Theobromine

Theobromine Chemical Properties
Melting point 345-350 °C
Boiling point 312.97°C (rough estimate)
density 1.50
FEMA 3591 | THEOBROMINE
refractive index 1.6700 (estimate)
Fp 290-295°C
storage temp. Inert atmosphere,Room Temperature
solubility H2O: slightly soluble
form solid
pka7.89(at 18℃)
color white
Odorodorless
Water Solubility slightly soluble, <0.1 g/100 mL at 18 ºC
Sublimation 290-295 ºC
Merck 14,9282
BRN 16464
InChIKeyYAPQBXQYLJRXSA-UHFFFAOYSA-N
LogP-0.78
CAS DataBase Reference83-67-0(CAS DataBase Reference)
IARC3 (Vol. 51) 1991
NIST Chemistry Reference1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-(83-67-0)
EPA Substance Registry SystemTheobromine (83-67-0)
Safety Information
Hazard Codes Xn,Xi,T,F
Risk 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
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 1
RTECS XH2275000
10-23
TSCA Yes
HS Code 29399990
Hazardous Substances Data83-67-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
3,7-Dimethyl-xanthine English
SigmaAldrich English
ACROS English
ALFA English
Theobromine Usage And Synthesis
DescriptionA 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.
DescriptionTheobromine 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.
Chemical PropertiesA methyl xanthine similar to caffeine. Theobromine has a bitter taste.
Chemical Propertieswhite to light yellow crystal powder
OccurrenceReported found in cocoa bean, cocoa powder, cola nut and tea.
UsesA metabolite of Caffeine.
Usesdiuretic, bronchodilator, cardiotonic
DefinitionChEBI: A dimethylxanthine having the two methyl groups located at positions 3 and 7. It is a purine alkaloid derived from cocoa tree.
General DescriptionOdorless white crystalline powder. Bitter taste. pH (saturated solution in water): 5.5-7.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileTheobromine may be sensitive to prolonged exposure to light. Theobromine has weakly acidic properties, combining with bases to forms salts. Theobromine also has even weaker basic properties, combining with acids to form salts which are decomposed in aqueous solution. .
HazardToxic by ingestion. Questionable carcinogen.
Fire HazardFlash point data for Theobromine are not available; however, Theobromine is probably combustible.
Flammability and ExplosibilityNonflammable
Safety ProfilePoison by ingestion. Moderately toxic by subcutaneous route. An experimental teratogen. Human systemic effects by ingestion: central nervous system and gastrointestinal changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as a diuretic, smooth muscle relaxant, cardiac stimulant, and vasoddator.
Purification MethodsIt crystallises from H2O. Its solubility in H2O is 0.06% at 15o and 1.25% at 100o, and it is poorly soluble in organic solvents. It forms salts with heavy metals and is a diuretic, vasodilator and a cardiac stimulant. [Lister Purines Part II, Fused Pyrimidines Brown Ed, Wiley-Interscience pp254-225 1971, ISBN 0-471-38205-1, Beilstein 26 H 457, 26 I 135, 26 II 264, 26 III/IV 2336.]
ReferencesBiltz, Max., Annalen, 423,320 (1921)
Dubosc., Chem. Zentr., IV, 956 (1932)
Gepner, Kreps., Chem. Abstr., 41,96 (1947)
Bohinc, Korber-Smid, J agodic., Farm. Vestn., (Ljubljana), 23, 143 (1972)


2,6-Dihydroxypurine beta-Tetralone Dehydroepiandrosterone N,N-Dimethylformamide HYDROCODONE Epiandrosterone acetate Tetrahydro-4H-pyran-4-one (-)-SPARTEINE HYDROMORPHONE Purine Dimethyl fumarate Theobromine Acetone oxime Dimethyl sebacate Dimethyl sulfoxide Dimethyl carbonate Dihydromyrcenol Dimethyl phthalate

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