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480-66-0

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480-66-0 Usage

Chemical Properties

Light Brown Solid

Uses

Different sources of media describe the Uses of 480-66-0 differently. You can refer to the following data:
1. Monoacetylphloroglucinol (MAPG) is small molecular weight phenolic metabolite belonging to the phloroglucinol (1,3,5-trihydroxybenzene) family, produced by bacteria including Pseudomonas strains. MAPG exhibits a broad range of biological activity albeit with mostly low potency. In the search for novel actives, MAPG and related metabolites are important metabolites for dereplication to eliminate leads due to high amounts of weakly potent actives. Although weakly active, this family appears to be important in the biocontrol of plant diseases by some Pseudomonas strains.
2. Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion
3. Induced choleresis in rats is mediated through multidrug resistance protein-2 (Mrp2). It enhances bile secretion.

Preparation

Preparation by reaction of acetic anhydride on phloroglucinol,with concentrated sulfuric acid at 130° (70%)with boron trifluoride at 10° (62.5–68%) with zinc chloride at 145–150° (50%)with Amberlite IR-120 or Zeokarb 225 (cation exchange resins, sulfonic acid type) at 160° (39%).

Definition

ChEBI: A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acid c glycans and glycopeptides.

Biological Activity

monoacetylphloroglucinol (mapg), small molecular weight phenolic metabolite, is produced via bacteria including pseudomonas strains. mapg is acetylated to form the broad-spectrum antibiotic, 2,4-diacetylphloroglucinol (dapg) by mapg acetyltransferase. in addition, mapg exerts fairly weak potency when exhibiting a broad range of antibiotic activity. even though weakly active, it seems that mapg is essential in the biocontrol of plant diseases by some pseudomonas strains [1].

Purification Methods

Crystallise the ketone from hot H2O (35mL/g). [Beilstein 8 IV 2729.]

references

[1]. hayashi, a., saitou, h., mori, t., matano, i., sugisaki, h., & maruyama, k. molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase frompseudomonassp. ygj3. bioscience, biotechnology, and biochemistry. 2012; 76(3): 559-566.

Check Digit Verification of cas no

The CAS Registry Mumber 480-66-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 0 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 480-66:
(5*4)+(4*8)+(3*0)+(2*6)+(1*6)=70
70 % 10 = 0
So 480-66-0 is a valid CAS Registry Number.

480-66-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L04156)  2',4',6'-Trihydroxyacetophenone hydrate, 98+%   

  • 480-66-0

  • 5g

  • 360.0CNY

  • Detail
  • Alfa Aesar

  • (L04156)  2',4',6'-Trihydroxyacetophenone hydrate, 98+%   

  • 480-66-0

  • 25g

  • 792.0CNY

  • Detail
  • Sigma-Aldrich

  • (91928)  2′,4′,6′-Trihydroxyacetophenonemonohydrate  matrix substance for MALDI-MS, ≥99.5%

  • 480-66-0

  • 91928-1G

  • 679.77CNY

  • Detail
  • Sigma-Aldrich

  • (91928)  2′,4′,6′-Trihydroxyacetophenonemonohydrate  matrix substance for MALDI-MS, ≥99.5%

  • 480-66-0

  • 91928-5G

  • 2,650.05CNY

  • Detail

480-66-0Synthetic route

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetonitrile
75-05-8

acetonitrile

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
Stage #1: 3,5-dihydroxyphenol; acetonitrile With hydrogenchloride; zinc(II) chloride In di-isopropyl ether at 0℃;
Stage #2: With water for 2h; Reflux;
96.2%
Stage #1: 3,5-dihydroxyphenol; acetonitrile With hydrogenchloride; zinc(II) chloride In diethyl ether at -20℃; for 2h;
Stage #2: With water for 2h; Reflux;
80%
With hydrogenchloride; zinc(II) chloride In diethyl ether for 6h; Cooling with ice;80.7%
1-(2,4,6-tris((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-one
265975-36-8

