Lipoate

Base Information

• Chemical Name: Lipoate
• CAS No.: 62-46-4
• Molecular Formula: C₈H₁₄O₂S₂
• Molecular Weight: 206.33
• Hs Code.: 2934999090
• European Community (EC) Number: 200-534-6
• Nikkaji Number: J1.695.521C
• Wikidata: Q27104127
• Mol file: 62-46-4.mol

Synonyms:Lipoicacid;lipoate;6,8-thioctate;62-46-4;liponate;5-(dithiolan-3-yl)pentanoate;6-thioctate;6-thiotate;6,8-thiotate;1,2-dithiolane-3-valerate;5-(dithiolan-3-yl)valerate;1,2-dithiolane-3-pentanoate;CHEBI:30313;5-(1,2-dithiolan-3-yl)valerate;5-(1,2-dithiolan-3-yl)pentanoate;5-[1,2]Dithiolan-3-yl-pentanoate;5-[3-(1,2-dithiolanyl)]pentanoate;5-(1,2-Dithiolane-3-yl)valeric acidanion;Q27104127

Chemical Property of Lipoate

Chemical Property:

• Appearance/Colour: slightly yellow crystalline powder
• Vapor Pressure: 3.07E-06mmHg at 25°C
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 362.5 °C at 760 mmHg
• Flash Point: 173 °C
• PSA: 87.90000
• Density: 1.218 g/cm³
• LogP: 2.78510
• Solubility.: Very slightly soluble in water, very soluble in dimethylformamide, freely soluble in methanol.
• Water Solubility.: 0.9 g/L (20℃)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 205.03569700
• Heavy Atom Count: 12
• Complexity: 145

Purity/Quality:

99%,food grade, ^*data from raw suppliers

Lipoic?acid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:
• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSSC1CCCCC(=O)[O-]
• Recent EU Clinical Trials: Sensory Motor Neuropathies of the sciatic nerve: a comparative evaluation of dextrorotatory enantiomer of thioctic acid and acetyl-L-carnitine.
• Description: Lipoic acid is a class of compounds belonging to the B class vitamins and is the growth factor of yeast and some kinds of microorganisms. It can play the role of coenzyme role in a multi-enzyme system that is responsible for catalyzing the acyl transfer effect in the reaction of oxidative decarboxylation of pyruvate into acetate and oxidative decarboxylation reaction of α-ketoglutarate into succinic acid.
• Uses: Alpha-lipoic acid is a kind of B vitamins and can be used for the treatment of acute and chronic hepatitis, cirrhosis, hepatic coma, fatty liver, diabetes, etc. other uses of lipoic acid are as follows:1. Neutralize free radicals.2. It is quickly absorbed and utilized by body cells.3. Can strengthen the role of other antioxidants.4. Can be concentrated on the inside and outside of cells and cell membranes.5. Promote normal gene expression.6. Chelate metal ions, or excrete toxic metals from the body.7. Alpha-lipoic acid is an antioxidant that is made naturally in the body and also found in foods. α-lipoic acid (ALA, thioctic acid) is an organosulfur component produced from plants, animals, and humans. It has various properties, among them great antioxidant potential and is widely used as a racemic drug for diabetic polyneuropathy-associated pain and paresthesia. It has been used in alternative medicine as a possibly effective aid in weight loss, treating diabetic nerve pain, healing wounds, lowering blood sugar, improving skin discoloration caused by vitiligo, and decreasing complications of coronary artery bypass graft (CABG) surgery.Alpha Lipoic Acid 600 mg | 45 Tablets

Technology Process of Lipoate

There total 105 articles about Lipoate 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: 70.0%

1,2-dithiolane-3-pentanoic acid methyl ester (46236-19-5) → Thioctic acid (1077-28-7,62-46-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 24h;

DOI:10.1055/s-2005-861867

Reference yield: 69.0%

5-(2,2-Dimethyl-3-oxo-3λ4-[1,3]dithian-4-yl)-pentanoic acid (88987-43-3) → Thioctic acid (1077-28-7,62-46-4)

Guidance literature:

With hydrogenchloride; In benzene; at 50 ℃; for 7h;

DOI:10.1055/s-2005-865217

Reference yield: 65.0%

6,8-Dibromoctansaeure (138152-63-3) → Thioctic acid (1077-28-7,62-46-4)

Guidance literature:

With piperidinium thiotungstate; In N,N-dimethyl-formamide; at 50 ℃; for 4h;

DOI:10.1021/jo00032a019

upstream raw materials:

5-((7R,10S)-7-Isopropyl-10-methyl-1-oxo-1λ⁴,5-dithia-spiro[5.5]undec-2-yl)-pentanoic acid

(S)-methyl lipoate

1,2-dithiolane-3-pentanoic acid methyl ester

α-dihydrolipoic acid

Downstream raw materials:

dihydrolipoic acid

trans-1,2-dithiane-4,5-diol

1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane

(4S,5R)-3-<5-(1,2-dithiolan-3-yl)-1-oxopentyl>-4-methyl-5-phenyloxazolidine-2-selone

Refernces

• 1、 -. "Preparation method of R-(+)-lipoic acid". Paragraph 0038; 0043; 0044; 0046; 0050; 0052; 0054. . Retrieved 2018/06/23.
• 2、 Chavan, Subhash P.,Pawar, Kailash P.,Praveen, Ch.,Patil, Niteen B.. "Chirality induction and chiron approaches to enantioselective total synthesis of α-lipoic acid". . p. 4213 - 4218. Retrieved 2015/06/02.