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Sigma-Aldrich

trans,trans-Dibenzylideneacetone

98%

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Synonym(s):
1,5-Diphenyl-1,4-pentadien-3-one, trans,trans-1,5-Diphenyl-1,4-pentadien-3-one
Linear Formula:
C6H5CH=CHCOCH=CHC6H5
CAS Number:
35225-79-7
Molecular Weight:
234.29
MDL number:
MFCD00004790
PubChem Substance ID:
24854806
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

104-107 °C (lit.)

solubility

acetone: soluble(lit.)
alcohol: slightly soluble(lit.)
chloroform: soluble(lit.)
diethyl ether: slightly soluble(lit.)
water: insoluble(lit.)

SMILES string

O=C(\C=C\c1ccccc1)/C=C/c2ccccc2

InChI

1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H/b13-11+,14-12+

InChI key

WMKGGPCROCCUDY-PHEQNACWSA-N

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Application

trans,trans-Dibenzylideneacetone was used as an additive in the copper-catalyzed N-arylation of imidazoles.
Reactant involved in:
  • Nazarov-like cyclization
  • Transfer hydrogenation
  • Lewis acid mediated condensation
  • Hetero-Diels-Alder reactions
  • Asymmetric 1,4-addition reactions
  • Michael addition reactions

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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Kiyomori A, et al.
Tetrahedron Letters, 40(14), 2657-2660 null
Regina Appiah-Opong et al.
European journal of medicinal chemistry, 43(8), 1621-1631 (2008-02-06)
Inhibition of cytochrome P450 (CYP) is a major cause of drug-drug interactions. In this work, inhibitory potentials of 33 curcumin analogues, i.e. 2,6-dibenzylidenecyclohexanone (A series), 2,5-dibenzylidenecyclopentanone (B series) and 1,4-pentadiene-3-one (C series) substituted analogues of curcumin towards recombinant human CYP1A2
Rahul Balasaheb Aher et al.
Bioorganic & medicinal chemistry letters, 21(10), 3034-3036 (2011-04-16)
A series of dibenzylideneacetones (A1-A12) and some of their pyrazolines (B1-B4) were synthesized and evaluated in vitro for blood stage antiplasmodial properties in Plasmodium falciparum culture using SYBR-green-I fluorescence assay. The compound (1E, 4E)-1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (A9) was found to be the
D Batovska et al.
European journal of medicinal chemistry, 42(1), 87-92 (2006-09-30)
A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with
Mengchao Cui et al.
Journal of medicinal chemistry, 54(7), 2225-2240 (2011-03-23)
A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward Aβ(1-42) aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position

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