1775-97-9,MFCD00075877
Catalog No.:AA0025AX

1775-97-9 | (E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥98%
in stock  
$93.00   $65.00
- +
5mg
≥98%
in stock  
$362.00   $253.00
- +
10mg
≥98%
in stock  
$578.00   $404.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0025AX
Chemical Name:
(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
CAS Number:
1775-97-9
Molecular Formula:
C17H16O4
Molecular Weight:
284.3065
MDL Number:
MFCD00075877
SMILES:
COc1cc(O)c(c(c1)OC)C(=O)/C=C/c1ccccc1
NSC Number:
51351
Properties
Computed Properties
 
Complexity:
360  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
1  
Formal Charge:
0  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
5  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
3.8  

Downstream Synthesis Route

[1]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1988,vol.27,p.67

[1]SyntheticCommunications,2008,vol.38,p.1815-1821

[1]Sipos,Zoltán;Kónya,Krisztina[Synthesis,2018,vol.50,#8,p.1610-1620]

Literature

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.

Journal: The journal of obstetrics and gynaecology research 20120801

Title: Flavokawain B, a kava chalcone, induces apoptosis in synovial sarcoma cell lines.

Journal: Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20120701

Title: Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity.

Journal: Journal of medicinal chemistry 20120412

Title: Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.

Journal: The Journal of nutritional biochemistry 20120401

Title: 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.

Journal: Journal of agricultural and food chemistry 20120307

Title: A synthetic chalcone as a potent inducer of glutathione biosynthesis.

Journal: Journal of medicinal chemistry 20120209

Title: Possible participation of nitric oxide/cyclic guanosine monophosphate/protein kinase C/ATP-sensitive K(+) channels pathway in the systemic antinociception of flavokawin B.

Journal: Basic & clinical pharmacology & toxicology 20110601

Title: Chalcone-based inhibitors against hypoxia-inducible factor 1--structure activity relationship studies.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-kappaB and MAPK signaling pathways.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101201

Title: Antinociceptive activity of a synthetic chalcone, flavokawin B on chemical and thermal models of nociception in mice.

Journal: European journal of pharmacology 20101125

Title: Flavokawain B, a kava chalcone, induces apoptosis via up-regulation of death-receptor 5 and Bim expression in androgen receptor negative, hormonal refractory prostate cancer cell lines and reduces tumor growth.

Journal: International journal of cancer 20101015

Title: 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.

Journal: Free radical biology & medicine 20100715

Title: Structure-activity relationship studies of chalcone leading to 3-hydroxy-4,3',4',5'-tetramethoxychalcone and its analogues as potent nuclear factor kappaB inhibitors and their anticancer activities.

Journal: Journal of medicinal chemistry 20091126

Title: Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.

Journal: Bioorganic & medicinal chemistry letters 20091001

Title: Anti-inflammatory activity of Flavokawain B from Alpinia pricei Hayata.

Journal: Journal of agricultural and food chemistry 20090722

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: In vitro cytotoxicity of nonpolar constituents from different parts of kava plant (Piper methysticum).

Journal: Journal of agricultural and food chemistry 20060419

Title: HPLC analysis of flavokavins and kavapyrones from Piper methysticum Forst.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051105

Title: Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.

Journal: Cancer research 20050415

Title: Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase.

Journal: Journal of natural products 20021101

Title: Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.

Journal: Journal of agricultural and food chemistry 20020213

Title: Rossette MC, et al. The In Vitro and In Vivo Antiangiogenic Effects of Flavokawain B. Phytother Res. 2017 Oct;31(10):1607-1613.

Title: Li X, et al. Flavokawain B targets protein neddylation for enhancing the anti-prostate cancer effect of Bortezomib via Skp2 degradation. Cell Commun Signal. 2019 Mar 18;17(1):25.

