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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
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



Global Trade Item Number

SKUGTIN
N17351-500G04061832113487
N17351-100G04061832113463
07039-10MG04061838647375
07039-50MG04061833380390
07039-500MG04061833380383
703904061838245526