Theobromine supplier | CasNO.83-67-0

Name
Theobromine
EINECS 201-494-2
CAS No. 83-67-0
Article Data57
CAS DataBase
Density 1.608 g/cm³
Solubility slightly soluble in water
Melting Point 345-350 °C
Formula C₇H₈N₄O₂
Boiling Point Sublimes 290-295oC
Molecular Weight 180.166
Flash Point 290-295°C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25-36-26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Theobromine(8CI);3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione;3,7-Dimethylxanthine;Diurobromine;NSC 5039;SC 15090;Santheose;Teobromin;Theosalvose;Theostene;Thesal;
PSA 72.68000
LogP -1.03970

Synthetic route

: 81281-47-2
1-amino-3,7-dimethylxanthine

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium nitrite In acetic acid	96%

: 1076-22-8
3-methylxanthine

: 77-78-1
dimethyl sulfate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine; dimethyl sulfate With sodium hydrogencarbonate In water; acetone at 55 - 60℃; for 4h; Stage #2: With hydrogenchloride In water at 80℃; pH=5 - 6; Product distribution / selectivity;	87%

: 3-methylxanthine disodium salt

: 77-78-1
dimethyl sulfate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
Stage #1: 3-methylxanthine disodium salt; dimethyl sulfate With sodium carbonate In acetone at 55 - 57℃; for 4h; Stage #2: With hydrogenchloride In water at 30℃; pH=6; Product distribution / selectivity;	84.9%

: 3,7,9-trimethylxanthinium hydrogensulfate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
at 260℃; for 1h;	66%

: 1076-22-8
3-methylxanthine

: 74-88-4
methyl iodide

A: 83-67-0
theobromine /

B: 86180-33-8
1,7,9-trimethylxanthinium iodide

Conditions

Conditions	Yield
at 110℃; for 1.5h; closed Kjeldahl flask;	A 61% B 28%

...Expand

: 94453-49-3
5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide; hydrochloride

: 57-13-6
urea

: 83-67-0
theobromine /

Conditions

Conditions	Yield
In melt 1) 140 deg C, 30 min 2) 170-175 deg C, 2h;	55%

: 3,7,9-trimethylxanthinium perchlorate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
In pyridine at 115℃; for 3h;	53%

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A: 58-55-9
theophylline

B: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium thiophenolate at 250℃; for 1.5h;	A 37% B 21%

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A: 58-55-9
theophylline

B: 83-67-0
theobromine /

C: 611-59-6
paraxanthine

Conditions

Conditions	Yield
With hepatic cytochrome P450 Enzymatic reaction;	A 7% B 12% C n/a

...Expand

: 58-55-9
theophylline

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium thiophenolate at 280℃; for 1.5h;	10%

: 14785-95-6
3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium hydroxide anschliessendes Behandeln mit Dimethylsulfat;

: 64-17-5
ethanol

: 519-41-5
3,7-dimethyl-3,7-dihydro-purine-2,6-dione, theobromine; salicylate

: 83-67-0
theobromine /

Conditions

Conditions	Yield
Ausscheidung;

: 3-methyl-5-(N-methyl-ureido)-3H-imidazole-4-carboxylic acid methylamide

: 64-19-7
acetic acid

: 83-67-0
theobromine /

Conditions

Conditions	Yield
Erhitzen ueber den Schmelzpunkt;

: 117882-90-3
3,7-dimethyl-8-trichloromethyl-3,7-dihydro-purine-2,6-dione

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With hydrogenchloride

: 80038-09-1
1-benzoyl-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

: furan-2,3,5(4H)-trione pyridine (1:1)

: 56-40-6
glycine

A: 495-69-2
Hippuric Acid

B: 83-67-0
theobromine /

Conditions

Conditions	Yield
at 20℃;

...Expand

: 77-78-1
dimethyl sulfate

: 69-89-6
xanthin

: 83-67-0
theobromine /

: 77-78-1
dimethyl sulfate

: 69-89-6
xanthin

A: 83-67-0
theobromine /

B: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
bei der Methylierung unter verschiedenen Bedingungen;

...Expand

: 69-89-6
xanthin

: 74-88-4
methyl iodide

: 83-67-0
theobromine /

Conditions

Conditions	Yield
at 100℃; Das Bleisalz liefert beim Erhitzen im Rohr;

