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A5752

Sigma-Aldrich

Adrenochrome

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Synonym(s):
3-Hydroxy-1-methyl-5,6-indolinedione
Empirical Formula (Hill Notation):
C9H9NO3
CAS Number:
Molecular Weight:
179.17
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Assay

>95% (HPLC)

Quality Level

form

powder

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

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1 of 4

This Item
214515N5625N2125
Adrenochrome

Sigma-Aldrich

A5752

Adrenochrome

Chromotrope FB Dye content 50 %

Sigma-Aldrich

214515

Chromotrope FB

Naphthol AS phosphate >99% (TLC), histochemical substrate

Sigma-Aldrich

N5625

Naphthol AS phosphate

form

powder

form

powder

form

powder

form

powder

εmax

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

εmax

-

εmax

-

εmax

-

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

storage temp.

room temp

storage temp.

−20°C

storage temp.

−20°C

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.

related product

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

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Customers Also Viewed

Slide 1 of 8

1 of 8

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
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
Adrenochrome-induced coronary artery constriction in the rat heart.
Karmazyn M, et al.
Journal of Pharmacology and Experimental Therapeutics, 219, 225-225 (1981)
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.
The oxidative metabolism of catecholamines in the brain: a review.
Smythies J and Galzigna L
Biochimica et Biophysica Acta, 1380, 159-159 (1998)

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