ChemicalBook > CAS DataBase List > 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE

4',6'-DIMETHOXY-2'-HYDROXYCHALCONE

Product Name
4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
CAS No.
1775-97-9
Chemical Name
4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
Synonyms
FlavoringB;Flavokavin B;FLAVOKAWIN B;FLAVOKAWAIN B;Flavokavain B;FLAVOKAVAIN B(P);Flavokawain B-RM;CARDAMONIN-4'-METHYL ETHER;4',6'-DIMETHOXY-2'-HYDROXYCHALCONE;2'-Hydroxy-4',6'-Dimethoxychalcone
CBNumber
CB4430922
Molecular Formula
C17H16O4
Formula Weight
284.31
MOL File
1775-97-9.mol
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4',6'-DIMETHOXY-2'-HYDROXYCHALCONE Property

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)
pka
6.84±0.40(Predicted)
form 
Solid
color 
Yellow to Dark Yellow
LogP
4.206 (est)
CAS DataBase Reference
1775-97-9(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHL83763
Product name
Flavokawain B
Purity
phyproof<SUP>&#174;</SUP> Reference Substance
Packaging
10 mg
Price
$549
Updated
2025/07/31
Cayman Chemical
Product number
19652
Product name
Flavokawain B
Purity
≥98%
Packaging
500μg
Price
$34
Updated
2024/03/01
Cayman Chemical
Product number
19652
Product name
Flavokawain B
Purity
≥98%
Packaging
1mg
Price
$65
Updated
2024/03/01
Cayman Chemical
Product number
19652
Product name
Flavokawain B
Purity
≥98%
Packaging
5mg
Price
$253
Updated
2024/03/01
Cayman Chemical
Product number
19652
Product name
Flavokawain B
Purity
≥98%
Packaging
10mg
Price
$404
Updated
2024/03/01
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4',6'-DIMETHOXY-2'-HYDROXYCHALCONE Chemical Properties,Usage,Production

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

4',6'-DIMETHOXY-2'-HYDROXYCHALCONE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE manufacturers

Shanghai Standard Technology Co., Ltd.
Product
Flavokawain B 1775-97-9
Price
US $0.00/mg
Min. Order
20mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-04-26
Career Henan Chemical Co
Product
4',6'-DIMETHOXY-2'-HYDROXYCHALCONE 1775-97-9
Price
US $3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1kg,5kg,50kg
Release date
2020-01-18

1775-97-9, 4',6'-DIMETHOXY-2'-HYDROXYCHALCONERelated Search:


  • CARDAMONIN-4'-METHYL ETHER
  • FLAVOKAWAIN B
  • FLAVOKAWIN B
  • DIMETHOXY-2'-HYDROXYCHALCONE, 4',6'-
  • (E)-1-(2-HYDROXY-4,6-DIMETHOXY-PHENYL)-3-PHENYL-PROPENONE
  • 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
  • 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one)
  • (E)-1-(2-Hydroxy-4,6-dimethoxy-phenyl)-3-phenyl-
  • FLAVOKAVAIN B(P)
  • Flavokavin B
  • (E)-2'-Hydroxy-4',6'-dimethoxychalcone
  • Flavokavain B
  • (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'-Hydroxy-4',6'-Dimethoxychalcone
  • 2-Propen-1-one,1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-
  • 4',6'-Dimethoxy-2'-hydroxychalcone (Flavokawain B)
  • FlavoringB
  • Flavokawain B-RM
  • Flavokawain B, chalcone isolated from kava
  • 1775-97-9
  • Chalcones
  • Plant Oils, Toxins, Phenolic Acids & Derivatives