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W222402

Sigma-Aldrich

Caffeine

anhydrous, 99%, FCC, FG

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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

biological source

synthetic

Quality Level

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

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

odorless

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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1 of 4

This Item
C773156396C0750
vibrant-m

W222402

Caffeine

vibrant-m

C7731

Caffeine

vibrant-m

56396

Caffeine

vibrant-m

C0750

Caffeine

organoleptic

odorless

organoleptic

-

organoleptic

-

organoleptic

-

food allergen

no known allergens

food allergen

-

food allergen

-

food allergen

-

biological source

synthetic

biological source

-

biological source

-

biological source

-

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

documentation

see Safety & Documentation for available documents

documentation

-

documentation

-

documentation

-

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.

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.

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Description
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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Caffeine for system suitability European Pharmacopoeia (EP) Reference Standard

Y0000787

Caffeine for system suitability

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
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
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
Christopher C Wendler et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 23(4), 1272-1278 (2008-12-18)
The purpose of this study was to determine both the short-term effects on cardiac development and embryo growth and the long-term effects on cardiac function and body composition of in utero caffeine exposure. Pregnant mice (C57BL/6) were exposed to hypoxia

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