2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

Base Information

• Chemical Name: 2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
• CAS No.: 497-76-7
• Molecular Formula: C12H16O7
• Molecular Weight: 272.255
• Hs Code.: 2938.90 CLASSIFICATION
• NSC Number: 4036
• DSSTox Substance ID: DTXSID20859416
• Wikidata: Q104937322
• ChEMBL ID: CHEMBL79041
• Mol file: 497-76-7.mol

Synonyms:4-Hydroxyphenyl hexopyranoside;NSC4036;p-Hydroxyphenyl .beta.-D-glucoside;Hydroquinone .beta.-D-glucopyranoside;p-Hydroxyphenyl .beta.-D-glucopyranoside;Hydroquinone-beta-D-glucopyranoside;.beta.-D-Glucopyranoside, 4-hydroxyphenyl;MFCD00016915;MFCD09838262;.beta.-Arbutin;(c) paragraph sign-Arbutin;SCHEMBL36352;MLS006012040;CHEMBL79041;SCHEMBL20468232;2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;DTXSID20859416;BJRNKVDFDLYUGJ-UHFFFAOYSA-N;HMS1648K06;HMS3655F18;BCP18027;BCP18147;BDBM50130191;STL451054;AKOS001581355;AKOS021730279;AC-8030;4-Hydroxyphenyl .beta.-D-glucopyranoside;SMR001215811;SY051904;SY056800;FT-0622464;FT-0649357;B2694-078258;2-Hydroxymethyl-6-(4-hydroxy-phenoxy)-tetrahydro-pyran-3,4,5-triol

Chemical Property of 2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

Chemical Property:

• Appearance/Colour: White needle crystal or powder
• Vapor Pressure: 1.9E-13mmHg at 25°C
• Melting Point: 195-198 °C
• Refractive Index: -65.5 ° (C=4, H2O)
• Boiling Point: 561.583 °C at 760 mmHg
• PKA: 10.10±0.15(Predicted)
• Flash Point: 293.435 °C
• PSA: 119.61000
• Density: 1.556 g/cm³
• LogP: -1.42910
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL hot, clear
• Water Solubility.: 10-15 g/100 mL at 20 ºC
• 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:

98% ^*data from raw suppliers

Arbutin 99.5+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
• Recent ClinicalTrials: Safety Evaluation of β-arbutin in Healthy Human Subjects
• Chemical Properties: Arbutin, also known as 尾-arbutin, is a hydroquinone glucoside. It is a soluble glycosylated phenol with two isomeric configurations: alpha (伪)-arbutin and beta (尾)-arbutin.
• Pharmacological Activities: Exhibits anti-inflammatory and antioxidant effects.; Protects cells from damage induced by high glucose and oxidative stress.; Inhibits lipopolysaccharide-induced lung injury by activating SIRT1, a histone deacetylase enzyme.; Shows potential in regulating NF-魏B signaling and cell apoptosis pathways.
• Cosmetic and Pharmaceutical Uses: Widely used in pharmaceutical and cosmetic industries due to potent inhibition of tyrosinase activity.; Both 伪- and 尾-arbutin are utilized for their anti-oxidative, anti-inflammatory, anti-microbial, and anti-cancer effects.; 伪-Arbutin exhibits 10-times greater tyrosinase inhibition compared to 尾-arbutin, making it more valuable for cosmetic formulations.
• Natural Sources and Extraction: Primary natural source of 尾-arbutin is bearberry leaves, also found in pears, wheat, coffee, and tea.; Extraction from plants hindered by low content, complicated process, and low purity.; Plant cell culture techniques explored for 尾-arbutin synthesis, but face challenges in yield, purification, and production scale-up.
• Chemical Synthesis: Chemical synthesis involves the glycosylation of glucose with hydroquinone, followed by the removal of protecting groups.; First studied in 1912, the synthesis process requires treatment with acetyl bromide and subsequent alkaline conditions to yield tetra-acetyl arbutin, which is then converted to 尾-arbutin.

Technology Process of 2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

There total 45 articles about 2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol 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: 99.0%

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) → arbutin (497-76-7)

Guidance literature:

With ammonia; water; In methanol; Microwave irradiation;

DOI:10.5012/bkcs.2010.31.7.1825

Reference yield: 95.2%

pentaacetate arbutin → arbutin (497-76-7)

Guidance literature:

With methanol; sodium methylate; at 50 ℃; for 2h; Large scale;

Reference yield: 95.0%

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) → arbutin (497-76-7)

Guidance literature:

With copper(I) oxide; sodium methylate; In methanol; at 0 - 80 ℃; for 4h;

upstream raw materials:

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

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

UDP-glucose

hydroquinone

Downstream raw materials:

6-O-triphenylmethylarbutin

β-D-glucopyranosyl-(1→6)-arbutin

2,3,4,4'-tetra-O-benzylarbutin

2-O-(hydroquinone-β-D-glucopyranoside-6-phosphoryl)-L-ascorbic acid

Refernces

• 1、 Lutterbach, Ralf,Stoeckigt, Joachim. "High-Field Formation of Arbutin from Hydroquinone by Cell-Suspension Cultures of Rauwolfia serpentina". . p. 2009 - 2011. Retrieved 1992.
• 2、 Choi, Seong Yeon,Jang, Hyeon Seok,Jeong, Birang,Kim, Juyeol,Kwon, Yong Soo,Lee, Jiho,Park, Jinyoung,Yang, Heejung. "α-Glucosidic hydroquinone derivatives from Viburnum erosum". . . Retrieved 2021/05/03.
• 3、 -. "Method for chemically synthesizing beta-arbutin". Paragraph 0004; 0006-0010. . Retrieved 2020/02/10.