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Merck
CN

50292

Aloin

analytical standard

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:
1415-73-2
Molecular Weight:
418.39
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329757585
EC Number:
215-808-0
Beilstein/REAXYS Number:
6077558
MDL number:
MFCD00151160

Key Documents

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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

InChI key

AFHJQYHRLPMKHU-OSYMLPPYSA-N

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

impurities

≤10.0% water (Karl Fischer)

application(s)

food and beverages

format

neat

storage temp.

2-8°C

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH9044
BCCH4742
BCCH2892
BCCG9033
BCCG2617

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Y Ishii et al.
Biological & pharmaceutical bulletin, 21(11), 1226-1227 (1998-12-16)
The cathartic effect of isobarbaloin, a stereoisomer of barbaloin (compound principally responsible for the cathartic activity of Aloe), was examined in male rats by oral administration. Individual differences in sensitivity in the laxative activity of isobarbaloin and barbaloin was not
Evandro L Duarte et al.
Langmuir : the ACS journal of surfaces and colloids, 24(8), 4041-4049 (2008-03-06)
Barbaloin is a bioactive glycosilated 1,8-dihydroxyanthraquinone present in several exudates from plants, such as Aloe vera, which are used for cosmetic or food purposes. It has been shown that barbaloin interacts with DMPG (dimyristoylphosphatidylglycerol) model membranes, altering the bilayer structure
Tetsuya Shindo et al.
Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan, 43(3), 115-121 (2002-09-20)
Four kinds of barbaloin (BA)-related compounds (A, B, C, D) in aloe drinks were isolated by using preparative HPLC. LC/MS analyses of these compounds showed the identical quasimolecular ion peak at m/z 833 [M-H]-. The chemical structures were mainly determined
Metabolism of barbaloin by intestinal bacteria.
M Hattori et al.
Chemical & pharmaceutical bulletin, 36(11), 4462-4466 (1988-11-01)
Determination of barbaloin in rat serum.
Y Ishii et al.
Chemical & pharmaceutical bulletin, 35(11), 4642-4644 (1987-11-01)
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