1-(2,4,6-tris((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-one

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With N,N,N',N'-tetramethylguanidine In acetonitrile at 50℃; for 1h;92%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetic acid butyl ester
123-86-4

acetic acid butyl ester

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With 4-chlorophenylethylamine; copper(I) bromide at 5℃; for 35h; Temperature; Reflux;92%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetic anhydride
108-24-7

acetic anhydride

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In ethyl acetate at 40℃; for 10h;90%
With boron trifluoride diethyl etherate In ethyl acetate at 40℃; for 10h;90%
With boron trifluoride diethyl etherate at 20℃; for 15h; Inert atmosphere;88%
2-(1-iminoethyl)phenyl-1,3,5-triol hydrochloride

2-(1-iminoethyl)phenyl-1,3,5-triol hydrochloride

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With water Heating;90%
With water for 3h; Reflux;20%
With water for 3h; Reflux;20%
With water for 1.5h; Heating;
In water for 2h; Reflux;
1-{4-[(tert-butyldimethylsilyl)oxy]-2,6-dihydroxyphenyl}ethan-1-one
139140-13-9

1-{4-[(tert-butyldimethylsilyl)oxy]-2,6-dihydroxyphenyl}ethan-1-one

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With KF-Al2O3 (basic) In acetonitrile for 18h; Ambient temperature;86%
1-[2,4,6-tris(acetyloxy)phenyl]ethanone
144152-27-2

1-[2,4,6-tris(acetyloxy)phenyl]ethanone

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With water; sodium acetate In ethanol for 5h; Reflux;86%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetyl chloride
75-36-5

acetyl chloride

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With carbon disulfide; aluminum (III) chloride In nitrobenzene at 20 - 50℃; for 1h;85.7%
Stage #1: 3,5-dihydroxyphenol With aluminum (III) chloride In dichloromethane; nitrobenzene at 0℃; Inert atmosphere;
Stage #2: acetyl chloride In dichloromethane; nitrobenzene at 0 - 90℃; for 4h; Inert atmosphere;
85%
Stage #1: 3,5-dihydroxyphenol With aluminum (III) chloride In nitrobenzene; 1,2-dichloro-ethane at 0℃; for 0.166667h; Friedel-Crafts Acylation; Inert atmosphere;
Stage #2: acetyl chloride In nitrobenzene; 1,2-dichloro-ethane for 5h; Friedel-Crafts Acylation; Inert atmosphere;
82.5%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetic acid
64-19-7

acetic acid

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With zinc(II) chloride at 140 - 145℃; for 2h; Friedel Crafts acylation;80%
With boron trifluoride
1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone
18065-05-9

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With triethylammonium formate; palladium on activated charcoal for 2h; Ambient temperature;75%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetic anhydride
108-24-7

acetic anhydride

A

2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

B

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With zinc(II) chloride at 145 - 150℃; for 0.25h;A 25%
B 50%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

benzene-1,4-diyl diacetate
1205-91-0

benzene-1,4-diyl diacetate

A

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

B

2,5-Dihydroxyacetophenone
490-78-8

2,5-Dihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 35%
B 40%
acetylacetone
123-54-6

acetylacetone

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

A

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

B

methyl orsellinate
3187-58-4

methyl orsellinate

Conditions
ConditionsYield
With n-butyllithium; sodium hydride In tetrahydrofuran; hexane for 48h; Heating;A 30%
B 8%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

Phenyl acetate
122-79-2

Phenyl acetate

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;30%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

A

4-methyl-5,7-dihydroxycoumarin
2107-76-8

4-methyl-5,7-dihydroxycoumarin

B

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene; acetyl chloride Erhitzen des Reaktionsprodukts mit wss. Salzsaeure;
2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With sodium hydroxide at 25℃;
With sodium methylate In methanol
1,3,5-triacetyl-2,4,6-trihydroxybenzene
2161-87-7

1,3,5-triacetyl-2,4,6-trihydroxybenzene

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With sodium hydroxide at 25℃;
Multi-step reaction with 2 steps
1: diluted NaOH-solution
2: diluted NaOH-solution / 25 °C
View Scheme
3-(3-ethoxycarbonyl-2,4,6-trihydroxy-phenyl)-3-oxo-propionic acid ethyl ester

