1,2-di-o-sinapoyl-beta-D-glucose

1, 2-di-o-sinapoyl-beta-D-glucose

formula | C_28H_32O_14 name | 1, 2-di-o-sinapoyl-beta-D-glucose IUPAC name | 3-(4-hydroxy-3, 5-dimethoxyphenyl)-2-propenoic acid [(2S, 3R, 4S, 5S, 6R)-4, 5-dihydroxy-2-[3-(4-hydroxy-3, 5-dimethoxyphenyl)-1-oxoallyloxy]-6-(hydroxymethyl)-3-tetrahydropyranyl] ester alternate names | 1, 2-bis-O-sinapoyl-beta-D-glucoside mass fractions | C (carbon) 56.8% | H (hydrogen) 5.44% | O (oxygen) 37.8%

Draw the Lewis structure of 1, 2-di-o-sinapoyl-beta-D-glucose. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 28 n_C, val + 32 n_H, val + 14 n_O, val = 228 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 28 n_C, full + 32 n_H, full + 14 n_O, full = 400 Subtracting these two numbers shows that 400 - 228 = 172 bonding electrons are needed. Each bond has two electrons, so in addition to the 76 bonds already present in the diagram add 10 bonds. To minimize formal charge oxygen wants 2 bonds and carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 10 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom rings are aromatic, so that the single and double bonds may be rearranged: Answer: | |

3D structure

molar mass | 592.55 g/mol

PubChem CID number | 440280 SMILES identifier | COC1=CC(=CC(=C1O)OC)C=CC(=O)OC2C(C(C(OC2OC(=O)C=CC3=CC(=C(C(=C3)OC)O)OC)CO)O)O InChI identifier | InChI=1S/C28H32O14/c1-36-16-9-14(10-17(37-2)23(16)32)5-7-21(30)41-27-26(35)25(34)20(13-29)40-28(27)42-22(31)8-6-15-11-18(38-3)24(33)19(12-15)39-4/h5-12, 20, 25-29, 32-35H, 13H2, 1-4H3/t20-, 25-, 26+, 27-, 28+/m1/s1