Chrysophal 8-O-glucoside

The Chrysophanol 8-O-beta-D-glucoside with CAS registry number of 13241-28-6 is also known as 8-Hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl β-D-glucopyranoside. The IUPAC name is 1-Hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione. In addition, the formula is C₂₁H₂₀O₉ and the molecular weight is 416.38.

Physical properties about Chrysophanol 8-O-beta-D-glucoside are: (1)ACD/LogP: 1.55; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 9; (4)#H bond donors: 5; (5)#Freely Rotating Bonds: 8; (6)Polar Surface Area: 98.75Ų; (7)Index of Refraction: 1.702; (8)Molar Refractivity: 101.08 cm³; (9)Molar Volume: 260.8 cm³; (10)Polarizability: 40.07×10^-24cm³; (11)Surface Tension: 86.7 dyne/cm ; (12)Density: 1.596 g/cm³; (13)Flash Point: 272.8 °C; (14)Enthalpy of Vaporization: 116.61 kJ/mol ; (15)Boiling Point: 763.2 °C at 760 mmHg ; (16)Vapour Pressure: 1.73E-24 mmHg at 25 °C.

Preparation of Chrysophanol 8-O-beta-D-glucoside: it is prepared by reaction of Chrysophanol 8-O-b-D-(6'-galloyl)-glucopyranoside. The reaction needs reagent MeONa and solvent methanol at the temperature of 20 °C. The yield is about 98%.

Uses of Chrysophanol 8-O-beta-D-glucoside: it is used to produce 1,8-dihydroxy-3-methyl-anthraquinone. The reaction occurs with reagents b-glucosidase, acetate buffer and solvent H₂O with PH of 5.0 at 37 °C for 16 hours. The yield is about 98%.

You can still convert the following datas into molecular structure:
1. SMILES: O=C3c2c(c(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)ccc2)C(=O)c4c3cc(cc4O)C
2. InChI: InChI=1/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1
3. InChIKey: WMMOMSNMMDMSRB-JNHRPPPUBD
4. Std. InChI: InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1
5. Std. InChIKey: WMMOMSNMMDMSRB-JNHRPPPUSA-N