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A0638

Adipic acid dihydrazide

≥98% (titration)

Synonym(s):

Hexanedihydrazide

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25 g

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100 g
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$595.00

About This Item

Linear Formula:
NH2NHCO(CH2)4CONHNH2
CAS Number:
1071-93-8
Molecular Weight:
174.20
UNSPSC Code:
12352127
NACRES:
NA.25
PubChem Substance ID:
24890442
EC Number:
213-999-5
Beilstein/REAXYS Number:
973863
MDL number:
MFCD00007614

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Quality Level

300

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

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.

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Adipic acid dihydrazide ≥98% (titration)

Sigma-Aldrich

A0638

Adipic acid dihydrazide

Adipic acid 99%

Sigma-Aldrich

A26357

Adipic acid

Adipic acid dihydrazide–Agarose saline suspension

Sigma-Aldrich

A0802

Adipic acid dihydrazide–Agarose

3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) powder

Sigma-Aldrich

D3669

3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester)

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

−20°C

reaction suitability

reagent type: cross-linking reagent

reaction suitability

-

reaction suitability

-

reaction suitability

reagent type: cross-linking reagent

form

powder

form

solid

form

saline suspension

form

powder

assay

≥98% (titration)

assay

99%

assay

-

assay

-

solubility

H2O: 100 mg/mL

solubility

H2O: soluble 23 g/L at 25 °C

solubility

-

solubility

chloroform: 50 mg/mL, DMF: soluble, acetone: soluble

mp

180-182 °C (lit.)

mp

151-154 °C (lit.)

mp

-

mp

-

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pictograms

Environment
GHS09

hcodes

H411

Hazard Classifications

Aquatic Chronic 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

302.0 °F - closed cup

flash_point_c

150 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000552789
0000554203
0000536920
0000536920
0000554203

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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
View All Related Papers

Global Trade Item Number

SKUGTIN
A0638-100G04061835326204
A0638-25G04061833334201

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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