Dihydrolipoic acid

Base Information

• Chemical Name: Dihydrolipoic acid
• CAS No.: 462-20-4
• Molecular Formula: C8H16O2S2
• Molecular Weight: 208.346
• Hs Code.: 2930909090
• European Community (EC) Number: 610-288-5
• UNII: 7NV2KHU5JA
• DSSTox Substance ID: DTXSID50861946
• Nikkaji Number: J86.722E
• Wikipedia: Dihydrolipoic_acid
• Wikidata: Q5276437
• Mol file: 462-20-4.mol

Synonyms:dihydrolipoate;dihydrolipoic acid;dihydrolipoic acid, (+-)-isomer;dihydrolipoic acid, sodium salt;dihydrothioctic acid

Chemical Property of Dihydrolipoic acid

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 3.47E-06mmHg at 25°C
• Melting Point: 60ºC
• Refractive Index: 1.526
• Boiling Point: 360.8 °C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 172 °C
• PSA: 114.90000
• Density: 1.134 g/cm³
• LogP: 2.24970
• Storage Temp.: +2C to +8C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 208.05917210
• Heavy Atom Count: 12
• Complexity: 128

Purity/Quality:

99.9% ^*data from raw suppliers

Lipoic acid, reduced ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CCC(=O)O)CC(CCS)S
• Uses: γ-Lipoic Acid, is a metabolite of α-Lipoic Acid (L468730), which is a over-the-counter nutritional supplements, that has been used as antioxidant. It is also fat-metabolism stimulator, and thus used a "weight loss" and "energy" supplement.

Technology Process of Dihydrolipoic acid

There total 25 articles about Dihydrolipoic 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: 100.0%

Thioctic acid (1077-28-7,62-46-4) → dihydrolipoic acid (462-20-4)

Guidance literature:

With sodium tetrahydroborate; sodium hydrogencarbonate; In water; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2010.07.118

Reference yield: 100.0%

(R)-1,2-dithiolane-3-pentanoic acid (1200-22-2) → dihydrolipoic acid (462-20-4)

Guidance literature:

With hydrogenchloride; sodium borohydrid; sodium hydrogencarbonate; In water;

Reference yield: 51.24%

2-oxide-β-lipoic acid (108015-78-7) → dihydrolipoic acid (462-20-4)

Guidance literature:

With hydrogenchloride; tetrabutylammomium bromide; sodium thiosulfate; In water; at 40 - 45 ℃;

upstream raw materials:

Thioctic acid

(+/-)-8-hydroxy-6-mercapto-octanoic acid

thiourea

2-(2-Benzoyloxyethyl)cyclohexanone

Downstream raw materials:

Thioctic acid

1,4-dithio-D,L-threitol

N,N'-dimethyl-N,N'-bis(mercaptoacetyl)hydrazine

6,8-bis[(dimethylarsanyl)thio]octanoic acid

Refernces

• 1、 Susumu, Kimihiro,Uyeda, H. Tetsuo,Medintz, Igor L.,Pons, Thomas,Delehanty, James B.,Mattoussi, Hedi. "Enhancing the stability and biological functionalities of quantum dots via compact multifunctional ligands". . p. 13987 - 13996. Retrieved 2007.
• 2、 Wu, Yuzhou,Chakrabortty, Sabyasachi,Gropeanu, Radu A.,Wilhelmi, Joerg,Xu, Yang,Er, Kai Shih,Kuan, Seah Ling,Koynov, Kaloian,Chan, Yinthai,Weil, Tanja. "PH-Responsive quantum dots via an albumin polymer surface coating". . p. 5012 - 5014. Retrieved 2010.
• 3、 Caldwell, Marissa A.,Albers, Aaron E.,Levy, Seth C.,Pick, Teresa E.,Cohen, Bruce E.,Helms, Brett A.,Milliron, Delia J.. "Driving oxygen coordinated ligand exchange at nanocrystal surfaces using trialkylsilylated chalcogenides". . p. 556 - 558. Retrieved 2011.
• 4、 Uyeda, H. Tetsuo,Medintz, Igor L.,Jaiswal, Jyoti K.,Simon, Sanford M.,Mattoussi, Hedi. "Synthesis of compact multidentate ligands to prepare stable hydrophilic quantum dot fluorophores". . p. 3870 - 3878. Retrieved 2005.
• 5、 Li, Dan,Chen, Zhenhua,Wan, Zhanghui,Yang, Tiezhu,Wang, Hao,Mei, Xifan. "One-pot development of water soluble copper nanoclusters with red emission and aggregation induced fluorescence enhancement". . p. 34090 - 34095. Retrieved 2016.
• 6、 Jensen, Andreas I.,Magnus, Charlotte B.,Straathof, Natan J. W.,Zhuravlev, Fedor. "Novel bifunctional [16]anes4-derived chelators for soft radiometals". supporting information. . Retrieved 2021/08/17.
• 7、 -. "Thioctic acid aldehyde derivatives, and preparation method and application thereof". Paragraph 0048-0050. . Retrieved 2019/11/20.