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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
Pricing and availability is not currently available.

biological source

Aloe barbadensis Miller leaves

Quality Level

200

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.[1] 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.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000421402
0000421401
0000421401
0000421402
0000373630

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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)
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
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
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
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
View All Related Papers

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. I studied some papers and found that aloin is a light sensitive compound, is it true?

    1 answer

    1. This material is considered light and air sensisitve. The product is packaged under nitrogen in white HDPE bottles.

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