3-(3-ethoxycarbonyl-2,4,6-trihydroxy-phenyl)-3-oxo-propionic acid ethyl ester

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With water at 160 - 170℃;
2-(5,7-dihydroxy-4-methylene-4H-chromen-2-yl)-phloroglucinol

2-(5,7-dihydroxy-4-methylene-4H-chromen-2-yl)-phloroglucinol

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetyl chloride
75-36-5

acetyl chloride

A

4-methyl-5,7-dihydroxycoumarin
2107-76-8

4-methyl-5,7-dihydroxycoumarin

B

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene Erhitzen des Reaktionsprodukts mit wss.HCl;
methyl 3,5,7-trioxooctanoate
23066-87-7

methyl 3,5,7-trioxooctanoate

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With potassium hydroxide
2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

A

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

B

4,6-dihydroxy-2-methoxyacetophenone
3602-54-8

4,6-dihydroxy-2-methoxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride In chlorobenzene for 1h; Heating;A 1.6 g
B 2.0 g
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

acetic acid
64-19-7

acetic acid

A

2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

B

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 100℃; for 2h;
1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

A

2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

B

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

C

2,6-dihydroxy-4-methoxy-acetophenone
7507-89-3

2,6-dihydroxy-4-methoxy-acetophenone

D

4,6-dihydroxy-2-methoxyacetophenone
3602-54-8

4,6-dihydroxy-2-methoxyacetophenone

Conditions
ConditionsYield
With aluminium trichloride In chlorobenzeneA n/a
B n/a
C n/a
D 29 % Chromat.
1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With pyridine hydrochloride
2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With In methanol; water
hydrogenchloride
7647-01-0

hydrogenchloride

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

diethyl ether
60-29-7

diethyl ether

acetonitrile
75-05-8

acetonitrile

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
nachfolgend Kochen des Reaktionsproduktes mit Wasser;
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

Resorcinol diacetate
108-58-7

Resorcinol diacetate

sulfuric acid
7664-93-9

sulfuric acid

A

2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

B

2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

C

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

1-<2.4.6-trihydroxy-phenyl>-ethanone-(1)-imine sulfate

1-<2.4.6-trihydroxy-phenyl>-ethanone-(1)-imine sulfate

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

Conditions
ConditionsYield
With water
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

dimethyl sulfate
77-78-1

dimethyl sulfate

2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone Inert atmosphere;100%
With potassium carbonate In acetone for 3h; Reflux;100%
With potassium carbonate In acetone at 66℃; for 2h; Inert atmosphere;100%
Dimethoxymethane
109-87-5

Dimethoxymethane

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone
65490-09-7

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

Conditions
ConditionsYield
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20 - 30℃; for 3.5h;
Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 10℃;
100%
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide at 20℃; for 2h; Inert atmosphere;
Stage #2: 2,4,6-trihydroxyacetophenone With diisopropylamine In dichloromethane for 3h; Inert atmosphere; Cooling with ice; regioselective reaction;
50%
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 20℃; for 3.5h;
Stage #2: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃;
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-{4-[(tert-butyldimethylsilyl)oxy]-2,6-dihydroxyphenyl}ethan-1-one
139140-13-9

1-{4-[(tert-butyldimethylsilyl)oxy]-2,6-dihydroxyphenyl}ethan-1-one

Conditions
ConditionsYield
Stage #1: 2,4,6-trihydroxyacetophenone; tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: With pyridinium p-toluenesulfonate In methanol for 4h; Inert atmosphere; Reflux;
99%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

acetic anhydride
108-24-7

acetic anhydride

3-Acetyl-5,7-bis(acetyloxy)-2-methyl-4H-1-benzopyran-4-one
1162-81-8

3-Acetyl-5,7-bis(acetyloxy)-2-methyl-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sodium acetate for 9h; Heating;98%
With sodium acetate
With sodium acetate for 10h; Heating;11.8 g
With sodium acetate for 10h; Heating / reflux;
With sodium acetate for 10h; Heating / reflux;
dimedone
3471-13-4

dimedone

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

isobutyraldehyde
78-84-2

isobutyraldehyde

2-(1-(3-acetyl-2,4,6-trihydroxy-5-(1-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-5,5-dimethylcyclohex-2-enone
1224866-14-1

