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Merck
CN

A0451

Aloin

from Curacao aloe, ~50%

Synonym(s):

1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone, 10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, Aloin A, Barbaloin

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About This Item

Empirical Formula (Hill Notation):
C21H22O9
CAS Number:
Molecular Weight:
418.39
UNSPSC Code:
41116107
NACRES:
NA.79
PubChem Substance ID:
EC Number:
215-808-0
Beilstein/REAXYS Number:
6077558
MDL number:
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Product Name

Aloin, from Curacao aloe, ~50%

InChI key

AFHJQYHRLPMKHU-OSYMLPPYSA-N

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

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)[C@H]2c3cccc(O)c3C(=O)c4c(O)cc(CO)cc24

biological source

Curacao aloe

form

powder

concentration

~50%

color

yellow to brown

mp

418.39  °C ((785.10 °F ))

solubility

pyridine: 50 mg/mL, clear, dark red to very dark red and red purple

storage temp.

room temp

Quality Level

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Biochem/physiol Actions

Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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K Shimpo et al.
Phytotherapy research : PTR, 15(8), 705-711 (2001-12-18)
We examined the modifying effect of whole-leaf Aloe arborescens Miller var. natalensis Berger (designated as 'ALOE') on azoxymethane (AOM)-induced aberrant crypt foci (ACF), putative preneoplastic lesions, in the rat colorectum. Male F344 rats (4 weeks old) were fed the basal
[Studies of aloe. II. Mechanism of cathartic effect].
Y Ishii et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 108(9), 904-910 (1988-09-01)
Jin-dong Chen et al.
Se pu = Chinese journal of chromatography, 20(4), 367-368 (2003-01-25)
Barbaloin in aloe capsule was quantitatively determined by high performance liquid chromatography with ODS column, a mixture of CH3OH-H2O (50:50, volume ratio) as mobile phase and UV detection at 298 nm. There was a good linear relationship within the range
Metabolism of barbaloin by intestinal bacteria.
M Hattori et al.
Chemical & pharmaceutical bulletin, 36(11), 4462-4466 (1988-11-01)
Jianniao Tian et al.
Chemical & pharmaceutical bulletin, 51(5), 579-582 (2003-05-09)
The fluorescence quenching reactions of barbaloin with bovine serum albumin (BSA) in pH 7.20 Tris-HCl buffer solution were studied. The quenching mechanism of BSA by barbaloin was interpreted using the Stern-Volmer (S-V) mechanism. The binding constant K values were 2.78

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