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497-76-7

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  • Best price cosmetic raw material pure natural beta and alpha arbutin

    Cas No: 497-76-7

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  • Beta Arbutin skin whitening 497-76-7/84380-01-8 Factory Supply Purity

    Cas No: 497-76-7

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497-76-7 Usage

The ideal whitening agent of whitening cosmetics

Arbutin is an ideal whitening agent of whitening cosmetics. It is also called the hydroquinone glucoside. There are two kinds of optical isomers, namely α and ?. The ? isomer has biological activity. At room temperature, it is white with pale yellow powder. It is soluble in water, methanol, ethanol, propylene glycol and glycerin aqueous solution, and it has no precipitation after dissolved. It is insoluble in chloroform, ether and petroleum ether, etc. Arbutin is always added in a lot of whitening skin care products. Arbutin is named for that it was founded in ericaceae plants of the genus bearberry leaves. Subsequently, it is also founded in the leaves of ericaceae vaccinium bilberry, rosaceae pyrus sand pear (european pear, small yamanashi), saxifragaceae saxifrage and other plants. It is used as drug and cosmetic additives after extracted. Arbutin can whiten skin and medicate freckle effectively. It can gradually reduce and eliminate skin freckles, melasma, hyperpigmentation, acne and age spots. It has higher security and no irritating, allergenic and other side effects. It has good compatibility with cosmetics components and ultraviolet irradiation stability. But arbutin is easily hydrolyzed, and it should be used under conditions of PH 5-7. In order to stabilize the performance, it is typically added an appropriate amount of antioxidants such as sodium bisulfate and vitamin E. Then it can get better effect of whitening, freckle, moisturizer, soft, wrinkle removal, anti-inflammatory. Arbutin can be used to eliminate swelling, promote wound healing without leaving scars. Besides, it also can inhibit the generation of dandruff.

Ursolic acid and α- arbutin

Ursolic acid is a kind of triterpene compounds that exists in the natural plant. It has many kinds of biological effects, like calm, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer and hypoglycaemic. In recent years, it is found that ursolic acid has the effect on resistance to get and promote cancer, and induction to F9 teratoma cell differentiation and anti-angiogenesis. It is likely to be low toxic and efficient new anti-cancer drugs. In addition, ursolic acid has obvious antioxidant function, so it is widely used as pharmaceutical and cosmetic ingredients. α-Arbutin can repair damaged skin that caused by ultraviolet radiation and regain transparency of skin. It is not easy to be decomposed by the β-glycosidase enzymes on the surface of the skin. Its effect is about 10 times of β-arbutin. It can stay for a long time in every corner of the skin, and protect skin from harm. Melanin is the reason for the formation of skin dull. α-Arbutin can rapidly permeate into deep skin, and inhibit the activity of tyrosinase that exists in the depths of the cuticle of chromoplast. Then it forms a dual effect on the surface of the skin, and inhibits the generation of melanin.

Is it suitable for using during the day?

Arbutin can reduce the formation of melanin through inhibiting the activity of the enzyme tyrosinase, which can generate melanin. The action principle is similar to whitening drugs hydroquinone. But hydroquinone has side effects and need so many precautions. Hydroquinone must be used below the doctor's guidance and monitoring. But there is glucose molecule in the structure of arbutin, which is not in hydroquinone. So its irritation is low. It is free to add arbutin to skin care products, and its concentration limit can be up to 7%. Arbutin reactive molecules can penetrate base layer to lighten spots deeply. It has strong therapeutic effect on hyperpigmentation left over by chloasma, black spot, sun spot, drug allergy. But if its concentration is low, then the effect of persistence will be weakened. So, 5% is the safest and most efficient concentration to lighten spot. When its concentration is 5%, its effect is faster than vitamin C, and more persistent and stable. More important, it won't produce irritating effect on the skin. Arbutin is absorbed by the skin and reduced to hydroquinone, which raises some doubts about the safety of arbutin. They think that arbutin may have a chance to produce side effects similar to hydroquinone. The most commonly heard says that "cosmetics contains arbutin cannot be used during the day, otherwise whitening fails, but more black". In fact, do not worry about that. Tests show that only the concentration of arbutin is more than 7% that it may be photosensitive. So 7% is a safety critical point. The concentration of ingredients added in skin care products has specific provision. The highest concentration is 7%. In this concentration range, arbutin is not enough to produce light sensitivity. But it does not have to be used away from light. When arbutin is absorbed by the skin and deposed by light, it will be reduced to hydroquinone and produce whitening effect. The concentration of hydroquinone in arbutin skin care products is lower than 20 PPM (that is twenty millionths). Hydroquinone won't cause side effects, like skin dark, within the limits of such a low concentration. If just because the skin care products contain arbutin so that we are afraid to use them during the day. That doesn't need unless that the skin care products containing arbutin also are added other maintenance components which need to be away from light. In a word, choose reliable brand of skin care products. Then regardless of what is painted, good sunscreen is necessary during the day.

