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MedKoo Cat#: 591711 | Name: Dibenzalacetone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dibenzylideneacetone is a synthetic curcumin analog leads to apoptotic cell death in Leishmania donovani.

Chemical Structure

Dibenzalacetone
CAS#538-58-9

Theoretical Analysis

MedKoo Cat#: 591711

Name: Dibenzalacetone

CAS#: 538-58-9

Chemical Formula: C17H14O

Exact Mass: 234.1045

Molecular Weight: 234.30

Elemental Analysis: C, 87.15; H, 6.02; O, 6.83

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 350.00 2 Weeks
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Related CAS #
No Data
Synonym
Dibenzalacetone; Dibenzalacetone; Dibenzylidene acetone; Distyryl ketone; NSC623642; NSC 623642; NSC-623642;
IUPAC/Chemical Name
1,4-Pentadien-3-one, 1,5-diphenyl-
InChi Key
WMKGGPCROCCUDY-PHEQNACWSA-N
InChi Code
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+
SMILES Code
O=C(/C=C/C1=CC=CC=C1)/C=C/C2=CC=CC=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 234.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chauhan IS, SubbaRao G, Shankar J, Chauhan LKS, Kapadia GJ, Singh N. Chemoprevention of Leishmaniasis: In vitro antiparasitic activity of dibenzalacetone, a synthetic curcumin analog leads to apoptotic cell death in Leishmania donovani. Parasitol Int. 2018 Jun 15. pii: S1383-5769(18)30035-7. doi: 10.1016/j.parint.2018.06.004. [Epub ahead of print] PubMed PMID: 29913255. 2: Dohutia C, Chetia D, Gogoi K, Sarma K. Design, in silico and in vitro evaluation of curcumin analogues against Plasmodium falciparum. Exp Parasitol. 2017 Apr;175:51-58. doi: 10.1016/j.exppara.2017.02.006. Epub 2017 Feb 7. PubMed PMID: 28188731. 3: El-Ablack FZ, Metwally MA, Khalil AM. Michael Reaction of 3-aAryl-2,4-Dicarboethoxy-5-Hydroxy-5-Methylcyclohexanones. Org Chem Int. 2015 Sep 1;5(5):311-323. PubMed PMID: 26689538; PubMed Central PMCID: PMC4681101. 4: Sedighi V, Azerang P, Sardari S. Antimycobacterial evaluation of novel [4,5-dihydro-1H-pyrazole-1-carbonyl]pyridine derivatives synthesized by microwave-mediated Michael addition. Drug Test Anal. 2015 Jun;7(6):550-4. doi: 10.1002/dta.1712. Epub 2014 Sep 14. PubMed PMID: 25219796. 5: Cyriac J, Paulose J, George M, Ramesh M, Srinivas R, Giblin D, Gross ML. The role of methoxy group in the Nazarov cyclization of 1,5-bis-(2-methoxyphenyl)-1,4-pentadien-3-one in the gas phase and condensed phase. J Am Soc Mass Spectrom. 2014 Mar;25(3):398-409. doi: 10.1007/s13361-013-0785-8. Epub 2014 Jan 11. PubMed PMID: 24415061; PubMed Central PMCID: PMC3930160. 6: Ud Din Z, Fill TP, de Assis FF, Lazarin-Bidóia D, Kaplum V, Garcia FP, Nakamura CV, de Oliveira KT, Rodrigues-Filho E. Unsymmetrical 1,5-diaryl-3-oxo-1,4-pentadienyls and their evaluation as antiparasitic agents. Bioorg Med Chem. 2014 Feb 1;22(3):1121-7. doi: 10.1016/j.bmc.2013.12.020. Epub 2013 Dec 23. PubMed PMID: 24398381. 7: Lee HE, Choi ES, Jung JY, You MJ, Kim LH, Cho SD. Inhibition of specificity protein 1 by dibenzylideneacetone, a curcumin analogue, induces apoptosis in mucoepidermoid carcinomas and tumor xenografts through Bim and truncated Bid. Oral Oncol. 2014 Mar;50(3):189-95. doi: 10.1016/j.oraloncology.2013.11.006. Epub 2013 Dec 3. PubMed PMID: 24309154. 8: Kapdi AR, Whitwood AC, Williamson DC, Lynam JM, Burns MJ, Williams TJ, Reay AJ, Holmes J, Fairlamb IJ. The elusive structure of Pd2(dba)3. Examination by isotopic labeling, NMR spectroscopy, and X-ray diffraction analysis: synthesis and characterization of Pd2(dba-Z)3 complexes. J Am Chem Soc. 2013 Jun 5;135(22):8388-99. doi: 10.1021/ja403259c. Epub 2013 May 23. PubMed PMID: 23701049. 9: Jarvis AG, Sehnal PE, Bajwa SE, Whitwood AC, Zhang X, Cheung MS, Lin Z, Fairlamb IJ. A remarkable cis- and trans-spanning dibenzylidene acetone diphosphine chelating ligand (dbaphos). Chemistry. 2013 May 3;19(19):6034-43. doi: 10.1002/chem.201203691. Epub 2013 Mar 11. PubMed PMID: 23495201. 10: 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. 11: Brinkevich SD, Ostrovskaya NI, Parkhach ME, Samovich SN, Shadyro OI. Effects of curcumin and related compounds on processes involving α-hydroxyethyl radicals. Free Radic Res. 2012 Mar;46(3):295-302. doi: 10.3109/10715762.2011.653966. Epub 2012 Feb 6. PubMed PMID: 22239556. 12: 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. 13: 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. 14: Jarvis AG, Whitwood AC, Fairlamb IJ. Cu(I) complexes containing a multidentate and conformationally flexible dibenzylidene acetone ligand (dbathiophos): application in catalytic alkene cyclopropanation. Dalton Trans. 2011 Apr 14;40(14):3695-702. doi: 10.1039/c0dt01612h. Epub 2011 Mar 2. PubMed PMID: 21369564. 15: 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. 16: Fairlamb IJ. pi-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(II). Org Biomol Chem. 2008 Oct 21;6(20):3645-56. doi: 10.1039/b811772a. Epub 2008 Sep 9. Review. PubMed PMID: 18843391. 17: Fairlamb IJ, O'Brien CT, Lin Z, Lam KC. Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone. Org Biomol Chem. 2006 Apr 7;4(7):1213-6. Epub 2006 Feb 21. PubMed PMID: 16557307. 18: Fairlamb IJ, Kapdi AR, Lee AF. Eta2-dba complexes of Pd(0): the substituent effect in Suzuki-Miyaura coupling. Org Lett. 2004 Nov 25;6(24):4435-8. PubMed PMID: 15548044. 19: Stambuli JP, Incarvito CD, Bühl M, Hartwig JF. Synthesis, structure, theoretical studies, and Ligand exchange reactions of monomeric, T-shaped arylpalladium(II) halide complexes with an additional, weak agostic interaction. J Am Chem Soc. 2004 Feb 4;126(4):1184-94. PubMed PMID: 14746489. 20: Scheeren CW, Machado G, Dupont J, Fichtner PF, Texeira SR. Nanoscale Pt(0) particles prepared in imidazolium room temperature ionic liquids: synthesis from an organometallic precursor, characterization, and catalytic properties in hydrogenation reactions. Inorg Chem. 2003 Jul 28;42(15):4738-42. PubMed PMID: 12870966.