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497-76-7

Basic Information
CAS No.: 497-76-7
Name: Arbutin
Molecular Structure:
Molecular Structure of 497-76-7 (Arbutin)
Formula: C12H16O7
Molecular Weight: 272.25 .
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
Transport Information:
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
133-89-1

UDP-glucose

123-31-9

hydroquinone

497-76-7

arbutin

Conditions
ConditionsYield
in Gegenwart eines Enzym-Praeparats aus Weizenkeimen;
With arbutin synthase Product distribution; Further Variations:; Reaction partners; Reagents; Enzymatic reaction;
123-31-9

hydroquinone

497-76-7

arbutin

Conditions
ConditionsYield
biotransformation with Rauwolfia cell culture;

(E)-(R)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-(4-acetoxy-phenoxy)-tetrahydro-pyran-2-ylmethyl ester

A

83945-54-4

(6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid

B

497-76-7

arbutin

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Heating;A 76 mg
B 191 mg
2444-19-1

4-hydroxyphenyl benzoate

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: quinoline; silver oxide
2: ammonia; methanol
View Scheme
56401-20-8

α-D-Glucopyranoside 1-(disodium phosphate)

123-31-9

hydroquinone

497-76-7

arbutin

Conditions
ConditionsYield
With cellobiose phosphorylase from Clostridium thermocellum In ethyl acetate at 50℃; for 48h; pH=6.5; Solvent; Enzymatic reaction;
492-62-6

alpha-D-glucopyranose

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium acetate / 4 h / 100 - 130 °C / 760.05 Torr / Large scale
2.1: triethylamine; boron trifluoride diethyl etherate / dichloromethane; toluene / 11 h / 30 - 40 °C / 760.05 Torr / Inert atmosphere; Large scale
2.2: 2 h / 15 - 20 °C / Large scale
3.1: methanol; sodium methylate / 2 h / 50 °C / Large scale
View Scheme

C21H22O10

A

22805-46-5

1-(4-hydroxyphenyl)-1,3-propanediol

B

497-76-7

arbutin

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0 - 20℃;A 2 mg
B 1 mg
50-99-7

D-glucose

71-43-2

benzene

A

123-31-9

hydroquinone

B

497-76-7

arbutin

Conditions
ConditionsYield
With arbutin synthase from Rauvolfia serpentina; cytochrome P450-BM3 monooxygenase from Bacillus megaterium A82F/V78F/A328F triple mutant In aq. phosphate buffer at 30℃; for 5h; pH=8;
492-61-5

β-D-glucose

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Prunus dulcis var. amara β-glucoside glucohydrolase, 68 kDa / aq. phosphate buffer / 70 h / 50 °C / pH 6 / Enzymatic reaction
2: Prunus dulcis var. amara β-glucoside glucohydrolase, 68 kDa / aq. phosphate buffer; tert-butyl alcohol / 24 h / 50 °C / pH 7 / Enzymatic reaction
View Scheme
604-69-3

β-D-glucose pentaacetate

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 10 h / 0 - 50 °C
2: sodium methylate; methanol / 5 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 10 h / 0 - 50 °C
2: sodium methylate; methanol / 5 h / 80 °C
View Scheme
99-96-7

4-hydroxy-benzoic acid

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
2: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
492-61-5

β-D-glucose

123-31-9

hydroquinone

497-76-7

arbutin

Conditions
ConditionsYield
With arbutin synthase (Q9AR73.1) from Rauvolfia serpentina Reagent/catalyst; Enzymatic reaction;
7400-08-0

p-Coumaric Acid

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NADH / aq. phosphate buffer / 8 h / 37 °C / pH 7.0 / Enzymatic reaction
2: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1.1: feruloyl-CoA synthetase / Enzymatic reaction
1.2: Enzymatic reaction
2.1: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
3.1: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
4.1: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1: E. coli (pET28a-TtAdo-BLPad) / aq. phosphate buffer / 6 h / 37 °C / pH 7.0 / Enzymatic reaction
2: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
3: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
4: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
Multi-step reaction with 5 steps
1: Bacillus licheniformis strain CGMCC 7172 phenolic acid decarboxylase / 6 h / Enzymatic reaction
2: oxygen; Thielavia terrestris NRRL 8126 aromatic dioxygenase TtAdo (XP_003653923) / 37 °C / pH 7.0 / Enzymatic reaction
3: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
4: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
5: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
2628-17-3

