Dibenzylideneacetone

• CAT Number: M010385
• CAS Number: 538-58-9
• Molecular Formula: C17H14O
• Molecular Weight: 234.298
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one
• InChI: 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+
• InChIKey: WMKGGPCROCCUDY-PHEQNACWSA-N
• SMILES: C1=CC=C(C=C1)C=CC(=O)C=CC2=CC=CC=C2

Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.

Reference

1: Cui M, Ono M, Kimura H, Liu B, Saji H. Synthesis and structure-affinity
relationships of novel dibenzylideneacetone derivatives as probes for β-amyloid
plaques. J Med Chem. 2011 Apr 14;54(7):2225-40. doi: 10.1021/jm101404k. Epub 2011
Mar 21. PubMed PMID: 21417461.

2: Yang Y, Cui M, Jin B, Wang X, Li Z, Yu P, Jia J, Fu H, Jia H, Liu B.
(99m)Tc-labeled dibenzylideneacetone derivatives as potential SPECT probes for in
vivo imaging of β-amyloid plaque. Eur J Med Chem. 2013 Jun;64:90-8. doi:
10.1016/j.ejmech.2013.03.057. Epub 2013 Apr 6. PubMed PMID: 23644192.

3: Yu HJ, Shin JA, Nam JS, Kang BS, Cho SD. Apoptotic effect of
dibenzylideneacetone on oral cancer cells via modulation of specificity protein 1
and Bax. Oral Dis. 2013 Nov;19(8):767-74. doi: 10.1111/odi.12062. Epub 2013 Jan
11. PubMed PMID: 23305452.

4: Prasad S, Yadav VR, Ravindran J, Aggarwal BB. ROS and CHOP are critical for
dibenzylideneacetone to sensitize tumor cells to TRAIL through induction of death
receptors and downregulation of cell survival proteins. Cancer Res. 2011 Jan
15;71(2):538-49. doi: 10.1158/0008-5472.CAN-10-3121. Epub 2010 Dec 2. PubMed
PMID: 21127198; PubMed Central PMCID: PMC3022089.

5: Cao B, Wang Y, Ding K, Neamati N, Long YQ. Synthesis of the pyridinyl
analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen-Schmidt
condensation, displaying diverse biological activities as curcumin analogues. Org
Biomol Chem. 2012 Feb 14;10(6):1239-45. doi: 10.1039/c1ob06773g. Epub 2011 Dec
19. PubMed PMID: 22179573.

6: Li Z, Cui M, Zhang J, Dai J, Zhang X, Chen P, Jia H, Liu B. Novel 1⁸F-labeled
dibenzylideneacetone derivatives as potential positron emission tomography probes
for in vivo imaging of β-amyloid plaques. Eur J Med Chem. 2014 Sep 12;84:628-38.
doi: 10.1016/j.ejmech.2014.07.070. Epub 2014 Jul 21. PubMed PMID: 25063945.

7: Anand P, Sung B, Kunnumakkara AB, Rajasekharan KN, Aggarwal BB. Suppression of
pro-inflammatory and proliferative pathways by diferuloylmethane (curcumin) and
its analogues dibenzoylmethane, dibenzoylpropane, and dibenzylideneacetone: role
of Michael acceptors and Michael donors. Biochem Pharmacol. 2011 Dec
15;82(12):1901-9. doi: 10.1016/j.bcp.2011.09.001. Epub 2011 Sep 8. Retraction in:
Biochem Pharmacol. 2016 Feb 15;102:144. PubMed PMID: 21924245; PubMed Central
PMCID: PMC3216474.