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Cas Database

855-97-0

855-97-0

Identification

  • Product Name:4H-1-Benzopyran-4-one,2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-

  • CAS Number: 855-97-0

  • EINECS:

  • Molecular Weight:342.348

  • Molecular Formula: C19H18 O6

  • HS Code:2932999099

  • Mol File:855-97-0.mol

Synonyms:Flavone,3',4',5,7-tetramethoxy- (6CI,7CI,8CI); 3',4',5,7-Tetramethoxyflavone;5,7,3',4'-Tetramethoxyflavone; Luteolin 5,7,3',4'-tetramethylether; Luteolintetramethyl ether; Tetramethyl camphoral

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:3,4,5,7-Tetramethoxyflavone
  • Packaging:10mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:3,4,5,7-Tetramethoxyflavone
  • Packaging:50mg
  • Price:$ 65
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:5,7,3',4'-Tetramethoxyflavone 99.08%
  • Packaging:50mg
  • Price:$ 150
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:5,7,3',4'-Tetramethoxyflavone 99.08%
  • Packaging:100mg
  • Price:$ 250
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:5,7,3',4'-Tetramethoxyflavone 99.08%
  • Packaging:10mg
  • Price:$ 100
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:5,7,3',4'-Tetramethoxyflavone 99.08%
  • Packaging:5mg
  • Price:$ 70
  • Delivery:In stock
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:3',4',5,7-Tetramethoxyflavone
  • Packaging:50 mg
  • Price:$ 40
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:3',4',5,7-Tetramethoxyflavone
  • Packaging:100 mg
  • Price:$ 60
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:3',4',5,7-Tetramethoxyflavone
  • Packaging:500 mg
  • Price:$ 220
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:3',4',5,7-Tetramethoxyflavone
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Relevant articles and documentsAll total 40 Articles be found

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao

, p. 12089 - 12108 (2021/09/06)

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma

Chen, Hongping,Ding, Haiyan,Hu, Yuan,Li, Dan,Liu, Youping,You, Qiang

, p. 12705 - 12716 (2021/11/17)

Polymethoxyflavones (PMFs) are a subgroup of flavonoids possessing various health benefits. 3,5,7,4′-Tetramethoxyflavone (1), 5,6,7,4′-tetramethylflavone (2), 3,7,3′,4′-tetramethoxyflavone (3), 5,7,3′,4′-tetramethoxyflavone (4), 5-hydroxy-3,7,2′,4′-tetramethoxyflavone (5), 3,5,7,2′,4′-pentamethoxyflavone (6), 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (7), 3-hydroxy-5,7,3′,4′-tetramethylflavone (8), 3,5,7,3′,4′-pentamethoxyflavone (9), 5-hydroxy-3,7,3′,4′,5′-pentamethoxyflavone (10), 3-hydroxy-5,7,3′,4′,5′-pentamethoxyflavone (11), and 3,5,7,3′,4′,5′-hexamethoxylflavone (12) were 12 bioactive and available PMFs. The aim of this study was to investigate the pharmacokinetic, metabolite, and antitumor activities as well as the structure-pharmacokinetic-antitumor activity relationships of these 12 PMFs to facilitate further studies of their medicinal potentials. The cytotoxicity of PMFs with a hydroxy group toward HeLa, A549, HepG2, and HCT116 cancer cell lines was generally significantly more potent than that of PMFs without a hydroxy group. Compounds 5, 7, 8, 10, and 11 were all undetectable in rat plasma, while compounds 1-4, 6, 9, and 12 were detectable. Both the number and position of hydroxy and methoxy groups played an important role in modulating PMF pharmacokinetics and metabolites.

Flavonoid-based inhibitors of the Phi-class glutathione transferase from black-grass to combat multiple herbicide resistance

Brazier-Hicks, Melissa,Coxon, Christopher R.,Cummins, Ian,Edwards, Robert,Eno, Rebecca F. M.,Freitag-Pohl, Stefanie,Hughes, David J.,Mitchell, Glynn,Moore, Jenny,Onkokesung, Nawaporn,Pohl, Ehmke,Schwarz, Maria,Steel, Patrick G.,Straker, Hannah E.,Wortley, David J.

, p. 9211 - 9222 (2021/11/16)

The evolution and growth of multiple-herbicide resistance (MHR) in grass weeds continues to threaten global cereal production. While various processes can contribute to resistance, earlier work has identified the phi class glutathione-S-transferase (AmGSTF1) as a functional biomarker of MHR in black-grass (Alopecurus myosuroides). This study provides further insights into the role of AmGSTF1 in MHR using a combination of chemical and structural biology. Crystal structures of wild-type AmGSTF1, together with two specifically designed variants that allowed the co-crystal structure determination with glutathione and a glutathione adduct of the AmGSTF1 inhibitor 4-chloro-7-nitro-benzofurazan (NBD-Cl) were obtained. These studies demonstrated that the inhibitory activity of NBD-Cl was associated with the occlusion of the active site and the impediment of substrate binding. A search for other selective inhibitors of AmGSTF1, using ligand-fishing experiments, identified a number of flavonoids as potential ligands. Subsequent experiments using black-grass extracts discovered a specific flavonoid as a natural ligand of the recombinant enzyme. A series of related synthetic flavonoids was prepared and their binding to AmGSTF1 was investigated showing a high affinity for derivatives bearing a O-5-decyl-α-carboxylate. Molecular modelling based on high-resolution crystal structures allowed a binding pose to be defined which explained flavonoid binding specificity. Crucially, high binding affinity was linked to a reversal of the herbicide resistance phenotype in MHR black-grass. Collectively, these results present a nature-inspired new lead for the development of herbicide synergists to counteract MHR in weeds. This journal is

Anti‐melanogenic properties of velutin and its analogs?

