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Thermo Scientific Chemicals 4-Epioxytetracycline, 'can be used as secondary standard'

Catalog No. AC257711000
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100 mg
Packaging:
Glass bottle
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AC257711000 100 mg Glass bottle
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Catalog No. AC257711000 Supplier Thermo Scientific Chemicals Supplier No. 257711000
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Description

4-Epioxytetracycline, CAS # 14206-58-7, is one of the main oxytetracycline metabolites that show antibacterial activity.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

General Description

  • 4-Epioxytetracycline is a metabolite of the oxytetracycline compound that displays antibacterial activity
  • It is the main degradation product derived from the oxytetracycline metabolization and has been detected in some biological samples
  • Its mechanism of action has been described to be related to the mitochondrial protein synthesis inhibition

Applications

  • In laboratory research it has been described that the treatment with 4-epioxytetracycline decreases the bacterial diversity of the intestinal microbiota and facilitates the proliferation of opportunistic pathogens in salmon
  • The use of 4-epioxytetracycline in animal models (wistar rats) resulted in a significant alteration of the gut microbiota and disorders in blood metabolomics
  • 4-Epioxytetracycline can be applied as a secondary reference standard during stability studies of oxytetracycline
  • 4-epioxytetracycline has been used in research studies to evaluate the degradation pathway and products of tetracyclines

Chemical Identifiers

CAS 14206-58-7
Molecular Formula C22H24N2O9
Molecular Weight (g/mol) 460.43
MDL Number MFCD00062825
InChI Key OWFJMIVZYSDULZ-DVJPNYBFSA-N
Synonym 4-epioxytetracyline, unii-73von8sry5, 4-epioxytetracycline, 73von8sry5, 4r,4ar,5s,5ar,6s,12as-4-dimethylamino-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide, hydroxy quatrimycin, oxytetracycline dihydrate specified impurity a ep, oxytetracycline hydrochloride specified impurity a ep, 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, 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
PubChem CID 54678403
IUPAC Name (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
SMILES CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O

Specifications

CAS Min % 96.0
CAS Max % 100.0
Melting Point 168.0°C
Color Beige-Green to Brown
Infrared Spectrum Authentic
Assay Percent Range 80% min. (as is,calculated)
Packaging Glass bottle
Quantity 100 mg
Merck Index 10, 6846
Specific Rotation − 247.00
Solubility Information Solubility in water: 0.5g/L. Other solubilities: 3.6g/L methanol
Formula Weight 460.43
Percent Purity ≥97.0% Total Base (on anhydrous substance), ≥80 wt% (as is, calculated) (HPLC)
Physical Form Powder
Chemical Name or Material 4-Epioxytetracycline, 97%
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Safety and Handling

Hazard Category GHS Signal Word: Warning
Hazard Statement GHS H Statement
Causes serious eye irritation.
Suspected of damaging the unborn child.
Precautionary Statement GHS P Statement
Wash face,hands and any exposed skin thoroughly after handling.
Wear protective gloves/protective clothing/eye protection/face protection.
Obtain special instructions before use.
IF exposed or concerned: Get medical
Recommended Storage 4°C

RUO – Research Use Only