Arbutin supplier | CasNO.497-76-7

Name
Arbutin
EINECS 207-850-3
CAS No. 497-76-7
Article Data38
CAS DataBase
Density 1.556 g/cm³
Solubility 10-15 g/100 mL at 20 °C in water
Melting Point 195-198 °C
Formula C₁₂H₁₆O₇
Boiling Point 561.583 °C at 760 mmHg
Molecular Weight 272.255
Flash Point 293.435 °C
Transport Information
Appearance White needle crystal or powder
Safety 22-24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
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;
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

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%

...Expand

: 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

: 133-89-1
UDP-glucose

: 123-31-9
hydroquinone

: 497-76-7
arbutin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In methanol for 2h; Heating;	A 76 mg B 191 mg

: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

: 123-31-9
hydroquinone

emulsin: emulsin

: 497-76-7
arbutin

...Expand

: 2444-19-1
4-hydroxyphenyl benzoate

: 497-76-7
arbutin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 492-61-5
β-D-glucose

: 497-76-7
arbutin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With arbutin synthase (Q9AR73.1) from Rauvolfia serpentina Reagent/catalyst; Enzymatic reaction;

: 7400-08-0
p-Coumaric Acid

: 497-76-7
arbutin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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.

Product Name

Arbutin

Synthetic route

Arbutin Chemical Properties

Arbutin Uses

Arbutin Production

Arbutin Safety Profile

Arbutin Specification

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