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Theobromine

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Identification
Molecular formula
C7H8N4O2
CAS number
83-67-0
IUPAC name
1,7-dimethyl-3H-purine-2,6-dione
State
State

Theobromine is typically a solid at room temperature. It is commonly used in its solid form in various chocolate and other cocoa-based products.

Melting point (Celsius)
357.00
Melting point (Kelvin)
630.00
Boiling point (Celsius)
290.00
Boiling point (Kelvin)
563.00
General information
Molecular weight
180.16g/mol
Molar mass
180.1640g/mol
Density
1.3730g/cm3
Appearence

Theobromine appears as a colorless, crystalline solid, often found in a powdered form. It is less crystalline in appearance and might present as a fine powder due to its extraction methods and preparation forms. The compound is a derivative of xanthine and a dimethyl derivative of xanthine, resulting in its pharmaceutical applications.

Comment on solubility

Solubility of 1,7-Dimethyl-3H-purine-2,6-dione

The solubility of 1,7-dimethyl-3H-purine-2,6-dione, commonly referred to as a derivative of purine, can be intriguing to study. This compound, with the chemical formula C7H8N4O2, presents interesting characteristics regarding its interaction with solvents. Here are some key points to consider:

  • Polar vs. Non-Polar Solvents: The presence of both polar and non-polar functional groups in the structure indicates that this compound may dissolve in a variety of solvents.
  • Water Solubility: Given that purine derivatives can exhibit limited solubility in water, 1,7-dimethyl-3H-purine-2,6-dione is generally considered slightly soluble.
  • Organic Solvents: Higher solubility may be observed in organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO).
  • Temperature Effect: As with many chemical compounds, increasing temperature may enhance solubility, allowing for better interaction with solvents.

In essence, the solubility of 1,7-dimethyl-3H-purine-2,6-dione can be influenced by various factors including the choice of solvent and environmental conditions. Understanding these interactions is fundamental in applications where this compound is utilized.

Interesting facts

Interesting Facts About 1,7-Dimethyl-3H-purine-2,6-dione

1,7-Dimethyl-3H-purine-2,6-dione, commonly known as theobromine, is a fascinating compound with a variety of roles in both nature and human consumption. Here are some intriguing aspects of this compound:

  • Natural Occurrence: Theobromine is primarily found in cacao beans, making it a significant component of chocolate. In fact, the name 'theobromine' derives from the Greek word 'theobroma', meaning "food of the gods."
  • Caffeine Cousin: Theobromine is chemically similar to caffeine and shares certain stimulatory effects, though it is much milder. This has led to its reputation as a relaxed form of 'pick-me-up'
  • Health Benefits: Studies suggest that theobromine may offer numerous health benefits, including:
    • Antioxidant properties, which can help combat oxidative stress in the body.
    • Potential cardiovascular benefits, such as improved heart health.
    • Diuretic effects, aiding in fluid balance and kidney function.
  • Biochemical Significance: In plants, theobromine is not only a secondary metabolite but also serves as a defense mechanism against herbivores. Its bitter taste can deter many animals from consuming cacao.
  • Uses in Medicine: Beyond its presence in popular treats, theobromine is used in medical applications, notably as an ingredient in some cough medicines due to its ability to relax the bronchial tubes.

As a chemical compound, 1,7-dimethyl-3H-purine-2,6-dione illustrates the complexities of biochemical interactions both in ecology and human health. It’s the perfect example of how a single compound can bridge the worlds of enjoyment and scientific discovery. Remember, with great chocolate comes great responsibility!

Synonyms
paraxanthine
1,7-Dimethylxanthine
611-59-6
p-Xanthine
1,7-Dimethyl-1H-purine-2,6(3H,7H)-dione
1,7-dimethyl-3H-purine-2,6-dione
1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl-
Xanthine, 1,7-dimethyl-
3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione
Caffeine Impurity F
1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
EINECS 210-271-9
NSC 400018
NSC-400018
1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione
BRN 0197907
Paraxanthine(72%)
DTXSID2052281
CHEBI:25858
1,7-dimethyl-Xanthine
MFCD00005727
Q3565Y41V7
CHEMBL1158
DTXCID2030853
5-26-13-00554 (Beilstein Handbook Reference)
CAFFEINE IMPURITY F [EP IMPURITY]
CAFFEINE MONOHYDRATE IMPURITY F [EP IMPURITY]
CAFFEINE IMPURITY F (EP IMPURITY)
CAFFEINE MONOHYDRATE IMPURITY F (EP IMPURITY)
pXanthine
UNII-Q3565Y41V7
2,6-Dihydroxy-1,7-dimethylpurine
PXT
1,7-Dimethyl-1H-purine-2,6-dione
Xanthine, 1,7dimethyl
Paraxanthine (Standard)
Spectrum2_001733
Spectrum3_000774
Spectrum4_001207
Spectrum5_001506
Lopac-D-5385
PARAXANTHINE [INCI]
Lopac0_000389
BSPBio_002448
KBioGR_001614
MLS000859929
DivK1c_000081
SCHEMBL232702
SPECTRUM2300170
SPBio_001806
SCHEMBL4651937
HMS500E03
KBio1_000081
KBio3_001668
1,7-Dimethylxanthine/Paraxanthine
NINDS_000081
HMS2231K19
HMS3261M19
HMS3370A12
HY-W016498R
SEA49041
6-hydroxy-1,7-dimethylpurin-2-one
Tox21_303803
Tox21_500389
BDBM50042210
CCG-39489
NSC400018
Paraxanthine (1,7-Dimethylxanthine)
1,7-Dimethylxanthine, ~98%, solid
AKOS015913484
CS-W017214
FP26762
HY-W016498
LP00389
SDCCGSBI-0050376.P003
3,7Dihydro1,7dimethyl1Hpurine2,6dione
IDI1_000081
NCGC00015347-01
NCGC00015347-02
NCGC00015347-03
NCGC00015347-04
NCGC00015347-05
NCGC00015347-06
NCGC00015347-07
NCGC00015347-09
NCGC00093817-01
NCGC00093817-02
NCGC00093817-03
NCGC00093817-04
NCGC00261074-01
NCGC00357087-01
AS-64037
CAS-611-59-6
SMR000326790
1HPurine2,6dione, 3,7dihydro1,7dimethyl
DB-005072
Eur J Pharmacol 179: 295 (1990)
1H-Purine-2, 3,7-dihydro-1,7-dimethyl-
D5696
EU-0100389
NS00010640
purine-2,6(1H,3H)-dione, 1,7-dimethyl-
D 5385
D94772
1,7-Dimethylxanthine (paraxathine, dimethyl-d6)
EN300-1666036
1HPurine2,6dione, 3,7dihydro1,7dimethyl (9CI)
A853055
Q419223
SR-01000075184
1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #
1,7-Dimethylxanthine 100 microg/mL in Acetonitrile
SR-01000075184-1
BRD-K24084088-001-02-2
BRD-K24084088-001-06-3
BRD-K24084088-001-11-3
Z1255430986
1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl-(9CI)
1,7-Dimethylxanthine;3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione
1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione (Paraxanthine; 1,7-Dimethylxanthine)
1,7-DIMETHYL-3,7-DIHYDRO- 1H-PURINE-2,6-DIONE (Caffeine Impurity F), Pharmaceutical Secondary Standard; Certified Reference Material
210-271-9
InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13