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

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

Specifications

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

• 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%

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

SDS

RUO – Research Use Only