Tetracycline hydrochloride

Base Information

• Chemical Name: Tetracycline hydrochloride
• CAS No.: 64-75-5
• Molecular Formula: C22H24N2O8^.HCl
• Molecular Weight: 480.902
• Hs Code.: 29413000
• Mol file: 64-75-5.mol

Synonyms:Neocycline B;Paltet;Panmycin hydrochloride;Partrex;Polyotic ointment;Purocyclina;Remicyclin;Riocyclin;Robitet;Subamycin;Supramycin;Tefilin;Tet-Cy;Tetrabakat;Tetrabid;Tetrabon;Tetrachel;Tetracompren;Tetracycline hydrochloride;Tetracyn;Tetralution;Tetrosol;Triphacyclin;Unicin;Vetquamycin 324;2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride (8CI);Achro;Achromycin hydrochloride;Ala-Tet;Ambracyn;Bristacycline;Cancycline-250;Criseociclina;Dumocyclin;Helvecyclin;Hostacycline;Medamycin;Tetracycline HCL;

Chemical Property of Tetracycline hydrochloride

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Vapor Pressure: 5.82E-27mmHg at 25°C
• Melting Point: 220-223 °C(lit.)
• Refractive Index: -253 ° (C=0.5, 0.1mol/L HCl)
• Boiling Point: 799.4 °C at 760 mmHg
• Flash Point: 437.3 °C
• PSA: 181.62000
• LogP: 1.28790
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: H2O: 10 mg/mL as a stock solution. Stock solutions should b
• Water Solubility.: 50 g/L

Purity/Quality:

99%, ^*data from raw suppliers

Tetracycline Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Tetracycline is a broad-spectrum antibiotic that prevents bacterial growth by inhibiting protein synthesis. It binds to a single site in the 30S ribosomal subunit which prevents attachment of aminoacyl tRNA to the ribosomal acceptor site. It is used in cell biology as a selective agent in cell culture systems. Tetracycline is toxic to prokaryotic and eukaryotic cells and selects for cells harboring the bacterial tetR gene, which are resistant to the antibiotic.
• Uses: Antibiotic substance produced by Streptomyces spp. Antiamebic; antibacterial; antirickettsial. Tetracycline hydrochloride is a salt prepared from tetracycline taking advantage of the basic dimethylamino group which protonates and readily forms the salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Tetracycline hydrochloride has broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-unit,s blocking protein synthesis. Tetracycline hydrochloride is used to induce apoptosis in osteoclasts. It is used to treat acne and other skin infections, respiratory tract infections like pneumonia, genital, urinary infections, leptospirosis, helicobacter pylori, taxoplasmosis, mycoplasma, psittacosis for dog and cats. It also works more effectively in animals that have tick-borne infections. It is also useful in cell culture applications.

Technology Process of Tetracycline hydrochloride

There total 17 articles about Tetracycline hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C36H32N2O9 → tetracycline hydrochloride (64-75-5)

Guidance literature:

C₃₆H₃₂N₂O₉; With hydrogen; palladium; In 1,4-dioxane; at 23 ℃; for 2h; under 760.051 Torr;

With hydrogenchloride; In methanol; water; acetonitrile; Inert atmosphere;

Reference yield:

TETRACYCLINE (60-54-8) → tetracycline hydrochloride (64-75-5)

Guidance literature:

With hydrogenchloride; In methanol; water;

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → tetracycline hydrochloride (64-75-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10.5 h / 23 °C / Inert atmosphere

2.1: methanol; hexane; benzene / 0.08 h / 23 °C / Inert atmosphere

2.2: 0.5 h

3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere

4.2: 18 h / 23 °C / Inert atmosphere

5.1: diethylazodicarboxylate; triphenylphosphine / toluene / 1.5 h / 0 °C / Inert atmosphere

5.2: 23 h / 0 - 23 °C / Inert atmosphere

6.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 0 - 23 °C / Inert atmosphere

7.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 36 h / 23 °C / Inert atmosphere

8.1: pyridinium hydrobromide perbromide / dichloromethane / 17 h / 23 °C / Inert atmosphere

8.2: 0.42 h / 0 °C / Inert atmosphere

9.1: 48 h / 85 °C / Inert atmosphere

10.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere

11.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 18 h / 23 - 35 °C / Darkness; Inert atmosphere

12.1: 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid / dichloromethane / 0.67 h / -78 - 0 °C / Inert atmosphere

12.2: air

13.1: palladium; hydrogen / 1,4-dioxane / 2 h / 23 °C / 760.05 Torr

13.2: Inert atmosphere

With n-butyllithium; 2-iodoxybenzoic acid; tetrabutyl ammonium fluoride; hydrogen; lithium trifluoromethanesulfonate; palladium; acetic acid; pyridinium hydrobromide perbromide; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; benzene; 9.1: |Diels-Alder Cycloaddition;

upstream raw materials:

TETRACYCLINE

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

(1S,2R,3S,6R)-2,3-Dihydroxy-7-oxa-bicyclo[4.1.0]hept-4-ene-3-carboxylic acid

(1S,2R,3R,6S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-4-ene-1-carboxylic acid methyl ester

Downstream raw materials:

carbon dioxide

water

TETRACYCLINE

piperidine hydrochloride

Refernces

• 1、 -. "SYNTHESIS OF TETRACYCLINES AND ANALOGUES THEREOF". Page/Page column 106-107. . Retrieved 2008/06/13.