Choe, Jung-Won,Heo, Hee-Young,Jung, Se-Hui,Kim, Jaehyun,Lee, Kooyeon

, (2021/06/03)

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

Discovery and synthesis of rocaglaol derivatives inducing apoptosis in HCT116 cells via suppression of MAPK signaling pathway

Yang, Hao-Jie,Li, Ya-Nan,Yan, Chen,Yang, Jue,Zeng, Yan-Rong,Yi, Ping,Li, Yan-Mei,Hao, Xiao-Jiang,Yuan, Chun-Mao

, (2021/03/16)

Six rocaglaol derivatives were isolated from Dysoxylum gotadhora, and those compounds showed good cytotoxic activity with IC50 values ranging from 10 to 350 ng/mL against five different cancer cells. Obviously, further total synthesis of rocaglaol derivatives for medical chemistry study is of great significance. Then, twenty six rocaglaol derivatives including 25 new compounds were designed, synthesized, and evaluated for their cytotoxic activities against three human cancer cell lines: human colon cancer cells (HCT116), colorectal cancer stem cells (P6C), and human red leukocyte leukemia cells (HEL), using MTT assay. Most of derivatives showed good cytotoxic activities, with the lowest IC50 being 3.2 nM for HEL cells, which was 169 times stronger than that of the positive control (doxorubicin). Further mechanism study indicated that 11k could significantly suppress MAPK pathway in HCT116 cells, which may responsible for induction of apoptosis and cell cycle arrest.

Process route upstream and downstream products

Process route

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With potassium carbonate; In acetone; for 10h; Reflux;
90.7%
With potassium carbonate; acetone;
With potassium carbonate; In acetone; for 4h; Inert atmosphere; Reflux;
With potassium hydroxide; In water; acetone;
2'-hydroxy-3,4,4',6'-tetramethoxychalcone
114021-60-2

2'-hydroxy-3,4,4',6'-tetramethoxychalcone

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With iodine; In dimethyl sulfoxide; Reflux;
76%
With hydrogenchloride; tetra-(n-butyl)ammonium iodide; In ethanol; for 96h; Heating;
67%
Multi-step reaction with 2 steps
1: 97 percent / K2CO3 / acetone / 2 h / Heating
With potassium carbonate; In acetone;
3-(3',4'-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-yn-1-one
1064710-43-5

3-(3',4'-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-yn-1-one

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With caesium carbonate; In acetone; at 20 ℃; for 0.166667h;
99%
2′-hydroxy-3,4,4′,6′-trimethoxychalcone

2′-hydroxy-3,4,4′,6′-trimethoxychalcone

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With iodine; In dimethyl sulfoxide; at 130 ℃; for 4.5h;
80%
diosmetin
520-34-3

diosmetin

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With potassium carbonate; In acetone; at 40 - 45 ℃;
42%
5,7-dimethoxy-4-chromanone
54107-66-3

5,7-dimethoxy-4-chromanone

2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
365564-10-9

2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen; In dimethyl sulfoxide; at 100 ℃; for 48h;
75%
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen; In dimethyl sulfoxide; at 100 ℃;
75%
(2S)-5,7,3',4'-tetramethoxyflavanone
74628-43-6

(2S)-5,7,3',4'-tetramethoxyflavanone

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 90 ℃; for 24h;
90%
2-chloro-5,7-dimethoxy-4H-chromen-4-one
67837-36-9

2-chloro-5,7-dimethoxy-4H-chromen-4-one

3,4-Dimethoxyphenylboronic acid
122775-35-3

3,4-Dimethoxyphenylboronic acid

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; tricyclohexylphosphine; In 1,4-dioxane; at 100 ℃; for 22h; Inert atmosphere;
71%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 18h; Inert atmosphere; Reflux;
69%
Acetic acid 2-[(Z)-2-bromo-3-(3,4-dimethoxy-phenyl)-acryloyl]-3,5-dimethoxy-phenyl ester
392302-53-3

Acetic acid 2-[(Z)-2-bromo-3-(3,4-dimethoxy-phenyl)-acryloyl]-3,5-dimethoxy-phenyl ester

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With sodium methylate; In methanol; at 0 - 5 ℃;
65%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

methyl iodide
74-88-4

methyl iodide

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
Conditions Yield
With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
84%

Global suppliers and manufacturers

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  • Amadis Chemical Co., Ltd.
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  • Shanghai Upbio Tech Co.,Ltd
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  • GIHI CHEMICALS CO.,LIMITED
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  • Finetech Industry Limited
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  • Antimex Chemical Limied
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