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T4500

Theobromine

≥98.0%, Phosphosdiesterase inhibitor

Synonym(s):

2,6-Dihydroxy-3,7-dimethylpurine, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 3,7-Dimethylxanthine

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About This Item

Empirical Formula (Hill Notation):
C7H8N4O2
CAS Number:
83-67-0
Molecular Weight:
180.16
NACRES:
NA.77
PubChem Substance ID:
24277679
UNSPSC Code:
41106305
EC Number:
201-494-2
MDL number:
MFCD00022830
Beilstein/REAXYS Number:
16464
Assay:
≥98.0%
Quality level:
200
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Product Name

Theobromine, ≥98.0%

Quality Level

200

assay

≥98.0%

mp

345-350 °C

solubility

H2O: slightly soluble, aqueous base: moderately soluble, ethanol: slightly soluble

SMILES string

[H]N1C(N(C)C2=C(N(C)C=N2)C1=O)=O

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)

InChI key

YAPQBXQYLJRXSA-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290)

General description

Theobromine is a methylxanthine alkaloid derivative, highly present in cocoa.

Application

Theobromine has been used:
  • to test in behavioural assay
  • as a food or dietary supplement
  • as a standard for theobromine quantification in brewed coffee samples

Biochem/physiol Actions

Theobromine possesses antitussive action and might be useful in treating acute and chronic cough. It is a catabolic product of caffeine and shows antioxidant and prooxidant properties.
Phosphosdiesterase inhibitor; weak adenosine receptor antagonist; diuretic; smooth muscle relaxant.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Theobromine is moderately soluble in aqueous base and is slightly soluble in water and ethanol.

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF0961
BCBZ9934
BCBW0621
BCBS4524
BCBQ1887V

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Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

A subset of enteroendocrine cells is activated by amino acids in the Drosophila midgut
Park JH, et al.
Febs Letters (2006)
Theobromine inhibits sensory nerve activation and cough
Usmani OS, et al.
Faseb Journal (2004)
Development of a chromatographic low pressure flow injection system: Application to the analysis of methylxanthines in coffee
Santos JR and Antonio OSS Rangel
Analytica Chimica Acta, 715(17), 57-63 (2012)
View All Related Papers

Global Trade Item Number

SKUGTIN
T4500-100G04061835546428
T4500-25G04061835559312