3555-86-0

Basic information

• Product Name: PHLOROBENZOPHENONE
• Synonyms: PHLOROBENZOPHENONE;2,4,6-TRIHYDROXYBENZOPHENONE;2,4,6-TRIHYDROXYBENZOPHENONE 97%;phenyl-(2,4,6-trihydroxyphenyl)methanone
• CAS NO: 3555-86-0
• Molecular Formula: C₁₃H₁₀O₄
• Molecular Weight: 230.22
• EINECS: 222-615-5
• Product Categories: Aromatic Benzophenones & Derivatives (substituted)
• Mol File: 3555-86-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 170–171°C
• Boiling Point: 332.2°C (rough estimate)
• Flash Point: 213.7 °C
• Appearance: /
• Density: 1.2683 (rough estimate)
• Vapor Pressure: 3.48E-07mmHg at 25°C
• Refractive Index: 1.4977 (estimate)
• Water Solubility: 3.1g/L(22 oC)
• CAS DataBase Reference: PHLOROBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: PHLOROBENZOPHENONE(3555-86-0)
• EPA Substance Registry System: PHLOROBENZOPHENONE(3555-86-0)

Safety Data

• Hazardous Substances Data: 3555-86-0(Hazardous Substances Data)

Usage

Definition

ChEBI: A benzenetriol that is benzophenone in which one of the phenyl groups is substituted at by hydroxy groups at positions 2, 4, and 6.

Preparation

Preparation by Fries rearrangement of phloroglucinol tribenzoate with aluminium chloride at 160–170° for 2 h (95%).

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 6734, 1967 DOI: 10.1021/ja01001a060Tetrahedron, 26, p. 5255, 1970 DOI: 10.1016/S0040-4020(01)98735-6

InChI:InChI=1/C13H10O4/c14-9-6-10(15)12(11(16)7-9)13(17)8-4-2-1-3-5-8/h1-7,14-16H

Synthetic route

2,4,6-trimethoxybenzophenone (3770-80-7) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 74h; Inert atmosphere; Schlenk technique;	100%
With boron tribromide In dichloromethane at -78 - 20℃; for 20h;	99%
With boron tribromide In dichloromethane at -78 - 20℃;	99%

3,5-dihydroxyphenol (108-73-6) + benzoyl chloride (98-88-4) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With aluminum (III) chloride In nitrobenzene at 65℃; for 3h; Inert atmosphere;	72%
With aluminum (III) chloride In nitrobenzene at 65℃; Friedel-Crafts Acylation;	65.8%
Stage #1: 3,5-dihydroxyphenol With aluminum (III) chloride In carbon disulfide; nitrobenzene at 55℃; for 0.5h; Friedel-Crafts Acylation; Stage #2: benzoyl chloride In carbon disulfide; nitrobenzene for 0.5h; Friedel-Crafts Acylation; Heating;	54%

2,4,6-trimethoxybenzophenone (3770-80-7) → cotoin (479-21-0) + 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Stage #1: 2,4,6-trimethoxybenzophenone With boron tribromide In dichloromethane at -78 - 20℃; for 48h; Inert atmosphere; Stage #2: With water In dichloromethane at 0 - 20℃; for 1.3h;	A 4% B 52%

3,5-dihydroxyphenol (108-73-6) + 1,4-dibenzoyloxybenzene (14210-97-0) → 2,5-dihydroxybenzophenone (2050-37-5) + 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;	A 50% B 40%

3,5-dihydroxyphenol (108-73-6) + benzoic acid phenyl ester (93-99-2) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;	25%

2-(α-phenylimino-benzyl)-phloroglucinol → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With hydrogenchloride

3,5-dihydroxyphenol (108-73-6) + benzonitrile (100-47-0) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With hydrogenchloride; diethyl ether; zinc(II) chloride Erhitzen des Reaktionsprodukts mit Wasser;
With diethyl ether
With hydrogenchloride; diethyl ether; zinc(II) chloride Man verwandelt das ausgeschiedene Ketimidhydrochlorid in das Sulfat und kocht dieses mit der 20-fachen Menge Wasser; Ausbeute 65prozent der Theorie;

7-Phenyl-3,5,7-trioxoheptansaeuremethylester (15148-46-6) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With sodium hydroxide at -5℃;

4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one (20851-38-1) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With lithium hydride

2,4,6-trihydroxy-benzophenone-imine; hydrochloride → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With water for 1.5h; Heating;

