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1-(5-hydroxy-5-methylhexyl)-3-methylxanthine

Product Name
1-(5-hydroxy-5-methylhexyl)-3-methylxanthine
CAS No.
107767-55-5
Chemical Name
1-(5-hydroxy-5-methylhexyl)-3-methylxanthine
Synonyms
HWA-138;1-(5-hydroxy-5-methylhexyl)-3-methylxanthine;3,7-Dihydro-1-(5-hydroxy-5-methylhexyl)-3-methyl-1H-purine-2,6-dione;1H-Purine-2,6-dione, 3,9-dihydro-1-(5-hydroxy-5-methylhexyl)-3-methyl-
CBNumber
CB81318128
Molecular Formula
C13H20N4O3
Formula Weight
280.32
MOL File
107767-55-5.mol
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1-(5-hydroxy-5-methylhexyl)-3-methylxanthine Property

Boiling point:
527.2±56.0 °C(Predicted)
Density 
1.270±0.06 g/cm3(Predicted)
pka
8.62±0.70(Predicted)
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Hazard and Precautionary Statements (GHS)

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1-(5-hydroxy-5-methylhexyl)-3-methylxanthine Chemical Properties,Usage,Production

Originator

HWA-138 ,Hoechst-Roussel

Manufacturing Process

1-(5-Hydroxy-5-methylhexyl)-3-methylxanthine may be prepared next way: 1). 1-Chloro-5-hydroxy-5-methylhexane:
A solution of 67.3 g (0.5 mol) of 1-chloro-5-hexanone in 50 ml of anhydrous ether is added dropwise to 44.9 g (0.6 mol) of methyl magnesium chloride in the form of a 20% strength solution in tetrahydrofuran and 200 ml of dry ether at 0° to 5°C, while stirring. The mixture is then subsequently stirred initially at room temperature for one hour and then while boiling under reflux for a further hour, the tertiary alkanolate formed is decomposed by addition of 50% strength aqueous ammonium chloride solution, the ether phase is separated off and the aqueous phase is extracted by shaking with ether. The combined ethereal extracts are washed in succession with aqueous sodium bisulfite solution and sodium bicarbonate solution as well as a little water, dried over sodium sulfate, filtered and concentrated in vacuo and the liquid residue is subjected to fractional distillation under reduced pressure. Yield: 64.1 g (85.1% of theory), boiling point (20 mbar) 95-97°C, refractive index nD25 =1.4489.
2). 7-Benzyl-3-methylxanthine:
20 g (0.5 mol) of sodium hydroxide dissolved in 200 ml of water are added to a suspension of 83 g (0.5 mol) of 3-methylxanthine in 500 ml of methanol, the mixture is stirred at 70°C for one hour, 85.5 g (0.5 mol) of benzyl bromide are then added dropwise at the same temperature and the reaction mixture is kept between 70°C and 80°C for 5 hours. It is then cooled and filtered cold with suction, the product on the suction filter is washed with water and dissolved in 1000 ml of 1 N sodium hydroxide solution under the influence of heat, the solution is filtered and the pH is brought slowly to 9.5 with 4 N hydrochloric acid, while stirring. The crystals are filtered off from the still warm solution, washed with water until free from chloride and dried in vacuum. Yield: 81.7 g (63.8% of theory), melting point: 262-264°C.
3). 7-Benzyl-1-(5-hydroxy-5-methylhexyl)-3-methylxanthine:
A mixture of 20.5 g (0.08 mol) of 7-benzyl-3-methylxanthine, 12.4 g (0.09 mol) of potassium carbonate and 13.61 g (0.09 mol) of above 1-chloro-5- hydroxy-5-methylhexane in 300 ml of dimethylformamide is heated at 110° to 120°C for 8 hours, while stirring, and is then filtered hot and the filtrate is evaporated under reduced pressure. The residue is taken up in chloroform, the mixture is washed first with 1 N sodium hydroxide solution and then with water until neutral and dried, the solvent is distilled off in vacuum and the solid residue is recrystallized from ethyl acetate, with the addition of petroleum ether Yield: 23.8 g (80.3% of theory), melting point: 109-111°C.
4). 1-(5-Hydroxy-5-methylhexyl)-3-methylxanthine:
14.8 g (0.04 mol) of the above mentioned 7-benzylxanthine are hydrogenated in 200 ml of glacial acetic acid over 1.5 g of palladium (5%) on active charcoal at 60°C under 3.5 bar in the course of 24 hours, while shaking. After cooling, the mixture is blanketed with nitrogen, the catalyst is filtered off, the filtrate is concentrated under reduced pressure and the solid residue is recrystallized from ethyl acetate. Yield of albifylline: 9.6 g (85.6% of theory), MP: 192-193°C.

Therapeutic Function

Vasodilator

1-(5-hydroxy-5-methylhexyl)-3-methylxanthine Preparation Products And Raw materials

Raw materials

Preparation Products

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1-(5-hydroxy-5-methylhexyl)-3-methylxanthine Suppliers

TargetMol Chemicals Inc.
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+1-781-999-5354 +1-00000000000
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marketing@targetmol.com
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United States
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Changzhou Bojia Biomedical Technology Co., Ltd.
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2122619822
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czbjpharma@126.com
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China
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TargetMol Chemicals Inc.
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15002134094
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marketing@targetmol.cn
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China
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TargetMol Chemicals Inc.
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+8613564774135
Email
zijue.cai@tsbiochem.com
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United States
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19885
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107767-55-5, 1-(5-hydroxy-5-methylhexyl)-3-methylxanthineRelated Search:


  • 1-(5-hydroxy-5-methylhexyl)-3-methylxanthine
  • 3,7-Dihydro-1-(5-hydroxy-5-methylhexyl)-3-methyl-1H-purine-2,6-dione
  • HWA-138
  • 1H-Purine-2,6-dione, 3,9-dihydro-1-(5-hydroxy-5-methylhexyl)-3-methyl-
  • 107767-55-5