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A5752

Sigma-Aldrich

Adrenochrome

>95% purity (HPLC), powder

Synonym(s):

3-Hydroxy-1-methyl-5,6-indolinedione

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About This Item

Empirical Formula (Hill Notation):
C9H9NO3
CAS Number:
54-06-8
Molecular Weight:
179.17
EC Number:
200-192-8
MDL number:
MFCD00069732
UNSPSC Code:
12171500
PubChem Substance ID:
24891016
NACRES:
NA.47

product name

Adrenochrome, ≥95% (HPLC)

Quality Level

200

Assay

≥95% (HPLC)

form

powder

color

red to brown

εmax

3-4.5 at 485-490 nm in water
9.0-10.5 at 299-304 nm in water

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

SMILES string

CN1CC(O)C2=CC(=O)C(=O)C=C12

InChI

1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3

InChI key

RPHLQSHHTJORHI-UHFFFAOYSA-N

Related Categories

Application

Adrenochrome has been used to study the effect of adrenochrome on coronary artery constriction in the rat heart.

Biochem/physiol Actions

Adrenochrome is an oxidation product of adrenaline. It has been implicated in cardiotoxicity. It is a short-lived cytotoxic molecule and is part of the leukocyte response used to kill bacteria. Adrenochrome is also suggested to exhibit psychotomimetic effects. It is used to determine superoxide dismutase activity.

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Viviana S Fluxá et al.
Nature protocols, 3(8), 1270-1277 (2008-08-21)
The adrenaline test for enzymes is a colorimetric enzyme assay based on the quantification of periodate-sensitive reaction products such as 1,2-diols and 1,2-aminoalcohols by back-titration of the oxidant with adrenaline to produce adrenochrome as an easily detectable red product. The
Adrenochrome-induced coronary artery constriction in the rat heart.
Karmazyn M, et al.
Journal of Pharmacology and Experimental Therapeutics, 219, 225-225 (1981)
Janna Shainsky et al.
Applied and environmental microbiology, 75(14), 4711-4719 (2009-05-26)
Enantiopure sulfoxides are prevalent in drugs and are useful chiral auxiliaries in organic synthesis. The biocatalytic enantioselective oxidation of prochiral sulfides is a direct and economical approach for the synthesis of optically pure sulfoxides. The selection of suitable biocatalysts requires
Maria Luisa Genova et al.
Archives of biochemistry and biophysics, 447(2), 167-173 (2006-02-21)
Complex I in bovine heart submitochondrial particles catalyses the NADH-supported generation of superoxide anion; adrenaline is oxidised by superoxide to adrenochrome that, on its hand, is reduced by Complex I, thus establishing a redox cycle that amplifies the superoxide production.
Cardiotoxicity of adrenochrome in isolated rabbit hearts assessed by epicardial NADH fluorescence.
Rump AF, et al.
Archives of Toxicology, 68, 571-571 (1994)
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