Product Name

  • Name

    8-O-acetyl shanzhiside methyl ester

  • EINECS
  • CAS No. 57420-46-9
  • Density 1.52g/cm3
  • Solubility
  • Melting Point
  • Formula C19H28O12
  • Boiling Point 634.2 °C at 760 mmHg
  • Molecular Weight 448.42
  • Flash Point 220 °C
  • Transport Information
  • Appearance
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 57420-46-9 (8-O-acetyl shanzhiside methyl ester)
  • Hazard Symbols
  • Synonyms Cyclopenta[c]pyran-4-carboxylic acid,7-(acetyloxy)-1-(a-Dglucopyranosyloxy)- 1,4a,5,6,7,7a-hexahydro-5- hydroxy-7-methyl-,methyl ester,(1S,4aS,5R,7S,7aS)-;Umbroside;
  • PSA 181.44000
  • LogP -2.46510

Synthetic route

acetic anhydride
108-24-7

acetic anhydride

barlerin
57420-46-9

barlerin

shanzhiside methyl ester hexaacetate
30021-44-4

shanzhiside methyl ester hexaacetate

Conditions
ConditionsYield
With pyridine at 50℃; for 3h;19 mg
With pyridine
With pyridine
barlerin
57420-46-9

barlerin

shanzhiside methyl ester
64421-28-9

shanzhiside methyl ester

Conditions
ConditionsYield
With potassium carbonate60 mg

8-O-Acetylshanzhiside methyl ester Specification

The 8-O-Acetylshanzhiside methyl ester with the CAS number 57420-46-9 is also called Barlerin. The systematic name is methyl (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1-(β-D-glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate. Its molecular formula is C19H28O12.

The properties of the 8-O-Acetylshanzhiside methyl ester are: (1)ACD/LogP: -2.76; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -2.76; (4)ACD/LogD (pH 7.4): -2.76; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 126.44 Å2; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 99.99 cm3; (15)Molar Volume: 294.8 cm3; (16)Polarizability: 39.64×10-24cm3; (17)Surface Tension: 72.9 dyne/cm; (18)Enthalpy of Vaporization: 107.42 kJ/mol; (19)Vapour Pressure: 9.42×10-19 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@@]2(C)C[C@@H](O)[C@@H]3C(/C(=O)OC)=C\O[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@H]23)C
(2)InChI: InChI=1/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1
(3)InChIKey: ARFRZOLTIRQFCI-NGQYDJQZBC

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