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| CAS No.: | 62-46-4 |
|---|---|
| Name: | Lipoic acid |
| Article Data: | 54 |
| Molecular Structure: | |
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| Formula: | C8H14O2S2 |
| Molecular Weight: | 206.33 |
| Synonyms: | 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid;1,2-dithiolane-3-pentanoic acid, (3R)-;α-Lipoic Acid; |
| EINECS: | 200-534-6 |
| Density: | 1.218 g/cm3 |
| Melting Point: | 48-52 °C(lit.) |
| Boiling Point: | 362.5 °C at 760 mmHg |
| Flash Point: | 173 °C |
| Solubility: | 0.9 g/L (20℃) |
| Appearance: | slightly yellow crystalline powder |
| Hazard Symbols: | R22:; |
| Risk Codes: | Xn:Harmful; ">  Xn:Harmful; |
| PSA: | 87.90000 |
| LogP: | 2.78510 |
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History
They administered intravenous ALA to 79 people with acute and severe liver damage at various medical centers across the United States and 75 recovered full liver function. Drs. Bartter and Berkson were appointed by the FDA as principal investigators for this therapeutic agent as an investigational drug and Dr. Berkson went on to use it successfully for the treatment of chronic liver disease.
The first human clinical studies using alpha-lipoic acid in the United States were conducted by Fredrick C. Bartter, Burton M. Berkson, and associates from the National Institutes of Health in the 1970’s.
Standards and Recommendations
Lipoic acid (CAS NO.62-46-4) is first called pyruvate oxidation factor by Irwin C. Gunsalus, the former chair of Biochemistry at the University of Illinois at Urbana-Champaign. The structure was determined in a collaboration of Gunsalus with Lester Reed and Eli Lilly; the synthetic compound designated α-lipoic acid proved to be the correct molecule. The configuration found in vivo was later found to be the R-enantiomer.This was after the observation by many groups that POF functioned as an essential growth factor for Enterococci, which lack the ability to make lipoate.
Specification
The Lipoic acid, with the CAS registry number 62-46-4 and EINECS registry number 200-534-6, is also called 1,2-Dithiolane-3-pentanoic acid. The molecular formula of this chemical is C8H14O2S2. Lipoic acid is also known as Heparlipon or Thioctic acid. It is biosynthesized by cleavage of Linoleic acid and is a coenzyme of oxoglutarate dehydrogenase. And it is used in dietary supplements.
The physical properties of Lipoic acid are as followings: (1)Melting Point: 60.5 °C; (2)Boiling Point: 162.5 °C; (3)log P (octanol-water): 3.400; (4)Water Solubility: 127 mg/L; (5)Vapor Pressure: 3.75E-05 mm Hg; (6)Henry's Law Constant: 1.64E-08 atm-m3/mole; (7)Atmospheric OH Rate Constant: 2.52E-10 cm3/molecule-sec.
You can still convert the following datas into molecular structure:
(1)SMILES: C1(CCSS1)CCCCC(=O)O
(2)InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 160mg/kg (160mg/kg) | Drugs in Japan Vol. 6, Pg. 454, 1982. | |
| mouse | LD50 | intravenous | 197mg/kg (197mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 278, 1964. | |
| mouse | LD50 | oral | 502mg/kg (502mg/kg) | Archives of Toxicology. Vol. 41, Pg. 79, 1978. | |
| mouse | LD50 | subcutaneous | 200mg/kg (200mg/kg) | Drugs in Japan Vol. 6, Pg. 454, 1982. | |
| rat | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972. |
| rat | LD50 | intravenous | 180mg/kg (180mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972. |
| rat | LD50 | oral | 1130mg/kg (1130mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972. |
| rat | LD50 | subcutaneous | 230mg/kg (230mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 68, Pg. 265, 1972. |