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156868

Sigma-Aldrich

(+)-N,N′-Diallyltartramide

≥99%

Synonym(s):

N,N′-Diallyl L-tartardiamide, N,N′-Diallyltartramide, DATD

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About This Item

Linear Formula:
[CH(OH)CONHCH2CH=CH2]2
CAS Number:
58477-85-3
Molecular Weight:
228.25
Beilstein:
1712934
EC Number:
261-277-3
MDL number:
MFCD00008640
UNSPSC Code:
12352002
PubChem Substance ID:
24849641
NACRES:
NA.22

Assay

≥99%

optical activity

[α]20/D +108°, c = 2.4 in H2O

mp

186-188 °C (lit.)

SMILES string

O[C@H]([C@@H](O)C(=O)NCC=C)C(=O)NCC=C

InChI

1S/C10H16N2O4/c1-3-5-11-9(15)7(13)8(14)10(16)12-6-4-2/h3-4,7-8,13-14H,1-2,5-6H2,(H,11,15)(H,12,16)/t7-,8-/m1/s1

InChI key

ZRKLEAHGBNDKHM-HTQZYQBOSA-N

Related Categories

General description

(+)-N,N′-Diallyltartramide can be used as a cross-linking agent during the preparation of hydrogels.

Application

(+)-N,N′-Diallyltartramide can be used as a crosslinking agent:
  • In the polymerization of soluble polyacrylamide gels for electrophoresis applications.
  • In the preparation of hydrogel containing cellulose, which is used as a component of an actuator capable of controlled soil irrigation.
  • In the synthesis of dendronized polymers, which are used to prepare hydrogels containing ciprofloxacin for controlled drug release.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A novel gel based on an ionic complex from a dendronized polymer and ciprofloxacin: Evaluation of its use for controlled topical drug release
Garcia MC, et al.
Materials Science and Engineering, C, 69(2), 236-246 (2016)
Electrophoresis and electrofocusing on polyacrylamide gel in the study of native macromolecules.
A Chrambach
Molecular and cellular biochemistry, 29(1), 23-46 (1980-01-16)
W R Springer
Analytical biochemistry, 195(1), 172-176 (1991-05-15)
A method is described in which individual proteins labeled with weak beta-emitting radionuclides, separated by polyacrylamide gel electrophoresis, and stained with silver are released from the gel by the use of the periodate soluble cross-linking agent N,N'-dialyltartardiamide. The radioactivity can
Post-synthesis modification of hydrogels. Total and partial rupture of crosslinks: Formation of aldehyde groups and re-crosslinking of cleaved hydrogels.
Wolfel A, et al.
Polymer (2017)
Roberto Sánchez-Sánchez et al.
Antimicrobial agents and chemotherapy, 63(7) (2019-05-08)
Previous studies on drug efficacy showed low protection against abortion and vertical transmission of Toxoplasma gondii in pregnant sheep. Bumped kinase inhibitors (BKIs), which are ATP-competitive inhibitors of calcium-dependent protein kinase 1 (CDPK1), were shown to be highly efficacious against
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