ChemicalBook > CAS DataBase List > 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one

Product Name
1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
CAS No.
20784-60-5
Chemical Name
1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
Synonyms
Guaiacol Impurity 14;4'-O-Methylbavachalcone;4''-O-Methylbavachalcone;O-Methylbroussochalcone B;4'-O-Methylbroussochalcone B;O-Methylbroussochalcone B, 4'-;O-Methylbroussochalcone B, 4’-;4''-O-Methylbavachalcone, 10 mM in DMSO;Methylbroussochalcone4'-O- B;4'-O-Methylbroussochalcone B, （4'-O-Methylbavachalcone）
CBNumber
CB82277802
Molecular Formula
C21H22O4
Formula Weight
338.4
MOL File
20784-60-5.mol
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1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one Property

Melting point:
169.9-170.1 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
Boiling point:
552.1±50.0 °C(Predicted)
Density 
1.181±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: 50 mg/mL (147.75 mM)
form 
Solid
pka
7.41±0.50(Predicted)
color 
Orange to yellow
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

ChemScene
Product number
CS-0017867
Product name
4'-O-Methylbavachalcone
Purity
99.64%
Packaging
5mg
Price
$168
Updated
2021/12/16
ChemScene
Product number
CS-0017867
Product name
4'-O-Methylbavachalcone
Purity
99.64%
Packaging
10mg
Price
$286
Updated
2021/12/16
AK Scientific
Product number
W1522
Product name
4'-O-MethylbroussochalconeB
Packaging
10mg
Price
$455
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
PXT0001297
Product name
4'-O-METHYLBROUSSOCHALCONE B
Purity
95.00%
Packaging
5MG
Price
$499.22
Updated
2021/12/16
AK Scientific
Product number
W1522
Product name
4'-O-MethylbroussochalconeB
Packaging
100mg
Price
$1096
Updated
2021/12/16
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1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one Chemical Properties,Usage,Production

Chemical Properties

Red needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Psoralea corylifolia Linn.

Uses

4'-O-Methylbavachalcone is a chalcone isolated from Psoralea corylifolia, inhibits severe acute respiratory syndrome coronavirus (SARS-CoV) papain-like protease (PLpro) activity, with an IC50 of 10.1 μM[1].

Synthesis

128961-13-7

20784-60-5

Compound 17a (51 mg, 0.13 mmol) was used as starting material, which was dissolved in methanol (5 mL) and stirred at room temperature. Carbon tetrabromide (CBr4, 4.5 mg, 0.013 mmol) was added to this solution and the reaction mixture was subsequently heated to reflux with continuous stirring for 2.5 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed under reduced pressure using a rotary evaporator. The resulting residue was purified by preparative thin layer chromatography (PLC) with the eluent being a mixed solvent of hashane/ethyl acetate, resulting in the target product (E)-1-(2-hydroxy-4-methoxy-5-(3-methyl-2-buten-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (Compound 5a, 35 mg, 84% yield) as yellow needle-like It is a yellow needle-like crystal. Its melting point is 169.9-170.1°C (EtOAc/hexane recrystallized); Rf value is 0.34 (33% EtOAc/hexane); infrared spectrum (KBr) νmax/cm-1: 3436, 3319, 3069, 2973, 2943, 2911, 2854, 2821, 2751, 2697, 2604, 1628, 1604, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544, 1544 1628, 1604, 1544, 1508, 1443, 1363, 1306, 1284, 1205, 1170, 1130, 1105; NMR hydrogen spectra (acetone-d6) δH: 1.58 (3H, d, J = 1.0 Hz, CH3), 1.59 (3H, s, CH3), 3.13 (2H, d, J = 7.2 Hz, Ph-CH2CH), 3.78 (3H, s, OCH3), 5.12-5.17 (1H, m, CCHCH2), 6.34 (1H, s, C2'H), 6.80 (2H, d, J = 8.6 Hz, C3H and C5H), 7.56 (2H, d, J = 8.6 Hz, C2H and C6H), 7.59 (1H d, J = 15.4 Hz, CαH), 7.70 (1H, d, J = 15.4 Hz, CβH), 7.80 (1H, s, C6'H), 8.93 (1H, s, OH), 13.51 (1H, s, OH); NMR carbon (acetone-d6) δC: 17.89, 25.88, 29.28, 56.28, 100.00, 114.16, 118.35, 122.38, 123.78, 127.56, 131.21, 131.74, 132.50, 145.15, 161.08, 165.09, 166.44, 192.89; high-resolution mass spectrometry (HRMS): measured value [M]+ 338.1530, calculated value c21h22o4 338.1518.

References

[1] 4'-O-Methylbavachalcone, et al. Phenolic phytochemical displaying SARS-CoV papain-like protease inhibition from the seeds of Psoralea corylifolia. J Enzyme Inhib Med Chem. 2014 Feb;29(1):59-63. DOI:10.3109/14756366.2012.753591

1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one Preparation Products And Raw materials

Raw materials

Preparation Products

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1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one Suppliers

China 129 India 1 United States 8 Global 138
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View Lastest Price from 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one manufacturers

Shanghai Standard Technology Co., Ltd.
Product
4'-O-Methylbroussochalcone B 20784-60-5
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2020-03-24
Career Henan Chemical Co
Product
1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one 20784-60-5
Price
US $9.80/KG
Min. Order
1KG
Purity
≥98%
Supply Ability
20 tons
Release date
2020-01-10

20784-60-5, 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-oneRelated Search:

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  • 1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
  • 4'-O-Methylbroussochalcone B
  • 2',4-Dihydroxy-4'-methoxy-5'-(3-methyl-2-butenyl)chalcone
  • 4'-O-Methylbavachalcone
  • O-Methylbroussochalcone B, 4'-
  • Methylbroussochalcone4'-O- B
  • O-Methylbroussochalcone B
  • 2-Propen-1-one, 1-[2-hydroxy-4-methoxy-5-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
  • 4'-O-Methylbroussochalcone B, （4'-O-Methylbavachalcone）
  • (2E)-1-[2-Hydroxy-4-methoxy-5-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
  • (E)-1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
  • O-Methylbroussochalcone B, 4’-
  • (E)-1-(2-Hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  • Guaiacol Impurity 14
  • 4''-O-Methylbavachalcone
  • 4''-O-Methylbavachalcone, 10 mM in DMSO
  • 20784-60-5