1,2,3-trimethoxybenzene (621-23-8) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / AlCl3 / CH2Cl2 / 12 h / 0 - 20 °C 2: 92 percent / boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: 7.5 g / AlCl3 / diethyl ether / 15 h / Ambient temperature 2: 5.1 g / HI / acetic anhydride / 4 h / 115 - 120 °C View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 2.2: 1.3 h / 0 - 20 °C View Scheme

benzoyl chloride (98-88-4) + (η-2,5-Ph2C4H2N)(Ph3P)2ReH2 → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / AlCl3 / CH2Cl2 / 12 h / 0 - 20 °C 2: 92 percent / boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

3,5-dihydroxyphenol (108-73-6) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ZnCl2; HCl / diethyl ether 2: H2O / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: AlCl3; diethyl ether 2: ethanolic HCl View Scheme

benzoyl chloride (98-88-4) + O5-benzoyl-O1,O2-isopropyliden-β-D-arabinofuranose → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 7.5 g / AlCl3 / diethyl ether / 15 h / Ambient temperature 2: 5.1 g / HI / acetic anhydride / 4 h / 115 - 120 °C View Scheme

N-phenyl-benzimidoyl chloride (4903-36-0) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; diethyl ether 2: ethanolic HCl View Scheme

1-phenylhexane-1,3,5-trione (1469-95-0) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) NaNH2, liq. NH3, Et2O, (ii) /BRN= 1900390/ 2: diethyl ether 3: aq. NaOH / -5 °C View Scheme

7-Phenyl-3,5,7-trioxo-heptansaeure (4809-02-3) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: aq. NaOH / -5 °C View Scheme

acide 2,4,6-trihydroxybenzoique (83-30-7) + benzene (71-43-2) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Friedel-Crafts reaction;
Stage #1: acide 2,4,6-trihydroxybenzoique; benzene With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Stage #2: With water at 4℃; for 24h; Cooling with ice;

benzoyl chloride (98-88-4) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 2.2: 1.3 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C 1.2: 12 h / 0 - 20 °C 2.1: boron tribromide / dichloromethane / 20 h / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2.1: boron tribromide / dichloromethane / 74 h / -78 - 20 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C 1.2: 0 - 20 °C 2.1: boron tribromide / dichloromethane / -78 - 20 °C View Scheme

<2-14C>malonyl-CoA + S-benzoyl coenzyme A (6756-74-7) → 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one (20851-38-1) + 4-hydroxy-6-phenyl-2H-pyran-2-one (5526-38-5) + 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With acridone synthase from Citrus Microcarpa pH=6.5 - 8.5; Enzymatic reaction;

S-benzoyl coenzyme A (6756-74-7) + S-(hydrogen malonyl)coenzyme A (524-14-1) → 2-benzoylphloroglucinol (3555-86-0)

Conditions	Yield
With recombinant type III polyketide synthase from Aquilaria sinensis In aq. phosphate buffer at 37℃; for 12h; pH=7.0; Enzymatic reaction;

UDP-glucose (133-89-1) + 2-benzoylphloroglucinol (3555-86-0) → phlorobenzophenone 3-C-β-D-glucoside

Conditions	Yield
With C-glycosyltransferase from Mangifera indica In methanol at 40℃; for 12h; pH=6.6; Enzymatic reaction;	100%
With Mangifera indica C-glycosyltransferase for 12h; Enzymatic reaction; stereospecific reaction;	4.5 mg

3,7-dimethyl-2,6-octadienal (141-27-5) + 2-benzoylphloroglucinol (3555-86-0) → 6-benzoyl-5-hydroxy-2,8-dimethyl-2,8-bis(4-methylpent-3-enyl)-2H,8H-benzo(1,2-b:3',4'-b')dipyran

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 36h;	95%

3,3-dimethyl acrylaldehyde (107-86-8) + 2-benzoylphloroglucinol (3555-86-0) → 6-benzoyl-5-hydroxy-2,2,8,8-tetramethyl-2H,8H-benzo(1,2-b:3',4'-b')dipyran (88662-01-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 36h;	94%

2-benzoylphloroglucinol (3555-86-0) + 2-benzylidene-indan-1,3-dione (5381-33-9) → 2-((3-benzoyl-2,4,6-trihydroxy-5-((3-hydroxy-1-oxo-1H-inden-2-yl)(phenyl)methyl)phenyl)(phenyl)methyl)-3-hydroxy-1H-inden-1-one

Conditions	Yield
Stage #1: 2-benzoylphloroglucinol With sodium hydride In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #2: 2-benzylidene-indan-1,3-dione In tetrahydrofuran for 1h;	92%
With sodium hydride In tetrahydrofuran at 20℃; Michael Addition;	643 mg

2-benzoylphloroglucinol (3555-86-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-benzoyl-2,4,6-trihydroxy-benzaldehyde

