[4,5-Dihydroxy-2-(2-hydroxycyclohexyl)oxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate

Base Information

• Chemical Name: [4,5-Dihydroxy-2-(2-hydroxycyclohexyl)oxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate
• CAS No.: 15732-48-6
• Molecular Formula: C21H28 O9
• Molecular Weight: 424.44
• Wikidata: Q105383029
• Mol file: 15732-48-6.mol

Synonyms:

Chemical Property of [4,5-Dihydroxy-2-(2-hydroxycyclohexyl)oxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate

Chemical Property:

• Vapor Pressure: 6.4E-19mmHg at 25°C
• Boiling Point: 671°C at 760 mmHg
• Flash Point: 233.6°C
• PSA: 145.91000
• Density: 1.42g/cm³
• LogP: 0.07630
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 424.17333247
• Heavy Atom Count: 30
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)O)OC2C(C(C(C(O2)CO)O)O)OC(=O)C=CC3=CC=C(C=C3)O
• General Description: Grandidentatin, also known as [(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[(1R,2S)-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate, is a glucoside isolated from the bark of *Populus grandidentata*. It is structurally characterized as *cis*-2-hydroxycyclohexyl 2-O-p-coumaroyl-β-D-glucopyranoside, where the p-coumaroyl group is esterified to the glucose moiety. Upon hydrolysis, it yields p-coumaric acid and grandidentin (*cis*-2-hydroxycyclohexyl β-D-glucopyranoside), with the aglucone identified as *cis*-1,2-cyclohexanediol. [(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[(1R,2S)-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate represents a natural product with a unique glycosidic linkage and phenolic esterification, contributing to the phytochemical diversity of *Populus* species.

Refernces

10.1021/jo01052a078

The research investigate the chemical composition of the bark of Populus grandidentata, specifically focusing on the isolation and characterization of a new glucoside, named grandidentatin. The researchers used various chemical methods, including ethanol extraction, hot-water extraction, alkaline hydrolysis with barium hydroxide, enzymatic hydrolysis with β-glucosidase, and methylation with methyl iodide and silver oxide. They also employed techniques such as paper chromatography and infrared spectroscopy to analyze the compounds. The key findings included the identification of grandidentatin as cis-2-hydroxycyclohexyl 2-O-p-coumaroyl-β-D-glucopyranoside and its hydrolysis products, such as p-coumaric acid and grandidentin (cis-2-hydroxycyclohexyl β-D-glucopyranoside). The study concluded that the p-coumaroyl group in grandidentatin is attached to the glucose moiety, and the aglucone is identified as cis-1,2-cyclohexanediol. The research provides valuable insights into the chemical structure and properties of grandidentatin, contributing to the understanding of the natural products found in the bark of Populus grandidentata.