ChemicalBook CAS DataBase List 1775-97-9

1775-97-9

Name	4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
CAS	1775-97-9
Molecular Formula	C17H16O4
MDL Number	MFCD00075877
Molecular Weight	284.31
MOL File	1775-97-9.mol

Synonyms

FlavoringB Flavokavin B FLAVOKAWIN B FLAVOKAWAIN B Flavokavain B FLAVOKAVAIN B(P) CARDAMONIN-4'-METHYL ETHER 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE 2'-Hydroxy-4',6'-Dimethoxychalcone DIMETHOXY-2'-HYDROXYCHALCONE, 4',6'- (E)-2'-Hydroxy-4',6'-dimethoxychalcone (E)-1-(2-Hydroxy-4,6-dimethoxy-phenyl)-3-phenyl- 4',6'-Dimethoxy-2'-hydroxychalcone (Flavokawain B) (E)-1-(2-HYDROXY-4,6-DIMETHOXY-PHENYL)-3-PHENYL-PROPENONE 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one) (E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one 2-Propen-1-one,1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-

Chemical Properties

Melting point	85-87°C
Boiling point	500.1±50.0 °C(Predicted)
density	1.203±0.06 g/cm3(Predicted)
storage temp.	-20°C Freezer
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	6.84±0.40(Predicted)
color	Yellow to Dark Yellow
Major Application	food and beverages
InChI	1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+
InChIKey	QKQLSQLKXBHUSO-CMDGGOBGSA-N
SMILES	O(C)c1c(c(cc(c1)OC)O)C(=O)\C=C\c2ccccc2
LogP	4.206 (est)
CAS DataBase Reference	1775-97-9(CAS DataBase Reference)

Safety Data

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Description

Flavokawain B is a natural chalcone first isolated from extracts of kava roots. It induces apoptosis in androgen receptor-negative, hormone-refractory prostate cancer cell lines (IC₅₀s = 32, 48, 6.2, and 3.9 μM for LAPC4, LNCaP, PC-3, and DU145 cells, respectively, treated for 48 hours), with increased expression of the proapoptotic protein Bim. Flavokawain B increases Bim expression and inhibits growth of DU145 xenografts in mice. It also increases Bim expression, promotes apoptosis, and induces cell cycle arrest in uterine leiomyosarcoma cells. However, flavokawain B is hepatotoxic, triggering oxidative stress, inhibiting NF-κB signaling, and activating MAPK pathways, culminating in HepG2 and L-02 cell death (LD₅₀s = 15 and 32 μM, respectively).

Chemical Properties

Pale yellow powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Piper methysticum Forst.

Uses

Flavokavain B is a secondary metabolite of the kava plant (Piper methysticum Forst. f., Piperaceae, which has anticancer properties and demonstrated oral efficacy in murine cancer models. ?Futhermore, it also has suspected roles in rare cases of kava-induced hepatotoxicity. In addition, it is a potential candidate for the development of novel antifungal phytotherapic products.

Definition

ChEBI: Flavokawain B is a member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2' and methoxy groups at positions 4' and 6'. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities. It has a role as a metabolite, an antileishmanial agent, an anti-inflammatory agent, an apoptosis inducer and an antineoplastic agent. It is a member of chalcones, a dimethoxybenzene and a member of phenols. It is functionally related to a trans-chalcone.

in vivo

Flavokawain B (1-2.5 μg/mL, 24 h) suppresses angiogenesis in a zebrafish model^[1].
Flavokawain B (50-200 mg/kg, i.p.) shows anti-inflammatory activities in LPS-induced mice^[4].
Flavokawain B (0.35-0.75 mg/kg, i.p., every 2 days, 27 days) significantly inhibits in vivo growth of human KB cell-derived tumor xenografts in nude mice^[5].
Flavokawain B (20-40 mg/kg, p.o., 7 days) inhibits NF-κB inflammatory signaling pathway activation in colitis mice by targeting TLR2^[10].
Flavokawain B (25 mg/kg, p.o., daily for a week) induces GSH-sensitive oxidative stress in mice through modulation of IKK/NF-κB and MAPK signaling pathways^[11].
Flavokawain B (10-20 mg/kg, i.g., 3 consecutive days) alleviates LPS-induced acute lung injury in mice via targeting myeloid differentiation factor 2^[12].
Flavokawain B (25 mg/kg, i.p., twice-a-week for 2 weeks) in combination with Cisplatin (HY-17394)/Gemcitabine (HY-17026) significantly inhibits tumor growth in a xenograft mouse (SNU-478 cells) model^[13].

Animal Model:	Nude mice injected human KB cell^[5]
Dosage:	0.35, 0.75 mg/kg
Administration:	Intraperitoneal injection (i.p.), every 2 days, 27 days
Result:	Showed no loss of body weight. Showed time-dependent growth inhibition of tumor. Showed tumor cell inactivity or regression. Showed augmentation of apoptotic DNA fragmentation.

References

[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] RAMEZ N. ESKANDER. Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line[J]. Journal of Obstetrics and Gynaecology Research, 2012, 38 8: 1086-1094. DOI: 10.1111/j.1447-0756.2011.01841.x
[3] PING ZHOU. Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways[J]. FASEB Journal, 2010, 24 12: 4722-4732. DOI: 10.1096/fj.10.163311

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