ALPHA-APO-OXYTETRACYCLINE Chemical Properties

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)

pka

1.62±0.58(Predicted)

form 

Powder

color 

Yellow-brown to brown

Stability:

Unstable in basic solution

InChIKey

DRKMHDAKULCOKQ-VUPCMTQJSA-N

SMILES

C1(C(N)=O)C(=O)[C@H](O)[C@@H](C2C3=C(C)C4C(=C(O)C=CC=4)C(O)=C3C(=O)O2)[C@@H](N(C)C)C=1O

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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

63

Safety Statements 

45-36/37

HS Code 

29413020

MSDS

• Language:English Provider:ACROS

ALPHA-APO-OXYTETRACYCLINE Usage And Synthesis

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.

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. 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.

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.

References

[1] 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
[2] B. 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 3: 263-271. DOI: 10.1007/s00244-001-0017-2
[3] N. HUE. PRELIMINARY STUDIES ON THE TOXIC EFFECTS OF DEGRADATION PRODUCTS OF OXYTETRACYCLINE AND CHLORTETRACYCLINE ON RATS[J]. Hue University Journal of Science: Natural Science, 2015, 438 1: 467-475. DOI: 10.17265/2161-6256/2015.12.004

ALPHA-APO-OXYTETRACYCLINE(18751-99-0)Related Product Information

• ALPHA-APO-OXYTETRACYCLINE,alpha-Apo-oxytetracycline, 'can be used as secondary standard'
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