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1200-22-2

R-alpha-Lipoic Acid

CAS: 1200-22-2

Molecular Formula: C8H14O2S2

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1200-22-2 - Names and Identifiers

Name R-alpha-Lipoic Acid
Synonyms D-lipoic acid
R-Alpha Lipoic Acid
R-alpha-Lipoic Acid
(R)-(+)-1,2-Dithiola
R(+)Alpha Lipoic Acid
R(+)alpha-lipoic acid
R-(+)-alpha-Lipoic acid
5-[(3R)-dithiolan-3-yl]valeric acid
5-[(3R)-dithiolan-3-yl]pentanoic acid
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
(R)-(+)-1,2-Dithiolane-3-Pentanoic Acid
(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
(R)-Thioctic Acid(R)-1,2-Dithiolane-3-valeric Acid
CAS 1200-22-2
EINECS 638-752-2
InChI InChI=1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1

1200-22-2 - Physico-chemical Properties

Molecular FormulaC8H14O2S2
Molar Mass206.33
Density1.218±0.06 g/cm3(Predicted)
Melting Point48-52°C(lit.)
Boling Point185-195 °C(Press: 0.5 Torr)
Specific Rotation(α)D23 +104° (c = 0.88 in benzene)
Flash Point>230°F
Solubility Soluble in Dimethyl Sulfoxide and Methanol
AppearanceYellow crystalline solid
ColorLight Yellow to Yellow Low-Melting
Merck14,9326
pKa5.4(at 25℃)
Storage Condition-20°C
Sensitive`sensitive` to light, heat, air and humidity
Refractive Index114 ° (C=1, EtOH)
MDLMFCD01631142
UseVitamin drugs, the effect is better than lipoic acid.
In vitro study 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.

1200-22-2 - Risk and Safety

Risk CodesR22 - Harmful if swallowed
R36/38 - Irritating to eyes and skin.
Safety DescriptionS20 - When using, do not eat or drink.
S36 - Wear suitable protective clothing.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S35 - This material and its container must be disposed of in a safe way.
WGK Germany3
HS Code29349990

1200-22-2 - Reference Information

found R-( )-lipoic acid is a yellow crystalline substance. Lipoic acid is a natural product with biological activity. In 1951, Raed et al. reported that a crystalline cofactor of a growth-promoting enzyme was isolated from treated insoluble liver tissue residues. Because of its high fat solubility and acidity (pka = 4.7), this compound was named lipoic acid.
physiological function lipoic acid is an endogenous antioxidant, which can remove free radicals in the body, promote the body to use glucose to synthesize vitamin C, and promote the synthesis of glutathione. It can effectively remove melanin and assist coenzymes in physiological metabolism that is beneficial to the body's immunity. Lipoic acid also has anti-inflammatory effect, can inhibit the activity of kinase, transforming factor, tumor necrosis factor and collagenase, and has anti-aging effect. Lipoic acid can preserve and regenerate other antioxidants, and has a good health effect on the human body. It is currently widely used in the prevention and treatment of heart disease, diabetes, liver disease and Alzheimer's disease.
The two enantiomers of lipoic acid show different biological activities. Among them, the R-type enantiomer is much more effective than the S-type. This may be due to the metabolism of lipoic acid, a large amount of R-type lipoic acid can penetrate the cell membrane and mitochondrial membrane into the cell and mitochondria It is reduced to dihydrolipoic acid, while only a small amount of S-type enters the cell and is reduced. Dihydrolipoic acid has stronger antioxidant capacity than lipoic acid. The regeneration of endogenous antioxidants and the repair of oxidative damage need to be achieved in the form of dihydrolipoic acid.
Biological activity ( )-α-Lipoic acid ((R)-( )-α-Lipoic acid, α-Lipoic acid, Alpha-Lipoic acid) is one of the physiological forms of thioctic acid. It is a powerful antioxidant that can reduce diabetic neurological symptoms. It has superior oxidation resistance than its racemate. R (+)-α-lipoic acid is an essential cofactor of the mitochondrial enzyme complex. R( )-α-lipoic acid inhibits NF-κB-dependent HIV-1 LTR activation.
TargetValue
use vitamin drugs, the effect is better than lipoic acid.
Last Update:2024-04-09 15:16:47
1200-22-2
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View History
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