Uses

Different sources of media describe the Uses of 497-76-7 differently. You can refer to the following data:
1. Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.
2. arbutin is used primarily for its anti-oxidant and bleaching properties. Arbutin is the active constituent of bearberry, and found in other plant sources, including wheat. It acts as a tyrosinase inhibitor by converting to hydroquinone, and thus can prevent melanin formation.
3. tyrosinase inhibitor, depigmentor, antitussive
4. Antibacterial;Tyrosinase inhibitor
5. Arbutin is a glycosylated hydroquinone extracted from bearberry plant. Arbutin is a known inhibitor of tyrosinase, which in turn prevents the formation of melanin. Arbutin is often used as a skin-ligh tening agent in cosmetic products.
6. veterinary drug

Description

Different sources of media describe the Description of 497-76-7 differently. You can refer to the following data:
1. Arbutin is a β-D-glucopyranoside HQ derivative and a plant-derived compound found in the dried leaves of several plant species, including blueberry, cranberry, bearberry, and pear trees. It suppresses tyrosinase activity without altering RNA expression.
2. Arbutin is a glycosylated hydroquinone that has been found in Arctostaphylos plants and has diverse biological activities, including tyrosinase inhibitory, antioxidant, and anti-inflammatory properties. It inhibits human tyrosinase activity in crude tyrosinase solution isolated from human melanocytes (IC50s = 5.7 and 18.9 mM using L-tyrosine and L-DOPA as substrates, respectively) as well as in intact melanocytes (IC50 = 0.5 mM). Arbutin (50 μM) inhibits hemolysis induced by the free radical generator AAPH in sheep erythrocytes and inhibits AAPH-induced decreases in cell viability in cultured human skin fibroblasts when used at concentrations greater than 125 μM. In an LPS-induced rat model of acute lung injury, arbutin (50 mg/kg) prevents increases in IL-1β, IL-6, and TNF-α levels in lung tissue and serum. Formulations containing arbutin have been used in the treatment of hyperpigmentation disorders.

Chemical Properties

Crystalline powder

Physical properties

Appearance: white powder. Solubility: soluble in hot water. Melting point: 198–201?°C

History

Arbutin is a hydroquinone compound with two epimers, α and β arbutin. The sources of α-arbutin and β-arbutin are completely different. β-arbutin can be prepared by plant extraction, plant cell culture, and artificial synthesis. Arbutin can relieve cough and asthma and has whitening effect. The Japanese cosmetics company Shiseido developed the arbutin as a whitening agent in the 1990s. Arbutin can not only reduce skin freckles, senile plaques, and chloasma but also relieve acne and improve healing after skin burns. Arbutin is the epimer of β-arbutin, and the spatial orientation of their glycosidic bonds is just the opposite. Alpha arbutin is generally prepared by different microbial enzymes. A molecule of glucose and a molecule of hydroquinone combine to form a molecule α-arbutin . Alpha arbutin improves ultraviolet burn scar. α-Arbutin can be used in a variety of skin whitening cosmetics since it is chemically stable.

Definition

ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.

Indications

Arbutin has bactericidal, anti-inflammatory, and whitening effects and is mainly used in whitening cosmetics.

Pharmacology

Arbutin could effectively inhibit the activity of tyrosinase in skin cells and block the formation of melanin without affecting cell proliferation . Furthermore, it could accelerate the decomposition and excretion of melanin and thereby reduce skin pigmentation and eliminate freckles. In addition, arbutin shows no toxicity, irritation, sensitization, and other side effects . Alpha arbutin is safer and has a stronger inhibitory effect on tyrosinase. At present the whitening cosmetics market in the developed countries has been almost monopolized by arbutin.

Clinical Use

Arbutin is mainly used in high-level cosmetics and has been formulated into skin cream, freckle cream, and senior pearl cream. Arbutin is a major component of medicine for treating burn and scald, characterized by rapid elimination of pain and swelling and fast healing, leaving no scars. Arbutin can also be used as raw materials for intestinal anti-inflammatory drug, with sterilization, anti-inflammatory effect, and nontoxic side effects.

