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18751-99-0

18751-99-0 Structure

18751-99-0 Structure
IdentificationBack Directory
[Name]

ALPHA-APO-OXYTETRACYCLINE
[CAS]

18751-99-0
[Synonyms]

β-Apo-oxytetracycline
b-Apo-oxytetracycline
BETA-APO-OXYTETRACYCLINE
ALPHA-APO-OXYTETRACYCLINE
Apooxytetracycline, beta-
beta-Apo-oxytetracycline, 'can be used as secondary standard'
[Molecular Formula]

C22H22N2O8
[MDL Number]

MFCD00062827
[MOL File]

18751-99-0.mol
[Molecular Weight]

442.42
Chemical PropertiesBack Directory
[Appearance]

yellow-brown to brown powder
[Melting point ]

200-204 °C
[Boiling point ]

742.4±60.0 °C(Predicted)
[density ]

1.62±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator, Under Inert Atmosphere
[solubility ]

Aqueous Base (Slightly), Methanol (Slightly, Heated, Sonicated)
[form ]

Powder
[pka]

1.62±0.58(Predicted)
[color ]

Yellow-brown to brown
[Stability:]

Unstable in basic solution
[EPA Substance Registry System]

1-Cyclohexene-1-carboxamide, 4-(1,3-dihydro-4,5-dihydroxy-9-methyl-3-oxonaphtho[2,3-c]furan-1-yl)-3-(dimethylamino)-2,5-dihydroxy-6-oxo- (18751-99-0)
Hazard InformationBack Directory
[Chemical Properties]

yellow-brown to brown powder
[Uses]

Oxytetracycline metabolite (absolute stereochemistry unknown)
[Uses]

β-Apooxytetracycline is a degradation product of oxytetracycline formed under acidic conditions. After initial dehydration to anhydrooxytetracycline, it undergoes an internal cyclisation of the C5-OH to the C12 ketone. The resulting cleavage of the C12-C12a bond generates two isomers, α- and β-apooxytetracycline. β-Apooxytetracycline is an important standard for monitoring oxytetracycline stability.
[Uses]

β-Apooxytetracycline is a degradation product of oxytetracycline formed under acidic conditions. An initial dehydration to anhydrooxytetracycline then undergoes an internal cyclisation of the C5-OH to the C12 ketone. The resulting cleavage of the C12-C12a bond generates two isomers, α- and β-apooxytetracycline. β-apooxytetracycline is an important standard for monitoring oxytetracycline stability.
[Description]

β-Apooxytetracycline is a potential impurity found in commercial preparations of oxytetracycline. β-Apooxytetracycline is a degradation product formed from oxytetracycline via acid hydrolysis. It has a relative potency of 0.1 compared with oxytetracycline for inhibiting the growth of aerobic sludge bacteria, an MIC50 value of 32 mg/L for tetracycline-sensitive strains of Pseudomonas, and MIC50 values of greater than 32 mg/L for tetracycline-sensitive strains of Agrobacterium, Moraxella, and Bacillus, as well as tetracycline-resistant strains of E. coli. β-Apooxytetracycline (10 mg/kg) is toxic to rats, decreasing body weight, disrupting blood cell counts, and inducing hepatocyte necrosis.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

63
[Safety Statements ]

45-36/37
[HS Code ]

29413020
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