53936-56-4

Basic information

• Product Name: Deoxyarbutin
• Synonyms: Deoxyarbutin;4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenol;Tetrahydropyranyloxyphenol;Phenol,4-[(tetrahydro-2H-pyran-2-yl)oxy]-;Deoxyarbutin 4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenol
• CAS NO: 53936-56-4
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.22706
• EINECS: 1308068-626-2
• Product Categories: Cosmetics;Inhibitors
• Mol File: 53936-56-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 88-89 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 349.779 °C at 760 mmHg
• Flash Point: 165.341 °C
• Appearance: /
• Density: 1.174
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 10.10±0.15(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Deoxyarbutin(CAS DataBase Reference)
• NIST Chemistry Reference: Deoxyarbutin(53936-56-4)
• EPA Substance Registry System: Deoxyarbutin(53936-56-4)

Safety Data

• Hazardous Substances Data: 53936-56-4(Hazardous Substances Data)

Usage

Description

Deoxyarbutin is a tyrosinase inhibitor (IC50 = 17.5 μM for mushroom tyrosinase). It reduces melanin content in isolated dark human melanocytes when used at a concentration of 1.56 μM. Topical administration of deoxyarbutin (5%) induces skin lightening in human skin mouse xenograft models. Deoxyarbutin also inhibits proliferation of B16/F10 murine melanoma cells (EC50 = 39.56 μM). It induces apoptosis and halts the cell cycle at the S phase in B16/F10 cells when used at a concentration of 50 μM. Deoxyarbutin (50 mg/kg) reduces tumor growth in a B16/F10 murine melanoma model.

Uses

Deoxyarbutin acts as a skin whitening agent through the inhibition of tyrosinase. A safer alternative to the use of hydroquinone and arbutin.

Preparation

Deoxyarbutin is a derivative of ?-arbutin, obtained by removal of hydroxyl groups from the glucose side-chain of ?-arbutin.

Synthetic route

4-benzyloxyphenyl 2-tetrahydropyranyl ether (53936-79-1) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; under 3000.3 Torr; for 3h; Autoclave;	100%
With aluminum oxide; hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; Product distribution / selectivity;	82%
With hydrogen; calcium carbonate; palladium on activated charcoal In ethyl acetate at 20℃; Product distribution / selectivity;	80%

2-(4-Acetoxyphenoxy)tetrahydropyran (134142-87-3) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With sodium perborate In methanol at 25℃; for 0.25h;	84%

3,4-dihydro-2H-pyran (110-87-2) + hydroquinone (123-31-9) → 2-(4-(tetrahydro-2H-pyran-2-yloxy)phenoxy)tetrahydro-2H-pyran (2139-44-8) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With iron(III) sulfate In acetone for 1h;	A 12% B 72%
With aluminium trichloride

3,4-dihydro-2H-pyran (110-87-2) + hydroquinone (123-31-9) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With ruthenium(III) acetate at 20℃; for 12h;	72%
With pyridinium p-toluenesulfonate In dichloromethane at 10 - 25℃; for 16h; Inert atmosphere;	52.7%
With pyridinium p-toluenesulfonate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	49.6%

(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide (36637-44-2) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With air In tetrahydrofuran at -25℃; under 12929 Torr; for 0.0566667h; Green chemistry;	64%

2-(4-allyloxy-phenoxy)-tetrahydro-pyran → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
With sodium acetate; nickel In N,N-dimethyl-formamide for 18h; Ambient temperature;	25%

4-Benzyloxyphenol (103-16-2) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / 20 °C / Inert atmosphere; Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 20 °C / 3000.3 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 20 °C / Inert atmosphere; Cooling with ice 2: pyridine; 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 50 °C / 3750.38 Torr View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 7 h / 20 °C / Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h / 50 °C / 3750.38 Torr View Scheme

3,4-dihydro-2H-pyran (110-87-2) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / 20 °C / Inert atmosphere; Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 20 °C / 3000.3 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 20 °C / Inert atmosphere; Cooling with ice 2: pyridine; 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 50 °C / 3750.38 Torr View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 7 h / 20 °C / Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h / 50 °C / 3750.38 Torr View Scheme

6-(2-acryloyloxyethoxy)capronic acid (777078-65-6) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C22H30O7 (1187579-83-4)

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide In chloroform at 20℃; Inert atmosphere; Cooling with ice;	94%

6-chloro-1-hexanol (2009-83-8) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C17H26O4 (161841-10-7)

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at 90 - 100℃; Inert atmosphere;	91%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;	91%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	84.9%

N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)propanamide

Conditions	Yield
With potassium carbonate In isopropyl alcohol for 3h; Reflux;	91%

phosphonic acid diethyl ester (762-04-9) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → O,O-diethyl O-4-tetrahydro-2H-2-pyranyloxyphenyl phosphate (866927-59-5)

