Isoliquiritin

C21H22O9CAS 5041-81-6418.40 g/mol

Open in Covalent MOL file
OOOOHOHOHHOHOOH
AcetalAlcoholAlkeneEtherKetonePhenol

Properties

Molecular formula
C21H22O9
Molar mass
418.40 g/mol
Exact mass
418.1264 Da
Melting point
185–186 °C (decomposes)
logP
0.17Crippen estimate
Polar surface area
156.9 Ų
H-bond donors / acceptors
6 / 9
Rotatable bonds
6
Stereocentres
S, R, S, S, Rin SMILES atom order
Double bonds
EE/Z, in SMILES order

Hazards

No GHS classification is on file for this compound. That is not evidence that it is harmless.

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Identifiers

CAS number
5041-81-6
SMILES
O=C(/C=C/c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1)c1ccc(O)cc1O
InChIKey
YNWXJFQOCHMPCK-LXGDFETPSA-N
InChI
InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1
Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR
Predicted ¹H NMR (400 MHz, CDCl₃) δ 7.74 (d, J = 7.7 Hz, 1H), 7.54 (d, J = 16.8 Hz, 1H), 7.33 (d, J = 7.7 Hz, 2H), 6.96 (d, J = 7.0 Hz, 1H), 6.85 (d, J = 7.7 Hz, 2H), 6.67 (d, J = 16.8 Hz, 1H), 6.49 (dd, J = 7.7, 1.6 Hz, 1H), 6.38 (d, J = 1.6 Hz, 1H), 5.30 (br s, 1H), 5.30 (br s, 1H), 4.91 (t, J = 7.0 Hz, 1H), 4.72 (t, J = 7.0 Hz, 1H), 4.41 (m, J = 7.0 Hz, 1H), 4.35 (m, J = 7.0 Hz, 1H), 3.95 (d, J = 7.0 Hz, 2H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H).
¹³C NMR
Predicted ¹³C NMR (101 MHz, CDCl₃) δ 190.8, 161.3, 159.1, 156.5, 140.5, 131.0, 129.8, 127.1, 126.1, 123.7, 116.8, 114.0, 108.3, 102.9, 85.7, 78.6, 78.1, 77.6, 62.5.
[M + H]+
[M + H]+ Calcd for C21H23O9 419.1337
[M + Na]+
[M + Na]+ Calcd for C21H22NaO9 441.1156
[M − H]−
[M − H]− Calcd for C21H21O9 417.1191
Elemental analysis
Anal. Calcd for C21H22O9: C, 60.28; H, 5.30.

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

6 names
  • 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-(β-D-glucopyranosyloxy)phenyl]-, (2E)-
  • Chalcone, 2′,4,4′-trihydroxy-, 4-β-D-glucopyranoside
  • 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-(β-D-glucopyranosyloxy)phenyl]-, (E)-
  • (2E)-1-(2,4-Dihydroxyphenyl)-3-[4-(β-D-glucopyranosyloxy)phenyl]-2-propen-1-one
  • Isoliquiritoside
  • 2′,4,4′-Trihydroxychalcone 4-(β-D-glucopyranoside)

Work with Isoliquiritin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Similar compounds

Isoliquiritin apioside120926-46-768 % similar Marein535-96-664 % similar Arbutin497-76-757 % similar α-Arbutin84380-01-857 % similar Piceid27208-80-657 % similar 2,3,5,4′-Tetrahydroxystilbene 2-O-β-D-glucoside82373-94-256 % similar Isoliquiritigenin961-29-556 % similar Helicide80154-34-355 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Same formula

Barbaloin1415-73-2 Aloin B28371-16-6 Barbaloin5133-19-7 Liquiritin551-15-5

Elsewhere

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