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A0451

Sigma-Aldrich

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:
1415-73-2
Molecular Weight:
418.39
Beilstein:
6077558
EC Number:
215-808-0
MDL number:
MFCD00151160
UNSPSC Code:
41116107
PubChem Substance ID:
24890427
NACRES:
NA.79

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

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

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

InChI key

AFHJQYHRLPMKHU-OSYMLPPYSA-N

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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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Y Ishii et al.
Biological & pharmaceutical bulletin, 17(4), 495-497 (1994-04-01)
Charcoal transport, as an indicator of the degree of peristalsis, and water content in the large intestine after the intracaecal administration of barbaloin, were measured simultaneously in the same rat. Charcoal transport was significantly accelerated at both 3.5 and 6.5
Q M Che et al.
Planta medica, 57(1), 15-19 (1991-02-01)
A strictly anaerobic bacterium, Eubacterium sp. BAR, was isolated from human feces as one of the intestinal bacteria capable of metabolizing barbaloin. The bacterium grew in PYF broth containing barbaloin and converted barbaloin to aloe-emodin anthrone. On the other hand
Q L Li et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 32(9), 691-694 (2001-10-13)
In 0.1 mol.L-1 H2SO4 solution, a well-defined reduction wave of barbaloin was obtained by single-sweep osciflopolarography. The peak potential was shown to be -0.75 V (vs SCE). The peak current is proportional to the concentration of barbaloin over the range
Tetsuya Shindo et al.
Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan, 43(3), 122-126 (2002-09-20)
The contents of barbaloin (BA), isoBA, aloin-dimers A, B, C, D and aloe-emodin (AE) in aloe drinks were investigated. BA and isoBA were detected in 30 of the 31 samples at the levels of 120-570 micrograms/mL and 120-580 micrograms/mL, respectively.
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