2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione CAS#: 19956-53-7

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2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione

Basic information Safety Supplier Related

2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione Basic information

Product Name:

2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione

Synonyms:

2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione
Lucidone
4-Cyclopentene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-4-methoxy-, (2Z)-
(2E)-2-[(2E)-1-Hydroxy-3-phenyl-2-propen-1-ylidene]-4-methoxy-4-cyclopentene-1,3-dione

CAS:

19956-53-7

MF:

C15H12O4

MW:

256.25

Mol File:

19956-53-7.mol

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2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione Chemical Properties

Melting point:: 166.5-168.5 °C
Boiling point:: 489.6±45.0 °C(Predicted)
Density: 1.30±0.1 g/cm3(Predicted)
pka: 4.50±1.00(Predicted)

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2-[(1Z,2E)-1-Hydroxy-3-phenyl-2-propenylidene]-4-methoxy-4-cyclopentene-1,3-dione Usage And Synthesis

Uses

Lucidone, an anti-inflammatory agent that can be isolated from the fruit of Lindera erythrocarpa Makino. Lucidone inhibits LPS-induced NO and PGE2 production in RAW 264.7 mouse macrophages. Lucidone also decreases TNF-α secretion, iNOS and COX-2 expression. Lucidone prevents NF-κB translocation and inhibits JNK and p38MAPK signals. Lucidone also has inhibitory activity against Dengue virus (DENV) (EC50=25 μM)[1][2].

Definition

ChEBI: Lucidone is an olefinic compound. It is functionally related to a cinnamic acid.

in vivo

Lucidone (1 mg/kg; intracranial injection; 3 times for 1 week) significantly increases the survival rate and body weight of DENV-infected mice^[2].

Animal Model:	DENV-infected ICR mice^[2]
Dosage:	0.4 mg/kg, 1 mg/kg
Administration:	Intracranial injection; 3 times dose at day 2, 4, 6 after DENV infection
Result:	Increased the survival rate and body weight of DENV-infected mice on day 7.

IC 50

p38 MAPK; JNK; p50; p65; COX-2; NF-κB; iNOS; IKK

References

[1] Senthil Kumar KJ, et aL. Lucidone inhibits iNOS and COX-2 expression in LPS-induced RAW 264.7 murine macrophage cells via NF-kappaB and MAPKs signaling pathways. Planta Med. 2009 Apr;75(5):494-500. DOI:10.1055/s-0029-1185309
[2] Chen WC, et al. Lucidone suppresses dengue viral replication through the induction of heme oxygenase-1. Virulence. 2018 Jan 1;9(1):588-603. DOI:10.1080/21505594.2017.1421893

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