R-(+)-alpha-Lipoic acid
R-alpha-Lipoic Acid
CAS: 1200-22-2
Molecular Formula: C8H14O2S2
R-(+)-alpha-Lipoic acid - 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 |
R-(+)-alpha-Lipoic acid - Physico-chemical Properties
| Molecular Formula | C8H14O2S2 |
| Molar Mass | 206.33 |
| Density | 1.218±0.06 g/cm3(Predicted) |
| Melting Point | 48-52°C(lit.) |
| Boling Point | 185-195 °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 |
| Appearance | Yellow crystalline solid |
| Color | Light Yellow to Yellow Low-Melting |
| Merck | 14,9326 |
| pKa | 5.4(at 25℃) |
| Storage Condition | -20°C |
| Sensitive | `sensitive` to light, heat, air and humidity |
| Refractive Index | 114 ° (C=1, EtOH) |
| MDL | MFCD01631142 |
| Use | Vitamin 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. |
R-(+)-alpha-Lipoic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/38 - Irritating to eyes and skin. |
| Safety Description | S20 - 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 Germany | 3 |
| HS Code | 29349990 |
R-(+)-alpha-Lipoic acid - 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. |
| Target | Value |
| use | vitamin drugs, the effect is better than lipoic acid. |
Last Update：2024-04-09 15:16:47
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