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I5659

Sigma-Aldrich

Idebenone

≥98% (HPLC), powder

Synonym(s):

2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

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About This Item

Empirical Formula (Hill Notation):
C19H30O5
CAS Number:
Molecular Weight:
338.44
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.25

product name

Idebenone, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

solubility

methanol: 50 mg/mL, clear to slightly hazy

storage temp.

room temp

SMILES string

O=C(C(OC)=C1OC)C(CCCCCCCCCCO)=C(C)C1=O

InChI

1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3

InChI key

JGPMMRGNQUBGND-UHFFFAOYSA-N

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General description

Idebenone is a short-chain benzoquinone drug.

Application

Idebenone has been used:
  • to treat mutant myocilin (mMYOC) cells for drug treatment assay
  • to validate C2C12 secondary cell screening assay
  • to treat obese mice, to test whether idebenone and CoQ10 bind directly to peroxisome proliferator-activated receptor (PPAR)LBDs, His-tagged PPARα, δ and γ LBDs

Biochem/physiol Actions

Idebenone is used in the treatment of visual impairment in adolescents and adults with Leber′s hereditary optic neuropathy (LHON). It serves as an antioxidant. It helps to guard the heart muscle against oxidative stress.
A short-chain Coenzyme Q analog that enhances superoxide formation, presumably by mediating electron transfer from N2 to oxygen.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carolyn P Ojano-Dirain et al.
The Laryngoscope, 122(11), 2543-2548 (2012-09-12)
Antioxidants have been shown to protect against aminoglycoside-induced hearing loss. Mitoquinone (MitoQ) is a mitochondria-targeted derivative of the antioxidant ubiquinone. MitoQ is attached to a lipophilic triphenylphosphonium (TPP) cation, which enables its accumulation inside the mitochondria several hundred-fold over the
Ruth Goldschmidt et al.
Bioorganic & medicinal chemistry, 21(4), 969-978 (2013-01-15)
Two new aza analogues of the neuroprotective agent idebenone have been synthesized and characterized. Their antioxidant activity, and ability to augment ATP levels have been evaluated in several different cell lines having suboptimal mitochondrial function. Both compounds were found to
Idebenone and reduced cardiac hypertrophy in Friedreich's ataxia
Hausse AO, et al.
Heart, 87(4), 346-349 (2002)
Persistence of the treatment effect of idebenone in Leber's hereditary optic neuropathy.
T Klopstock et al.
Brain : a journal of neurology, 136(Pt 2), e230-e230 (2013-02-08)
Visual improvement with the use of idebenone in the treatment of Wolfram syndrome.
Simon R Bababeygy et al.
Journal of neuro-ophthalmology : the official journal of the North American Neuro-Ophthalmology Society, 32(4), 386-389 (2012-12-01)

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