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294381

Sigma-Aldrich

N,N′-(1,2-Dihydroxyethylene)bisacrylamide

97%

Synonym(s):

N,N′-Bisacryloyl-1,2-dihydroxy-1,2-ethylenediamine, DHEBA

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About This Item

Linear Formula:
[H2C=CHCONHCH(OH)-]2
CAS Number:
868-63-3
Molecular Weight:
200.19
Beilstein:
1941875
EC Number:
212-780-1
MDL number:
MFCD00008624
UNSPSC Code:
12162002
PubChem Substance ID:
24857712
NACRES:
NA.23
Pricing and availability is not currently available.

Quality Level

200

Assay

97%

form

solid

mp

156 °C (dec.) (lit.)

SMILES string

OC(NC(=O)C=C)C(O)NC(=O)C=C

InChI

1S/C8H12N2O4/c1-3-5(11)9-7(13)8(14)10-6(12)4-2/h3-4,7-8,13-14H,1-2H2,(H,9,11)(H,10,12)

InChI key

ZMLXKXHICXTSDM-UHFFFAOYSA-N

General description

N,N′-(1,2-Dihydroxyethylene)bisacrylamide, commonly referred to as DHEBA or bis-acrylamide. It is used as a crosslinking agent in various biomedical applications. Its structure includes two acrylamide groups linked by a dihydroxyethylene bridge, which enhances its reactivity and ability to form hydrogels. In the biomedical field, DHEBA is primarily utilized in the synthesis of hydrogels that can be used for drug delivery systems, tissue engineering scaffolds, and biosensors. The hydrophilic nature of the compound allows for the formation of hydrogels that can retain water and biological molecules, making them suitable for applications that require biocompatibility and bioactivity.[1][2][3]

Application

N,N′-(1,2-Dihydroxyethylene)bisacrylamide can be used as:
  • A crosslinker in the synthesis of hydrogel microparticles with a porous hydrogel structure. This porosity is essential for enhancing biomolecule accessibility and mass transport, which are critical for the performance of biosensing applications.
  • A cross-linking agent in the preparation of molecularly imprinted polymers, that can selectively bind to oxidized low-density lipoprotein (oxLDL). The cross-linking enhances the mechanical stability and structural integrity of the polymer matrix.
  • A cross-linking agent in the preparation of hydrogels or polymer matrices that support biological imaging applications.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000431142
0000431142
0000425994
0000425994
0000396476

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Gisela Giorgi et al.
Experimental physiology, 100(10), 1199-1216 (2015-06-06)
What is the central question of this study? The aim was to explore the role and hitherto unclear mechanisms of action of iron proteins in protecting the lung against the harmful effects of iron accumulation and the ability of pulmonary
Suticha Chunta et al.
Analytica chimica acta, 1116, 27-35 (2020-05-12)
Oxidized-low-density lipoprotein (oxLDL) is well-recognized as an actual patho-atherogenic lipoprotein: elevated serum concentration of oxLDL increases the risk for developing atherosclerosis, leading to coronary artery disease (CAD). Herein, we report an approach for sensing oxLDL directly in serum with molecularly
Suticha Chunta et al.
Talanta, 221, 121549-121549 (2020-10-21)
Very-low-density lipoprotein (VLDL) contributes to the buildup of atherosclerotic plaque in the arteries and can lead to coronary heart disease. In clinical laboratory testing, the cholesterol content of VLDL (VLDL-C) cannot be assessed directly by the enzymatic colorimetric assay as
Martin Zeilinger et al.
Sensors (Basel, Switzerland), 19(10) (2019-05-28)
Food standards and quality control are important means to ensure public health. In the last decade, melamine has become a rather notorious example of food adulteration: Spiking products with low-cost melamine in order to feign high amino acid content exploits
U Neumann et al.
Analytical biochemistry, 206(1), 1-5 (1992-10-01)
A simple and rapid method for the quantitation of proteins separated either by sodium dodecyl sulfate-electrophoresis or by isoelectric focusing in slab gels is presented. The method is based on the solubility of polyacrylamide gels crosslinked with N, N'-1, 2-dihydroxyethylenebisacrylamide
View All Related Papers

Questions

1–4 of 4 Questions  

  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/449/386/product-dating-information-mk.pdf

      Helpful?

  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

      Helpful?

  3. How can I make 2% dheba for my expansion microscopy protocol? It seems that  it doesn’t dissolve easily in water. 

    1 answer

    1. This product is not tested for solubility.

      A literature search yielded the following: "Cross-linking agent for polyacrylamide gel electrophoresis that produces a gel which is soluble in dilute periodic acid or dilute aqueous solutions of bases". This information is from 'Polyacrylamide gels with modified cross-linkages' (P B O'Connell and C J Brady, Analytical biochemistry, 76(l), undefined (1976-11-1))

      There is also a recommendation to incubate at 50 °C for 16 hours until solubilized (in Periodic acid).

      Helpful?

  4. Where do you store the powder form of DHEBA? Does it need to be desiccated after opening?

    1 answer

    1. Storage conditions are at ambient temperatures in accordance with section 7 of the Safety Data Sheet.
      https://www.sigmaaldrich.com/sds/aldrich/294381?userType=new_user
      This product is not indicated as hygroscopic or moisture sensitive. Desiccator storage is not a requirement, but the reagent should be stored tightly closed under dry conditions.

      Helpful?

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