FComEx: Theobromine (PC000882)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:12 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000882

FoodDB Record

FDB000455

Chemical Information

Name

Theobromine

Description

Theobromine, also known as diurobromine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Theobromine is an extremely weak basic (essentially neutral) compound (based on its pKa). Theobromine is an isomer of theophylline, as well as paraxanthine. Theobromine exists in all living organisms, ranging from bacteria to humans. Within humans, theobromine participates in a number of enzymatic reactions. In particular, theobromine and formaldehyde can be biosynthesized from caffeine through the action of the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In addition, theobromine can be converted into 3,7-dimethyluric acid through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, theobromine is involved in caffeine metabolism. Theobromine is a bitter tasting compound. Outside of the human body, Theobromine is found, on average, in the highest concentration within a few different foods, such as cocoa powders, chocolates, and cocoa beans and in a lower concentration in other candies, cakes, and soy milks. Theobromine has also been detected, but not quantified in, several different foods, such as hyacinth beans, oyster mushrooms, tamarinds, milk (other mammals), and watercress. This could make theobromine a potential biomarker for the consumption of these foods. Theobromine and caffeine are similar in that they are related alkaloids. A necropsy and toxicology report performed at the University of New Hampshire in 2015 confirmed they died of heart failure caused by theobromine after they consumed 41 kilograms (90 lb) of chocolate and doughnuts placed at the site as bait.

CAS Number

83-67-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1H-Purine-2,6-dione, 3, 7-dihydro-3,7-dimethyl-	biospider
1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-	biospider
1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI)	biospider
2,6-Dihydroxy-3,7-dimethyl-purine	biospider
2,6-Dihydroxy-3,7-dimethylpurine	biospider
3-7-DIMETHYLXANTHINE	biospider
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione	biospider
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 9CI	db_source
3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione	biospider
3,7-Dimethyl-xanthine	biospider
3,7-dimethylpurine-2,6-dione	biospider
3,7-Dimethylxanthine	db_source
Diurobromine	db_source
FEMA 3591	db_source
Santheose	db_source
Teobromin	biospider
Theobromin	biospider
Theobromine [ban]	biospider
Theobrominum	biospider
Theosalvose	biospider
Theostene	biospider
Thesal	db_source
Thesodate	biospider
Xanthine, 3,7-dimethyl-	biospider

Chemical Formula

C7H8N4O2

IUPAC name

3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

InChI Identifier

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

Isomeric SMILES

CN1C=NC2=C1C(=O)NC(=O)N2C

Average Molecular Weight

180.164

Monoisotopic Molecular Weight

180.06472552

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents