EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

flavokawain B
2'-hydroxy-4',6'-dimethoxychalcone

Supplier Sponsors

Name:(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
CAS Number: 1775-97-9Picture of molecule3D/inchi
FDA UNII: R9WC6SM4UQ
Nikkaji Web:J816.775C
MDL:MFCD00075877
XlogP3-AA:3.80 (est)
Molecular Weight:284.31132000
Formula:C17 H16 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 500.00 to 501.00 °C. @ 760.00 mm Hg (est)
Flash Point: 366.00 °F. TCC ( 185.80 °C. ) (est)
logP (o/w): 4.206 (est)
Soluble in:
 water, 17.57 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Flavokawain B 98%
BOC Sciences
For experimental / research use only.
Flavokawain B 98%
Odor: characteristic
Use: Flavokawain B is a chalcone isolated from Piper methysticum with strong antiangiogenic activity.
Coompo
For experimental / research use only.
Flavokawain B from Plants ≥98%
Odor: characteristic
Use: Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-?B and MAPK signaling pathways. Flavokawain B acts through ROS generation and GADD153 up-regulation to regulate the expression of Bcl-2 family members, thereby inducing mitochondrial dysfunction and apoptosis in HCT116 cells. A potent anti-inflammatory. Flavokawain B significantly inhibited production of NO and PGE2 in LPS-induced RAW 264.7 cells. Robust mechanisms for Flavokawain B induction of apoptosis preferentially for hormone-refractory prostate cancer and the potential usefulness of FKB for prevention and treatment of hormone-refractory prostate cancer in an adjuvant setting.
ExtraSynthese
For experimental / research use only.
Flavokawain B
Santa Cruz Biotechnology
For experimental / research use only.
Flavokawain B
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for flavokawain B usage levels up to:
 not for fragrance use.
 
Recommendation for flavokawain B flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5356121
National Institute of Allergy and Infectious Diseases:Data
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Chemidplus:0001775979
 
References:
 (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5356121
Pubchem (sid):135269659
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB33691
FooDB:FDB011797
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 kava
Search Trop Picture
 
Synonyms:
2',4'-dimethoxy-6'-hydroxychalcone
(E)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-phenyl-propenone
(E)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-phenylpropenone
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one
(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone
2'-hydroxy-4',6'-dimethoxychalcone
2-propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-
2-propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (E)-
 

Articles:

PubMed:The flavokawains: uprising medicinal chalcones.
PubMed:Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin.
PubMed:Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.
PubMed:Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-kappaB and MAPK signaling pathways.
PubMed:Anti-inflammatory activity of Flavokawain B from Alpinia pricei Hayata.
PubMed:In vitro cytotoxicity of nonpolar constituents from different parts of kava plant (Piper methysticum).
PubMed:HPLC analysis of flavokavins and kavapyrones from Piper methysticum Forst.
PubMed:Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.
PubMed:The chalcones cardamonin and flavokawain B inhibit the differentiation of preadipocytes to adipocytes by activating ERK.
PubMed:Chalcones suppress fatty acid-induced lipid accumulation through a LKB1/AMPK signaling pathway in HepG2 cells.
PubMed:The flavokawains: uprising medicinal chalcones.
PubMed:Flavokawain B, a kava chalcone, inhibits growth of human osteosarcoma cells through G2/M cell cycle arrest and apoptosis.
PubMed:Peripheral antinociception of a chalcone, flavokawin B and possible involvement of the nitric oxide/cyclic guanosine monophosphate/potassium channels pathway.
PubMed:Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.
PubMed:Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice.
PubMed:The chalcone flavokawain B induces G2/M cell-cycle arrest and apoptosis in human oral carcinoma HSC-3 cells through the intracellular ROS generation and downregulation of the Akt/p38 MAPK signaling pathway.
PubMed:Flavokawain B, a kava chalcone, induces apoptosis in synovial sarcoma cell lines.
PubMed:Flavokawain B induces apoptosis of human oral adenoid cystic cancer ACC-2 cells via up-regulation of Bim and down-regulation of Bcl-2 expression.
PubMed:Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.
PubMed:Herbal hepatotoxicity by kava: update on pipermethystine, flavokavain B, and mould hepatotoxins as primarily assumed culprits.
PubMed:Possible participation of nitric oxide/cyclic guanosine monophosphate/protein kinase C/ATP-sensitive K(+) channels pathway in the systemic antinociception of flavokawin B.
PubMed:Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-kappaB and MAPK signaling pathways.
PubMed:Flavokawain B, a novel chalcone from Alpinia pricei Hayata with potent apoptotic activity: Involvement of ROS and GADD153 upstream of mitochondria-dependent apoptosis in HCT116 cells.
PubMed:Anti-inflammatory activity of Flavokawain B from Alpinia pricei Hayata.
PubMed:HPLC analysis of flavokavins and kavapyrones from Piper methysticum Forst.
 
Notes:
Found in kava (Piper methysticum), FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
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