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Merck
CN

19772

(R)-Dihydrolipoic acid

analytical standard

Synonym(s):

(R)-6,8-Dimercaptooctanoic acid, (R)-Dihydro-α-lipoic acid, R-DHLA

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About This Item

Empirical Formula (Hill Notation):
C8H16O2S2
CAS Number:
119365-69-4
Molecular Weight:
208.34
UNSPSC Code:
85151701
MDL number:
MFCD10566606
Beilstein/REAXYS Number:
1722776

Key Documents

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SMILES string

OC(=O)CCCC[C@@H](S)CCS

grade

analytical standard

assay

≥95.0% (HPLC)

optical activity

[α]/D -11±2°, c = 1 in ethanol

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

storage temp.

2-8°C

Biochem/physiol Actions

R-DHLA regenerates the antioxidants vitamin C, thioredoxin and glutathione which in turn can recycle vitamin E.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

signalword

Warning

pictograms

Exclamation mark
GHS07

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

12 - Non Combustible Liquids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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J H Prehn et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 12(1), 78-87 (1992-01-01)
It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation. We tested dihydrolipoate for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia
H Kataoka
Journal of chromatography. B, Biomedical sciences and applications, 717(1-2), 247-262 (1998-12-01)
The analysis of lipoic acid and related compounds, such as its reduced form dihydrolipoic acid, its amide form lipoamide and other analogues, in biological and food samples is important in biochemistry, nutritional and clinical chemistry. This review summarizes the chromatographic
Michael L Koenig et al.
Neurotoxicity research, 5(4), 265-272 (2003-07-02)
One consequence of trauma to the CNS is the production and liberation, from damaged tissue, of large amounts of oxygen-centered free radicals or reactive oxygen species (ROS). An excessive production of ROS can overwhelm the endogenous antioxidant defense system resulting
B C Scott et al.
Free radical research, 20(2), 119-133 (1994-02-01)
A detailed evaluation of the antioxidant and pro-oxidant properties of lipoic acid (LA) and dihydrolipoic acid (DHLA) was performed. Both compounds are powerful scavengers of hypochlorous acid, able to protect alpha 1-antiproteinase against inactivation by HOCl. LA was a powerful
Soichiro Satoh et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 854(1-2), 109-115 (2007-04-28)
The simultaneous determination of alpha-lipoic acid (LA) and DHLA (reduced form of LA) was carried out by HPLC with fluorescence detection. DHLA in the sample was first labeled with ABD-F at room temperature for 10 min and then the LA
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