Conditions	Yield
With trichlorophosphate In ethyl acetate at 20℃; Inert atmosphere;	91%
With trichlorophosphate In ethyl acetate	79%

2-benzoylphloroglucinol (3555-86-0) + 2-(2-methylpropylidene)-1H-indene-1,3(2H)-dione (22123-54-2) → 2-(1-(3-benzoyl-2,4,6-trihydroxy-5-(1-(3-hydroxy-1-oxo-1H-inden-2-yl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-1H-inden-1-one

Conditions	Yield
Stage #1: 2-benzoylphloroglucinol With sodium hydride In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #2: 2-(2-methylpropylidene)-1H-indene-1,3(2H)-dione In tetrahydrofuran for 1h;	77%
With sodium hydride In tetrahydrofuran at 20℃; Michael Addition;	486 mg

2-benzoylphloroglucinol (3555-86-0) + acetic acid (64-19-7) → 2-acetyl-4-benzoylphloroglucinol (31188-65-5)

Conditions	Yield
With boron trifluoride	76%

trans-geranyl bromide (6138-90-5) + 2-benzoylphloroglucinol (3555-86-0) → (E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone (70219-87-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;	63%

2-benzoylphloroglucinol (3555-86-0) + prenyl bromide (870-63-3) → phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (93796-20-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;	63%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;	62%

bromethyl methyl ether (13057-17-5) + 2-benzoylphloroglucinol (3555-86-0) → (2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;	60%

2-benzoylphloroglucinol (3555-86-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-phen-1-one

Conditions	Yield
Stage #1: 2-benzoylphloroglucinol With 1H-imidazole In acetone for 0.0833333h; Stage #2: tert-butyldimethylsilyl chloride In acetone at 20℃; for 2h; regioselective reaction;	58%

geranyl diphosphate (763-10-0) + 2-benzoylphloroglucinol (3555-86-0) → (E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone (70219-87-3) + (E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzophenone

Conditions	Yield
With Aspergillus terreus aromatic prenyltransferase; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 2h; pH=7.5; Enzymatic reaction;	A 54.72% B 0.62%

2-benzoylphloroglucinol (3555-86-0) + chloromethyl methyl ether (107-30-2) → (2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

Conditions	Yield
Stage #1: 2-benzoylphloroglucinol With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: chloromethyl methyl ether In acetone at 20℃; for 1h; Inert atmosphere; Schlenk technique;	50%

2-benzoylphloroglucinol (3555-86-0) + 2-chloro-4-nitrophenyl β-D-xylopyranoside → C18H18O8

Conditions	Yield
With recombinant Streptomyces venezuelae ISP5230 GT1 Sv0189 glycosyltransferase; UDP In aq. phosphate buffer at 20℃; pH=7.0; Enzymatic reaction;	50%

2-benzoylphloroglucinol (3555-86-0) + isoprene (78-79-5) → 8-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran (63565-07-1) + 6-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran (86606-14-6) + 6-Benzoyl-5-hydroxy-2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-benzo<1,2-b:3,4-b'>dipyran (83611-02-3)

Conditions	Yield
With phosphoric acid In xylene at 30 - 35℃; for 12h;	A 30% B 48% C 7%

2-benzoylphloroglucinol (3555-86-0) + prenyl bromide (870-63-3) → phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone (70219-84-0) + phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (93796-20-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 45℃; for 24h;	A 48% B 13%

2-benzoylphloroglucinol (3555-86-0) + prenyl bromide (870-63-3) → phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone (70219-84-0)

Conditions	Yield
With potassium hydroxide at 0℃; for 2h;	45%
With potassium hydroxide In water at 0℃; for 1.33h;	34%
With potassium hydroxide In water at 0℃; for 1.33333h; Inert atmosphere;	34%

C17H35S(1+)*BF4(1-) + 2-benzoylphloroglucinol (3555-86-0) → 2,6-dihydroxy-4-prenyloxybenzophenone (70219-83-9) + phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (93796-20-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 7h;	A 10% B 42%

geranyl bromide (6138-90-5) + 2-benzoylphloroglucinol (3555-86-0) → phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (70219-87-3, 76015-48-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;	42%

allyl iodid (556-56-9) + 2-benzoylphloroglucinol (3555-86-0) → (3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone (1570098-55-3)

Conditions	Yield
Stage #1: 2-benzoylphloroglucinol With potassium hydroxide In water at 20℃; Inert atmosphere; Stage #2: allyl iodid In water at 20 - 60℃; for 0.666667h; Inert atmosphere; Stage #3: With 1.3-propanedithiol In water at 60℃; for 0.0833333h; Inert atmosphere;	36%

