(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol
• CAS No.: 85026-55-7
• Molecular Formula: C15H20O6
• Molecular Weight: 296.32
• Hs Code.: 38061010
• European Community (EC) Number: 617-106-3,875-664-5
• UNII: SVS3GU8AY8
• ChEMBL ID: CHEMBL4175856
• DSSTox Substance ID: DTXSID60904535
• Nikkaji Number: J430.836K,J2.573.236G
• Wikidata: Q15424776
• Wikipedia: Rosin_(chemical)
• Mol file: 85026-55-7.mol

Synonyms:colophonium;colophony;pine resin;pine tar resin;pitch tar;rosin

Chemical Property of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 1.35E-12mmHg at 25°C
• Melting Point: 75-81 °C
• Refractive Index: 1.613
• Boiling Point: 542.4 °C at 760 mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 281.8 °C
• PSA: 0.00000
• Density: 1.36 g/cm³
• LogP: 0.00000
• Solubility.: chloroform: 0.1 g/mL, clear, strongly yellow
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 296.12598835
• Heavy Atom Count: 21
• Complexity: 328

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rosin 98% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CCOC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Description: Rosin is a light yellow to reddish brown, transparent, vitreous substance with a thermoplastic nature.
• Uses: Rosin is mainly used in the manufacture of soaps, paints, adhesives, and soldering fluxes.In the pharmaceutical industry, rosin is a raw material for several creams and ointments.Rosin is used in a variety of applications for its ability to increase friction.

Technology Process of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

There total 10 articles about (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]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: 95.0%

cinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6743-85-7) → (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol (85026-55-7)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/j.tetlet.2005.04.023

Reference yield: 70.0%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) + rutin (153-18-4) → (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol (85026-55-7)

Guidance literature:

With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger; In aq. phosphate buffer; dimethyl sulfoxide; at 35 ℃; for 8h; pH=5; Enzymatic reaction;

DOI:10.1002/cssc.201700136

Reference yield: 20.0%

3-Phenylpropenol (104-54-1) + 4-nitrophenyl-β-D-glucoside (2492-87-7) → (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol (85026-55-7)

Guidance literature:

With phosphate buffer; β-glucosidase; at 30 ℃; for 16h;

DOI:10.1016/S0957-4166(99)00228-1

upstream raw materials:

cinnamylalcohol 9-O-(6'-O-α-L-arabinofuranosyl)-β-D-glucopyranoside

cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside

3-Phenylpropenol

4-nitrophenyl-β-D-glucoside

Downstream raw materials:

D-Glucose

(Z)-cinnamyl alcohol

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

(2E)-3-phenyl-2-propen-1-ol