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Theobromine

Name: Theobromine
Brand: SIGMA

≥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%

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Properties

Product Name

Theobromine, ≥98.0%

Quality Segment

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)

Description

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

Phosphosdiesterase inhibitor; weak adenosine receptor antagonist; diuretic; smooth muscle relaxant.

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.

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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This Item	PHR1837	42993	D5385
Sigma-Aldrich T4500 Theobromine	Supelco PHR1837 Theobromine	Supelco 42993 Theobromine	Sigma-Aldrich D5385 1,7-Dimethylxanthine
description ≥98.0%	description Pharmaceutical Secondary Standard; Certified Reference Material	description analytical standard	description ~98%, solid
assay ≥98.0%	assay -	assay ≥99.0% (HPLC)	assay ~98%
Quality Level 200	Quality Level 300	Quality Level 100	Quality Level 200
solubility aqueous base: moderately soluble, H₂O: slightly soluble, ethanol: slightly soluble	solubility -	solubility -	solubility H₂O: 1 mg/mL, ethanol: 0.6 mg/mL, 0.1 M NaOH: 2 mg/mL
Gene Information human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) rat ... Adora1(29290)	Gene Information -	Gene Information -	Gene Information human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140) rat ... Adora1(29290), Adora2a(25369)
mp 345-350 °C	mp 345-350 °C	mp 345-350 °C	mp 294-296 °C (lit.)

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Pictograms

GHS07

Signal Word

Warning

Hazard Codes

H302,H319

Precautionary Statements

P264 - P280 - P301 + P312 - P305 + P351 + P338 - P337 + P313 - P501

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 (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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