beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl

Base Information

• Chemical Name: beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl
• CAS No.: 138-52-3
• Molecular Formula: C13H18O7
• Molecular Weight: 286.282
• Hs Code.: 29389090
• NSC Number: 5751
• Wikidata: Q105178875
• ChEMBL ID: CHEMBL315895
• Mol file: 138-52-3.mol

Synonyms:D-Salicin;NSC5751;Saligenin-.beta.-D-glucopyranoside;.beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl;2-(Hydroxymethyl)phenyl hexopyranoside;D-(-)-Salicin;Salicoside;o-(Hydroxymethyl)phenyl .beta.-D-glucopyranoside;MFCD00006590;2-(Hydroxymethyl)phenyl-.beta.-d-glucopyranoside;Benzyl alcohol, o-glucoside;MLS006011842;CHEMBL315895;SCHEMBL4533731;SCHEMBL21984844;SCHEMBL23623699;BDBM85510;NGFMICBWJRZIBI-UHFFFAOYSA-N;HMS3656E09;2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol;NSC_5145;BBL033791;STL371942;2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]tetrahydropyran-3,4,5-triol;AKOS025247673;CAS_138-52-3;NCI60_004404;SMR001550505;SY038043;VS-12279;FT-0603347;68329186-F80B-4F42-872B-6B53458EE17E

Chemical Property of beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 6.85E-13mmHg at 25°C
• Melting Point: 197-200 °C
• Refractive Index: -62 ° (C=3, H2O)
• Boiling Point: 549.1 °C at 760 mmHg
• PKA: 12.80±0.70(Predicted)
• Flash Point: 285.9 °C
• PSA: 119.61000
• Density: 1.504 g/cm³
• LogP: -1.64240
• Storage Temp.: Store at RT.
• Solubility.: 36g/l
• Water Solubility.: 36 g/L (15 ºC), 250 g/L (60 ºC)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.10525291
• Heavy Atom Count: 20
• Complexity: 300

Purity/Quality:

100% Natural & No pollution ^*data from raw suppliers

Salicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37-37-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CO)OC2C(C(C(C(O2)CO)O)O)O
• Description: D(-)-Salicin is a traditional medicine which has been known to exhibit anti-inflammation and other therapeutic activities, it can inhibit the LPS-induced inflammation in RAW264.7 cells and mouse models.
• Uses: analgesic, antipyretic H1 antihistamine (nonsedating) Standard substrate in evaluating enzyme Preparations contg b-glucosidase: Weidenhagen, Z. Ver. Zucker-Ind. 79, 591 (1929). D-(-)-Salicin has been used:to study its in vitro anticoagulant and antiplatelet activitiesas a standard in high performance liquid chromatography method (HPLC) for quantitation of salicin from willow plantas a tastant in taste threshold assayas a constituent of nutrient agar-salicin medium for selective isolation of Lactobacillus paracasei

Technology Process of beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl

There total 19 articles about beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl 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%

2-(hydroxymethyl)phenyl-2-O-acetyl-β-D-glucopyranoside → D-(-)-salicin (138-52-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/acs.jnatprod.9b00570

Reference yield: 99.0%

2-(hydroxymethyl)phenyl-6-O-acetyl-β-D-glucopyranoside (19764-02-4) → D-(-)-salicin (138-52-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/acs.jnatprod.9b00570

Reference yield: 46.0%

2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate (29836-40-6) → D-(-)-salicin (138-52-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1021/np034052o

upstream raw materials:

helicin acetate

2-[[[(1-hydroxy-6-oxo-2-cyclohexen-1-yl)carbonyl]hydroxy]methyl]phenyl-β-D-glucopyranoside

2-methyl-benzyl alcohol

Sucrose

Downstream raw materials:

Penta-O-(isopropoxycarbonyl)salicin

(1R,2R)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside

(1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside

Refernces

• 1、 Romanova, Dariya A.,Avetyan, David L.,Belyanin, Maxim L.,Stepanova, Elena V.. "Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration". . p. 888 - 893. Retrieved 2020/03/30.
• 2、 Shimoda, Kei,Katsuragi, Hisashi. "Enzymatic resolution of (RS)-1-phenylalkyl β-D-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-D-glucosides via plant xylosyltransferase". experimental part. p. 2060 - 2065. Retrieved 2010/10/21.