A0638
Adipic acid dihydrazide
≥98% (titration)
Sinónimos:
Hexanedihydrazide
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About This Item
Fórmula lineal:
NH2NHCO(CH2)4CONHNH2
Número de CAS:
Peso molecular:
174.20
Beilstein/REAXYS Number:
973863
EC Number:
MDL number:
UNSPSC Code:
12352127
PubChem Substance ID:
NACRES:
NA.25
Productos recomendados
Quality Level
assay
≥98% (titration)
form
powder
reaction suitability
reagent type: cross-linking reagent
mp
180-182 °C (lit.)
solubility
H2O: 100 mg/mL
storage temp.
−20°C
SMILES string
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)
InChI key
IBVAQQYNSHJXBV-UHFFFAOYSA-N
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General description
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
Biochem/physiol Actions
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.
Other Notes
Note that the hydrazone bond may be stabilized by selective reduction using, for example, sodium cyanoborohydride.
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 2
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
302.0 °F - closed cup
flash_point_c
150 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
Certificados de análisis (COA)
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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
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