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

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

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%

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

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