Quotation Request
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Additional Info:
SDS
Tags:1775-97-9 Molecular Formula|1775-97-9 MDL|1775-97-9 SMILES|1775-97-9 (E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Catalog No.: AA0025AX
1775-97-9,MFCD00075877
1775-97-9 | (E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
Pack Size: 1mg
Purity: ≥98%
in stock
$93.00 $65.00
Pack Size: 5mg
Purity: ≥98%
in stock
$362.00 $253.00
Pack Size: 10mg
Purity: ≥98%
in stock
$578.00 $404.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0025AX
Chemical Name: (E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
CAS Number: 1775-97-9
Molecular Formula: C17H16O4
Molecular Weight: 284.3065
MDL Number: MFCD00075877
SMILES: COc1cc(O)c(c(c1)OC)C(=O)/C=C/c1ccccc1
NSC Number: 51351
Properties
Complexity: 360  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 1  
Formal Charge: 0  
Heavy Atom Count: 21  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 5  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 3.8  
Downstream Synthesis Route
1775-97-9    480-39-7 

[1]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1988,vol.27,p.67

1775-97-9    480-39-7 

[1]SyntheticCommunications,2008,vol.38,p.1815-1821

1775-97-9    520-28-5 

[1]Sipos,Zoltán;Kónya,Krisztina[Synthesis,2018,vol.50,#8,p.1610-1620]

Literature fold

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry20121115

Title: Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.

Journal: The journal of obstetrics and gynaecology research20120801

Title: Flavokawain B, a kava chalcone, induces apoptosis in synovial sarcoma cell lines.

Journal: Journal of orthopaedic research : official publication of the Orthopaedic Research Society20120701

Title: Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity.

Journal: Journal of medicinal chemistry20120412

Title: Flavokawain B inhibits growth of human squamous carcinoma cells: Involvement of apoptosis and cell cycle dysregulation in vitro and in vivo.

Journal: The Journal of nutritional biochemistry20120401

Title: 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.

Journal: Journal of agricultural and food chemistry20120307

Title: A synthetic chalcone as a potent inducer of glutathione biosynthesis.

Journal: Journal of medicinal chemistry20120209

Title: Possible participation of nitric oxide/cyclic guanosine monophosphate/protein kinase C/ATP-sensitive K(+) channels pathway in the systemic antinociception of flavokawin B.

Journal: Basic & clinical pharmacology & toxicology20110601

Title: Chalcone-based inhibitors against hypoxia-inducible factor 1--structure activity relationship studies.

Journal: Bioorganic & medicinal chemistry letters20110101

Title: Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-kappaB and MAPK signaling pathways.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology20101201

Title: Antinociceptive activity of a synthetic chalcone, flavokawin B on chemical and thermal models of nociception in mice.

Journal: European journal of pharmacology20101125

Title: Flavokawain B, a kava chalcone, induces apoptosis via up-regulation of death-receptor 5 and Bim expression in androgen receptor negative, hormonal refractory prostate cancer cell lines and reduces tumor growth.

Journal: International journal of cancer20101015

Title: 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.

Journal: Free radical biology & medicine20100715

Title: Structure-activity relationship studies of chalcone leading to 3-hydroxy-4,3',4',5'-tetramethoxychalcone and its analogues as potent nuclear factor kappaB inhibitors and their anticancer activities.

Journal: Journal of medicinal chemistry20091126

Title: Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.

Journal: Bioorganic & medicinal chemistry letters20091001

Title: Anti-inflammatory activity of Flavokawain B from Alpinia pricei Hayata.

Journal: Journal of agricultural and food chemistry20090722

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology20060501

Title: In vitro cytotoxicity of nonpolar constituents from different parts of kava plant (Piper methysticum).

Journal: Journal of agricultural and food chemistry20060419

Title: HPLC analysis of flavokavins and kavapyrones from Piper methysticum Forst.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences20051105

Title: Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.

Journal: Cancer research20050415

Title: Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase.

Journal: Journal of natural products20021101

Title: Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.

Journal: Journal of agricultural and food chemistry20020213

Title: Rossette MC, et al. The In Vitro and In Vivo Antiangiogenic Effects of Flavokawain B. Phytother Res. 2017 Oct;31(10):1607-1613.

Title: Li X, et al. Flavokawain B targets protein neddylation for enhancing the anti-prostate cancer effect of Bortezomib via Skp2 degradation. Cell Commun Signal. 2019 Mar 18;17(1):25.

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