Purification Methods

The glycoside from Protea exima is purified by recrystallisation from H2O or moist EtOAc (as monohydrate), after chromatography through silica Gel using EtOAc/MeOH. Crystallisation from EtOH/CHCl3 gives crystals m 199-200o with intermediate melting at 164o and resolidifying. The pentaacetate crystallises from EtOH in fine needles with m 145-146o, [] D 20 -28.2o (c 2, Me2CO). [Robinson & Waters J Chem Soc 2729 1930, IR, NMR, MS: Perold et al. J Chem Soc, Perkin Trans 1 239 1979, Beilstein 17/7 V 110.]

Check Digit Verification of cas no

The CAS Registry Mumber 497-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 7 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 497-76:
(5*4)+(4*9)+(3*7)+(2*7)+(1*6)=97
97 % 10 = 7
So 497-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9+,10+,11-,12-/m1/s1

497-76-7 Well-known Company Product Price

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  • TCI America

  • (A0522)  Arbutin  >95.0%(HPLC)

  • 497-76-7

  • 5g

  • 190.00CNY

  • Detail
  • TCI America

  • (A0522)  Arbutin  >95.0%(HPLC)

  • 497-76-7

  • 25g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (L14945)  Arbutin, 98+%   

  • 497-76-7

  • 1g

  • 122.0CNY

  • Detail
  • Alfa Aesar

  • (L14945)  Arbutin, 98+%   

  • 497-76-7

  • 5g

  • 328.0CNY

  • Detail
  • Sigma-Aldrich

  • (66468)  Arbutin  analytical standard

  • 497-76-7

  • 66468-50MG

  • 995.67CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000806)  Arbutin  European Pharmacopoeia (EP) Reference Standard

  • 497-76-7

  • Y0000806

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (00890590)  Arbutin  primary pharmaceutical reference standard

  • 497-76-7

  • 00890590-50MG

  • 2,231.19CNY

  • Detail

497-76-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name hydroquinone O-β-D-glucopyranoside

1.2 Other means of identification

Product number -
Other names 4-Hydroxyphenyl-β-D-glucopyranosidep

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:497-76-7 SDS

497-76-7Synthetic route

4-hydroxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
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

arbutin
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

pentaacetate arbutin

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
With methanol; sodium methylate at 50℃; for 2h; Large scale;95.2%
p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
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

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
With copper(I) oxide; sodium methylate In methanol at 0 - 80℃; for 4h;95%
β-D-glucose
492-61-5

β-D-glucose

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
With SArbutin 5 In aq. phosphate buffer at 37℃; for 24h; pH=7.0;92%
hydroquinone
123-31-9

hydroquinone

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

2-nitrophenyl β-D-glucopyranoside

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
With Na acetate buffer; butan-1-ol for 8h; β-glucuronidase from bovine liver;91.2%
4-acetoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
14698-56-7

4-acetoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

arbutin
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%
D-glucose
50-99-7

D-glucose

hydroquinone
123-31-9

hydroquinone

A

arbutin
497-76-7

arbutin

B

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

4-hydroxyphenyl α-D-glucopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide at 100℃; for 10h;A 4%
B 11%
hydroquinone
123-31-9

hydroquinone

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

α-D-glucopyranosyl-1-phosphate

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

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
With methanol; ammonia
UDP-glucose
133-89-1

UDP-glucose

hydroquinone
123-31-9

hydroquinone

arbutin
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;
hydroquinone
123-31-9

hydroquinone

arbutin
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

(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

(6R)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid
83945-54-4

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

B

arbutin
497-76-7

arbutin

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

4-hydroxyphenyl benzoate

arbutin
497-76-7

arbutin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: quinoline; silver oxide
2: ammonia; methanol
View Scheme
α-D-Glucopyranoside 1-(disodium phosphate)
56401-20-8

α-D-Glucopyranoside 1-(disodium phosphate)

hydroquinone
123-31-9

hydroquinone

arbutin
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;
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

arbutin
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

C21H22O10

A

1-(4-hydroxyphenyl)-1,3-propanediol
22805-46-5

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

B

arbutin
497-76-7

arbutin

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

D-glucose

benzene
71-43-2

benzene

A

hydroquinone
123-31-9

hydroquinone

B

arbutin
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;
β-D-glucose
492-61-5

