Theobromine

Base Information

• Chemical Name: Theobromine
• CAS No.: 83-67-0
• Molecular Formula: C7H8N4O2
• Molecular Weight: 180.166
• Hs Code.: 29399990
• European Community (EC) Number: 201-494-2
• NSC Number: 757407,5039
• UNII: OBD445WZ5P
• DSSTox Substance ID: DTXSID9026132
• Nikkaji Number: J3.874A
• Wikipedia: Theobromine
• Wikidata: Q206844
• NCI Thesaurus Code: C87684
• RXCUI: 10437
• Metabolomics Workbench ID: 38208
• ChEMBL ID: CHEMBL1114
• Mol file: 83-67-0.mol

Synonyms:Theobromine

Chemical Property of Theobromine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 345-350 °C
• Refractive Index: 1.737
• Boiling Point: Sublimes 290-295oC
• PKA: 7.89(at 18℃)
• Flash Point: 290-295°C
• PSA: 72.68000
• Density: 1.608 g/cm³
• LogP: -1.03970
• Storage Temp.: Refrigerator
• Solubility.: H2O: slightly soluble
• Water Solubility.: slightly soluble,
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 180.06472551
• Heavy Atom Count: 13
• Complexity: 267

Purity/Quality:

99%, ^*data from raw suppliers

Theobromine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 22-24/25-36-26-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC2=C1C(=O)NC(=O)N2C
• Recent ClinicalTrials: Effects of a Cocoa Shot on the Human Brain
• Recent EU Clinical Trials: A Multicentre, Double-Blind, Placebo-Controlled, Adaptive Pivotal Study of the Efficacy and Safety of Oral BC1036 in the Management of Cough
• Description: A purine alkaloid which is present in a number of plants, particularly Theobroma coco and kola nuts. The alkaloid sublimes at 290°C and may be purified by this method when it forms colourless, rhombic microcrystals. It is soluble in 1600 parts of H20 at 17°C, insoluble in cold Et20 or ligroin. It is a weak base and the salts are decomposed by H20. The perchlorate forms colourless crystals of the monohydrate which decompose at 271-3°C; the mercurinitrate is also crystalline and has a melting point above 300°C. The mercury salt is obtained as colourless crystals which darken at 29S-300°C and melt at 310°C. One imino group is present yielding alkyl derivative, e.g. the N-methyl compound identical with Caffeine (q.v.); the N~ethyl derivative, m.p. 164-SoC, forming an aurichloride, m.p. 226°C; N-propyl, m.p. 136°C giving an aurichloride, m.p. 9SoC; N-butyl, m.p. 119°C and the N-iso butyl, m.p. 129-130oC also giving an aurichloride,m.p. 97°C. The alkaloid also furnishes a methochloride as colourless rods, m.p. 320-340°C (dec.) which is very soluble in H20 and the methoaurichloride, m.p. 265°C (dec.).Like Caffeine (q.v.) and Theophylline (q.v.), the alkaloid and its salts are mild stimulants and also possess a diuretic action. Theobromine is a methylxanthine alkaloid and derivative of caffeine that has been found in cocoa beans and has diverse biological activities. It is an adenosine A1 receptor antagonist (IC50s = 200-280 μM in radioligand binding assays using rat brain membranes). Theobromine (150 μg/ml) increases AMPK phosphorylation and inhibits adipocyte differentiation, ERK and JNK phosphorylation, and IL-6 and TNF-α production in 3T3-L1 preadipocytes cultured in differentiation medium. It inhibits decreases in renal cortex SIRT1 activity and increases in NADPH oxidase-dependent reactive oxygen species (ROS) production, as well as reduces kidney hypertrophy and albuminuria in a spontaneously hypertensive rat model of streptozotocin-induced diabetes when administered at a dose of 5 mg/kg per day. Theobromine is toxic to dogs with an LD50 value of 250 to 500 mg/kg.
• Uses: A metabolite of Caffeine. diuretic, bronchodilator, cardiotonic

Technology Process of Theobromine

There total 65 articles about Theobromine 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: 96.0%

1-amino-3,7-dimethylxanthine (81281-47-2) → theobromine / (83-67-0)

Guidance literature:

With sodium nitrite; In acetic acid;

Reference yield: 87.0%

3-methylxanthine (1076-22-8) + dimethyl sulfate (77-78-1) → theobromine / (83-67-0)

Guidance literature:

3-methylxanthine; dimethyl sulfate; With sodium hydrogencarbonate; In water; acetone; at 55 - 60 ℃; for 4h;

With hydrogenchloride; In water; at 80 ℃; pH=5 - 6; Product distribution / selectivity;

Reference yield: 84.9%

3-methylxanthine disodium salt + dimethyl sulfate (77-78-1) → theobromine / (83-67-0)

Guidance literature:

3-methylxanthine disodium salt; dimethyl sulfate; With sodium carbonate; In acetone; at 55 - 57 ℃; for 4h;

With hydrogenchloride; In water; at 30 ℃; pH=6; Product distribution / selectivity;

upstream raw materials:

3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine

ethanol

3,7-dimethyl-3,7-dihydro-purine-2,6-dione, theobromine; salicylate

3-methylxanthine

Downstream raw materials:

1-(3-trimethylsilylpropyl)theobromine

1-n-Butyl-3,7-dimethylxanthine

pentoxyphylline

3,7-Dimethyl-1-propylxanthine

Refernces

• 1、 Ovcharova et al.. "-". . . Retrieved 1970.
• 2、 -. "Method for preparing a theobromine (by machine translation)". Paragraph 0079. . Retrieved 2017/03/08.
• 3、 Schimpl, Flávia Camila,Kiyota, Eduardo,Mayer, Juliana Lischka Sampaio,Gon?alves, José Francisco De Carvalho,Da Silva, José Ferreira,Mazzafera, Paulo. "Molecular and biochemical characterization of caffeine synthase and purine alkaloid concentration in guarana fruit". . p. 25 - 36. Retrieved 2014/08/18.