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Merck

07039

(R)-(+)-α-Lipoic acid

≥98.0% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C8H14O2S2
CAS Number:
Molecular Weight:
206.33
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.32
MDL number:
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Quality Level

assay

≥98.0% (HPLC)

optical purity

enantiomeric excess: ≥98.0% (HPLC)

mp

48-52 °C (lit.)

storage temp.

−20°C

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

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


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Storage Class

11 - Combustible Solids

wgk

WGK 3



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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
Annette Maczurek et al.
Advanced drug delivery reviews, 60(13-14), 1463-1470 (2008-07-29)
Alzheimer's disease (AD) is a progressive neurodegenerative disorder that destroys patient memory and cognition, communication ability with the social environment and the ability to carry out daily activities. Despite extensive research into the pathogenesis of AD, a neuroprotective treatment -