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Key Documents

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07039

Sigma-Aldrich

(R)-(+)-α-Lipoic acid

≥98.0% (HPLC)

Sinónimos:

(R)-(+)-1,2-Dithiolane-3-pentanoic acid, (R)-6,8-Dithiooctanoic acid, (R)-6,8-Thioctic acid

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About This Item

Fórmula empírica (notación de Hill):
C8H14O2S2
Número de CAS:
1200-22-2
Peso molecular:
206.33
MDL number:
MFCD01631142
UNSPSC Code:
12352202
PubChem Substance ID:
329748332
NACRES:
NA.32

Quality Level

100
200

assay

≥98.0% (HPLC)

optical purity

enantiomeric excess: ≥98.0% (HPLC)

mp

48-52 °C (lit.)

storage temp.

−20°C

SMILES string

OC(=O)CCCC[C@@H]1CCSS1

InChI

1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1

InChI key

AGBQKNBQESQNJD-SSDOTTSWSA-N

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Biochem/physiol Actions

(R)-(+)-α-Lipoic acid was shown to significantly increase pyruvate oxidation while abrogating fatty acid oxidation in rat hepatocytes. These effects make R-(+)-α-Lipoic acid a promising treatment option for the treatment of Type II diabetes. It is a biological antioxidant with prooxidant activities, its therapeutic potential is widely investigated, e.g. in the treatment for Alzheimer′s disease.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

identity confirmed by LC-MS

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Thioctic acid containing impurity B European Pharmacopoeia (EP) Reference Standard

Y0000545

Thioctic acid containing impurity B

Valerian standardised dry extract European Pharmacopoeia (EP) Reference Standard

Y0000583

Valerian standardised dry extract

Parthenolide ≥98% (HPLC)

Sigma-Aldrich

P0667

Parthenolide

Jennie L Walgren et al.
Metabolism: clinical and experimental, 53(2), 165-173 (2004-02-10)
R-(+)-alpha-lipoic acid (R-LA) is the naturally occurring enantiomer of LA. It is a strong antioxidant and cofactor of key metabolic enzyme complexes catalyzing the decarboxylation of alpha-keto acids. Racemic LA (rac-LA) has shown promise in treating diabetic polyneuropathy, and some
Dove J Keith et al.
Pharmacological research, 66(3), 199-206 (2012-05-23)
Lipoic acid (LA) shows promise as a beneficial micronutrient toward improving elder health. Studies using old rats show that (R)-α-LA (R-LA) significantly increases low molecular weight antioxidants that otherwise decline with age. Despite this rationale for benefiting human health, little
Takashi Yamada et al.
Neurochemistry international, 59(7), 1003-1009 (2011-10-13)
Growing evidence suggests that α-lipoic acid (LA) has neuroprotective effects in various pathological conditions including brain ischemia and neurodegeneration. While anti-oxidative activity has been thought to play a central role in LA-mediated neuroprotection, the precise mechanism and the effect of
L Packer et al.
Free radical biology & medicine, 19(2), 227-250 (1995-08-01)
alpha-Lipoic acid, which plays an essential role in mitochondrial dehydrogenase reactions, has recently gained considerable attention as an antioxidant. Lipoate, or its reduced form, dihydrolipoate, reacts with reactive oxygen species such as superoxide radicals, hydroxyl radicals, hypochlorous acid, peroxyl radicals
Christiane Iserman et al.
bioRxiv : the preprint server for biology (2020-06-27)
A mechanistic understanding of the SARS-CoV-2 viral replication cycle is essential to develop new therapies for the COVID-19 global health crisis. In this study, we show that the SARS-CoV-2 nucleocapsid protein (N-protein) undergoes liquid-liquid phase separation (LLPS) with the viral
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