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Deoxyarbutin
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Name

Deoxyarbutin

 EINECS 1308068-626-2
CAS No. 53936-56-4 Density 1.174 g/cm3
PSA 38.69000 LogP 2.29760
Solubility N/A Melting Point 83-88℃
Formula C11H14O3 Boiling Point 349.779 °C at 760 mmHg
Molecular Weight 194.23 Flash Point 165.341 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 53936-56-4 (Deoxyarbutin) Hazard Symbols N/A
Synonyms

4-(Tetrahydro-2H-pyran-2-yloxy)phenol;

Article Data 22

Deoxyarbutin Synthetic route

53936-79-1

4-benzyloxyphenyl 2-tetrahydropyranyl ether

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
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%
134142-87-3

2-(4-Acetoxyphenoxy)tetrahydropyran

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
With sodium perborate In methanol at 25℃; for 0.25h;84%
110-87-2

3,4-dihydro-2H-pyran

123-31-9

hydroquinone

A

2139-44-8

2-(4-(tetrahydro-2H-pyran-2-yloxy)phenoxy)tetrahydro-2H-pyran

B

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
With iron(III) sulfate In acetone for 1h;A 12%
B 72%
With aluminium trichloride
110-87-2

3,4-dihydro-2H-pyran

123-31-9

hydroquinone

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
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%
36637-44-2

(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

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

2-(4-allyloxy-phenoxy)-tetrahydro-pyran

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
With sodium acetate; nickel In N,N-dimethyl-formamide for 18h; Ambient temperature;25%
103-16-2

4-Benzyloxyphenol

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
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
110-87-2

3,4-dihydro-2H-pyran

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions
ConditionsYield
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
777078-65-6

6-(2-acryloyloxyethoxy)capronic acid

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

1187579-83-4

C22H30O7

Conditions
ConditionsYield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide In chloroform at 20℃; Inert atmosphere; Cooling with ice;94%
2009-83-8

6-chloro-1-hexanol

53936-56-4

4-(tetrahydro-2H-2-pyranyloxy)phenol

161841-10-7

C17H26O4

Conditions
ConditionsYield
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%

Deoxyarbutin Specification

The Deoxyarbutin with CAS registry number of 53936-56-4 is also known as Phenol,4-[(tetrahydro-2H-pyran-2-yl)oxy]-. The systematic name is 4-(Tetrahydro-2H-pyran-2-yloxy)phenol. In addition, the formula is C11H14O3 and the molecular weight is 194.23.

Physical properties about Deoxyarbutin are: (1)ACD/LogP: 1.50; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 38.69 Å2; (7)Index of Refraction: 1.552; (8)Molar Refractivity: 52.841 cm3; (9)Molar Volume: 165.414 cm3; (10)Polarizability: 20.948×10-24cm3; (11)Surface Tension: 46.085 dyne/cm; (12)Density: 1.174 g/cm3; (13)Flash Point: 165.341 °C; (14)Enthalpy of Vaporization: 61.778 kJ/mol; (15)Boiling Point: 349.779 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. SMILES: O(c1ccc(O)cc1)C2OCCCC2
2. InChI: InChI=1/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
3. InChIKey: GFBCWCDNXDKFRH-UHFFFAOYAE
4. Std. InChI: InChI=1S/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
5. Std. InChIKey: GFBCWCDNXDKFRH-UHFFFAOYSA-N

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