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Name Arbutin
EINECS207-850-3
CAS No. 497-76-7
Density1.556 g/cm³
PSA119.61000
LogP-1.42910
Solubility10-15 g/100 mL at 20 °C in water
Melting Point195-198 °C
FormulaC₁₂H₁₆O₇
Boiling Point561.583 °C at 760 mmHg
Molecular Weight272.255
Flash Point293.435 °C
Transport InformationN/A
AppearanceWhite needle crystal or powder
Safety22-24/25-36-26
Risk Codes20/21/22-36/37/38
Molecular Structure
Hazard SymbolsXn
SynonymsXn
Article Data38

Arbutin Synthetic route

: 6129-66-4, 124431-77-2, 125095-10-5, 125095-11-6, 142393-05-3
4-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 497-76-7
arbutin

Conditions

Conditions	Yield
With ammonia; water In methanol Microwave irradiation;	99%
Stage #1: 4-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside With sodium methylate In methanol for 4h; Heating / reflux; Stage #2: With acetic acid In methanol for 0.5h; AcOH was added after cooling; Stirring;	80%
With methanol; sodium methylate
Multi-step reaction with 2 steps 1: acetic anhydride / toluene / 1.5 h / 60 °C 2: ammonium chloride / water / 2 h / 70 °C View Scheme
With methanol; sodium methylate at 80℃; for 5h;

: pentaacetate arbutin

: 497-76-7
arbutin

Conditions

Conditions	Yield
With methanol; sodium methylate at 50℃; for 2h; Large scale;	95.2%

: 2872-65-3, 14581-81-8, 17042-40-9, 84380-06-3, 105260-62-6
p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 497-76-7
arbutin

Conditions

Conditions	Yield
With copper(I) oxide; sodium methylate In methanol at 0 - 80℃; for 4h;	95%

: 492-61-5
β-D-glucose

: 7400-08-0
p-Coumaric Acid

: 497-76-7
arbutin

Conditions

Conditions	Yield
With SArbutin 5 In aq. phosphate buffer at 37℃; for 24h; pH=7.0;	92%

: 123-31-9
hydroquinone

: 2816-24-2
2-nitrophenyl β-D-glucopyranoside

: 497-76-7
arbutin

Conditions

Conditions	Yield
With Na acetate buffer; butan-1-ol for 8h; β-glucuronidase from bovine liver;	91.2%

: 14698-56-7
4-acetoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 497-76-7
arbutin

Conditions

Conditions	Yield
With ammonium chloride In water at 70℃; for 2h; Concentration;	90%
With di(n-butyl)tin oxide In methanol for 8h; Heating;	87.7%
Stage #1: 4-acetoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside With sodium methylate In methanol for 4h; Heating / reflux; 28% NaOMe; Stage #2: With acetic acid In methanol for 0.5h; AcOH was added after cooling; Stirring;	81%

: 50-99-7
D-glucose

: 123-31-9
hydroquinone

A: 497-76-7
arbutin

B: 497-76-7, 84380-01-8, 90706-69-7, 125095-12-7, 125095-13-8
4-hydroxyphenyl α-D-glucopyranoside

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dimethyl sulfoxide at 100℃; for 10h;	A 4% B 11%

: 123-31-9
hydroquinone

: 59-56-3
α-D-glucopyranosyl-1-phosphate

: 497-76-7
arbutin

Conditions

Conditions	Yield
With recombinant cellobiosephosphorylase from C. thermocellum In ethyl acetate at 50℃; for 48h; pH=6.5; Enzymatic reaction;	1.6%

: 123-31-9
hydroquinone

: 5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7
n-butyl β-D-glucopyranoside

: 497-76-7
arbutin

Conditions

Conditions	Yield
With Prunus dulcis var. amara β-glucoside glucohydrolase, 68 kDa In aq. phosphate buffer; tert-butyl alcohol at 50℃; for 24h; pH=7; Enzymatic reaction;	0.14%

: 380153-99-1
4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate

: 497-76-7
arbutin

Conditions

Conditions	Yield
With methanol; ammonia

Arbutin Chemical Properties

IUPAC Name: 2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
CAS: 497-76-7
Molecular formula: C₁₂H₁₆O₇
Molecular Weight: 272.25
EINECS: 207-850-3
Density: 1.556g/cm³
Melting Point: 199-201^oC
H bond acceptors: 7
H bond donors: 5
Freely Rotating Bonds: 8
Polar Surface Area: 119.61Å²
Index of Refraction: 1.65
Molar Refractivity: 63.84 cm³
Molar Volume: 174.9 cm³
Surface Tension: 73.4 dyne/cm
Flash Point: 293.4 °C
Enthalpy of Vaporization: 88.85 kJ/mol
Boiling Point: 561.6 °C at 760 mmHg
Vapour Pressure: 1.9E-13 mmHg at 25°C
Water Solubility: 10-15g/100 mL at 20^oC
Sensitive: Hygroscopic
Merck: 14,773
BRN: 89673
Product Categories: Biochemistry; Glucose; Glycosides; Sugars; Natural Plant Extract

Arbutin Uses

Arbutin (CAS NO.497-76-7) was found to have depigmenting action in human melanocytes in culture. It can inhibit tyrosinase and thus prevents the formation of melanin. So it is used as a skin-lightening agent.It has also been used as food addition agent.

Arbutin Production

Arbutin (CAS NO.497-76-7) is extracted from bearberry plant in the genus Arctostaphylos. It is present in the leaves of bearberry, blueberry, cranberry and pear. It is also found in wheat, and is concentrated in pear skins.

Arbutin Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Harmful Xn
Risk Statements: 20/21/22-36/37/38
20/ 21/22(Harmful by inhalation,in contact with skin and if swallowed)
36/37/38 (Irritating to the eyes piratory system and skin)
Safety Statements: 22-24/25-36-26
22(Do not breathe dust)
24/25(Avoid contact with skin and eyes)
36(Wear suitable protective clothing)
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3
RTECS: CE8863000
F: 3-10-23

Arbutin Specification

Arbutin , with CAS number of 497-76-7, can be called (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol ; Arbutoside ; Hydroquinone-O-beta-D-glucopyranoside ; Hydroquinone .beta.-D-glucopyranoside ; p-Hydroxyphenyl beta-D-glucoside ; 4-Hydroxyphenyl-beta-D-glucopyranoside . Arbutin (CAS NO.497-76-7) should be stored in a cool, dry place with a tightly closed container.

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Product Name

Arbutin

Arbutin Synthetic route

Arbutin Chemical Properties

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Arbutin Production

Arbutin Safety Profile

Arbutin Specification

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