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497-76-7

Basic Information
CAS No.: 497-76-7
Name: Arbutin
Article Data: 38
Molecular Structure:
Molecular Structure of 497-76-7 (Arbutin)
Formula: C12H16O7
Molecular Weight: 272.255
Synonyms: .beta.-D-Glucopyranoside, 4-hydroxyphenyl;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;Arbutoside;Hydroquinone beta-D-glucopyranoside;2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;beta-D-Glucopyranoside, 4-hydroxyphenyl- (9CI);hexopyranoside, 4-hydroxyphenyl;(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;beta-Arbutin;Ursin;Uvasol;4-hydroxyphenyl hexopyranoside;4-Hydroxyphenyl-beta-D-glucopyranoside;p-Hydroxyphenyl beta-D-glucopyranoside;(3R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;4-Hydroxyphenyl beta-D-glucopyranoside;4-hydroxyphenyl β-D-glucopyranoside;β-Arbutin;4-Hydroxyphenyl-β-D-glucopyranoside;
EINECS: 207-850-3
Density: 1.556 g/cm3
Melting Point: 195-198 °C
Boiling Point: 561.583 °C at 760 mmHg
Flash Point: 293.435 °C
Solubility: 10-15 g/100 mL at 20 °C in water
Appearance: White needle crystal or powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 22-24/25-36-26
PSA: 119.61000
LogP: -1.42910
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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

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: 199-201oC
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 20oC
Sensitive: Hygroscopic
Merck: 14,773
BRN: 89673
Product Categories: Biochemistry; Glucose; Glycosides; Sugars; Natural Plant Extract

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.

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.

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: HarmfulXn
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

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.