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B6906

Sigma-Aldrich

Aloin

from Aloe barbadensis Miller leaves, ≥97%

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:
12352201
PubChem Substance ID:
24891938
NACRES:
NA.25

biological source

Aloe barbadensis Miller leaves

Assay

≥97%

form

powder

solubility

methanol: 100 mg/mL, clear to very slightly hazy, light yellow to yellow

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

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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Related Categories

Application

Aloin, a natural mixed diastereomer (A/B) anthracycline from aloe plant, may be studied as a chemopreventive factor and antineoplastic agent. Aloin inhibits angiogenesis, enhances melanogenesis and regulates transglutaminase activity. Aloin may be used to assess its activity as a selective phosphodiesterase inhibitor. Aloin A is used as a stabilizer in the preparation of gold and silver nanoparticles.

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.

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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Claudio Tabolacci et al.
Life sciences, 87(9-10), 316-324 (2010-07-14)
Aloe-emodin (AE), a natural hydroxyanthraquinone compound, has been reported as a potential anticancer agent. We studied the antineoplastic properties of AE on highly metastatic B16-F10 melanoma murine cells. Cell proliferation was assessed by cell counting and viability was investigated using
Angelo Gismondi et al.
Amino acids, 38(1), 257-262 (2009-02-13)
The aim of this study was to collect evidences on the role of transglutaminase (TG, E.C.2.3.2.13) in the antineoplastic properties exerted by nimesulide (NMS), a non-steroidal anti-inflammatory drug, on murine B16-F10 melanoma cells. Treatment of melanoma cells with nimesulide produces
Mahmoud A Elsohly et al.
Journal of AOAC International, 90(1), 28-42 (2007-03-22)
Methods using liquid chromatography/mass spectrometry (LC/MS) and LC with diode array detection (DAD) in the UV range (LC/UV) were developed for the determination of low levels of the anthraquinones aloe-emodin and aloin-A (barbaloin) in aloe-based products. The methods were used
Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation.
Tabolacci C, Rossi S, Lentini A, et al.
Amino Acids, doi: 10-doi: 10 (2011)
Mi-Young Park et al.
Nutrition research and practice, 2(1), 17-21 (2008-04-01)
Aloin is a physiologically active anthraquinone present in aloe. There are two isomers of aloin, aloin A and aloin B, occurring as a mixture of diastereomers. The objective of this study was to determine the bioavailability and tissue distribution of
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