2-(1-(3-acetyl-2,4,6-trihydroxy-5-(1-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-5,5-dimethylcyclohex-2-enone

Conditions
ConditionsYield
Stage #1: dimedone; isobutyraldehyde With piperidine In dichloromethane at 20℃; for 0.25h; Mannich reaction;
Stage #2: With hydrogenchloride; ammonium chloride In water
Stage #3: 2,4,6-trihydroxyacetophenone With sodium hydride In tetrahydrofuran at 20℃; for 3h; Friedel Crafts alkylation;
96%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

acetic anhydride
108-24-7

acetic anhydride

acetic acid 5-acetoxy-2-acetyl-3-hydroxyphenyl ester
17820-33-6

acetic acid 5-acetoxy-2-acetyl-3-hydroxyphenyl ester

Conditions
ConditionsYield
With pyridine; dmap at 60℃; for 3h;95%
With pyridine; dmap at 60℃; for 3h;95%
With pyridine for 5h; Ambient temperature;38%
With pyridine
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2,4,6-tri-MOM phloracetophenone
36804-11-2

2,4,6-tri-MOM phloracetophenone

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.75h;95%
With sodium hydride In N,N-dimethyl-formamide at 85℃; for 4h; Temperature;95%
Stage #1: 2,4,6-trihydroxyacetophenone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.75h; Inert atmosphere;
83%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(2,4,6-tris((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-one
265975-36-8

1-(2,4,6-tris((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; silylation;95%
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 3h;91%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

benzyl bromide
100-39-0

benzyl bromide

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone
18065-05-9

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;95%
With potassium carbonate In N,N-dimethyl-formamide94%
With potassium carbonate In acetonitrile for 3h; Reflux;91%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

Conditions
ConditionsYield
With tin(IV) chloride In 1,2-dichloro-ethane Heating;95%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

acetyl chloride
75-36-5

acetyl chloride

3-acetyl-5,7-dihydroxy-2-methyl-chromen-4-one
1022-78-2

3-acetyl-5,7-dihydroxy-2-methyl-chromen-4-one

Conditions
ConditionsYield
Stage #1: 2,4,6-trihydroxyacetophenone With potassium carbonate In tetrahydrofuran at 20 - 50℃; for 1h;
Stage #2: acetyl chloride In tetrahydrofuran for 4h; Heating / reflux;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In pyridine at 80 - 90℃; for 7h;51%
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

2,4,6-tri-MOM phloracetophenone
36804-11-2

2,4,6-tri-MOM phloracetophenone

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 3h;95%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate; dimethyl sulfate In acetone94.4%
With dimethylsulfide; potassium carbonate In acetone at 20℃;
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone
65490-09-7

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

Conditions
ConditionsYield
Stage #1: 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere;
Stage #2: chloromethyl methyl ether In dichloromethane at 0 - 20℃;
94%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.25h; Inert atmosphere;94%
With potassium carbonate In acetone Reflux;90%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one
108956-90-7

1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-ethan-1-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 0.5h;94%
With 1H-imidazole In N,N-dimethyl-formamide for 2h;92%
With triethylamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;83%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-acetyl-5-hydroxy-1,3-phenylene bis(4-methylbenzenesulfonate)
68097-14-3

4-acetyl-5-hydroxy-1,3-phenylene bis(4-methylbenzenesulfonate)

Conditions
ConditionsYield
With potassium carbonate In acetone Inert atmosphere; Reflux;94%
With potassium carbonate In acetone for 5h; Reflux;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

2,4,6-tris(trimethylsilyloxy)acetophenone

2,4,6-tris(trimethylsilyloxy)acetophenone

Conditions
ConditionsYield
With triethylamine In diethyl ether at 7℃; Heating;93%
Farnesal
502-67-0

