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62-46-4

Basic Information
CAS No.: 62-46-4
Name: Lipoic acid
Molecular Structure:
Molecular Structure of 62-46-4 (Lipoic acid)
Formula: C8H14O2S2
Molecular Weight: 206.32
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;
Safety:
Transport Information:
PSA: 87.90000
LogP: 2.78510
Downstream Products
119365-69-4
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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.