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31741 Supelco

Tetracycline hydrochloride

VETRANAL®, analytical standard

  • CAS Number 64-75-5

  • Empirical Formula (Hill Notation) C22H24N2O8 · HCl

  • Molecular Weight 480.90

  •  Beilstein/REAXYS Number 3844873

  •  EC Number 200-593-8

  •  MDL number MFCD00078142

  •  PubChem Substance ID 329753913

  •  E Number E701

  •  NACRES NA.24

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Properties

Related Categories Additional Standards, Analytical Standards, Analytical/Chromatography, Antibiotics Standards, Chromatography,
Quality Level   100
grade   analytical standard
product line   VETRANAL®
form   neat
shelf life   limited shelf life, expiry date on the label
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
mp   220-223 °C (lit.)
Featured Industry   Cleaning Products
Cosmetics
Food and Beverages
Forensics and Toxicology
Personal Care
Pharmaceutical (small molecule)
format   neat
storage temp.   2-8°C
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
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
InChI key   XMEVHPAGJVLHIG-FMZCEJRJSA-N

Description

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.

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.

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.

Caution

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.

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 Sigma-Aldrich Chemie GmbH

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
WGK 2
RTECS 
QI9100000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

HPLC Analysis of Tetracycline Antibiotics on Ascentis® Express C18

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Tetracycline Antibiotics on Ascentis® Express C18
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Metabolites, Separation

LC/MS/MS Analysis of Tetracycline Antibiotics on Kromasil® Eternity™ C18

From our library of Articles, Sigma-Aldrich presents LC/MS/MS Analysis of Tetracycline Antibiotics on Kromasil® Eternity™ C18
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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