Farnesal

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

C38H52O4

C38H52O4

Conditions
ConditionsYield
With ethylenediamine diacetic acid In dichloromethane at 20℃; for 10h;93%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

1-(2-hydroxy-4,6-diisopropylsilyloxyphenyl)ethanone
1198596-15-4

1-(2-hydroxy-4,6-diisopropylsilyloxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 2,4,6-trihydroxyacetophenone With triethylamine In dichloromethane; water at -78 - 20℃; Inert atmosphere;
Stage #2: triisopropylsilyl trifluoromethanesulfonate In dichloromethane; water at -78℃; for 1h; Inert atmosphere;
93%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

acetic anhydride
108-24-7

acetic anhydride

2,4-diacetylphloroglucinol
2161-86-6

2,4-diacetylphloroglucinol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; acetic acid for 21h; Heating;92%
With boron trifluoride diethyl etherate at 20℃; for 24h; Acetylation;90%
Stage #1: 2,4,6-trihydroxyacetophenone; acetic anhydride With boron trifluoride diethyl etherate In acetic acid Marchand reaction; Reflux;
Stage #2: With sodium hydroxide In methanol for 5h;
Stage #3: With hydrogenchloride In methanol; water
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

2',4',6'-tris(2-chlorobenzoyloxy)acetophenone
920006-70-8

2',4',6'-tris(2-chlorobenzoyloxy)acetophenone

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 3h;92%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

2-hydroxy-4,6-dimethoxyacetophenone
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 0 - 70℃; for 10h;92%
With potassium carbonate In acetone for 3h; Reflux;88%
2-iodo-propane
75-30-9

2-iodo-propane

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

1-(2-hydroxy-4,6-diisopropoxyphenyl)ethanone
93344-48-0

1-(2-hydroxy-4,6-diisopropoxyphenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere;92%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

ethyl phloroglucinol
94632-41-4

ethyl phloroglucinol

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride In methanol; water for 12h;91%
With amalgamated zinc; ethanol; acetic acid weiteres Reagens: wss. HCl;
With hydrogenchloride; sodium cyanoborohydride In methanol for 24h;100 % Spectr.
With dimethylamine borane In tetrahydrofuran for 24h; Heating;
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3'-formyl-2',4',6'-trihydroxyacetophenone
62018-55-7

3'-formyl-2',4',6'-trihydroxyacetophenone

Conditions
ConditionsYield
Stage #1: 2,4,6-trihydroxyacetophenone; N,N-dimethyl-formamide With trichlorophosphate In ethyl acetate at 20℃; for 1h; Vilsmeier-Haack Formylation;
Stage #2: In water; ethyl acetate
91%
With trichlorophosphate at 20℃;70%
With trichlorophosphate In ethyl acetate at 20℃; for 1h; Vilsmeier-Haack Formylation; Cooling with ice;64.7%
With trichlorophosphate In ethyl acetate at 20℃; for 0.5h; Vilsmeier-Haack formylation;
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone
65490-09-7

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;91%
Stage #1: bromethyl methyl ether; 2,4,6-trihydroxyacetophenone With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.333333h; Cooling with ice;
Stage #2: bromethyl methyl ether In dichloromethane for 12.3h;
75.5%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 3℃; for 3h; Inert atmosphere;74.5%
With potassium carbonate In acetone for 3h; Heating;68%
With potassium carbonate In acetone for 3h; Reflux;68%
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

isobutyryl chloride
79-30-1

isobutyryl chloride

1-(3-acetyl-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one

1-(3-acetyl-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one

Conditions
ConditionsYield
With silica sulphuric acid In neat (no solvent) at 60℃; Friedel-Crafts Acylation; Green chemistry;91%
With methanesulfonic acid; acetic acid In neat (no solvent) at 80℃; for 0.25h; Temperature; Friedel-Crafts Acylation; Inert atmosphere;

480-66-0Relevant articles and documents

Synthesis, photoluminescence and biological properties of terbium(III) complexes with hydroxyketone and nitrogen containing heterocyclic ligands

Poonam,Kumar, Rajesh,Boora, Priti,Khatkar, Anurag,Khatkar,Taxak

, p. 304 - 310 (2016)

