Lipoic acid

Base Information

• Chemical Name: Lipoic acid
• CAS No.: 1200-22-2
• Deprecated CAS: 57828-26-9
• Molecular Formula: C8H14O2S2
• Molecular Weight: 206.33
• Hs Code.: 29349990
• European Community (EC) Number: 638-752-2
• UNII: VLL71EBS9Z
• DSSTox Substance ID: DTXSID20152651
• Nikkaji Number: J9.331I
• Wikipedia: Lipoic_acid
• Wikidata: Q27887203
• NCI Thesaurus Code: C171728
• Pharos Ligand ID: FWWQC89NSQGD
• Metabolomics Workbench ID: 1887
• ChEMBL ID: CHEMBL134342
• Mol file: 1200-22-2.mol

Synonyms:Acid, alpha-Lipoic;Alpha Lipogamma;alpha Lipoic Acid;Alpha Lipon Stada;alpha Liponaure Heumann;Alpha Liponsaure Sofotec;alpha Liponsaure von ct;Alpha Lippon AL;alpha Vibolex;Alpha-Lipogamma;alpha-Lipoic Acid;Alpha-Lipon Stada;alpha-Liponaure Heumann;Alpha-Liponsaure Sofotec;alpha-Liponsaure von ct;Alpha-Lippon AL;alpha-Vibolex;Alphaflam;AlphaLipogamma;AlphaLipon Stada;alphaLiponaure Heumann;AlphaLiponsaure Sofotec;alphaLiponsaure von ct;AlphaLippon AL;alphaVibolex;Azulipont;biomo lipon;biomo-lipon;biomolipon;duralipon;espa lipon;espa-lipon;espalipon;Fenint;Injekt, Thiogamma;Juthiac;Lipoic Acid;Liponsaure ratiopharm;Liponsaure-ratiopharm;Liponsaureratiopharm;MTW Alphaliponsaure;MTW-Alphaliponsaure;MTWAlphaliponsaure;Neurium;Pleomix Alpha;Pleomix Alpha N;Pleomix-Alpha;Pleomix-Alpha N;PleomixAlpha;PleomixAlpha N;Thioctacid;Thioctacide T;Thioctic Acid;Thiogamma Injekt;Thiogamma oral;Tromlipon;Verla Lipon;Verla-Lipon;VerlaLipon

Chemical Property of Lipoic acid

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 114 ° (C=1, EtOH)
• Boiling Point: 362.5 °C at 760 mmHg
• PKA: 5.4(at 25℃)
• Flash Point: 173 °C
• PSA: 87.90000
• Density: 1.218 g/cm³
• LogP: 2.78510
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 206.04352203
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-α-Lipoic acid ^*data from reagent suppliers

Safty Information:

• Statements: 22-36/38
• Safety Statements: 20-36-26-35

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CSSC1CCCCC(=O)O
• Isomeric SMILES: C1CSS[C@@H]1CCCCC(=O)O
• Recent ClinicalTrials: Lipoic Acid for Progressive Multiple Sclerosis (MS)
• Recent EU Clinical Trials: The effects of lipoic acid on glycaemic control in type 2 diabetes.
• Uses: α-Lipoic acid has been used as a reference standard for the analysis of α-lipoic acid in human plasma by high performance liquid chromatography coupled to electron capture detector (HPLC-ECD), in various food matrices and dietary supplements by HPLC combined with coulometric electrode array detector (CEAD) as well as electrospray ionization mass spectrometer (ESI-MS). It may be used as a reference standard for the determination of α-lipoic acid in human urine by isocratic reversed-phase HPLC and in α-lipoic acid capsules by HPLC with chemiluminescence detection.

Technology Process of Lipoic acid

There total 175 articles about Lipoic acid 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: 99.8%

(S)-6,8-dichlorooctanoic acid ethylester → (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2)

Guidance literature:

(S)-6,8-dichlorooctanoic acid ethylester; With sodium sulfide; sulfur; In water; at 80 ℃; for 2h;

With water; sodium hydroxide; at 80 ℃; for 8h; Temperature;

Reference yield: 96.1%

[ethyl (5R)-5-(1,2-dithiolan-3yl)pentanoate] (104726-74-1) → (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2)

Guidance literature:

With ethanol; water; sodium hydroxide; at 50 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 96.0%

(+)-isopropyl lipoate (97961-65-4) → (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2)

Guidance literature:

With water; potassium carbonate; In methanol; at 22 ℃; for 40h;

DOI:10.1016/S0040-4039(00)98830-0

upstream raw materials:

Thioctic acid

(R)-6,8-dimercaptooctanoic acid

(S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid

(+)-isopropyl lipoate

Downstream raw materials:

(R)-6,8-dimercaptooctanoic acid

C₃₁H₅₃NO₇S₂Si

C₅₈H₆₃NO₆S₃

(R)-N-(5-acetyl-2-hydroxy-3-methoxyphenyl)-5-(1,2-dithiolan-3-yl)pentanamide

Refernces

• 1、 Elliott, John D.,Steele, John,Johnson, William S.. "ASYMMETRIC SYNTHESIS VIA ACETAL TEMPLATES. 12. HIGHLY DIASTEREOSELECTIVE COUPLING REACTIONS WITH A KETENE ACETAL. AN EFFICIENT, ASYMMETRIC SYNTHESIS OF R-(+)-α-LIPOIC ACID.". . p. 2535 - 2538. Retrieved 1985.
• 2、 Bloch, Robert,Bortolussi, Michel,Girard, Christian,Seck, Matar. "Stereocontrolled reactions induced by a thermolabile group. Synthesis of optically active 1,3-diols". . p. 453 - 462. Retrieved 1992.
• 3、 -. "Preparation method of R-lipoic acid". Paragraph 0039; 0065-0067; 0085-0087; 0105-0106. . Retrieved 2021/07/31.
• 4、 -. "Preparation method of R-lipoic acid tromethamine salt". Paragraph 0028; 0036; 0038; 0045; 0047; 0054. . Retrieved 2021/05/12.