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C0750

Sigma-Aldrich

Caffeine

powder, ReagentPlus®

Synonym(s):
1,3,7-Trimethylxanthine
Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
Beilstein:
17705
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

product line

ReagentPlus®

form

powder

mp

234-236.5 °C (lit.)

solubility

H2O: 15 mg/mL

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 a widely ingested pharmacologically active substance. It belongs to the class of methylxanthines. It is a naturally occurring alkaloid found in coffee, cocoa and other plants. Caffeine might be associated with osteoporosis, cardiovascular risk, arrhythmia and gastrointestinal disturbances. Caffeine is used to treat orthostatic hypotension, bronchopulmonary dysplasia and apnea of prematurity (AOP).

Application

Caffeine has been used:
  • to study its impact on the fluorescence of Petunia nuclei
  • as a stimulant to induce c-fos expression in rodents
  • as a component of defined media for the development of bovine oocytes in vitro

Packaging

5, 100, 500 g in poly bottle
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.

Caution

Keep tightly sealed.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

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

Effects of caffeine and chlorogenic acid on propidium iodide accessibility to DNA: consequences on genome size evaluation in coffee tree
Noirot M, et al.
Annals of Botany, 92(2), 259-264 (2003)
A simple method for immunohistochemical staining of zebrafish brain sections for c-fos protein expression
Chatterjee D, et al.
Zebrafish, 12(6), 414-420 (2015)
Metabolic effects of spices, teas, and caffeine
Westerterp-Plantenga M, et al.
Physiology & Behavior, 89(1), 85-91 (2006)
Apnea of prematurity: from cause to treatment
Zhao J, et al.
European Journal of Pediatrics, 170(9), 1097-1105 (2011)
Effects of caffeine on human health
Nawrot P, et al.
Food Additives and Contaminants, 20(1), 1-30 (2003)

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