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SML0737

Sigma-Aldrich

MitoTEMPO

≥98% (HPLC), powder, antioxidant

Synonym(s):

(2-(2,2,6,6-Tetramethylpiperidin-1-oxyl-4-ylamino)-2-oxoethyl)triphenylphosphonium chloride, Mito-TEMPO

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About This Item

Empirical Formula (Hill Notation):
C29H35N2O2P · Cl
CAS Number:
1334850-99-5
Molecular Weight:
510.03
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

MitoTEMPO, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to light brown

solubility

H2O: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

[P+](CC(=O)NC4CC(N(C(C4)(C)C)[O])(C)C)(c3ccccc3)(c2ccccc2)c1ccccc1.[Cl-]

InChI

1S/C29H34N2O2P.ClH/c1-28(2)20-23(21-29(3,4)31(28)33)30-27(32)22-34(24-14-8-5-9-15-24,25-16-10-6-11-17-25)26-18-12-7-13-19-26;/h5-19,23H,20-22H2,1-4H3;1H

InChI key

WKKFJIJNGHNQQW-UHFFFAOYSA-N

Application

MitoTEMPO has been used as a mitochondria-targeted antioxidant.

Biochem/physiol Actions

MitoTEMPO is a mitochondrially targeted antioxidant, a specific scavenger of mitochondrial superoxide. MitoTEMPO is a combination of the antioxidant piperidine nitroxide TEMPO with the lipophilic cation triphenylphosphonium, giving MitoTEMPO the ability to pass through lipid bilayers with ease and accumulate several hundred-fold in mitochondria. Mitochondrial dysfunction and oxidative stress contribute to a variety of disorders involving cardiovascular, kidney, liver disorders, Parkinson′s and Alzheimer′s disease.

Other Notes

Light sensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000227251
0000289606
0000289606
0000297835
0000227251

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Caveolin 1-related autophagy initiated by aldosterone-induced oxidation promotes liver sinusoidal endothelial cells defenestration
Xiaoying L, et al.
Redox Biology, 508-521 (2017)
Modulation of mitochondrial antiviral signaling by human herpesvirus 8 interferon regulatory factor 1
Young KH, et al.
Journal of Virology (2016)
Yike Yang et al.
Antioxidants & redox signaling, 34(2), 118-136 (2020-04-02)
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