ALPHA-APO-OXYTETRACYCLINE

Base Information

• Chemical Name: ALPHA-APO-OXYTETRACYCLINE
• CAS No.: 18751-99-0
• Molecular Formula: C₂₂H₂₂N₂O₈
• Molecular Weight: 442.425
• Hs Code.: 29413020
• Mol file: 18751-99-0.mol

Synonyms:b-Apo-5-oxytetracycline; b-Apooxytetracycline; b-Apoterramycin

Chemical Property of ALPHA-APO-OXYTETRACYCLINE

Chemical Property:

• Melting Point: 200-204 °C
• Boiling Point: 742.4±60.0 °C(Predicted)
• PKA: 1.62±0.58(Predicted)
• PSA: 170.62000
• Density: 1.62±0.1 g/cm3(Predicted)
• LogP: 1.25860
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Aqueous Base (Slightly), Methanol (Slightly, Heated, Sonicated)

Purity/Quality:

98%Min ^*data from raw suppliers

β-Apo-oxytetracycline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 63
• Safety Statements: 45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• 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.
• 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. 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.

Technology Process of ALPHA-APO-OXYTETRACYCLINE

There total 4 articles about ALPHA-APO-OXYTETRACYCLINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ (3S)-4t-[(R)-4,5-dihydroxy-9-methyl-3-oxo-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-3r-dimethylamino-2,5ξ-dihydroxy-6-oxo-cyclohex-1-enecarboxylic acid amide (2869-27-4,18695-01-7,18751-99-0)

Guidance literature:

With hydrogenchloride; α-apoterramycin;

DOI:10.1021/ja01118a001

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + Oxytetracycline (79-57-2) → (3S)-4t-[(R)-4,5-dihydroxy-9-methyl-3-oxo-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-3r-dimethylamino-2,5ξ-dihydroxy-6-oxo-cyclohex-1-enecarboxylic acid amide (2869-27-4,18695-01-7,18751-99-0)

Guidance literature:

DOI:10.1021/ja01118a001

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + Oxytetracycline (79-57-2) → (3S)-4t-[(R)-4,5-dihydroxy-9-methyl-3-oxo-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-3r-dimethylamino-2,5ξ-dihydroxy-6-oxo-cyclohex-1-enecarboxylic acid amide (2869-27-4,18695-01-7,18751-99-0) + terrinolide (569-33-5)

Guidance literature:

DOI:10.1021/ja01118a001

upstream raw materials:

hydrogenchloride

Oxytetracycline

Downstream raw materials:

8,9-dihydroxy-4-methyl-3-(2,3,5-trihydroxy-phenyl)-3H-naphtho[2,3-c]furan-1-one