: 541-41-3
chloroformic acid ethyl ester

: 115377-65-6
3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid amide; compound with perchloric acid

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium hydroxide; triethylamine 1.) MeCN, r. t., 1.5 h, 2.) r. t., 10 min; Yield given. Multistep reaction;

: 86180-29-2
7,9-dimethylxanthinium iodide

A: 83-67-0
theobromine /

B: 552-62-5
7-methylxanthine

Conditions

Conditions	Yield
at 230℃; for 0.75h; Title compound not separated from byproducts;

: 7,9-dimethylxanthinium hydrogensulfate

A: 83-67-0
theobromine /

B: 552-62-5
7-methylxanthine

Conditions

Conditions	Yield
at 250℃; for 0.25h; Title compound not separated from byproducts;

: 5752-21-6
7,9-dimethylxanthinium betaine

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With iodine at 250℃; for 1h;

: 86180-34-9
3,7,9-trimethylxanthinium chloride

: 83-67-0
theobromine /

Conditions

Conditions	Yield
at 260℃; for 0.75h; Yield given;

: 90198-42-8
3-methyl-4-methylamino-5-methylformylaminouracil

A: 83-67-0
theobromine /

B: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
fusion;

: 86180-33-8
1,7,9-trimethylxanthinium iodide

: 83-67-0
theobromine /

Conditions

Conditions	Yield
at 230℃; for 0.25h; Yield given;

: (5-Carbamoyl-1-methyl-1H-imidazol-4-yl)-methyl-carbamic acid ethyl ester

: 83-67-0
theobromine /

Conditions

Conditions	Yield
With sodium hydroxide for 0.166667h; Heating; Yield given;

: 93079-86-8
3,7-dimethyl-6-(5-oxohexyloxy)-3,7-dihydro-2H-purin-2-one

A: 83-67-0
theobromine /

B: 21856-89-3
6-hydroxy-2-hexanone

Conditions

Conditions	Yield
With hydrogenchloride

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A: 50-00-0
formaldehyd

B: 83-67-0
theobromine /

Conditions

Conditions	Yield
With Tris-HCl buffer; 1,4-dihydronicotinamide adenine dinucleotide; Pseudomonas putida No. 352 at 25℃; Product distribution; various substrates, enzyme activity;

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A: 58-55-9
theophylline

B: 83-67-0
theobromine /

C: 5415-44-1
1,3,7-trimethyl-7,9-dihydro-3H-purine-2,6,8-trione

Conditions

Conditions	Yield
With dihydrogen peroxide In water Product distribution; Mechanism; Irradiation; other reagent;

...Expand

: 83-67-0
theobromine /

: 872-17-3
11-chloroundec-1-ene

: 156918-64-8
1-(10-undecenyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide	100%

: 83-67-0
theobromine /

: 6280-87-1
δ-chlorovaleronitrile

: 5-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanenitrile

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 3h;	100%

: 83-67-0
theobromine /

: 89359-54-6
9-bromo-1-nonene

: 156918-55-7
1-(8-nonenyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
In dimethyl sulfoxide	99%
In dimethyl sulfoxide	99%
In dimethyl sulfoxide	99%
In dichloromethane; dimethyl sulfoxide	99%

: 83-67-0
theobromine /

: 2695-47-8
6-Bromo-1-hexene

: 58999-18-1
1-(hex-5-enyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
In water; dimethyl sulfoxide	98%
In water; dimethyl sulfoxide	95.5%

: 83-67-0
theobromine /

: 13154-13-7
(E)-1-bromohex-1-ene

: 58999-18-1
1-(hex-5-enyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
In water; dimethyl sulfoxide	98%
In water; dimethyl sulfoxide	98%
In water; dimethyl sulfoxide
In water; dimethyl sulfoxide

: 83-67-0
theobromine /

: 13154-13-7
(E)-1-bromohex-1-ene

A: 58999-18-1
1-(hex-5-enyl)-3,7-dimethylxanthine

B: 154719-57-0
1-(5,6-oxidohexyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
In water; dimethyl sulfoxide	A 98% B n/a
In water; dimethyl sulfoxide	A 98% B n/a

