108015-78-7

Basic information

• Product Name: rac-Lipoic Acid Impurity 1 (S-Oxide)
• Synonyms: rac-Lipoic Acid Impurity 1 (S-Oxide);Rac-Lipoic Acid Impurity D;Thioctic acid Impurity 2
• CAS NO: 108015-78-7
• Molecular Formula: C₈H₁₄O₃S₂
• Molecular Weight: 222.32
• Mol File: 108015-78-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Air Sensitive, Temperature Sensitive
• CAS DataBase Reference: rac-Lipoic Acid Impurity 1 (S-Oxide)(CAS DataBase Reference)
• NIST Chemistry Reference: rac-Lipoic Acid Impurity 1 (S-Oxide)(108015-78-7)
• EPA Substance Registry System: rac-Lipoic Acid Impurity 1 (S-Oxide)(108015-78-7)

Safety Data

• Hazardous Substances Data: 108015-78-7(Hazardous Substances Data)

Usage

Uses

β-2-Lipoic Acid is a constituent or an effective substance of camomiles.

Upstream product

• 1077-28-7 Thioctic acid 
• 1200-22-2 (R)-1,2-dithiolane-3-pentanoic acid 
• 46236-19-5 1,2-dithiolane-3-pentanoic acid methyl ester 

Downstream Products

• 949885-99-8 5-(2-Oxo-2λ⁴-[1,2]dithiolan-3-yl)-pentanoic acid {(S)-1-[(S)-1-(4-chloro-benzyl)-2-ethylcarbamoyl-2-hydroxy-ethylcarbamoyl]-2-methyl-propyl}-amide 
• 462-20-4 dihydrolipoic acid 

Relevant articles and documents

Cyclic Thiosulfinates and Cyclic Disulfides Selectively Cross-Link Thiols while Avoiding Modification of Lone Thiols

This work addresses the need for chemical tools that can selectively form cross-links. Contemporary thiol-selective cross-linkers, for example, modify all accessible thiols, but only form cross-links between a subset. The resulting terminal "dead-end" modifications of lone thiols are toxic, confound cross-linking-based studies of macromolecular structure, and are an undesired, and currently unavoidable, byproduct in polymer synthesis. Using the thiol pair of Cu/Zn-superoxide dismutase (SOD1), we demonstrated that cyclic disulfides, including the drug/nutritional supplement lipoic acid, efficiently cross-linked thiol pairs but avoided dead-end modifications. Thiolate-directed nucleophilic attack upon the cyclic disulfide resulted in thiol-disulfide exchange and ring cleavage. The resulting disulfide-tethered terminal thiolate moiety either directed the reverse reaction, releasing the cyclic disulfide, or participated in oxidative disulfide (cross-link) formation. We hypothesized, and confirmed with density functional theory (DFT) calculations, that mono-S-oxo derivatives of cyclic disulfides formed a terminal sulfenic acid upon ring cleavage that obviated the previously rate-limiting step, thiol oxidation, and accelerated the new rate-determining step, ring cleavage. Our calculations suggest that the origin of accelerated ring cleavage is improved frontier molecular orbital overlap in the thiolate-disulfide interchange transition. Five- to seven-membered cyclic thiosulfinates were synthesized and efficiently cross-linked up to 104-fold faster than their cyclic disulfide precursors; functioned in the presence of biological concentrations of glutathione; and acted as cell-permeable, potent, tolerable, intracellular cross-linkers. This new class of thiol cross-linkers exhibited click-like attributes including, high yields driven by the enthalpies of disulfide and water formation, orthogonality with common functional groups, water-compatibility, and ring strain-dependence.

Preparation method of lipoic acid impurity A

The invention relates to a preparation method of a lipoic acid impurity A, and belongs to the field of compound synthesis. The invention aims to overcome the defects of complex operation and harsh reaction conditions in the prior art, and provides the preparation method of the lipoic acid impurity A. The preparation method is mild in condition and high in product purity. The preparation method comprises the following steps: (1) dissolving lipoic acid in a reaction solvent, adding an oxidant for reaction, and removing solids and the solvent after the reaction is completed to obtain a compound B; (2) respectively adding the compound B, sodium thiosulfate and a catalyst into water, then adding hydrochloric acid, carrying out hydrolysis ring-opening reaction, and filtering after the reaction is completed to obtain a compound C; and (3) respectively adding the compound C, sodium sulfide and formaldehyde into the reaction solvent for reaction, extracting after the reaction is completed, drying, and purifying to obtain a compound D lipoic acid impurity A. The method is mild in condition, and the prepared lipoic acid impurity A is high in purity.

Preparation method of thioctic acid oxidation impurities

The invention relates to a chemical preparation method of thioctic acid oxidation impurities, and belongs to the technical field of medicine synthesis. The structural formula of the thioctic acid oxidation impurities is shown in the description. The preparation method of the thioctic acid oxidation impurities comprises the following steps: preparing an ester from thioctic acid and an alcohol in an organic solvent under the action of a condensing agent; dissolving the obtained alcohol ester compound of thioctic acid in an organic solvent, processing the obtained solution by an oxidant to generate four oxidation products of thioctate, and carrying out column chromatography purification according to the Rf vale difference of the compounds to obtain four intermediate compounds; and respectively hydrolyzing the four intermediate compounds in an alkaline aqueous solution to obtain the four thioctic acid oxidation impurity compounds I, II, III and IV. The preparation method of the thioctic acid oxidation impurity compounds has the advantages of obtaining of single oxidation impurities, simplicity, easiness in implementation, and easiness in enforcement.