2196-18-1

Basic information

• Product Name: α,4'-Dihydroxy-3'-methoxypropiophenone
• Synonyms: 4-(2-Hydroxypropionyl)-2-methoxyphenol;α,4'-Dihydroxy-3'-methoxypropiophenone;1-(3-Methoxy-4-hydroxyphenyl)-3-hydroxypropane-1-one;1-(4-Hydroxy-3-methoxyphenyl)-3-hydroxy-1-propanone;3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone;4-(3-Hydroxypropionyl)-2-methoxyphenol;β-Hydroxypropiovanillone;beta-Hydroxypropiovanillone
• CAS NO: 2196-18-1
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.1999
• Mol File: 2196-18-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 408.2°Cat760mmHg
• Flash Point: 165.4°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 2.14E-07mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: α,4'-Dihydroxy-3'-methoxypropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: α,4'-Dihydroxy-3'-methoxypropiophenone(2196-18-1)
• EPA Substance Registry System: α,4'-Dihydroxy-3'-methoxypropiophenone(2196-18-1)

Safety Data

• Hazardous Substances Data: 2196-18-1(Hazardous Substances Data)

Usage

General Description

α,4'-Dihydroxy-3'-methoxypropiophenone, also known as dihydroxypropiophenone, is a naturally occurring chemical compound found in certain plant species. It is a phenolic compound with two hydroxy groups and one methoxy group attached to a propiophenone backbone. This chemical has been studied for its potential antioxidant, anti-inflammatory, and anti-cancer properties. It may also have potential as a natural preservative in food and cosmetic products.α,4'-Dihydroxy-3'-methoxypropiophenone is of interest to researchers for its potential applications in various fields and for its role in the biochemistry and pharmacology of plants.

InChI:InChI=1/C10H12O4/c1-14-10-6-7(2-3-9(10)13)8(12)4-5-11/h2-3,6,11,13H,4-5H2,1H3

Synthetic route

3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (7182-42-5) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
With sodium hydroxide In water at 20 - 65℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; Industrial scale;	100%

β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone (22317-34-6) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere;	A 99% B 96%
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;	A 69% B 74%

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + 2-methoxy-phenol (90-05-1) + 1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2)

Conditions	Yield
With oxygen; rose bengal In acetonitrile at 13℃; Irradiation;	A 28 % Chromat. B 15 % Chromat. C 30 % Chromat.

3-acetoxy-1-<4-hydroxy-3-methoxy-phenyl>-propanone-(1) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
With water; barium carbonate

3-bromo-1-<4-hydroxy-3-methoxy-phenyl>-propanone-(1) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
With sodium hydroxide

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 69 percent / Br2 / CHCl3; CCl4 / 1) 5 deg C, 20 min, 2) 5 deg C -> 40 deg C, 2 h 2: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 3: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 4: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 5: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone (22317-34-6) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 2: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

3-methoxy-4-benzyloxy-α-bromoacetophenone (1835-12-7) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 2: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 3: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 4: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one (22317-29-9) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxygen; N-hydroxyphthalimide / acetone / 30 h / 20 °C / 760.05 Torr / Irradiation 2: N-ethyl-N,N-diisopropylamine; formic acid / acetonitrile / 24 h / 20 °C / Inert atmosphere; Irradiation View Scheme

pinoresinol (7452-03-1) → 3,4-Dihydroxybenzoic acid (99-50-3) + 3-methoxy-4-hydroxybenzoic acid (121-34-6) + 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1)

Conditions	Yield
With potassium superoxide; sphingobacterium sp. T2 manganese superoxide dismutase In dimethyl sulfoxide for 1h; pH=7.8; Inert atmosphere; Enzymatic reaction;

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → coniferol (458-35-5) + 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + 1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one (2983-65-5) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
With 4ZnS*In2S3 In water; acetonitrile for 20h; Inert atmosphere; UV-irradiation;

1-(4-hydroxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (56122-34-0) → 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + 1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one (2983-65-5) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
With 4ZnS*In2S3 In water; acetonitrile for 16h; Inert atmosphere; UV-irradiation;

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → 3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (7182-42-5)

Conditions	Yield
With hydrogenchloride at 90℃; for 0.5h;	96%

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propanol (3063-86-3)

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In water at 26℃; for 24h;	79%
With lithium aluminium tetrahydride In diethyl ether

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) + acetic anhydride (108-24-7) → ω-hydroxypropioguaiacone diacetate (107682-24-6)

Conditions	Yield
In pyridine for 24h; Ambient temperature;	2 mg

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → 3,3-bis(4-hydroxy-3-methoxyphenyl)-1-propanol

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / water / 24 h / 26 °C 2: methanesulfonic acid / water / 22.5 h / 65 °C View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → coniferol (458-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / water / 24 h / 26 °C 2: triethylamine / isopropyl alcohol / 48 h / 85 - 90 °C View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C20H32O4Si + C20H32O4Si

Conditions

Yield

Multi-step reaction with 4 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / toluene / 16 h / -78 °C / Inert atmosphere; Resolution of racemate View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C19H26O5 + C15H20O4 + C19H26O5

Conditions

Yield

Multi-step reaction with 4 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine / toluene / 16 h / -78 °C / Inert atmosphere; Resolution of racemate View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C23H34O5Si

Conditions

Yield

Multi-step reaction with 5 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C19H32O5Si

Conditions

Yield

Multi-step reaction with 7 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C19H30O5Si

Conditions

Yield

Multi-step reaction with 8 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C19H30O6Si

Conditions

Yield

Multi-step reaction with 9 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → C18H31NO4Si

Conditions

Yield

Multi-step reaction with 15 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: sodium acetate; hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C 8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere 9.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere 10.1: thionyl chloride / dichloromethane / 0.75 h / 20 °C / Inert atmosphere 10.2: 1.5 h / Inert atmosphere 11.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere 12.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / -78 °C / Inert atmosphere 13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 13.2: 1 h / Inert atmosphere 14.1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 15.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → 1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)prop-2-en-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (2196-18-1) → 1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)prop-2-en-1-ol (1491173-73-9)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / Inert atmosphere 1.2: 2 h / Inert atmosphere 2.1: dmap; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C / Inert atmosphere View Scheme

Upstream product

• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 7452-03-1 pinoresinol 
• 56122-34-0 3-(4-hydroxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol 
• 22317-34-6 β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone 
• 7182-42-5 3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone 
• 22317-29-9 1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 
• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 

Downstream Products

• 1124-63-6 3-cyclohexylpropan-1-ol 
• 77866-58-1 trans-4-propylcyclohexanol 
• 458-35-5 coniferol 
• 7182-42-5 3-chloro-1-(4-hydroxy-3-methoxyphenyl)-1-propanone 
• 1491173-73-9 1-(4-((tert-butyldimethylsilyl)oxy)-3-methoxyphenyl)prop-2-en-1-ol 
• 2983-65-5 1-(4-hydroxy-3-methoxyphenyl)-2-propene-1-one 

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