Methylarbutin

Base Information

• Chemical Name: Methylarbutin
• CAS No.: 6032-32-2
• Molecular Formula: C₁₃H₁₈O₇
• Molecular Weight: 286.282
• Hs Code.: 29389090
• European Community (EC) Number: 804-152-6
• UNII: F9MW5FU0XH
• DSSTox Substance ID: DTXSID501032087
• Nikkaji Number: J8.335F
• Wikidata: Q27155152
• Mol file: 6032-32-2.mol

Synonyms:4-methoxyphenylglucoside;p-methoxyphenyl beta-D-glucopyranoside

Chemical Property of Methylarbutin

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Vapor Pressure: 1.34E-11mmHg at 25°C
• Melting Point: 176 °C
• Refractive Index: 1.6
• Boiling Point: 519 °C at 760 mmHg
• PKA: 12.72±0.70(Predicted)
• Flash Point: 267.7 °C
• PSA: 108.61000
• Density: 1.427 g/cm³
• LogP: -1.12610
• Storage Temp.: Freezer
• Water Solubility.: Soluble in DMSO or water
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.10525291
• Heavy Atom Count: 20
• Complexity: 292

Purity/Quality:

98%, ^*data from raw suppliers

4-Methoxyphenyl b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: In cosmetics as skin lightening agent.

Technology Process of Methylarbutin

There total 40 articles about Methylarbutin 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: 100.0%

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) → 4-methoxyphenyl β-D-glucopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9)

Guidance literature:

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside; With methanol; sodium methylate; at 20 ℃;

With acidic ion-exchange resin; In methanol; at 20 ℃;

DOI:10.1071/CH08517

Reference yield: 100.0%

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1055/s-2003-40324

Reference yield: 92.0%

4-methoxy-phenol (150-76-5) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-methoxyphenyl β-D-glucopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9)

Guidance literature:

With calcium hydroxide; In water; at 20 ℃; for 1h;

DOI:10.1038/s41557-018-0041-8

upstream raw materials:

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

sodium methylate

4-methoxy-phenol

β-D-glucose pentaacetate

Downstream raw materials:

4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

p-methoxyphenyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

4-methoxyphenyl 3,6-di-O-allyl-β-D-galactopyranoside

p-methoxyphenyl 3,4,6-tri-O-benzoyl-β-D-galactopyranoside

Refernces

• 1、 Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang. "Synthesis of nature product kinsenoside analogues with anti-inflammatory activity". supporting information. . Retrieved 2020/12/02.
• 2、 Chen, Xi,Diaz, Sandra,Kooner, Anoopjit Singh,Santra, Abhishek,Varki, Ajit,Yu, Hai. "Chemoenzymatic Synthesis of Sialosides Containing 7- N- or 7,9-Di- N-acetyl Sialic Acid as Stable O-Acetyl Analogues for Probing Sialic Acid-Binding Proteins". . p. 14381 - 14397. Retrieved 2021/11/01.