Cas no 40846-94-4 (N-Hydroxysuccinimidyl Lipoate)

N-Hydroxysuccinimidyl Lipoate (NHS-Lipoate) is a reactive ester derivative of lipoic acid, widely utilized in bioconjugation and crosslinking applications. Its key advantage lies in the succinimidyl ester group, which enables efficient coupling with primary amines under mild conditions, forming stable amide bonds. The lipoate moiety provides additional functionality, including antioxidant properties and the ability to participate in redox reactions. This compound is particularly valuable in protein modification, surface functionalization, and the synthesis of biomolecular probes. Its solubility in organic solvents and controlled reactivity make it a versatile reagent for site-specific labeling and immobilization strategies in biochemical and biotechnological research.
N-Hydroxysuccinimidyl Lipoate structure
N-Hydroxysuccinimidyl Lipoate structure
Product Name:N-Hydroxysuccinimidyl Lipoate
CAS No:40846-94-4
MF:C12H17NO4S2
MW:303.397680997849
MDL:MFCD09028032
CID:2633901
PubChem ID:53259805
Update Time:2025-05-19

N-Hydroxysuccinimidyl Lipoate Chemical and Physical Properties

Names and Identifiers

    • alpha-lipoic acid-NHS
    • (2,5-dioxopyrrolidin-1-yl) 5-(dithiolan-3-yl)pentanoate
    • 2,5-Dioxopyrrolidin-1-yl 5-(1,2-Dithiolan-3-yl)pentanoate
    • 5-(1,2-Dithiolan-3-yl)pentanic Acid 2,5-Dioxopyrrolidin-1-yl Ester
    • Thioctic Acid N-Hydroxysuccinimide Ester
    • LCZC1182
    • C70383
    • DL-alpha-Lipoic acid NHS
    • ALPHA-LIPOICACID-NHS
    • DA-68905
    • DL-f inverted question mark-Lipoic Acid-NHS
    • 40846-94-4
    • AKOS027472998
    • 2,5-Pyrrolidinedione, 1-[[5-(1,2-dithiolan-3-yl)-1-oxopentyl]oxy]-
    • STL476790
    • DL-
    • DL-Alpha-lipoicacid-nhs
    • L0345
    • 1-{[5-(1,2-dithiolan-3-yl)pentanoyl]oxy}pyrrolidine-2,5-dione
    • AS-72152
    • SCHEMBL2633200
    • BP-22515
    • A1-03868
    • DL-Alpha-lipoic acid-nhs
    • MFCD09028032
    • CS-0115098
    • HY-141336
    • A-Lipoic Acid-NHS
    • DTXSID40693233
    • FL177264
    • DL-a-Lipoic acid NHS
    • DL-a-Lipoic Acid-NHS
    • N-Hydroxysuccinimidyl Lipoate
    • MDL: MFCD09028032
    • Inchi: 1S/C12H17NO4S2/c14-10-5-6-11(15)13(10)17-12(16)4-2-1-3-9-7-8-18-19-9/h9H,1-8H2
    • InChI Key: WBCUIGFYTHUQHZ-UHFFFAOYSA-N
    • SMILES: S1C(CCS1)CCCCC(=O)ON1C(CCC1=O)=O

Computed Properties

  • Exact Mass: 303.06
  • Monoisotopic Mass: 303.06
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 7
  • Complexity: 359
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 114A^2
  • XLogP3: 1.1

Experimental Properties

  • Density: 1.36±0.1(20.0000℃)
  • Melting Point: 93.0 to 97.0 deg-C

N-Hydroxysuccinimidyl Lipoate Security Information

  • Storage Condition:-20°C

N-Hydroxysuccinimidyl Lipoate Customs Data

  • HS CODE:29349990

N-Hydroxysuccinimidyl Lipoate Pricemore >>

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Additional information on N-Hydroxysuccinimidyl Lipoate

Recent Advances in N-Hydroxysuccinimidyl Lipoate (CAS 40846-94-4) Research: A Comprehensive Review

N-Hydroxysuccinimidyl Lipoate (NHS-Lipoate, CAS 40846-94-4) has emerged as a critical reagent in bioconjugation and drug delivery systems due to its unique chemical properties. This compound, which combines the lipoic acid moiety with an N-hydroxysuccinimide (NHS) ester, enables efficient covalent coupling of biomolecules such as proteins, peptides, and antibodies. Recent studies have highlighted its applications in targeted drug delivery, nanotechnology, and metabolic research, making it a focal point in chemical biology and pharmaceutical sciences.

A 2023 study published in Bioconjugate Chemistry demonstrated the use of NHS-Lipoate in the development of redox-responsive drug delivery systems. The researchers utilized the disulfide bond in lipoic acid to create stimuli-sensitive nanocarriers that release therapeutic payloads in reducing environments, such as tumor tissues. This approach significantly improved the specificity and efficacy of chemotherapy agents, reducing off-target effects. The study also emphasized the stability of NHS-Lipoate under physiological conditions, which is crucial for in vivo applications.

In another breakthrough, a team from MIT reported the application of NHS-Lipoate in protein labeling and imaging (Nature Methods, 2024). By conjugating fluorescent probes to antibodies via NHS-Lipoate, they achieved high-resolution imaging of intracellular targets with minimal background noise. The researchers attributed this success to the compound's rapid reaction kinetics and compatibility with aqueous buffers, which are essential for live-cell imaging. This method opens new avenues for studying dynamic biological processes at the molecular level.

Recent advancements in metabolic engineering have also leveraged NHS-Lipoate for enzyme immobilization. A 2024 paper in ACS Catalysis described its use in creating stable biocatalysts for industrial applications. The lipoic acid moiety provided a robust anchor for enzymes on solid supports, while the NHS ester facilitated covalent attachment. This dual functionality resulted in biocatalysts with enhanced operational stability and reusability, addressing key challenges in green chemistry and sustainable manufacturing.

Despite these promising developments, challenges remain in optimizing the pharmacokinetics of NHS-Lipoate-conjugated therapeutics. A review in Advanced Drug Delivery Reviews (2023) highlighted the need for further studies on the in vivo fate of these conjugates, particularly their clearance mechanisms and potential immunogenicity. Future research directions may focus on engineering derivatives of NHS-Lipoate with improved biodistribution profiles while retaining its advantageous reactivity.

In conclusion, NHS-Lipoate (CAS 40846-94-4) continues to play a pivotal role in advancing bioconjugation strategies and therapeutic delivery systems. Its unique chemical properties bridge the gap between synthetic chemistry and biological applications, offering versatile solutions across multiple domains of chemical biology and medicine. As research progresses, we anticipate novel applications emerging in areas such as theranostics, personalized medicine, and biomaterials science.

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