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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:
58186-27-9
Molecular Weight:
338.44
MDL number:
MFCD00274552
UNSPSC Code:
12352204
PubChem Substance ID:
329815386
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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Mary Kearney et al.
The Cochrane database of systematic reviews, 4(4), CD007791-CD007791 (2012-04-20)
Friedreich ataxia is a rare inherited autosomal recessive neurological disorder, characterised initially by unsteadiness in standing and walking, slowly progressing to wheelchair dependency usually in the late teens or early twenties. It is associated with slurred speech, scoliosis and pes
Idebenone maintains survival of mutant myocilin cells by inhibiting apoptosis
Guan Y, et al.
Chinese Medicine, 129(16), 2001-2001 (2016)
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)
Primary and secondary drug screening assays for Friedreich ataxia
Cotticelli MG, et al.
Journal of Biomolecular Screening, 17(3), 303-313 (2012)
Oliver Gamondi et al.
Drug metabolism letters, 6(2), 120-123 (2012-09-15)
We investigated the damage caused by oxidative stress using the yeast Saccharomyces cerevisiae as a model biological system. After inducing oxidative stress with menadione, we were able to evaluate the extent of cellular oxidative stress by utilizing 2',7'-dichlorofluorescein diacetate (DCFH-DA)
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