alpha-lipoic acid-NHS

Base Information

• Chemical Name: alpha-lipoic acid-NHS
• CAS No.: 40846-94-4
• Molecular Formula: C12H17NO4S2
• Molecular Weight: 303.403
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID40693233
• Nikkaji Number: J1.895.274B
• Mol file: 40846-94-4.mol

Synonyms:40846-94-4;alpha-lipoic acid-NHS;DL-Alpha-lipoic acid-nhs;2,5-DIOXOPYRROLIDIN-1-YL 5-(1,2-DITHIOLAN-3-YL)PENTANOATE;Thioctic acid N-hydroxysuccinimide ester;1-{[5-(1,2-dithiolan-3-yl)pentanoyl]oxy}pyrrolidine-2,5-dione;2,5-Pyrrolidinedione, 1-[[5-(1,2-dithiolan-3-yl)-1-oxopentyl]oxy]-;(2,5-dioxopyrrolidin-1-yl) 5-(dithiolan-3-yl)pentanoate;DL-Alpha-lipoicacid-nhs;DL-alpha-Lipoic acid NHS;ALPHA-LIPOICACID-NHS;LCZC1182;SCHEMBL2633200;DTXSID40693233;MFCD09028032;STL476790;AKOS027472998;AS-72152;BP-22515;HY-141336;CS-0115098;DL-f inverted question mark-Lipoic Acid-NHS;L0345;C70383;1,2-Dithiolane-3-pentanoic acid succinimidyl ester;A1-03868

Chemical Property of alpha-lipoic acid-NHS

Chemical Property:

• Melting Point: 95 °C
• PSA: 114.28000
• Density: 1.36±0.1(20.0000℃)
• LogP: 2.24560
• Solubility.: Soluble in DMSO, DMF, DCM
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 303.05990037
• Heavy Atom Count: 19
• Complexity: 359

Purity/Quality:

NLT 98% ^*data from raw suppliers

DL-α-Lipoic Acid-NHS ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSSC1CCCCC(=O)ON2C(=O)CCC2=O
• Description: alpha-lipoic acid-NHS contains a lipoic acid group and a terminal NHS group. The NHS group can participate in reactions with primary amine groups to form amide bonds.

Technology Process of alpha-lipoic acid-NHS

There total 2 articles about alpha-lipoic acid-NHS 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: 98.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Thioctic acid (1077-28-7,62-46-4) → thioctic acid-N-hydroxysuccinimide ester (40846-94-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.201301930

Reference yield: 98.0%

di(succinimido) carbonate (74124-79-1) + Thioctic acid (1077-28-7,62-46-4) → thioctic acid-N-hydroxysuccinimide ester (40846-94-4)

Guidance literature:

di(succinimido) carbonate; Thioctic acid; In acetonitrile;

With triethylamine; In acetonitrile; at 20 ℃; for 2h; Darkness;

DOI:10.1039/d1cc03648c

Reference yield: 99.0%

1-(2,4-dichlorobenzyl)piperazine (51619-56-8) + thioctic acid-N-hydroxysuccinimide ester (40846-94-4) → 1-(4-(2,4-dichlorobenzyl)piperazin-1-yl)-5-(1,2-dithiolan-3-yl)pentan-1-one (1589517-88-3)

Guidance literature:

In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.5012/bkcs.2013.34.11.3322

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Thioctic acid

di(succinimido) carbonate

Downstream raw materials:

5-([1,2]dithiolan-3-yl)pentanoic acid N-{3-[5-([1,2]dithiolan-3-yl)pentanoylamino]propyl}amide

C₁₈H₂₇O₃NS₂

(R)-1,2-dithiolane-3-pentanoic acid

2-(5-(1,2-dithiolan-3-yl)pentanamido)ethyl dihydrogen phosphate

Refernces

• 1、 Pramanik, Anup K.,Siddikuzzaman,Palanimuthu, Duraippandi,Somasundaram, Kumaravel,Samuelson, Ashoka G.. "Biotin Decorated Gold Nanoparticles for Targeted Delivery of a Smart-Linked Anticancer Active Copper Complex: In Vitro and in Vivo Studies". . p. 2874 - 2885. Retrieved 2016.
• 2、 Stvolinsky,Antonova,Kulikova,Lopachev,Abaimov,Al-Baidani,Lopacheva,Fedorova,Kaplun,Sorokoumova. "Lipoylcarnosine: Synthesis, Study of Physico-Chemical and Antioxidant Properties, Biological Activity". . p. 308 - 315. Retrieved 2018.
• 3、 Ramsey, Alexandra V.,Bischoff, Amanda J.,Francis, Matthew B.. "Enzyme Activated Gold Nanoparticles for Versatile Site-Selective Bioconjugation". . p. 7342 - 7350. Retrieved 2021.
• 4、 Shi, Lei,Jing, Chao,Ma, Wei,Li, Da-Wei,Halls, Jonathan E.,Marken, Frank,Long, Yi-Tao. "Plasmon resonance scattering spectroscopy at the single-nanoparticle level: Real-time monitoring of a click reaction". . p. 6011 - 6014. Retrieved 2013.
• 5、 Bolognesi, Maria Laura,Bergamini, Christian,Fato, Romana,Oiry, Jo?l,Vasseur, Jean-Jacques,Smietana, Michael. "Synthesis of new lipoic acid conjugates and evaluation of their free radical scavenging and neuroprotective activities". . p. 688 - 696. Retrieved 2014.
• 6、 Jin, Ho,Nam, Jutaek,Park, Joonhyuck,Jung, Sungho,Im, Kyuhyun,Hur, Jaehyun,Park, Jong-Jin,Kim, Jong-Min,Kim, Sungjee. "Strong polyelectrolyte quantum dot surface for stable bioconjugation and layer-by-layer assembly applications". . p. 1758 - 1760. Retrieved 2011.
• 7、 Berg, Keimpe J. van den,Feringa, Ben L.,Flapper, Jitte,Sieredzinska, Bianka,Zhang, Qi. "Photo-crosslinking polymers by dynamic covalent disulfide bonds". supporting information. p. 9838 - 9841. Retrieved 2021/10/08.