alpha-Arbutin

Base Information

• Chemical Name: alpha-Arbutin
• CAS No.: 84380-01-8
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.255
• Hs Code.: 2938909090
• European Community (EC) Number: 440-470-8,617-561-8
• UNII: 72VUP07IT5
• DSSTox Substance ID: DTXSID20233358
• Nikkaji Number: J593.405B
• Wikidata: Q27110235
• RXCUI: 1363429
• Metabolomics Workbench ID: 68234
• ChEMBL ID: CHEMBL226495
• Mol file: 84380-01-8.mol

Synonyms:alpha-Arbutin;84380-01-8;4-Hydroxyphenyl a-D-glucopyranoside;alpha arbutin;4-hydroxyphenyl alpha-D-glucopyranoside;a-Arbutin;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;UNII-72VUP07IT5;alpha-D-Glucopyranoside, 4-hydroxyphenyl;72VUP07IT5;CHEBI:29710;4-Hydroxyphenyl-alpha-D-glucopyranoside;PubChem16460;AC1L4KBI;Alpha Arbutine;Alfa Arbutina;alpha-Arbutoside;MFCD09838262;I+/--Arbutin;ORISTAR AAT;.ALPHA.-ARBUTIN;ALPHA-ARBUTIN [INCI];SCHEMBL435261;CHEMBL226495;ALPHA-ARBUTIN [WHO-DD];4-hydroxyphenyl-D-lucopyranoside;f inverted question mark-Arbutin;DTXSID20233358;alpha-Arbutin, analytical standard;AMY22497;HY-N3002;a-D-Glucopyranoside, 4-hydroxyphenyl;s5112;AKOS015905235;CCG-267174;DB14109;N-CYCLOPROPYL-N-HYDROXYGUANIDINE;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol;AC-34884;AS-15466;CS-0022901;EN300-7406351;P-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE;4-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE;A840768;W-203913;Q27110235

Chemical Property of alpha-Arbutin

Chemical Property:

• Appearance/Colour: White Crystalline powder
• Vapor Pressure: 1.9E-13mmHg at 25°C
• Melting Point: 195-196 °C
• Refractive Index: 1.65
• Boiling Point: 561.6 °C at 760 mmHg
• PKA: 10.10±0.15(Predicted)
• Flash Point: 293.4 °C
• PSA: 119.61000
• Density: 1.556 g/cm³
• LogP: -1.42910
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 272.08960285
• Heavy Atom Count: 19
• Complexity: 279

Purity/Quality:

99%, ^*data from raw suppliers

a-Arbutin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Description: Arbutin is naturally found in plant sources such as Bearberry, Cranberry and Mulberry, which essentially prevents the formation of melanin (the pigment that creates skin colour). The chemically synthesised version of this plant extract is known as Alpha Arbutin which is used as a topical skin brightening agent to treat sun spots, pigmentation and scars caused by sun damage and breakouts. It also has antioxidant properties, which protect the skin from potential sun damage. Along with Retinol, it is a fairly common ingredient in anti-ageing products to treat age spots, fine lines and wrinkles.
• Uses: more stable analog of b-Arbutin alpha-Arbutin is a component used in the skin-whitening cosmetics. α-Arbutin may be used as an analytical reference standard for the determination of the analyte in cosmetics by high-performance liquid chromatography with UV detection (HPLC-UV) method.
• Biological Functions: Alpha arbutin acts as a tyrosinase competitive inhibitor and also slows melanosome maturation (the organelles that synthesize and store melanin or pigment).3 This is significant because it works on two different mechanisms of pigmentation. Melanin is derived from the amino acid tyrosine and this conversion is regulated by the enzyme tyrosinase. Alpha arbutin is similar in structure to tyrosine, which fits into tyrosinase, needed for melanogenesis. This means that alpha arbutin is reversibly competing with tyrosine for a spot on the enzyme and not inhibiting cell viability, so therefore is not cytotoxic. By targeting tyrosinase, the rate-limiting enzyme in melanin formation, as well as slowing production of the organelles that produce melanin, alpha arbutin is a potent skin brightening agent.

Technology Process of alpha-Arbutin

There total 16 articles about alpha-Arbutin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyde (896100-81-5) → 4-hydroxyphenyl α-D-glucopyranoside (497-76-7,84380-01-8,90706-69-7,125095-12-7,125095-13-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; at 20 ℃; for 1.5h;

DOI:10.1016/j.carres.2006.04.022

Reference yield: 96.0%

O-p-acetoxyphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucose (612802-12-7) → 4-hydroxyphenyl α-D-glucopyranoside (497-76-7,84380-01-8,90706-69-7,125095-12-7,125095-13-8)

Guidance literature:

With methanol; sodium methylate; at 25 ℃; for 2h; Temperature;

Reference yield: 11.0%

D-glucose (50-99-7) + hydroquinone (123-31-9,8027-02-9) → arbutin (497-76-7) + 4-hydroxyphenyl α-D-glucopyranoside (497-76-7,84380-01-8,90706-69-7,125095-12-7,125095-13-8)

Guidance literature:

With toluene-4-sulfonic acid; In dimethyl sulfoxide; at 100 ℃; for 10h;

DOI:10.1246/cl.1983.1487

upstream raw materials:

D-glucose

hydroquinone

Sucrose

maltopentaose

Downstream raw materials:

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

Refernces

• 1、 -. "A method of preparing α-arbutine". Paragraph 0028-0029. . Retrieved 2017/06/29.
• 2、 De Winter, Karel,Desmet, Tom,Devlamynck, Tim,Van Renterghem, Lisa,Verhaeghe, Tom,Pelantova, Helena,Kren, Vladimir,Soetaert, Wim. "Biphasic catalysis with disaccharide phosphorylases: Chemoenzymatic synthesis of α- D -glucosides using sucrose phosphorylase". . p. 781 - 787. Retrieved 2014/07/08.