Tetracycline hydrochloride
SIAL/31741 - VETRANAL®, analytical standard
CAS Number: 64-75-5
Empirical Formula (Hill Notation): C22H24N2O8 · HCl
Molecular Weight: 480.90
EC Number: 200-593-8
MDL Number: MFCD00078142
Linear Formula: C22H24N2O8 · HCl
Product Type: Chemical
| application(s) | cleaning products cosmetics food and beverages forensics and toxicology personal care pharmaceutical (small molecule) |
| format | neat |
| grade | analytical standard |
| InChI | 1S/C22H24N2O8.ClH/c1-21(3 |
| InChI key | XMEVHPAGJVLHIG-FMZCEJRJSA |
| mp | 220-223 °C (lit.) |
| product line | VETRANAL® |
| Quality Level | 100  |
| shelf life | limited shelf life, expiry date on the label |
| SMILES string | Cl.CN(C)[C@H]1[C@@H]2C[C@ |
| storage temp. | 2-8°C |
| technique(s) | gas chromatography (GC): suitable |
| HPLC: suitable |
| 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. |
| 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. |
| Legal Information: | VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH |
| 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. |
| Symbol |    GHS07,GHS08,GHS09 |
| Signal word | Warning |
| Hazard statements | H315 - H319 - H335 - H361fd - H410 |
| Precautionary statements | P201 - P202 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313 |
| Hazard Codes | Xn |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | WGK 2 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 220-223 °C (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 41116107 |