lipoic acid

Names

[ Name ]:
lipoic acid

[Synonym ]:
Thioctic acid
MFCD01631142
(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
DL-Thioctic acid
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
5-(1,2-Dithiolan-3-yl)pentanoic acid
(R)-1,2-Dithiolane-3-valeric Acid
(R)-Alpha-Lipoic Acid
1,2-Dithiolane-3-pentanoic acid
5-[(3R)-dithiolan-3-yl]pentanoic acid
(R)-(+)-α-Lipoic acid
(R)-6,8-Thioctic acid
(R)-Thioctic Acid
(±)-1,2-Dithiolane-3-valeric acid
(R)-6,8-Dithiooctanoic acid
6,8-Dihydrothioctic acid
lipoic acid
UNII:73Y7P0K73Y
(R)-α-Lipoic Acid

Biological Activity

[Description]:

Lipoic acid ((R)-(+)-α-Lipoic acid) is an antioxidant, which is an essential cofactor of mitochondrial enzyme complexes. (R)-(+)-α-Lipoic acid is more effective than racemic Lipoic acid.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Mitochondrial Metabolism

Natural Products >> Acids and Aldehydes

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vitro]

Lipoic acid ((R)-(+)-α-Lipoic acid) is the form biosynthesized in humans which is essential for aerobic metabolism. Lipoic acid ((R)-(+)-α-Lipoic acid) is the nutritionally and therapeutically preferred form due to its "vitamin-like" role in metabolism. Lipoic acid ((R)-(+)-α-Lipoic acid) and S-(-)-α-Lipoic acid) constitute the racemic mixture Lipoic acid. Only the Lipoic acid ((R)-(+)-α-Lipoic acid) exists in nature and is an essential cofactor of four mitochondrial enzyme complexes. Lipoic acid ((R)-(+)-α-Lipoic acid) has been suggested to be nutritionally and therapeutically preferred form as antioxidant[1].

[References]

[1]. Nasole E, et al. Effects of alpha lipoic acid and its R+ enantiomer supplemented to hyperbaric oxygen therapy on interleukin-6, TNF-α and EGF production in chronic leg wound healing. J Enzyme Inhib Med Chem. 2014 Apr;29(2):297-302.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
362.5±11.0 °C at 760 mmHg

[ Melting Point ]:
46-49ºC

[ Molecular Formula ]:
C₈H₁₄O₂S₂

[ Molecular Weight ]:
206.326

[ Flash Point ]:
173.0±19.3 °C

[ Exact Mass ]:
206.043518

[ PSA ]:
87.90000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.562

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
C

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

2-Styrylchromones: novel strong scavengers of reactive oxygen and nitrogen species.

Bioorg. Med. Chem. 15 , 6027-36, (2007)

2-Styrylchromones are a small group of naturally occurring chromones, vinylogues of flavones (2-phenylchromones). Natural and synthetic 2-styrylchromones have been tested in different biological syste...

Synthesis and antioxidant properties of new chromone derivatives.

Bioorg. Med. Chem. 17 , 7218-26, (2009)

Nowadays, the recognition of the benefits of antioxidants is eliciting an increasingly interest in the search for new molecules with improved activity. The aim of the present work was to search for im...

Synthesis and biological evaluation of 3,7-diazabicyclo[4.3.0]nonan-8-ones as potential nootropic and analgesic drugs.

J. Med. Chem. 54 , 2512-6, (2011)

A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates...