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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
Pricing and availability is not currently available.

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

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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 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
STBC2848V
58396LM
40396DM
01596CK
07696AM

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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)
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)
E C Hahn et al.
Journal of virological methods, 15(1), 41-52 (1987-01-01)
The behavior of proteins on acrylamide gels cross-linked with low concentrations of N,N'-diallyltartardiamide (DATD) has been studied from a theoretical and practical point of view. Modifications in methodology and a technique for calculation of apparent molecular weights (MWs) allowed accurate
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
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