2-benzoylphloroglucinol (3555-86-0) + ethyl propanoylacetate (4949-44-4) → 6-benzoyl-4-ethyl-5,7-dihydroxy-2H-chromen-2-one (1313524-58-1)

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 2h; Pechmann reaction;	27%

3,7-dimethyl-2,6-octadienal (141-27-5) + 2-benzoylphloroglucinol (3555-86-0) → [5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-6-yl]phenylmethanone (933983-29-0) + [5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-8-yl]phenylmethanone (933997-22-9, 163634-65-9)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0℃; for 6h;	A 11% B 26%

dimethylallyl diphosphate (358-72-5) + 2-benzoylphloroglucinol (3555-86-0) → C23H26O4 + phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (93796-20-4)

Conditions	Yield
With Aspergillus terreus aromatic prenyltransferase; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 2h; pH=7.5; Enzymatic reaction;	A 5.29% B 22.06%

2-benzoylphloroglucinol (3555-86-0) + allyl bromide (106-95-6) → (3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone (1570098-55-3)

Conditions	Yield
With potassium hydroxide In water at 0 - 20℃; for 1.33333h; Inert atmosphere;	22%

2-benzoylphloroglucinol (3555-86-0) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 6-benzoyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one (213834-81-2)

Conditions	Yield
With sulfuric acid; acetic acid In nitrobenzene at 20℃; for 2h; Pechmann reaction;	15%

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 100-47-0 benzonitrile 
• 93-99-2 benzoic acid phenyl ester 
• 83-30-7 acide 2,4,6-trihydroxybenzoique 
• 71-43-2 benzene 
• 3770-80-7 2,4,6-trimethoxybenzophenone 
• 98-88-4 benzoyl chloride 
• 6756-74-7 S-benzoyl coenzyme A 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 4809-02-3 7-Phenyl-3.5.7-trioxo-heptansaeure 
• 1469-95-0 1-phenylhexane-1,3,5-trione 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 621-23-8 1,2,3-trimethoxybenzene 
• 14210-97-0 1,4-dibenzoyloxybenzene 

Downstream Products

• 24258-38-6 2-oxo-4-phenyl-2H-chromene-5,7-diyl diacetate 
• 70219-83-9 2,6-dihydroxy-4-prenyloxybenzophenone 
• 70219-84-0 phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone 
• 83611-02-3 6-Benzoyl-5-hydroxy-2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-benzo<1,2-b:3,4-b'>dipyran 
• 83611-04-5 6-benzoyl-5,7-dihydroxy-2,2-dimethyl-3-(3-methylbut-2-enyl)chroman 
• 93796-20-4 phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone 
• 93796-19-1 8-benzoyl-5,7-dihydroxy-2,2-dimethyl-3-(3-methylbut-2-enyl)chroman 
• 93796-21-5 2-benzoyl-3,5-dihydroxy-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 
• 93796-22-6 4-benzoyl-3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 
• 80472-57-7 5,7-dihydroxy-3,4-diphenyl-coumarin 
• 93-58-3 benzoic acid methyl ester 
• 93796-23-7 2,4,6-trihydroxy-3-isopentylbenzophenone 
• 93796-30-6 2-benzoyl-3,5-dihydroxy-6-isopentyl-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 
• 93796-31-7 6-benzoyl-3,5-dihydroxy-2-isopentyl-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 

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In this study, an effective route to synthesize fluorine-containing prenylated benzophenones was developed. Friedel–Crafts acylation and electrophilic aromatic substitution reactions were the key reactions of this synthesis to achieve these fluorinated prenylated benzophenones. The use of DBU in the prenylation step achieved only the C-prenylated benzophenones, whereas K2CO3 produced the C- and O-prenylated benzophenones.

The Natural Product Elegaphenone Potentiates Antibiotic Effects against Pseudomonas aeruginosa

Natural products represent a rich source of antibiotics that address versatile cellular targets. The deconvolution of their targets via chemical proteomics is often challenged by the introduction of large photocrosslinkers. Here we applied elegaphenone, a largely uncharacterized natural product antibiotic bearing a native benzophenone core scaffold, for affinity-based protein profiling (AfBPP) in Gram-positive and Gram-negative bacteria. This study utilizes the alkynylated natural product scaffold as a probe to uncover intriguing biological interactions with the transcriptional regulator AlgP. Furthermore, proteome profiling of a Pseudomonas aeruginosa AlgP transposon mutant provided unique insights into the mode of action. Elegaphenone enhanced the elimination of intracellular P. aeruginosa in macrophages exposed to sub-inhibitory concentrations of the fluoroquinolone antibiotic norfloxacin.