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07039

Sigma-Aldrich

(R)-(+)-α-Lipoic acid

≥98.0% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C8H14O2S2
Numéro CAS:
1200-22-2
Poids moléculaire :
206.33
Numéro MDL:
MFCD01631142
Code UNSPSC :
12352202
ID de substance PubChem :
329748332
Nomenclature NACRES :
NA.32

Niveau de qualité

100
200

Essai

≥98.0% (HPLC)

Pureté optique

enantiomeric excess: ≥98.0% (HPLC)

Pf

48-52 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

AGBQKNBQESQNJD-SSDOTTSWSA-N

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Actions biochimiques/physiologiques

(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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Remarque sur l'analyse

identity confirmed by LC-MS

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
BCCH9072
BCCG5212
BCCC5807
BCBZ5450
BCBS7542V

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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
Kate Petersen Shay et al.
Biochimica et biophysica acta, 1790(10), 1149-1160 (2009-08-12)
Alpha-lipoic acid (LA) has become a common ingredient in multivitamin formulas, anti-aging supplements, and even pet food. It is well-defined as a therapy for preventing diabetic polyneuropathies, and scavenges free radicals, chelates metals, and restores intracellular glutathione levels which otherwise
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
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