...Expand

: 83-67-0
theobromine /

: 86444-90-8
8-iodotheobromine

Conditions

Conditions	Yield
With iodine In acetonitrile for 1.5h; Heating;	97%

: 83-67-0
theobromine /

: 2695-48-9
8-Bromo-1-octene

: 1-(7-octenyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
In dimethyl sulfoxide	97%
In dimethyl sulfoxide	97%

: 83-67-0
theobromine /

: 111-83-1
1-bromo-octane

: 103976-48-3
3,7-dimethyl-1-octyl-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	96%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere; Schlenk technique;	88%
With potassium hydroxide; Aliquat 336 1.) 80 deg C, 2 h, 2.) 1 h; Yield given. Multistep reaction;

: 83-67-0
theobromine /

: 142-28-9
1,3-Dichloropropane

: 74409-52-2
1-(3-chloropropyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-2,6-purinedione

Conditions

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 2h; Heating;	96%

: 83-67-0
theobromine /

: 100-39-0
benzyl bromide

: 1243688-83-6
3,7-dimethyl-9-benzylxanthinium bromide

Conditions

Conditions	Yield
With potassium iodide for 24h; Reflux; Inert atmosphere;	96%

: 83-67-0
theobromine /

: 2273-93-0
2,6-dichloro-7-methylpurine

Conditions

Conditions	Yield
With trichlorophosphate; phosphorus trichloride Substitution;	95%
With trichlorophosphate at 140℃;
With N,N-diethylaniline; trichlorophosphate at 130℃; for 18h; Inert atmosphere;
With trichlorophosphate at 140℃;

: 83-67-0
theobromine /

: 100-39-0
benzyl bromide

: 55247-90-0
1-benzyl-3,7-dimethylxanthine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique;	95%
Stage #1: theobromine / With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide	89%
With caesium carbonate In toluene; acetonitrile for 18h;	80%

: 83-67-0
theobromine /

: 106-95-6
allyl bromide

: 2530-99-6
N-allyltheobromine

Conditions

Conditions	Yield
Stage #1: theobromine /; allyl bromide With sodium t-butanolate In N,N-dimethyl-formamide at 150℃; for 12h; Stage #2: In N,N-dimethyl-formamide at 100℃; for 12h;	95%
With potassium carbonate In N,N-dimethyl-formamide	80%
With hydrogenchloride In dimethyl sulfoxide	42%

: 83-67-0
theobromine /

: 10297-06-0
1-chloro-5-hexyne

: 1-(hex-5-yn-1-yl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 2h;	95%

: 83-67-0
theobromine /

: 12-phosphotungstic acid*29H2O

: 64-17-5
ethanol

: O40PW12(3-)*3C7H9N4O2(1+)*1.5C2H6O

Conditions

Conditions	Yield
Stage #1: theobromine /; 12-phosphotungstic acid*29H2O In water at 70 - 80℃; Stage #2: ethanol	95%

...Expand

: 74-83-9
methyl bromide

: 83-67-0
theobromine /

A: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

B: 7280-81-1
3-benzyladenine

Conditions

Conditions	Yield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;	A 94% B n/a

...Expand

: 624-76-0
Iodoethanol

: 83-67-0
theobromine /

: 1507-14-8
1-(2-hydroxyethyl)-3,7-dimethyl-3,7-dihydropurine-2,6-dione

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 4h;	94%
Stage #1: theobromine / With potassium carbonate In N,N-dimethyl-formamide Reflux; Stage #2: Iodoethanol for 18h; Reflux;	68%

: 83-67-0
theobromine /

1-propylhalide: 1-propylhalide

: 63906-63-8
3,7-Dimethyl-1-propylxanthine

Conditions

Conditions	Yield
Stage #1: theobromine / With sodium hydride In dimethyl sulfoxide at 60℃; for 0.333333h; Inert atmosphere; Stage #2: 1-propylhalide In dimethyl sulfoxide at 60℃; Inert atmosphere;	94%

: 83-67-0
theobromine /

: 14267-92-6
1-chloro-4-pentyne

: 3,7-dimethyl-1-(pent-4-yn-1-yl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 2h;	94%

: 83-67-0
theobromine /

: 5,8-dioxa-spiro[3,4]octane-2-ylmethyl methanesulfonate

: 1-(5,8-dioxa-spiro[3,4]octane-2-ylmethyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)dione