4-Vinylphenol

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: oxygen; Thielavia terrestris NRRL 8126 aromatic dioxygenase TtAdo (XP_003653923) / 37 °C / pH 7.0 / Enzymatic reaction
2: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
3: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
4: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
123-08-0

4-hydroxy-benzaldehyde

497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: vanillin dehydrogenase from genom of Pseudomonas putida KT2440 (NC_002947.4) / Enzymatic reaction
2: 4-hydroxybenzoate 1-hydroxylase MNX1 from yeast Candida parapsilosis strain CDC317 / 2 h / Enzymatic reaction
3: arbutin synthase (Q9AR73.1) from Rauvolfia serpentina / Enzymatic reaction
View Scheme
106-95-6

allyl bromide

497-76-7

arbutin

848940-03-4

(2S,3R,4S,5S,6R)-2-(4-Allyloxy-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;100%
Stage #1: arbutin With sodium hydroxide
Stage #2: allyl bromide In N,N-dimethyl-formamide for 24h;
99%
54519-07-2

vinyl ester of 3-phenylpropionic acid

497-76-7

arbutin

1277161-57-5

6'-O-(3-phenylpropionyl)arbutin

Conditions
ConditionsYield
With immobilized lipase from Penicillium expansum In tetrahydrofuran at 50℃; for 4h; Enzymatic reaction; regioselective reaction;93%
108-05-4

vinyl acetate

497-76-7

arbutin

10338-88-2

6'-O-acetylarbutin

Conditions
ConditionsYield
With CSL lipase In tetrahydrofuran at 60℃; for 2.5h; Temperature; Reagent/catalyst; Microwave irradiation;92.5%
76-83-5

trityl chloride

497-76-7

arbutin

180297-88-5

6-O-triphenylmethylarbutin

Conditions
ConditionsYield
With pyridine at 20℃; for 23h; tritylation;91%
112-38-9

10-undecenoic acid

497-76-7

arbutin

6-O-ω-undecylenoyl p-hydroxyphenyl β-D-glucopyranoside

Conditions
ConditionsYield
Candida antarctica-derived lipase In 1,4-dioxane; dimethyl sulfoxide at 40℃; for 168h; Product distribution / selectivity; Molecular sieve;91%
Candida antarctica-derived lipase In 1,4-dioxane at 40℃; for 168h; Product distribution / selectivity; Molecular sieve;
95063-02-8

vinyl ester of 4-phenylbutyric acid

497-76-7

arbutin

1277161-61-1

6'-O-(4-phenylbutyryl)arbutin

Conditions
ConditionsYield
With immobilized lipase from Penicillium expansum In tetrahydrofuran at 50℃; for 5h; Enzymatic reaction; regioselective reaction;91%
1186473-08-4

vinyl ester of 5-phenylvaleric acid

497-76-7

arbutin

1277161-64-4

6'-O-(5-phenylvaleryl)arbutin

Conditions
ConditionsYield
With immobilized lipase from Penicillium expansum In tetrahydrofuran at 50℃; for 5.5h; Enzymatic reaction; regioselective reaction;90%
17719-70-9, 3098-92-8

cinnamic acid vinyl ester

497-76-7

arbutin

221688-07-9

6'-O-cinnamoyl-arbutin

Conditions
ConditionsYield
With immobilized lipase from Penicillium expansum In tetrahydrofuran at 50℃; for 68h; Enzymatic reaction; regioselective reaction;88%
18120-64-4

vinyl ester of phenylacetic acid

497-76-7

arbutin

1277161-53-1

6'-O-phenylacetyl-arbutin

Conditions
ConditionsYield
With immobilized lipase from Penicillium expansum In tetrahydrofuran at 50℃; for 72h; Enzymatic reaction; regioselective reaction;87%
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  • Casno:

    497-76-7

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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.