1-Theobromineacetic acid

Base Information

• Chemical Name: 1-Theobromineacetic acid
• CAS No.: 5614-56-2
• Molecular Formula: C9H10 N4 O4
• Molecular Weight: 238.203
• Hs Code.: 2933990090
• European Community (EC) Number: 227-034-0
• UNII: 6XL1I8J8NT
• DSSTox Substance ID: DTXSID50204672
• Nikkaji Number: J8.028D
• Wikidata: Q27265676
• ChEMBL ID: CHEMBL67109
• Mol file: 5614-56-2.mol

Synonyms:3,7-dimethylxanthine-1-methanecarboxylic acid

Chemical Property of 1-Theobromineacetic acid

Chemical Property:

• Vapor Pressure: 1.66E-13mmHg at 25°C
• Melting Point: 260 °C
• Boiling Point: 562.9°Cat760mmHg
• PKA: 3.61±0.10(Predicted)
• Flash Point: 294.2°C
• PSA: 99.12000
• Density: 1.64g/cm³
• LogP: -1.48170
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 238.07020481
• Heavy Atom Count: 17
• Complexity: 385

Purity/Quality:

99% ^*data from raw suppliers

(3,7-DIMETHYL-2,6-DIOXO-2,3,6,7-TETRAHYDRO-1H-PURIN-1-YL)ACETIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC2=C1C(=O)N(C(=O)N2C)CC(=O)O

Technology Process of 1-Theobromineacetic acid

There total 5 articles about 1-Theobromineacetic acid 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: 93.0%

tert-butyl 2-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)acetate → 1-Theobromineacetic acid (5614-56-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 4h; Cooling with ice;

Reference yield: 66.0%

(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purine-1-yl) acetic acid ethyl ester (75449-03-5) → 1-Theobromineacetic acid (5614-56-2)

Guidance literature:

With water; potassium hydroxide; In acetone; for 30h; Reflux;

DOI:10.2174/1570180811666140718162449

Reference yield:

theobromine / (83-67-0) → 1-Theobromineacetic acid (5614-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetone / Heating

2: sodium hydroxide / acetone; water / Heating

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; sodium hydroxide; In water; acetone;

DOI:10.1515/hc-2014-0200

upstream raw materials:

theobromine /

chloroacetic acid

(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-purine-1-yl) acetic acid ethyl ester

Downstream raw materials:

N-(1-Acetyl-2,3,6,7-tetrahydro-3,7-dimethyl-2,6-dioxo-1H-purine)-N,N'-dicyclohexylurea

2,3,6,7-Tetrahydro-3,7-dimethyl-2,6-dioxo-1H-purine-1-acetic acid 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purin-7-yl)ethyl ester

1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purin-7-yl)ethyl ester

Refernces

• 1、 Ma, Ting,Ma, Qi-Sheng,Yu, Bin,Liu, Hong-Min. "Discovery of the theobromine derivative MQS-14 that induces death of MGC-803 cells mainly through ROS-mediated mechanisms". . p. 76 - 86. Retrieved 2019/07/02.
• 2、 Zygmunt, Maigorzata,Zmudzki, Pawe?,Ch?oń-Rzepa, Grazyna,Sapa, Jacek,Paw?owski, Maciej. "Synthesis and analgesic activity of 3,7-dimethylpurine-2,6-dion-1-yl derivatives of acetic and butanoic acid". . p. 1204 - 1213. Retrieved 2015/03/31.