Conditions	Yield
With triethylamine In tetrachloromethane	88%

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) + 3-(4-bromobutoxy)oxetane (202982-89-6) → 2-{4-[4-(oxetan-3-yloxy)-butoxy]-phenoxy}-tetrahydro-pyran (202983-46-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Etherification;	87%

poly(methacrylic acid) (79-41-4) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C15H18O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 16h; Inert atmosphere; Cooling with ice;	83.6%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 7h; Inert atmosphere; Cooling with ice;	9 g

4-Methyl-1-pentanol (626-89-1) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → 2-[4-{(4-methylpentyl)oxy}phenoxy]tetrahydropyran

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	78%

3-bromo-2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene 1-oxide (847386-22-5) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → 2-(4-fluorophenyl)-6-methoxy-3-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)benzo[b]thiophene-1-oxide

Conditions	Yield
Stage #1: 4-(tetrahydro-2H-2-pyranyloxy)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: 3-bromo-2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene 1-oxide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	75%

C27H16ClNO4 + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C38H29NO7

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 3h;	75%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C16H16O4

Conditions	Yield
Stage #1: 2-chloromethyl-3-chloroprop-1-ene; 4-(tetrahydro-2H-2-pyranyloxy)phenol With sodium hydride In N,N-dimethyl-formamide Substitution; Stage #2: In ethanol alcoholysis; acidic solution;	74%

1-bromo-butane (109-65-9) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C15H22O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 16h;	56%

ethylene dibromide (106-93-4) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → 2-(4-(2-bromoethoxy)phenoxy)tetrahydro-2H-pyran

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 24h; Reflux;	46%
In tetrahydrofuran for 24h; Reflux; Alkaline conditions;

chloroform (67-66-3) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → 2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde

Conditions	Yield
With sodium hydroxide In ethanol at 70℃; for 3h; Reimer-Tiemann reaction;	41%

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) + 2-bromoethanol (540-51-2) → 2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)ethanol (777084-12-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	32%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; for 4h;

N-(6’-fluoro-2-methyl-5‘-morpholino-[3,3‘-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → N-(2-methyl-5'-morpholino-6'-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)-[3,3'-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide

Conditions	Yield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 15 - 140℃; for 2h; Microwave irradiation;	29%

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) + 3-(2-chloromethylphenoxy)-2-(2-chloromethylphenoxymethyl)propene → C40H44O8

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 70℃; Alkylation;

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) + chloromethyl polystyrene resin → chloromethyl polystyrene resin derivatized with quinol monotetrahydropyranyl ether

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 55℃; for 16h;	111.5 g

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → 4,13-dimethylene-2,6,11,15-tetraoxa-tricyclo[14.2.2.27,10]docosa-1(19),7(22),8,10(21),16(20),17-hexaene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 1 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C40H40O8

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 24 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C60H60O12

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 4 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → TIMEOUT: 5s

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 4 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C30H28O6

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 70 °C 2: H3O+ / ethanol View Scheme

4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C48H44O8

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / dimethylformamide / 70 °C 2: H3O+ / ethanol 3: 38 percent / NaH / dimethylformamide / 70 °C View Scheme

4-[4-(3-ethyloxetane-3-ylmethoxy)butyloxy]benzoic acid (503474-64-4) + 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4) → C23H28O6 (677033-32-8)

Conditions	Yield
Stage #1: 4-[7-(3-ethyl-3-oxetanyl)-1,6-dioxaheptyl]benzoic acid; 4-(tetrahydro-2H-2-pyranyloxy)phenol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 123-31-9 hydroquinone 
• 103-16-2 4-Benzyloxyphenol 
• 36637-44-2 (4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide 
• 134142-87-3 2-(4-Acetoxyphenoxy)tetrahydropyran 
• 53936-79-1 4-benzyloxyphenyl 2-tetrahydropyranyl ether 

Downstream Products

• 777084-12-5 2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)ethanol 
• 1352299-25-2 4-[2-(2-azidoethoxy)ethoxy]phenol 
• 1352299-26-3 methyl 2,3,4-tri-O-benzyl-6-O-{4-[2-(2-azidoethoxy)ethoxy]phenyl}-α-D-glucopyranoside 
• 1352299-27-4 methyl 2,3,4-tri-O-benzyl-6-O-{4-[2-(2-(tridecafluorohexanecarboxamido)ethoxy)ethoxy]phenyl}-α-D-glucopyranoside 
• 1435950-96-1 C₃₃H₄₁NO₈ 
• 1435950-97-2 C₂₃H₂₅NO₆ 
• 1092853-38-7 3-(4-hydroxyphenoxy)propyl acrylate 

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