Oxytetracycline EP Impurity D
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| Category | Others |
| Catalog number | BBF-04355 |
| CAS | 18695-01-7 |
| Molecular Weight | 442.42 |
| Molecular Formula | C22H22N2O8 |
| Purity | >95% by HPLC |
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Description
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. alpha-Apooxytetracycline is an important standard for monitoring oxytetracycline stability.
Specification
| Related CAS | 1361013-47-9 (Deleted CAS) |
| Synonyms | (3S,4S,5S)-4-[(1R)-4,5-Dihydroxy-9-methyl-3-oxo-1,3-dihydronaphtho[2,3-c]furan-1-yl]-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohex-1-ene-1-carboxamide; 1-Cyclohexene-1-carboxamide, 4-[(1R)-1,3-dihydro-4,5-dihydroxy-9-methyl-3-oxonaphtho[2,3-c]furan-1-yl]-3-(dimethylamino)-2,5-dihydroxy-6-oxo-, (3S,4S,5S)-; α-Apo-oxytetracycline; α-Apooterramycin; alpha-Apo-terramycin; alpha-Apooxytetracycline; (3S,4S,5S)-4-[(1R)-1,3-Dihydro-4,5-dihydroxy-9-methyl-3-oxonaphtho[2,3-c]furan-1-yl]-3-(dimethylamino)-2,5-dihydroxy-6-oxo-1-cyclohexene-1-carboxamide; α-Apooxytetracycline; α-Apoterramycin; Oxytetracycline Dihydrate EP Impurity D; Oxytetracycline Hydrochloride EP Impurity D |
| Storage | Store at 2-8°C under inert atmosphere |
| IUPAC Name | (3S,4S,5S)-4-[(1R)-4,5-dihydroxy-9-methyl-3-oxo-1H-benzo[f][2]benzofuran-1-yl]-3-(dimethylamino)-2,5-dihydroxy-6-oxocyclohexene-1-carboxamide |
| Canonical SMILES | CC1=C2C=CC=C(C2=C(C3=C1C(OC3=O)C4C(C(=C(C(=O)C4O)C(=O)N)O)N(C)C)O)O |
| InChI | InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)20(32-22(12)31)13-15(24(2)3)17(27)14(21(23)30)19(29)18(13)28/h4-6,13,15,18,20,25-28H,1-3H3,(H2,23,30)/t13-,15-,18-,20-/m0/s1 |
| InChI Key | DRKMHDAKULCOKQ-MLZJRGSSSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Dark Yellow to Green Solid |
| Boiling Point | 742.4±60.0°C (Predicted) |
| Melting Point | 200°C |
| Density | 1.62±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1.Determination of oxytetracycline and its degradation products by high-performance liquid chromatography-tandem mass spectrometry in manure-containing anaerobic test systems.
Loke ML1, Jespersen S, Vreeken R, Halling-Sørensen B, Tjørnelund J. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jan 5;783(1):11-23.
This paper describes the development of a HPLC-MS-MS (ESI) method with baseline separation of oxytetracycline, 4-epi-oxytetracycline, alpha-apo-oxytetracycline and beta-apo-oxytetracycline using an XTerra column and an MeOH-MilliQ-water (containing 8 mM formic acid) mobile phase. Limits of quantification for aqueous standards were in the range of 0.004 to 0.008 microM. The linear range tested was 0.003 to 0.5 microM and in one case up to 17 microM. An experiment simulating the degradation of oxytetracycline in manure was set up and free concentrations of the four antibiotics were determined during 6 months. Oxytetracycline (>0.02 microM) was observed up till 6 months after spiking. No important increase in free concentrations of the degradation products was observed.
2.Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river.
Li D1, Yang M, Hu J, Ren L, Zhang Y, Li K. Environ Toxicol Chem. 2008 Jan;27(1):80-6.
This study investigated the occurrence and fate of oxytetracycline (OTC) and its related substances, 4-epi-oxytetracycline (EOTC), alpha-apo-oxytetracycline (alpha-apo-OTC), and beta-apo-oxytetracycline (beta-apo-OTC), in a wastewater treatment plant (WWTP) treating OTC production wastewater and a river receiving the effluent from the WWTP using liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS). The percent removal of OTC in the WWTP was 38.0 +/- 10.5%, and the concentration of OTC was still up to 19.5 +/- 2.9 mg/L in the treated outflow. The concentration slightly decreased along the river, from 641 +/- 118 microg/L at site R2 (discharging point) to 377 +/- 142 microg/L at site R4 ( approximately 20 km from site R2), which was still higher than the minimal inhibition concentration of OTC reported ( approximately 250 microg/L). On the other hand, the total amount of its related substances in the treated effluent was less than 5% of OTC.
3.Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS.
Halling-Sørensen B1, Lykkeberg A, Ingerslev F, Blackwell P, Tjørnelund J. Chemosphere. 2003 Mar;50(10):1331-42.
The fate of oxytetracyclines (OTCs) in soil interstitial water was investigated and the structure of a number of degradation products elucidated in a time-related experiment. A previously developed separation method for LC-MS-MS able to base separate and quantify OTC and three of its epimers and degradation products was applied. Compounds detected were 4-epi-oxytetracycline (EOTC) (t(R)=3.0 min), OTC (t(R)=4.4 min), alpha-apo-oxytetracycline (alpha-apo-OTC) (t(R)=11.4 min) and beta-apo-oxytetracycline (beta-apo-OTC) (t(R)=18.4 min). Furthermore, we tentatively identified 4-epi-N-desmethyl-oxytetracycline (E-N-DM-OTC) (t(R)=3.0 min), N-desmethyl-oxytetracycline (N-DM-OTC) (t(R)=3.5), N-didesmethyl-oxytetracycline (N-DDM-OTC), 4-epi-N-didesmethyl-oxytetracycline (E-N-DDM-OTC) (t(R)=3.7 and 4.7 min) and 2-acetyl-2-decarboxamido-oxytetracycline (t(R)=8.7) in all samples. Most compounds were only present in trace concentrations (less than 2%) relative to the parent OTC.
4.The degradation of oxytetracycline during thermal treatments of chicken and pig meat and the toxic effects of degradation products of oxytetracycline on rats.
Nguyen V1, Nguyen V2, Li C3, Zhou G3. J Food Sci Technol. 2015 May;52(5):2842-50. doi: 10.1007/s13197-014-1306-x. Epub 2014 Apr 1.
The formation oxytetracycline (OTC) degradation products in chicken and pork under two different methods of cooking were studied. Samples of chicken and pig muscles previously dosed with OTC residues were subjected to boiling or microwave treatment, and the residues were extracted in a mixture of citrate buffer-MeOH (75:25 v/v), and then analyzed by high performance liquid chromatography with photodiode array detection using a XBridgeTM C18 reverse-phase chromatographic column. Thermal treatment resulted in the degradation of OTC and the concentrations of the degradation products α-apo-oxytetracycline (α-apo-OTC) and β-apo-oxytetracycline (β-apo-OTC) in muscle samples amounted to 0.7 to 1.2 % of the initial OTC content. The toxic effects of the degradation products of oxytetracycline, α-apo-OTC and β-apo-OTC were studied in rats. Male rats received oral doses of 10 mg/kg body weight/day of either α-apo-OTC, β-apo-OTC, 90 days. The results of this study suggest that the toxic effects of β-apo-OTC treatment could damage liver and kidney tissues of rats, as well as lead to the degeneration and necrosis in the hepatocytes.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
