Theobromine Chemical Properties

Melting point:

345-350 °C

Boiling point:

312.97°C (rough estimate)

Density 

1.50

refractive index 

1.6700 (estimate)

FEMA 

3591 | THEOBROMINE

Flash point:

290-295°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

H₂O: slightly soluble

form 

solid

pka

7.89(at 18℃)

color 

white

Odor

odorless

Water Solubility 

slightly soluble, <0.1 g/100 mL at 18 ºC

Sublimation 

290-295 ºC

Merck 

14,9282

BRN 

16464

InChIKey

YAPQBXQYLJRXSA-UHFFFAOYSA-N

LogP

-0.78

CAS DataBase Reference

83-67-0(CAS DataBase Reference)

IARC

3 (Vol. 51) 1991

NIST Chemistry Reference

1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-(83-67-0)

EPA Substance Registry System

Theobromine (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

F 

10-23

TSCA 

Yes

HS Code 

29399990

Hazardous Substances Data

83-67-0(Hazardous Substances Data)

MSDS

• Language:English Provider:3,7-Dimethyl-xanthine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Theobromine Usage And Synthesis

Description

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.

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.

Chemical Properties

A methyl xanthine similar to caffeine. Theobromine has a bitter taste.

Chemical Properties

white to light yellow crystal powder

Occurrence

Reported found in cocoa bean, cocoa powder, cola nut and tea.

Uses

A metabolite of Caffeine.

Uses

diuretic, bronchodilator, cardiotonic

Definition

ChEBI: A dimethylxanthine having the two methyl groups located at positions 3 and 7. It is a purine alkaloid derived from cocoa tree.

General Description

Odorless white crystalline powder. Bitter taste. pH (saturated solution in water): 5.5-7.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Theobromine 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. .

Hazard

Toxic by ingestion. Questionable carcinogen.

Fire Hazard

Flash point data for Theobromine are not available; however, Theobromine is probably combustible.

Flammability and Explosibility

Non flammable

Safety Profile

Poison 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 Methods

It 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.]

References

Biltz, 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)

Theobromine(83-67-0)Related Product Information

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• ETHANE
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