Theophylline-7-acetic acid Chemical Properties

Melting point:

270-272 °C

Boiling point:

269-271 C

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly)

form 

Solid

pka

3.72±0.10(Predicted)

color 

White

Merck 

14,24

BRN 

279221

LogP

-0.490 (est)

CAS DataBase Reference

652-37-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

UO7451300

HS Code 

2939.59.0000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Theophylline-7-acetic acid Usage And Synthesis

Chemical Properties

White Solid

Uses

Bronchospasm;Adenosine receptor antagonist

Definition

ChEBI: 2-(1,3-dimethyl-2,6-dioxo-7-purinyl)acetic acid is an oxopurine.

Synthesis

General method: LiOH-H2O (1.5 eq.) was added in batches to a stirred solution of ester compounds 2a-2b (1.0 eq.) dissolved in THF (10 v/v) and H2O (10 v/v) at room temperature, and the reaction mixture was stirred continuously for 2 hr. The reaction progress was monitored by TLC. Upon completion of the reaction, THF was removed by concentration under reduced pressure, acidified to acidity with aqueous KHSO4, and subsequently extracted with a solvent mixture of 5% methanol and dichloromethane. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the target solid products 3a-3b. 4.2.3 Synthesis of 2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetic acid (3a): compound 2a (5 g, 18.78 mmol) was dissolved in 100 mL of THF:H2O (1:1) mixed solvent, LiOH-H2O (1.18 g, 28.18 mmol) was added, and the product was extracted as described in the The above general method was operated to give the white solid product 3a (4.1 g, 91% yield).1H NMR (400 MHz, DMSO-d6) δ: 13.27 (brs, 1H), 8.04 (s, 1H), 5.07 (s, 2H), 3.44 (s, 3H), 3.20 (s, 3H); m/z (ES)+: 239.04 [M +H]+.

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 379 - 396
[2] MedChemComm, 2017, vol. 8, # 1, p. 176 - 183
[3] Ricerca Scientifica, 1952, vol. 22, p. 1596,1599
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2527 - 2534
[5] Heterocyclic Communications, 2015, vol. 21, # 1, p. 13 - 18

Theophylline-7-acetic acid(652-37-9)Related Product Information

• Theophylline
• N,N-Dimethylformamide
• DIOXOPROMETHAZINE HCL
• Selenium dioxide
• Dimethyl sulfoxide
• Dimethyl fumarate
• Ethyl acetate
• Trichloroacetic acid
• Glycine
• Dimethyl sulfate
• ETHANE
• Dimethyl carbonate
• Aminophylline
• Ethyl 2-(Chlorosulfonyl)acetate
• Acetic acid
• Trifluoroacetic acid
• Dimethyl ether
• 1,4-Dioxane