ChemicalBook > CAS DataBase List > 4-Epioxytetracycline

4-Epioxytetracycline

Product Name
4-Epioxytetracycline
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;C13179000 4-epi-Oxytetracycline;4-Epioxytetracycline 100 μg/ml Methanol;Oxytetracycline Hydrochloride EP Impurity A;4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY ST;Oxytetracycline EP Impurity A/4-epi-Oxytetracycline
CBNumber
CB4500795
Molecular Formula
C22H24N2O9
Formula Weight
460.43
MOL File
14206-58-7.mol
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4-Epioxytetracycline Property

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)
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Safety

HS Code 
29413020
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
27987
Product name
Epioxytetracycline
Packaging
1mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
27987
Product name
Epioxytetracycline
Packaging
10mg
Price
$783
Updated
2024/03/01
Cayman Chemical
Product number
27987
Product name
Epioxytetracycline
Packaging
5mg
Price
$423
Updated
2024/03/01
TRC
Product number
O877505
Product name
4-epi-Oxytetracycline
Packaging
25mg
Price
$255
Updated
2021/12/16
AK Scientific
Product number
1702DM
Product name
4-Epi-Oxytetracycline
Packaging
10mg
Price
$387
Updated
2021/12/16
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4-Epioxytetracycline Chemical Properties,Usage,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

Uses

Epioxytetracycline is a degradation product of oxytetracycline formed by the epimerisation of the dimethylamino group at C4 in solution at neutral to acidic pH. The epimerisation is associated with a loss of antibiotic activity. Epioxytetracycline is an important standard for monitoring oxytetracycline stability.

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 Suppliers

BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
Standardpharm Co. Ltd.
Tel
86-714-3992388
Email
overseasales1@yongstandards.com
Country
United States
ProdList
14332
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
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View Lastest Price from 4-Epioxytetracycline manufacturers

Apeloa production Co.,Limited
Product
4-Epioxytetracycline 14206-58-7
Price
US $1.00/g
Min. Order
1g
Purity
0.98
Supply Ability
1000
Release date
2024-07-18
Career Henan Chemical Co
Product
4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY STANDARD', 97 14206-58-7
Price
US $1.00/g
Min. Order
1g
Purity
≥98%
Supply Ability
g/kg/Ton
Release date
2019-12-25

14206-58-7, 4-EpioxytetracyclineRelated Search:


  • 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
  • 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'
  • Oxytetracycline EP Impurity A
  • 4-EPIOXYTETRACYCLINE, 'CAN BE USED AS SECONDARY ST
  • [4R-(4α,4aβ,5β,5aβ,6α,12aβ]-
  • Oxytetracycline 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
  • 4-EPIOXYTETRACYCLINE
  • (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
  • 4-Epioxytetracycline 100 μg/ml Methanol
  • C13179000 4-epi-Oxytetracycline
  • 14206-58-7
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Amines
  • Chiral Reagents