The ternary terbium(III) complexes [Tb(HDAP)3·biq], [Tb(HDAP)3·dmph] and [Tb(HDAP)3·bathophen] were prepared by using methoxy substituted hydroxyketone ligand HDAP (2-hydroxy-4,6-dimethoxyacetophenone) and an ancillary ligand 2,2-biquinoline or 5,6-dimethyl-1,10-phenanthroline or bathophenanthroline respectively. The ligand and synthesized complexes were characterised based on elemental analysis, FT-IR and 1H NMR. Thermal behaviour of the synthesized complexes illustrates the general decomposition patterns of the complexes by thermogravimetric analysis. Photophysical properties such as excitation spectra, emission spectra and luminescence decay curves of the complexes were investigated in detail. The main green emitting peak at 548 nm can be attributed to 5D4 → 7F5 of Tb3+ ion. Thus, these complexes might be used to make a bright green light-emitting diode for display purpose. In addition the in vitro antibacterial activities of HDAP and its Tb(III) complexes against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and antifungal activities against Candida albicans and Aspergillus niger are reported. The Tb3+ complexes were found to be more potent antimicrobial agent as compared to the ligand. Among all these complexes, [Tb(HDAP)3·bathophen] exhibited excellent antimicrobial activity which proves its potential usefulness as an antimicrobial agent. Furthermore, in vitro antioxidant activity tests were carried out by using DPPH method which indicates that the complexes have considerable antioxidant activity when compared with the standard ascorbic acid.

Frutescone A-G, Tasmanone-Based Meroterpenoids from the aerial parts of Baeckea frutescens

Hou, Ji-Qin,Guo, Cui,Zhao, Jian-Juan,He, Qi-Wei,Zhang, Bao-Bao,Wang, Hao

, p. 1448 - 1457 (2017)

Frutescone A-G [(1-6), (+)-7, (-)-7], a new group of naturally occurring tasmanone-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens L. Compounds 1 and 4 featured a rare carbon skeleton with an unprecedented oxa-spiro[5.8] tetradecadiene ring system, existing as two favored equilibrating conformers in CDCl3 solution, identified by variable-temperature NMR. The regioselective syntheses of 4-7 were achieved in a concise manner by a biomimetically inspired key hetero-Diels-Alder reaction "on water". Compounds 1, 4, and 5 exhibited moderate cytotoxicities in vitro.

Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate

Qin, Xu-Jie,Rauwolf, Tyler J.,Li, Pan-Pan,Liu, Hui,McNeely, James,Hua, Yan,Liu, Hai-Yang,Porco, John A.

, p. 4291 - 4296 (2019)

Rhodomyrtusials A–C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syntheses of six isolates were achieved in six steps utilizing a reactive enetrione intermediate generated in situ from a readily available hydroxy-endoperoxide precursor.

Application of myrtle ketone compound in preparation of novel coronavirus SARS-CoV-2 medicine

-

Paragraph 0045; 0048-0050, (2021/12/07)

The invention discloses application of myrtle ketone compounds in preparation of novel coronavirus SARS-CoV-2 medicaments. The myrtle ketone compound has obvious inhibition effect on novel coronavirus SARS-CoV-2. Mechanisms include, but are not limited to, inhibition of new coronavirus SARS-CoV-2 into cells, preventing the replication of new coronavirus SARS-CoV-2 in the host cell, and timely modulating apoptosis of infected cells. To the myrtle ketone compound provided by the invention, the novel coronavirus SARS-CoV-2 has a remarkable inhibiting effect, and the cytotoxicity is relatively small. It can therefore be used for the prophylaxis or treatment of neoplastic pneumonitis. The invention is expected to provide new candidate drug molecules for clinic treatment of nebrodensis.

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Hu, Caijuan,Li, Guoxun,Mu, Yu,Wu, Wenxi,Cao, Bixuan,Wang, Zixuan,Yu, Hainan,Guan, Peipei,Han, Li,Li, Liya,Huang, Xueshi

supporting information, p. 6008 - 6020 (2021/05/06)

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

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