FComEx: Caffeine (PC000488)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:53 UTC

Update date

2017-01-19 02:36:25 UTC

FoodComEx ID

PC000488

FoodDB Record

FDB002100

Chemical Information

Name

Caffeine

Description

Component of coffee beans (Coffea arabica), many other Coffea subspecies, chocolate (Theobroma cacao), tea (Camellia thea), kolanut (Cola acuminata) and several other Cola subspecies and several other plants. It is used in many cola-type beverages as a flavour enhancer. Caffeine is found in many foods, some of which are black cabbage, canola, jerusalem artichoke, and yellow bell pepper.

CAS Number

58-08-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Methyl-theobromine	biospider
1-Methyltheobromine	biospider
1,3,7-Trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine	biospider
1,3,7-Trimethyl-2,6-dioxopurine	biospider
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione	biospider
1,3,7-Trimethylpurine-2,6-dione	biospider
1,3,7-Trimethylxanthine	db_source
3,7-dihydro-1,3,7-Trimethyl-1H-purin-2,6-dion	ChEBI
3,7-dihydro-1,3,7-Trimethyl-1H-purine-2,6-dione	HMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, 9CI	db_source
7-Methyl theophylline	biospider
7-Methyltheophylline	ChEBI
Anhydrous caffeine	ChEBI
Anhydrous caffeine (jp15)	HMDB
Cafeina	ChEBI
Cafeine	ChEBI
Caffein	biospider
Cafipel	db_source
Coffein	ChEBI
Coffeine	db_source
FEMA 2224	db_source
Guaranine	db_source
Hycomine	HMDB
Koffein	ChEBI
Lanorinal	HMDB
Mateina	ChEBI
Methyltheobromide	biospider
Methyltheobromine	db_source
Methylxanthine theophylline	HMDB
Monohydrate caffeine	HMDB
Propoxyphene	HMDB
Teina	ChEBI
Thein	biospider
Theine	db_source

Chemical Formula

C8H10N4O2

IUPAC name

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

InChI Identifier

InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChI Key

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Isomeric SMILES

CN1C=NC2=C1C(=O)N(C)C(=O)N2C

Average Molecular Weight

194.1906

Monoisotopic Molecular Weight

194.080375584

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

Substituents

Xanthine
Purinone
6-oxopurine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Vinylogous amide
Imidazole
Azole
Urea
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine alkaloid (CHEBI:27732 )
trimethylxanthine (CHEBI:27732 )
Purine alkaloids (C07481 )
a small molecule (1-3-7-TRIMETHYLXANTHINE )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-0.07	HANSCH,C ET AL. (1995)
Experimental Water Solubility	21.6 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 236° (phase transition at 141°)	DFC

Foods of Origin