W222402

Sigma-Aldrich

Caffeine

anhydrous, 99%, FCC, FG

Synonym(s):
1,3,7-Trimethylxanthine
Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
FEMA Number:
2224
Beilstein/REAXYS Number:
17705
EC Number:
Council of Europe no.:
11741
MDL number:
PubChem Substance ID:
Flavis number:
16.016
NACRES:
NA.21

Quality Level

biological source

synthetic

grade

FG
Halal
Kosher
anhydrous

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 182.1180

assay

99%

form

powder

mp

234-236.5 °C (lit.)

solubility

H2O: soluble 18.7 g/L at 16 °C

Documentation

see Safety & Documentation for available documents

Featured Industry

Flavors and Fragrances

Organoleptic

odorless

food allergen

no known allergens

SMILES string

CN1C(=O)N(C)c2ncn(C)c2C1=O

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

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General description

Caffeine is an addictive psychoactive compound, consumed mostly in the form of brewed coffee, instant coffee, tea and caffeinated soft drinks. Caffeine is reported to be an allergen and causes anaphylaxis. It is added to common analgesics such as paracetamol, ibuprofen and aspirin for enhancing their analgesic efficacy. It is a plant-derived drug and has been detected in low doses in the floral nectar and pollen of Citrus. Determination of caffeine in beverages by square-wave voltammetry using Nafion-ruthenium oxide pyrochlore chemically modified electrode has been reported. Caffeine acts as an antagonist of adenosine A1 receptors (A1R) and A2AR at non-toxic doses. Chronic consumption of caffeine is reported to prevent the memory impairment in type 2 diabetic mice.

Application

Caffeine (1,3,7-Trimethylxanthine) has been used in a study to determine the benefits of co-ingestion of carbohydrate and caffeine on rugby performance.
Caffeine is the suitable reagent used to investigate effect of its exposure during embryogenesis.

Packaging

10, 25 kg in fiber drum
1 kg in poly bottle

Biochem/physiol Actions

A central nervous system stimulant believed to act through adenosine receptors and monoamine neurotransmitters. It is an adenosine receptor antagonist and adenosine 3′,5′-cyclic monophosphate (cAMP) phosphodiesterase inhibitor. Thus, levels of cAMP increase in cells following treatment with caffeine. It has been reported to affect cellular calcium levels, releasing calcium from intracellular stores. It overrides the cell cycle effects of various chemicals such as protease inhibitors, preventing apoptosis; and it has been shown to inhibit cellular DNA repair mechanisms.

Other Notes

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pictograms

Exclamation mark

signalword

Warning

hcodes

hazcat

Acute Tox. 4 Oral

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 1

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

J M Zen et al.
The Analyst, 123(5), 1145-1147 (1998-08-26)
A Nafion-ruthenium oxide pyrochlore chemically modified electrode is used for the determination of caffeine in beverages by square-wave voltammetry. Compared to a bare glassy carbon electrode, the chemically modified electrode exhibits a marked enhancement of the current response. A linear...
Kumiya Sugiyama et al.
Asia Pacific allergy, 5(1), 55-56 (2015-02-06)
We report a rare case of anaphylaxis due to caffeine intake. A 27-year-old woman suffered her first episode of anaphylaxis and a positive skin prick test suggested that the anaphylaxis was due to an IgE-mediated hypersensitivity reaction to caffeine. She...
Simon P Roberts et al.
Journal of sports sciences, 28(8), 833-842 (2010-06-04)
In this study, we investigated the effect of ingesting carbohydrate alone or with caffeine on performance of a rugby union-specific shuttle running protocol. On three occasions, at least one week apart in a counterbalanced trial order, eight male rugby union...
K S Kendler et al.
The American journal of psychiatry, 156(2), 223-228 (1999-02-16)
Caffeine is by far the most commonly consumed psychoactive substance. The use and abuse of most other licit and illicit psychoactive drugs have been shown to be substantially heritable. However, the impact of genetic factors on caffeine consumption, heavy use...
João M N Duarte et al.
PloS one, 7(4), e21899-e21899 (2012-04-20)
Diabetic conditions are associated with modified brain function, namely with cognitive deficits, through largely undetermined processes. More than understanding the underlying mechanism, it is important to devise novel strategies to alleviate diabetes-induced cognitive deficits. Caffeine (a mixed antagonist of adenosine...

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