Page last updated: 2024-12-09

(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one, also known as **chalcone**, is an important organic compound that has been extensively studied for its potential applications in various fields. Let's break down its structure and significance.

**Structure and Properties:**

* **Chalcone** is a yellow crystalline solid with a characteristic aromatic odor.
* It consists of a **penta-1,4-dien-3-one** backbone, which is a five-carbon chain with alternating double and single bonds and a ketone group at the third carbon.
* Two **4-methoxyphenyl** groups (benzene rings with a methoxy group at the para position) are attached at the first and fifth carbons of the chain.
* The (1E,4E) designation indicates the configuration of the double bonds, meaning they are in a trans (E) configuration.

**Importance in Research:**

Chalcone is a versatile molecule with numerous applications in research, including:

* **Pharmacology:**
* **Anti-inflammatory and analgesic properties:** Chalcone and its derivatives have shown promise in treating inflammatory diseases like arthritis, and reducing pain.
* **Anti-cancer activity:** Chalcone analogs have exhibited activity against various cancer cell lines, demonstrating potential as anti-cancer drugs.
* **Antimicrobial activity:** Chalcones have shown effectiveness against bacteria, fungi, and viruses, suggesting potential use in antimicrobial therapies.
* **Antioxidant properties:** Chalcones can scavenge free radicals, protecting cells from oxidative damage and potentially preventing diseases like heart disease and cancer.

* **Materials Science:**
* **Organic electronics:** Chalcones can serve as building blocks for organic semiconductors used in solar cells, LEDs, and other electronic devices.
* **Liquid crystals:** Chalcone derivatives have been incorporated into liquid crystal displays due to their optical properties and ability to align in response to electric fields.

* **Agricultural Research:**
* **Pesticide and fungicide development:** Chalcone analogs have been investigated for their potential as natural pesticides and fungicides, offering a more environmentally friendly approach to pest control.

**Why is Chalcone Important for Research?**

Chalcone's importance stems from its unique combination of features:

* **Biological activity:** Its diverse biological properties, including anti-inflammatory, anti-cancer, and antimicrobial effects, make it a promising lead compound for drug discovery.
* **Structural versatility:** The chalcone scaffold can be easily modified by attaching different substituents to the phenyl rings, allowing for the synthesis of a wide range of derivatives with tailored properties.
* **Natural occurrence:** Chalcones are found in various plants, suggesting their potential for developing natural remedies and agrochemicals.

**In Summary:**

(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one, or chalcone, is a crucial molecule in research due to its biological activity, structural flexibility, and potential applications in pharmaceuticals, materials science, and agriculture.

Cross-References

ID SourceID
PubMed CID715840
CHEMBL ID584437
CHEBI ID183767
SCHEMBL ID2744098
SCHEMBL ID2744101

Synonyms (58)

Synonym
50764-85-7
bis(4-methoxybenzylidene)acetone
MEGXP0_001779
nsc-677239
1,4-pentadien-3-one, 1,5-bis(4-methoxyphenyl)-
nsc 401196
1,4-pentadien-3-one, 1,5-bis(p-methoxyphenyl)-
(1e,4e)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one
1,4-pentadien-3-one, 1,5-bis(4-methoxyphenyl)-, (1e,4e)-
nsc677239
nsc-401196
2051-07-2
STK325157
HMS1552C13
AKOS001325277
1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one
di-p-anisylideneacetone
CHEMBL584437 ,
go-y013
CHEBI:183767
37951-12-5
BBL002419
di-(4,4'-dimethoxy)-benzylidene-acetone
(1e,4e)-1,5-bis(4-methoxyphenyl)-3-penta-1,4-dienone
A816101
F0415-0075
dianisylidene acetone
1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one
AB01134828-03
SCHEMBL2744098
SCHEMBL2744101
(1e,4e)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one #
dianisylideneacetone
IOZVKDXPBWBUKY-LQIBPGRFSA-N
di(4-methoxybenzylidene)acetone
trans,trans-bis(4-methoxybenzylidene)acetone
trans,trans-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one
trans,trans-bis(4-methoxystyryl) ketone
B4467
trans,trans-bis(4-methoxybenzal)acetone
AS-67184
AS-69064
bdbm50488795
(1e,4e)-1,5-bis(4-methoxyphenyl)-1,4-pentadien-3-one
mfcd00014901
1,5-di(4-methoxyphenyl)penta-1,4-dien-3-one
Z234853558
NCGC00336197-01
1,5-bis-(4-methoxy-phenyl)-penta-1,4-dien-3-one
D89083
1,5-bis(p-methoxyphenyl)-1,4-pentadien-3-one
C1T5NW58W3 ,
go-y-013
A873973
1,5-bis-(4-methoxyphenyl)-3-pentadienone
unii-c1t5nw58w3
CS-W014550
DTXSID401347720
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
methoxybenzenesAny aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1415617Antifungal activity against fluconazole-resistant Candida tropicalis clinical isolate 087 in presence of 8 ug/ml fluconazole by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID1415618Antifungal activity against fluconazole-resistant Candida krusei clinical isolate 2159 in presence of 8 ug/ml fluconazole by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID1415616Antifungal activity against fluconazole-resistant Candida albicans clinical isolate 103 in presence of 8 ug/ml fluconazole by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID594784Cytotoxic activity against human HeLa cells after 24 to 48 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10
Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors.
AID664956Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID664955Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID458185Growth inhibition of human HCT116 cells after 48 hrs by MTS assay2010Bioorganic & medicinal chemistry, Feb, Volume: 18, Issue:3
Structure-activity relationship of C5-curcuminoids and synthesis of their molecular probes thereof.
AID593867Displacement of [125I]IMPY from amyloid beta (1 to 42) aggregate after 2 hrs by gamma counting2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for β-amyloid plaques.
AID1415613Antifungal activity against fluconazole-resistant Candida krusei clinical isolate 2159 by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID1415615Antifungal activity against fluconazole-resistant Candida tropicalis clinical isolate 087 by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID1415614Antifungal activity against fluconazole-resistant Candida albicans clinical isolate 103 by broth microdilution method2017MedChemComm, May-01, Volume: 8, Issue:5
Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant
AID594786Antiplasmodial activity against blood stage of chloroquine-sensitive Plasmodium falciparum 3D7 infected in human O positive erythrocytes after 48 hrs by SYBR green-I based fluorescence assay2011Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10
Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors.
AID664957Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID594785Antiplasmodial activity against blood stage of chloroquine-resistant Plasmodium falciparum isolate RKL9 infected in human O positive erythrocytes after 48 hrs by SYBR green I-based fluorescence assay2011Bioorganic & medicinal chemistry letters, May-15, Volume: 21, Issue:10
Dibenzylideneacetone analogues as novel Plasmodium falciparum inhibitors.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's8 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.36

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.36 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]