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Merck

B6906

Aloin

from Aloe barbadensis Miller leaves, ≥97%

Sinónimos:

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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Acerca de este artículo

Fórmula empírica (notación de Hill):
C21H22O9
Número CAS:
Peso molecular:
418.39
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
215-808-0
Beilstein/REAXYS Number:
6077558
MDL number:
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biological source

Aloe barbadensis Miller leaves

Quality Level

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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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

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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Zeljka Krpetić et al.
Langmuir : the ACS journal of surfaces and colloids, 25(13), 7217-7221 (2009-06-10)
A novel use of two components of Cape aloe, aloin A and aloesin, acting as stabilizers in the preparation of gold and silver nanoparticles, is reported. Stable water-soluble particles of different size and shape are prepared by varying the reaction
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
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
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

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