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 3.5h;	93%

: 83-67-0
theobromine /

: 77-78-1
dimethyl sulfate

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions

Conditions	Yield
potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature;	92%
With sodium hydroxide

: 83-67-0
theobromine /

: 18904-08-0
2,6-dithiotheobromine

Conditions

Conditions	Yield
With Lawessons reagent; aluminum oxide for 0.116667h; microwave irradiation;	92%
With kerosine

: 83-67-0
theobromine /

: 1119-51-3
bromopentene

: 1-(Pent-4-enyl)-3,7-dimethyl-xanthine

Conditions

Conditions	Yield
In water; dimethyl sulfoxide; Petroleum ether	92%

: 83-67-0
theobromine /

: (5-oxohexyl) mesylate

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 50℃; for 16h;	91.1%

: 83-67-0
theobromine /

: 4286-55-9
1-bromo-6-hexanol

: 56395-71-2
1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
In water; dimethyl sulfoxide	91%
In water; dimethyl sulfoxide	91%

ethanol-dichloromethane: ethanol-dichloromethane

: 83-67-0
theobromine /

: 4286-55-9
1-bromo-6-hexanol

: 56395-71-2
1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
In water; dimethyl sulfoxide	91%
In water; dimethyl sulfoxide	91%

...Expand

: 83-67-0
theobromine /

: zirconyl chloride octahydrate

: ZrO(C5H2N4(O)2(CH3)2)2(C5HN4(O)2(CH3)2)Cl(H2O)

Conditions

Conditions	Yield
In ethanol Zr-compound refluxed in ethanol/triethyl orthoformate for 2 h; N-compound added and refluxed for 36 h; cooled to room temp.; filtered; washed with acetone; elem. anal.;	91%

: 83-67-0
theobromine /

: 2417-72-3
Methyl 4-(bromomethyl)benzoate

: 4-((3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl)benzoic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 25 - 110℃; for 3h; Inert atmosphere;	91%

Theobromine Specification

The Theobromine, also known as xantheose, is an organic compound with the formula C₇H₈N₄O₂. It belongs to the product categories of Heterocyclic Compounds; Alkaloids; Alkaloids (Others); Biochemistry; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. Its EINECS registry number is 201-494-2. With the CAS registry number 83-67-0, its IUPAC name is 3,7-dimethylpurine-2,6-dione. What's more, this chemical is a white to light yellow crystal which can be used as a metabolite of caffeine.

Physical properties of Theobromine: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 6.331; (5)ACD/KOC (pH 7.4): 6.312; (6)#H bond acceptors: 6; (7)#H bond donors: 1; (8)Index of Refraction: 1.737; (9)Molar Refractivity: 45.057 cm³; (10)Molar Volume: 112.05 cm³; (11)Surface Tension: 65.77 dyne/cm; (12)Density: 1.608 g/cm³.

Preparation of Theobromine: this chemical is the primary alkaloid found in cocoa and chocolate. Theobromine can also be found in small amounts in the kola nut (1.0-2.5%), the guarana berry, ilex guayusa, and the tea plant.

Uses: In modern medicine, theobromine is used as a vasodilator (a blood vessel widener), a diuretic (urination aid), and heart stimulant. In addition, possible future uses of theobromine in such fields as cancer prevention have been patented. Theobromine has also been used in birth defect experiments involving mice and rabbits. A decreased fetal weight was noted in rabbits following forced feeding, but not after other administration of theobromine. Birth defects were not seen in rats.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing. Finally, you must avoid contacting it with skin and eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN1C=NC2=C1C(=O)NC(=O)N2C
(2)InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
(3)InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	oral	200mg/kg (200mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1372, 1986.
dog	LD50	oral	300mg/kg (300mg/kg)		Toxicology and Applied Pharmacology. Vol. 53, Pg. 481, 1980.
human	TDLo	oral	26mg/kg (26mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 113, 1946.
mouse	LD50	intraperitoneal	552mg/kg (552mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Acta Pharmaceutica Vol. 46, Pg. 93, 1996.
mouse	LD50	oral	837mg/kg (837mg/kg)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982.
mouse	LD50	subcutaneous	530mg/kg (530mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 601, 1956.
rabbit	LDLo	subcutaneous	1gm/kg (1000mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat	LD50	oral	1265mg/kg (1265mg/kg)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982.

Product Name

Theobromine

Synthetic route

Theobromine Specification

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