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A7687

Sigma-Aldrich

Aloe-emodin

≥95% (HPLC)

Synonym(s):

1,8-Dihydroxy 3-hydroxymethylanthraquinone, 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone, 3-Hydroxymethylchrysazine, Rhabarberone

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
481-72-1
Molecular Weight:
270.24
Beilstein:
2059062
EC Number:
207-571-7
MDL number:
MFCD00017373
UNSPSC Code:
12352205
PubChem Substance ID:
24891267
NACRES:
NA.79

biological source

plant root (Rheum palmatum)

Assay

≥95% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

yellow to brown

storage temp.

2-8°C

SMILES string

OCc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1

InChI

1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2

InChI key

YDQWDHRMZQUTBA-UHFFFAOYSA-N

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General description

Aloe-emodin is a hydroxyanthraquinone found naturally in aloe plants.

Application

Aloe-emodin has been used as a standard in high performance liquid chromatography (HPLC) for separation and identification of phenolic compounds in Aloe arborescens Miller var. natalensis Berger (Kidachi aloe).

Biochem/physiol Actions

Aloe-emodin exhibits antibacterial, antiviral, anti-inflammatory and hepatoprotective effects.
Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

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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Evaluation of aloin and aloe-emodin as anti-inflammatory agents in aloe by using murine macrophages
Park MY, et al.
Bioscience, Biotechnology, and Biochemistry, 73(4), 828-832 (2009)
Radical-scavenging effects of Aloe arborescens Miller on prevention of pancreatic islet B-cell destruction in rats
Beppu H, et al.
Journal of Ethnopharmacology, 89(1), 37-45 (2003)
Yiqun Du et al.
Journal of B.U.ON. : official journal of the Balkan Union of Oncology, 24(2), 746-753 (2019-05-28)
To study the anticancer effects of aloe emodin against the MIAPaCa-2 and PANC-1 human pancreatic adenocarcinoma cancer cell lines by evaluating its effect on autophagic cell death, mitochondrial membrane potential (ΛΨm) loss and cell cycle arrest. The MTT assay was
Mildred Acevedo-Duncan et al.
International immunopharmacology, 4(14), 1775-1784 (2004-11-09)
Aloe-emodin (1,8-dihydroy-3-[hydroxymethyl]-anthraquione) purified from Aloe vera leaves has been reported to have antitumor activity. The objectives of our research were to determine how aloe-emodin regulates the cell cycle, cell proliferation and protein kinase C (PKC) during glioma growth and development.
Jun-ming Guo et al.
Acta pharmacologica Sinica, 28(12), 1991-1995 (2007-11-23)
The aim of this study was to investigate the effects of aloe-emodin, a natural compound from the root and rhizome of Rheum palmatum, on the growth of human cervical cancer cells, HeLa. HeLa cells were treated with various concentrations of
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