Barbaloin

C21H22O9CAS 5133-19-7418.40 g/mol

Open in Covalent MOL file
OHOOOHOHOHHOHOHO
AlcoholEtherKetonePhenol

Properties

Molecular formula
C21H22O9
Molar mass
418.40 g/mol
Exact mass
418.1264 Da
Melting point
148–149 °C
logP
-0.89Crippen estimate
Polar surface area
167.9 Ų
H-bond donors / acceptors
7 / 9
Rotatable bonds
3
Stereocentres
S, S, R, S, R, Rin SMILES atom order

Hazards

Warning
Irritant (GHS07)

Aggregated from 50 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Identifiers

CAS number
5133-19-7
SMILES
O=C1c2c(O)cccc2[C@H]([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2cc(CO)cc(O)c21
InChIKey
AFHJQYHRLPMKHU-OSYMLPPYSA-N
InChI
InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,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 7.38 (t, J = 7.7 Hz, 1H), 6.91 (dd, J = 7.7, 1.6 Hz, 1H), 6.84 (d, J = 1.6 Hz, 1H), 6.75 (dd, J = 7.7, 1.6 Hz, 1H), 6.68 (d, J = 1.6 Hz, 1H), 5.30 (br s, 1H), 5.30 (br s, 1H), 4.73 (m, J = 7.0 Hz, 1H), 4.72 (t, J = 7.0 Hz, 1H), 4.71 (s, 2H), 4.69 (m, J = 7.0 Hz, 1H), 4.41 (m, J = 7.0 Hz, 1H), 4.41 (t, 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), 2.00 (br s, 1H).
¹³C NMR
Predicted ¹³C NMR (101 MHz, CDCl₃) δ 196.7, 157.0, 156.9, 151.6, 151.5, 145.9, 133.5, 122.9, 122.0, 118.7, 117.2, 112.8, 111.3, 92.7, 86.7, 79.1, 78.6, 78.6, 65.5, 62.8, 49.1.
[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.

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

Names and synonyms

9 names
  • 9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-
  • 9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (S)-
  • Anthrone, 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-
  • (10S)-10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
  • Aloin
  • Aloin A
  • Barbaloin A
  • NSC 407305
  • 10-Epi-Aloin B

Work with Barbaloin

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

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Aloin B28371-16-6Diastereomer Barbaloin1415-73-2

Similar compounds

Sennoside C37271-16-264 % similar Sennoside D37271-17-364 % similar Aloe-emodin 8-O-β-D-glucopyranoside33037-46-656 % similar Sennoside B128-57-454 % similar Sennoside A81-27-654 % similar Aloe emodin481-72-147 % similar Chrysophanol 8-O-β-D-glucopyranoside13241-28-643 % similar Trilobatin4192-90-939 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Same formula

Isoliquiritin5041-81-6 Liquiritin551-15-5

Elsewhere

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