Oxytetracycline EP Impurity E
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| Category | Others |
| Catalog number | BBF-04361 |
| CAS | 18751-99-0 |
| 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. beta-Apooxytetracycline is an important standard for monitoring oxytetracycline stability.
Specification
| Related CAS | 1361013-49-1 (Deleted CAS) |
| Synonyms | (3S,4S,5R)-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-[(3R)-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,5R)-; beta-Apooxytetracycline; β-Apooxytetracycline; beta-Apo-oxytetracycline; β-Apo-oxytetracycline; (3S,4S,5R)-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; β-Apo-5-oxytetracycline; β-Apoterramycin; Oxytetracycline Dihydrate EP Impurity E; Oxytetracycline Hydrochloride EP Impurity E |
| Storage | Store at 2-8°C under inert atmosphere |
| IUPAC Name | (3S,4S,5R)-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-VPZFNDQJSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Orange-brown Solid |
| Boiling Point | 742.4±60.0°C (Predicted) |
| Melting Point | 200-204°C |
| Density | 1.62±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. The effect of cooking on veterinary drug residues in food: 4. Oxytetracycline
G Shearer, W H Farrington, M D Rose, J Bygrave Food Addit Contam . 1996 Apr;13(3):275-86. doi: 10.1080/02652039609374409.
The heat stability of oxytetracycline (OTC) in water and vegetable oil was investigated. Results showed that the drug was unstable in water at 100 degrees C with a half-life of about 2 min, but more stable in oil at 180 degrees C where the half-life was about 8 min. The effect of a range of cooking processes including microwaving, boiling, roasting, grilling, braising and frying on OTC residues in incurred animal tissues was investigated. Substantial net reductions in OTC of 35-94% were observed, with temperature during cooking having the largest impact on the loss. Migration from the tissue into the surrounding liquid or meat juices was observed during the cooking processes. Diode-array analysis of heat-treated OTC standard solutions indicated that no individual closely related compound such as 4-epioxytetracycline, alpha- or beta-apooxytetracycline formed a significant proportion of the breakdown products. OTC was not evenly distributed throughout the tissue, but the effects of this were minimized by selecting adjacent samples for cooking and for the raw control. The findings of this investigation showed that the effect of cooking on residues of OTC should be considered before data obtained from measurements on raw tissue are used for consumer exposure estimates and dietary intake calculations.
2. Quantitative analysis of oxytetracycline and related substances by high-performance liquid chromatography
E Roets, H Vanderhaeghe, N H Khan, J Hoogmartens J Chromatogr . 1987 Sep 18;405:229-45. doi: 10.1016/s0021-9673(01)81765-9.
Isocratic high-performance liquid chromatography on PLRP-S 8-microns poly(styrene-divinylbenzene) copolymer allows complete separation of oxytetracycline, 4-epioxytetracycline, tetracycline, anhydrooxytetracycline, alpha- and beta-apooxytetracycline. The mobile phase was tert.-butanol-0.2 M phosphate buffer pH 8.0-0.02 M tetrabutylammonium sulphate pH 8-0.0001 M sodium ethylenediaminetetraacetate pH 8.0-water (5.9:10:5:10:78.1, m/v/v/v/v). With this isocratic method, 2-acetyl-2-decarboxamidooxytetracycline is only partly resolved from oxytetracycline. The separation and the detection limits can be improved by the use of gradient elution. Gradient elution was used for the comparison of official standards and for the analysis of a number of commercial samples, and to monitor the stability of oxytetracycline hydrochloride during storage in the solid state for about 6 years at various temperatures.
3. C(18) columns for the simultaneous determination of oxytetracycline and its related substances by reversed-phase high performance liquid chromatography and UV detection
Helen A Archontaki, C G Smyrniotakis J Pharm Biomed Anal . 2007 Jan 17;43(2):506-14. doi: 10.1016/j.jpba.2006.07.048.
Simultaneous determination of oxytetracycline, 4-epioxytetracycline, alpha-apooxytetracycline, tetracycline and beta-apooxytetracycline on C(18) columns has been accomplished using a high performance liquid chromatographic method with UV detection. Separation was achieved on a Hypersil BDS RP-C(18) column (250 mm x 4.6 mm) and on a Waters C(18) Symmetry column (150 mm x 3.9mm), 5 microm particle size each. These columns were equilibrated with mobile phases consisted of methanol-acetonitrile-0.1M phosphate buffer pH 8.0 (12.5:12.5:75, v/v/v) and (15:15:70, v/v/v), respectively. The flow rate was 1.0 ml/min and the total elution time was 15 and 5 min, respectively. Both methods were applied to oxytetracycline raw material, human and veterinary formulations, where the excipients did not interfere. External standard calibration curves were linear for 4-epioxytetracycline, oxytetracycline, alpha-apooxytetracycline, tetracycline and beta-apooxytetracycline in the concentration range of 0.27-200 microM, 0.05-200 microM, 0.03-200 microM, 0.35-200 microM and 0.20-200 microM on column A and 0.08-200 microM, 0.15-200 microM, 0.09-200 microM, 0.25-200 microM and 0.47-200 microM on column B, respectively. Day-to-day relative standard deviation of the determination for every component was less than 3%. Concerning the first column, limits of detection and quantification of the above compounds were in the concentration ranges of 10-106 nM and 30-352 nM, respectively, whereas on the second column these ranges became 27-144 nM and 81-475 nM, respectively. Recovery of the separated compounds was 95-105%.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
