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Merck

04471

(R)-(+)-α-Lipoic acid

analytical standard

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:
1200-22-2
Molecular Weight:
206.33
NACRES:
NA.24
PubChem Substance ID:
329747929
UNSPSC Code:
85151701
MDL number:
MFCD01631142

Product Name

(R)-(+)-α-Lipoic acid, analytical standard

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

SMILES string

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

InChI key

AGBQKNBQESQNJD-SSDOTTSWSA-N

grade

analytical standard

assay

≥98.0% (HPLC)

optical activity

[α]/D +115±5°, c = 1% in ethanol

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

48-52 °C (lit.)

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

2-8°C

Quality Level

100

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Application

α-Lipoic acid has been used as a reference standard for the analysis of α-lipoic acid in human plasma by high performance liquid chromatography coupled to electron capture detector (HPLC-ECD), in various food matrices and dietary supplements by HPLC combined with coulometric electrode array detector (CEAD) as well as electrospray ionization mass spectrometer (ESI-MS).
It may be used as a reference standard for the determination of α-lipoic acid in human urine by isocratic reversed-phase HPLC and in α-lipoic acid capsules by HPLC with chemiluminescence detection.

General description

α-Lipoic acid is an antioxidant which is generally present in plants, animals and many other microorganisms.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM4461
BCCJ1193
BCCJ7476
BCCF6166
BCCF6165

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W Witt et al.
Journal of chromatography. B, Biomedical sciences and applications, 705(1), 127-131 (1998-03-14)
A new method for the quantitation of lipoic acid in plasma and tissues based on the selective precolumn derivatization of thiols with the fluorescent label monobromobimane is described. After extraction with diethyl ether, the dithiolane ring of lipoic acid is
Determination of lipoic acid in human plasma by HPLC-ECD using liquid-liquid and solid-phase extraction: Method development, validation and optimization of experimental parameters.
Khan, et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 878(28), 2782-2788 (2010)
Determination of lipoic acid by flow-injection and high-performance liquid chromatography with chemiluminescence detection.
Wolyniec, et al.
Talanta, 96(2), 223-229 (2012)
High-performance liquid chromatographic assay for $\alpha$-lipoic acid and five of its metabolites in human plasma and urine.
Teichert, et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 769(2), 269-281 (2002)
Arjumand I Durrani et al.
Journal of pharmaceutical and biomedical analysis, 45(4), 694-699 (2007-09-21)
Alpha-lipoic acid is an antioxidant used both in the prevention and treatment of various oxidative stress related diseases. It is an important constituent of some dietary supplements and can also be found in plant and animal sources. A rapid method
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