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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/REAXYS Number:
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.)

functional group

amide
hydroxyl

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.[1][2]

Application

(+)-N,N′-Diallyltartramide can be used as a crosslinking agent:
  • In the polymerization of soluble polyacrylamide gels for electrophoresis applications.[3]
  • In the preparation of hydrogel containing cellulose, which is used as a component of an actuator capable of controlled soil irrigation.[4]
  • In the synthesis of dendronized polymers, which are used to prepare hydrogels containing ciprofloxacin for controlled drug release.[5]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBC2848V
58396LM
40396DM
01596CK
07696AM

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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
Novel poly (NIPA-co-AAc) functional hydrogels with potential application in drug controlled release.
Cuggino JC, et al.
Molecular Pharmaceutics, 11(7), 2239-2249 (2014)
Towards new formulations for polyacrylamide matrices, as investigated by capillary zone electrophoresis
Righetti PG, et al.
Journal of Chromatography A, 638(2), 165-178 (1993)
L Orbán et al.
Electrophoresis, 12(4), 241-246 (1991-04-01)
The Ferguson plot in polyacrylamide gel electrophoresis (PAGE)(15%CDATD, moving boundary electrophoresis buffer system operative at pH 8.9, 4 degrees C, 8 mA/cm2 of gel) of DNA fragments up to 9.4 kb in size was found to exhibit a linear segment
Liquid scintillation counting of polyacrylamide gels crosslinked with N,N'-methylene-bis-acrylamide and N,N'-diallyltartardiamide.
P A Moore
Analytical biochemistry, 108(1), 151-155 (1980-10-01)
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