Unstable in Solution
EPA Substance Registry System 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4R,4aR,5S,5aR,6S,12aS)- (14206-58-7)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H319-H361
Precautionary statements  P201-P202-P264-P280-P305+P351+P338-P308+P313-P337+P313-P405-P501
HS Code  29413020
NFPA 704
0
2 0

4-Epioxytetracycline Chemical Properties,Uses,Production

Description

Epioxytetracycline is a metabolite of Oxytetracycline. It has been found in swine manure compost and wastewater and is considered a pollutant. This highly pure metabolite can be used as a secondary reference standard during stability studies of oxytetracycline. It can also be used to study the degradation pathway and products of tetracyclines.

Chemical Properties

greenish-beige to brownish powder

Mode of action

Oxytetracycline causes inhibition of protein synthesis. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome.
In an acellular model system of protein synthesis using ribosomes from tetracycline-sensitive and resistant strains of E. coli in the synthesis of polyphenylalanine, Oxytetracycline showed inhibitory activity along with minocycline. 4-Epioxytetracycline and beta-apo-oxytetracycline had competing properties with respect to oxytetracycline at the stage of penetration through the cell membrane but did not, however, suppress the synthesis of polyphenylalanine.

References

1] I V BELIAVSKAIA. [Study of the mechanism of action of minocycline and of certain other tetracycline group compounds].[J]. Antibiotiki, 1976, 21 3: 242-245.
[2] BENT HALLING-S?RENSEN J. T G Sengel?v. Toxicity of Tetracyclines and Tetracycline Degradation Products to Environmentally Relevant Bacteria, Including Selected Tetracycline-Resistant Bacteria[J]. Archives of Environmental Contamination and Toxicology, 2002, 42 1: 263-271. DOI:10.1007/s00244-001-0017-2.
[3] ANNE KRUSE LYKKEBERG . Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS[J]. Journal of pharmaceutical and biomedical analysis, 2004, 34 2: Pages 325-332. DOI:10.1016/S0731-7085(03)00500-4.
[4] RICHENG XUAN. Hydrolysis and photolysis of oxytetracycline in aqueous solution.[J]. Journal of Environmental Science and Health Part B-pesticides Food Contaminants and Agricultural Wastes, 2010, 45 1: 73-81. DOI:10.1080/03601230903404556.
[5] HONGXING HAN. Impact of 4-epi-oxytetracycline on the gut microbiota and blood metabolomics of Wistar rats[J]. Scientific Reports, 2016, 6 1. DOI:10.1038/srep23141.

4-Epioxytetracycline Preparation Products And Raw materials

Raw materials

Preparation Products

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4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY STANDARD', 97 4-Epioxytetracycline, 'can be used as secondary standard', 97% 4-Epioxytetracycline,97%,'can be used as secondary standard' 4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY ST [4R-(4α,4aβ,5β,5aβ,6α,12aβ]- Oxytetracycline IMpurity A 4-EPIOXYTETRACYCLINE Oxytetracycline EP Impurity A/4-epi-Oxytetracycline (4R,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Oxytetracycline EP Impurity A Oxytetracycline Impurity 1(Oxytetracycline EP Impurity A) 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4R,4aR,5S,5aR,6S,12aS)- 4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY STANDARD', 97 USP/EP/BP Oxytetracycline Hydrochloride EP Impurity A (4R,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide(4-epioxytetracycline), 4-Epi-Oxytetracycline, EvoPure 14206-58-7 Intermediates & Fine Chemicals Pharmaceuticals Amines Chiral Reagents