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37919

Supelco

Anhydrotetracycline hydrochloride

VETRANAL®, analytical standard

Synonym(s):

(4S,4aS,12aS)-4-(Dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide monohydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H22N2O7 · HCl
CAS Number:
13803-65-1
Molecular Weight:
462.88
Beilstein:
4228856
MDL number:
MFCD00151453
UNSPSC Code:
41116107
PubChem Substance ID:
329755727
NACRES:
NA.24
Pricing and availability is not currently available.

grade

analytical standard

Quality Level

100

Agency

EPA 1694

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

storage condition

under inert gas

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

clinical testing

format

neat

SMILES string

Cl[H].[H][C@@]12Cc3c(C)c4cccc(O)c4c(O)c3C(=O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

InChI

1S/C22H22N2O7.ClH/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28;/h4-6,11,16,25-27,31H,7H2,1-3H3,(H2,23,30);1H/t11-,16-,22-;/m0./s1

InChI key

XBSQEFHDCDFNJU-WPJNXPDPSA-N

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General description

Anhydrotetracycline (ATC) is a degradation product of tetracycline hydrochloride, a widely used antibiotic in animal breeding.[1]

Application

The analytical standard can be used as follows:
  • Terahertz (THz) spectroscopy-based temperature-dependent quantitative and qualitative analysis of the antibiotic, tetracycline hydrochloride, and its three major metabolites
  • Simultaneous analysis of tetracycline hydrochloride and its degradation products in a pharmaceutical formulation by Resonance Raman Spectroscopy to study stress-induced stability of the drug
  • Development and validation of a liquid chromatography-tandem mass spectroscopy (LC-MS/MS) method to determine 21 antibiotic residues used as veterinary medicinal products in honey samples
  • Estimation of eight tetracycline antibiotics in various environmental water samples by dispersive liquid-liquid microextraction (DLLME) followed by an ultra-high pressure liquid chromatography (UHPLC)-tunable ultraviolet detection (TUV)

Other Notes

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360D

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9210
BCCK3339
BCCJ1168
BCCG9640
BCCF4540

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Susceptibility of Escherichia coli and Enterococcus faecium isolated from pigs and broiler chickens to tetracycline degradation products and distribution of tetracycline resistance determinants in E. coli from food animals
Sengelov G, et al.
Veterinary Microbiology, 95, 91-101 (2003)
Francesca Boldrin et al.
Nucleic acids research, 38(12), e134-e134 (2010-04-22)
Tightly regulated gene expression systems represent invaluable tools for studying gene function and for the validation of drug targets in bacteria. While several regulated bacterial promoters have been characterized, few of them have been successfully used in mycobacteria. In this
Marta Gratacós-Cubarsí et al.
Journal of agricultural and food chemistry, 55(11), 4610-4616 (2007-05-10)
Tetracycline (TC) and 4-epitetracycline (4eTC) degradation, as well as anhydrotetracycline (ATC) and 4-epianhydrotetracycline (4eATC) formation, has been evaluated in thermally treated chicken breast, pig loin, and pig loin with added back-fat. Samples containing TC and 4eTC residues were submitted to
Christine R Whetstine et al.
Applied and environmental microbiology, 75(20), 6553-6558 (2009-08-25)
We developed a single-plasmid-based regulatable protein expression system for Borrelia burgdorferi. Expression of a target gene is driven by P(ost), a hybrid B. burgdorferi ospA-tetO promoter, from a recombinant B. burgdorferi plasmid constitutively expressing TetR. The system was tested using
Wyndham W Lathem et al.
Science (New York, N.Y.), 315(5811), 509-513 (2007-01-27)
Primary pneumonic plague is transmitted easily, progresses rapidly, and causes high mortality, but the mechanisms by which Yersinia pestis overwhelms the lungs are largely unknown. We show that the plasminogen activator Pla is essential for Y. pestis to cause primary
View All Related Papers

Questions

1–6 of 6 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. For how long can I store anhydrotetracycline hydrochloride dissolved in DMSO at -20°C?

    1 answer

    1. The stability of this compound in solution has not been investigated. In general, solutions prepared fresh are recommended. However, various sources report that this material is stable when stored in Dimethylformamide at -20°C. The stability in anhydrous DMSO is expected to similar. No time frame is provided. This information has not been validated. Note that this product is packaged under nitrogen. Stock solutions should be stored likewise.

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  4. What is the correct temperature for storing ATC in the form of powder?

    1 answer

    1. This product is stored at room temperature.

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  5. How can I dissolve anhydrotetracycline hydrochloride?

    1 answer

    1. Anhydrotetracycline hydrochloride can be dissolved in any of several different organic solvents:1.  Ethanol:  2 mg/mL2.  DMSO:  10 mg/mL3.  DMF:  10 mg/mL.

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  6. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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