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A0638

Sigma-Aldrich

Adipic acid dihydrazide

≥98% (titration)

Synonyme(s) :

Hexanedihydrazide

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About This Item

Formule linéaire :
NH2NHCO(CH2)4CONHNH2
Numéro CAS:
Poids moléculaire :
174.20
Numéro Beilstein :
973863
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352127
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Niveau de qualité

Pureté

≥98% (titration)

Forme

powder

Pertinence de la réaction

reagent type: cross-linking reagent

Pf

180-182 °C (lit.)

Solubilité

H2O: 100 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

NNC(=O)CCCCC(=O)NN

InChI

1S/C6H14N4O2/c7-9-5(11)3-1-2-4-6(12)10-8/h1-4,7-8H2,(H,9,11)(H,10,12)

Clé InChI

IBVAQQYNSHJXBV-UHFFFAOYSA-N

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Description générale

Adipic acid dihydrazide is a homobifunctional cross-linking reagent that is specific for aldehydes. This results in relatively stable hydrazone linkages. Adipic acid dihydrazide is generally used in the linking of glycoproteins, like antibodies, in a site-specific fashion following periodate oxidation. Oxidation and coupling may be performed at pH 5.0 due to the low pKa of the hydrazide which avoids competition by primary amines.

Application

Adipic acid dihydrazide has been used:
  • in the preparation of reactive premix to synthesize the porous biomaterial
  • for the crosslinking of methacrylated chondroitin sulfate (MA-CS) coating using carbodiimide-based chemistry for the production and characterization of methacrylated chondroitin sulfate magnetic nanoparticles (MA-CS MNPs)
  • for the covalent labeling of rhamnolipids, pyochelin, and vancomycin with Abberior STARNHS ester dye

Actions biochimiques/physiologiques

Adipic acid dihydrazide (ADH) is a low molecular weight compound that comprises a hydrazide group at each end. This leads to the supply of extra adsorption sites for heavy metals that maintain or elevate the adsorption capacities of the cross-linked adsorbents. ADH is used as a crosslinker in various fields, like making mechanical latexes films and injectable oxidized hyaluronic acid hydrogel.

Autres remarques

Note that the hydrazone bond may be stabilized by selective reduction using, for example, sodium cyanoborohydride.

Pictogrammes

Environment

Mentions de danger

Conseils de prudence

Classification des risques

Aquatic Chronic 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

302.0 °F - closed cup

Point d'éclair (°C)

150 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

Bartosz Gerard Gdaniec et al.
iScience, 25(1), 103669-103669 (2022-01-15)
Efficient delivery of toxic compounds to bacterial competitors is essential during interspecies microbial warfare. Rhamnolipids (RLPs) are glycolipids produced by Pseudomonas and Burkholderia species involved in solubilization and uptake of environmental aliphatic hydrocarbons and perform as biosurfactants for swarming motility.
Tulsidas G Shrivastav et al.
Journal of immunoassay & immunochemistry, 33(1), 1-17 (2011-12-21)
The introduction of spacers in coating steroid antigen or enzyme conjugates or immunogen is known to exert an influence on the sensitivity of steroid enzyme immunoassays. We have introduced different homobifunctional spacers having varying atomic length (3 to 10) between
U Heimgartner et al.
The Biochemical journal, 267(3), 585-591 (1990-05-01)
After periodate oxidation and incubation with a dihydrazide, cross-linking of the two heavy chains of immunoglobulins G from several species proceeds specifically through their oligosaccharides. We have used malonic acid dihydrazide, adipic acid dihydrazide and dithiodipropionic acid dihydrazide. The last
Lin-Song Li et al.
Pharmaceuticals (Basel, Switzerland), 14(2) (2021-02-03)
Functionalized gold nanoparticles (AuNPs) have been successfully used in many fields as a result of having low cytotoxicity, good biocompatibility, excellent optical properties, and their ability to target cancer cells. Here, we synthesized AuNP carriers that were modified by hyaluronic
Xuefeng Yang et al.
Carbohydrate polymers, 256, 117574-117574 (2021-01-24)
To meet the demands of various therapeutic tasks, injectable hydrogels with tunable mechanical properties and degradability are highly desired. Herein, we developed an injectable chitin hydrogel system with well-manipulated mechanical properties and degradability through dynamic acylhydrazone crosslinking catalyzed by 4-amino-DL-phenylalanine

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