β-D-glucose

arbutin
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
β-D-glucose pentaacetate
604-69-3

β-D-glucose pentaacetate

arbutin
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
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

arbutin
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
β-D-glucose
492-61-5

β-D-glucose

hydroquinone
123-31-9

hydroquinone

arbutin
497-76-7

arbutin

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

p-Coumaric Acid

arbutin
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
4-Vinylphenol
2628-17-3

4-Vinylphenol

arbutin
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
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

arbutin
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
allyl bromide
106-95-6

allyl bromide

arbutin
497-76-7

arbutin

(2S,3R,4S,5S,6R)-2-(4-Allyloxy-phenoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
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%
vinyl ester of 3-phenylpropionic acid
54519-07-2

vinyl ester of 3-phenylpropionic acid

arbutin
497-76-7

arbutin

6'-O-(3-phenylpropionyl)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%
vinyl acetate
108-05-4

vinyl acetate

arbutin
497-76-7

arbutin

6'-O-acetylarbutin
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%
trityl chloride
76-83-5

trityl chloride

arbutin
497-76-7

arbutin

6-O-triphenylmethylarbutin
180297-88-5

6-O-triphenylmethylarbutin

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

10-undecenoic acid

arbutin
497-76-7

arbutin

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

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;
vinyl ester of 4-phenylbutyric acid
95063-02-8

vinyl ester of 4-phenylbutyric acid

arbutin
497-76-7

arbutin

6'-O-(4-phenylbutyryl)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%
vinyl ester of 5-phenylvaleric acid
1186473-08-4

vinyl ester of 5-phenylvaleric acid

arbutin
497-76-7

arbutin

6'-O-(5-phenylvaleryl)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%
cinnamic acid vinyl ester
17719-70-9, 3098-92-8

cinnamic acid vinyl ester

arbutin
497-76-7

arbutin

6'-O-cinnamoyl-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%
vinyl ester of phenylacetic acid
18120-64-4

vinyl ester of phenylacetic acid

arbutin
497-76-7

arbutin

6'-O-phenylacetyl-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%

497-76-7Relevant articles and documents

Multienzymic synthesis of poly(hydroquinone) for use as a redox polymer

Wang, Ping,Martin, Brett D.,Parida, Sanghamitra,Rethwisch, David G.,Dordick, Jonathan S.

, p. 12885 - 12886 (1995)

-

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Zhao, Mingtao,Hong, Xulin,Abdullah,Yao, Ruilian,Xiao, Yi

, p. 838 - 847 (2021/02/09)

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

Preparation method of glucoside and derivatives thereof

-

Paragraph 0030-0031; 0034; 0035; 0039, (2020/04/02)

The invention discloses a preparation method of glucoside and derivatives thereof. According to the method, all hydroxyl groups on a sugar molecule structure are acetylated, a ligand containing phenolic hydroxyl groups is prepared at the same time, then boron trifluoride-diethyl ether is used as a catalyst, the two substances are condensed to obtain tetraacetylated glucoside, and finally acetyl protecting groups are removed to obtain the required glucoside. The method can selectively catalyze hemiacetal hydroxyl of monosaccharide to react with hydroxyl to obtain glucoside, and the product is single. The method is simple in production operation and low in equipment requirement, can be used for synthesizing glucoside and derivatives thereof with similar structures, is green and environment-friendly, and can be used for large-scale production.

Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds

Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.

, p. 246 - 260 (2019/02/03)

β-Glucosidase from bitter almonds was immobilized on epoxy group-functionalized beads for catalyzing salidroside synthesis in a two-step process with n-butyl-β-D-glucoside (BG) as the glucosyl donor. The formation of salidroside ((0.59 ± 0.02) M) at a yield of 39.04%±1.25% was accomplished in 8 h by the transglucosylation of immobilized β-glucosidase at pH?8.0 and 50 °C when the ratio of BG to tyrosol was 1:2 (mol/mol). A study on the influence of different glycosyl acceptors demonstrated that the yield of the glucosylation reaction of phenylmethanol and cyclohexanol was higher than that of either phenol or cyclohexanol. This may account for the selectivity of the immobilized enzyme towards the alcoholic hydroxyl group of tyrosol in the salidroside synthesis reaction. A study on the synthesis of BG via the reverse hydrolysis of immobilized β-glucosidase showed that a yield of 78.04%±2.2% BG can be obtained with a product concentration of (0.23 ± 0.015) M.

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