31741
Tetracycline hydrochloride
VETRANAL®, analytical standard
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About This Item
Empirical Formula (Hill Notation):
C22H24N2O8 · HCl
CAS Number:
Molecular Weight:
480.90
NACRES:
NA.24
E Number:
E701
PubChem Substance ID:
UNSPSC Code:
41116107
EC Number:
200-593-8
MDL number:
Beilstein/REAXYS Number:
3844873
Product Name
Tetracycline hydrochloride, VETRANAL®, analytical standard
InChI key
XMEVHPAGJVLHIG-FMZCEJRJSA-N
InChI
1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
SMILES string
Cl.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O
grade
analytical standard
product line
VETRANAL®
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
mp
220-223 °C (lit.)
application(s)
cleaning products
cosmetics
food and beverages
forensics and toxicology
personal care
pharmaceutical (small molecule)
format
neat
storage temp.
2-8°C
Quality Level
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Application
Tetracycline (TCH) has been used in studies of multidrug resistance and potential side effects including acute pancreatitis. It is recommended for use in cell culture applications at 10 mg/L. TCH is also used as a reference standard in LC/MS/MS method for tetracycline residue analysis in biological samples.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Biochem/physiol Actions
Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.
Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.
Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.
Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.
Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.
Disclaimer
This product should be frozen below 0°C and protected from light and moisture. In these conditions, the product has been shown to retain activity for 4 years. Stock solutions should be stored at -20°C and are stable at 37°C for 4 days.
General description
Tetracycline hydrochloride (TCH) is a broad-spectrum polyketide antibiotic with clinical uses in treating bacterial infections such as Rocky Mountain spotted fever, typush fever, tick fevers, Q fever, and Brill-Zinsser disease and to treat upper respiratory infections and acne. It also helps as an alternate drug for penicillin.
Preparation Note
The product is freely soluble in water, soluble in methanol and ethanol but is insoluble in ether and hydrocarbons. In water, the product yields a clear, yellow-orange solution with heating and in 95% ethanol, 50 mg dissolved in 4 mL with heating yields a clear, yellow-green solution. Tetracycline is rapidly destroyed by alkali hydroxide solutions and standing water solutions become turbid due to hydrolysis and precipitation. The potency of tetracycline is reduced in solutions with pH below 2.
Legal Information
VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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A molecular imprinted membrane for molecular discrimination of tetracycline hydrochloride.
Trotta, F., et al.
Journal of Membrane Science, 254.1, 13-19 (2005)
Yasuhiro Igarashi et al.
Journal of natural products, 74(4), 670-674 (2011-03-11)
A new spirotetronate-class polyketide, maklamicin (1), was isolated from the culture extract of an endophytic actinomycete of the genus Micromonospora. The structure and relative configuration of 1 were elucidated by interpretation of NMR and other spectroscopic data, and the absolute
Ruiling Qi et al.
Colloids and surfaces. B, Biointerfaces, 110, 148-155 (2013-05-29)
Fabrication of nanofiber-based drug delivery system with controlled release property is of general interest in biomedical sciences. In this study, we prepared an antibiotic drug tetracycline hydrochloride (TCH)-loaded halloysite nanotubes/poly(lactic-co-glycolic acid) composite nanofibers (TCH/HNTs/PLGA), and evaluated the drug release and
T Bouchery et al.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases, 19(2), 131-140 (2013-02-13)
Symbiotic associations between eukaryotes and microorganisms are frequently observed in nature, and range along the continuum between parasitism and mutualism. The genus Wolbachia contains well-known intracellular bacteria of arthropods that induce several reproductive phenotypes that benefit the transmission of the
Zhijie Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5004-5009 (2013-03-12)
Reported here is a piggyBac transposon-based expression system for the generation of doxycycline-inducible, stably transfected mammalian cell cultures for large-scale protein production. The system works with commonly used adherent and suspension-adapted mammalian cell lines and requires only a single transfection
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