Lipoamide

Base Information

• Chemical Name: Lipoamide
• CAS No.: 940-69-2
• Deprecated CAS: 3206-73-3
• Molecular Formula: C8H15 N O S2
• Molecular Weight: 205.345
• Hs Code.: 2934999090
• European Community (EC) Number: 213-375-2,221-710-9
• NSC Number: 759236,90787
• UNII: Q1GT04827L
• DSSTox Substance ID: DTXSID2046541
• Nikkaji Number: J25.390A
• Wikipedia: Lipoamide
• Wikidata: Q63611085
• Metabolomics Workbench ID: 4496
• ChEMBL ID: CHEMBL1403899
• Mol file: 940-69-2.mol

Synonyms:1,2-dithiolane-3-valeramide;6,8-thioctic amide;alpha-lipoic amide;lipamide;lipoamide;lipoamide, (+-)-isomer

Chemical Property of Lipoamide

Chemical Property:

• Vapor Pressure: 1.39E-06mmHg at 25°C
• Melting Point: 127-129 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 399.2 °C at 760 mmHg
• PKA: 16.59±0.40(Predicted)
• Flash Point: 195.2 °C
• PSA: 93.69000
• Density: 1.169 g/cm³
• LogP: 2.88610
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly, Heated, Sonicated), Ethanol (Slightl
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 205.05950645
• Heavy Atom Count: 12
• Complexity: 152

Purity/Quality:

99% ^*data from raw suppliers

(±)-α-Lipoamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:Harmful if swallowed.
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Amides, Other
• Canonical SMILES: C1CSSC1CCCCC(=O)N
• Uses: (±)-α-Lipoamide may be used in treatment of insulin resistance by stimulating mitochondrial biogenesis. When used in combination with Alprostadil, it has shown to have a good therapeutic effect on early diabetic nephropathy.

Technology Process of Lipoamide

There total 6 articles about Lipoamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

thioctic acid-N-hydroxysuccinimide ester (40846-94-4) → lipoamide (940-69-2,165171-77-7,3206-73-3)

Guidance literature:

With ammonium hydroxide; In dichloromethane; acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.08.150

Reference yield: 34.0%

Thioctic acid (1077-28-7,62-46-4) → lipoamide (940-69-2,165171-77-7,3206-73-3)

Guidance literature:

With ammonium hydroxide; immobilized Candida antarctica Lipase B; In 1,4-dioxane; water; at 50 ℃; for 72h; Reagent/catalyst; Sealed tube; Enzymatic reaction;

DOI:10.1016/j.tetlet.2018.04.049

Reference yield:

dihydrolipoamide (3884-47-7) → lipoamide (940-69-2,165171-77-7,3206-73-3)

Guidance literature:

With oxidized dithiothreitol; Equilibrium constant; pH 7.0;

DOI:10.1021/ja00526a042

upstream raw materials:

Thioctic acid

dihydrolipoamide

2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

thioctic acid-N-hydroxysuccinimide ester

Downstream raw materials:

NAD

n-octanamide

dihydrolipoamide

2-Methyl-benzoic acid methyl ester

Refernces

• 1、 Manova, Daniela,Gallier, Florian,Tak-Tak, Lotfi,Yotava, Lyubov,Lubin-Germain, Nadège. "Lipase-catalyzed amidation of carboxylic acid and amines". supporting information. p. 2086 - 2090. Retrieved 2018/05/04.
• 2、 Molina Portela, Maria P.,Stoppani, Andres O.M.. "Redox cycling of β-lapachone and related o-naphthoquinones in the presence of dihydrolipoamide and oxygen". . p. 275 - 283. Retrieved 2007/10/03.