Doxycycline hydrochloride

Base Information

• Chemical Name: Doxycycline hydrochloride
• CAS No.: 10592-13-9
• Molecular Formula: C₂₂H₂₄N₂O₈*ClH
• Molecular Weight: 480.902
• Hs Code.: 29413000
• Mol file: 10592-13-9.mol

Synonyms:2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride (8CI);2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride, (4S,4aR,5S,5aR,6R,12aS)- (9CI);2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,monohydrochloride, [4S-(4a,4aa,5a,5aa,6a,12aa)]-;2-Naphthacenecarboxamide,4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-,hydrochloride (6CI);6-Deoxyoxytetracycline hydrochloride;6-Desoxy-5-hydroxytetracycline hydrochloride;Deoxy-5-hydroxytetracyclinehydrochloride;Deoxyoxytetracycline hydrochloride;Doxylin;Idocyklin;Vibramycin hyclate;Vibramycin hydrochloride;a-6-Deoxy-5-hydroxytetracyclinehydrochloride;

Chemical Property of Doxycycline hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 195-201℃
• Boiling Point: 762.6 °C at 760 mmHg
• Flash Point: 415 °C
• PSA: 181.62000
• Density: 1.63 g/cm³
• LogP: 1.15470
• Storage Temp.: 0-6°C
• Solubility.: H2O: 50 mg/mL, clear, yellow-green
• Water Solubility.: Soluble in water.

Purity/Quality:

98%min ^*data from raw suppliers

Doxycycline Hydrochloride, Ready Made Solution ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: antibiotic Doxycycline hydrochloride is a salt prepared from doxycycline taking advantage of the basic dimethylamino group which protonates and readily forms a salt in hydrochloric acid solutions. The hydrochloride is the preferred formulation for pharmaceutical applications. Like all tetracyclines, doxycycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal subunits, blocking protein synthesis. Doxycycline hydrochloride, is used to eliminate Borrelia burgdorferi and Anaplasma phagocytophilum in rodent reservoirs and to eliminate Ixodes scapularis ticks. It is a broad spectrum inhibitor used to inhibit matrix metalloproteinases (MMP), such as type 1 collagenase in studies on wound healing and tissue remodeling.

Technology Process of Doxycycline hydrochloride

There total 16 articles about Doxycycline 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: 90.0%

C37H34N2O10 → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

C₃₇H₃₄N₂O₁₀; With hydrogen; palladium; In tetrahydrofuran; methanol; at 23 ℃; for 2h; under 760.051 Torr;

With hydrogenchloride; In methanol; water; HPLC;

DOI:10.1021/ja806629e

Reference yield: 90.0%

doxycycline (564-25-0,10597-92-9,7164-70-7,7264-10-0) → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

With hydrogenchloride; In methanol; water;

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

Multi-step reaction with 15 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: triphenylphosphine; carbon tetrabromide / acetonitrile / 0.33 h / 0 - 23 °C

6.1: triethylamine / acetonitrile / 0.5 h / 0 - 23 °C

7.1: (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine / dichloromethane / 20 h / 23 °C

8.1: phosphorous acid trimethyl ester / methanol / 36 h

9.1: dmap / dichloromethane / 2 h / 23 °C

10.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C

11.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 12 h / 23 °C / Darkness

12.1: triethylamine / tetrahydrofuran / 0.67 h / 0 °C

13.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

13.2: 2 h / -75 - 0 °C / Inert atmosphere

14.1: hydrogen fluoride; water / acetonitrile / 60 h / 23 °C / Inert atmosphere

15.1: palladium; hydrogen / methanol; tetrahydrofuran / 2 h / 23 °C / 760.05 Torr

15.2: Inert atmosphere

With dmap; n-butyllithium; carbon tetrabromide; N,N,N,N,-tetramethylethylenediamine; 2-iodoxybenzoic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; water; hydrogen; lithium trifluoromethanesulfonate; palladium; acetic acid; (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; benzene; 13.1: |Michael Addition / 13.2: |Dieckmann Condensation;

upstream raw materials:

doxycycline

(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:

(4S,4aR,5S,5aR,6R,12aS)-3,5,10,12,12a-pentahydroxy-6-methyl-4-(methylamino)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

malonic acid

doxycycline

Refernces

• 1、 Sun, Cuixiang,Wang, Qiu,Brubaker, Jason D.,Wright, Peter M.,Lerner, Christian D.,Noson, Kevin,Charest, Mark,Siegel, Dionicio R.,Wang, Yi-Ming,Myers, Andrew G.. "A robust platform for the synthesis of new tetracycline antibiotics". supporting information; experimental part. p. 17913 - 17927. Retrieved 2009/07/18.