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Emodin-8-glucoside

CAT: 0804-HY-N0311-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0311-01Size:1 mg
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Description
Emodin-8-glucoside is an anthraquinone derivative that can be isolated from Aloe vera. Emodin-8-glucoside is the inhibitor for MAPK with an inhibition constant of 430.14 pM. Emodin-8-glucoside exhibits moderate inhibitory activity against rat lens aldose reductase (ALAR) and topoisomerases II with IC50s of 14.4 μM and 66 μM. Emodin-8-glucoside exhibits antioxidant, anti-inflammatory and anti-fibrotic activities. Emodin-8-glucoside can cross the blood brain barrier[1][2][3][4][5].
CAS Number
23313-21-5
UNSPSC
12352005
Hazard Statement
H302
Target
Aldose Reductase; p38 MAPK; SOD; Topoisomerase
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/emodin-8-glucoside.html
Purity
99.35
Solubility
DMSO : 50 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C1C2=C(C=C(C)C=C2O)C(C3=CC(O)=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)=C13)=O
Molecular Formula
C21H20O10
Molecular Weight
432.38
Precautions
H302
References & Citations
[1]Kim J M, et al. Constituents of the fruits of Rumex japonicus with Inhibitory Activity on Aldose Reductase[J]. Journal of Applied Biological Chemistry, 2008, 51 (1) : 13-16.|[2]Hwangbo K, et al., Inhibition of DNA topoisomerases I and II of compounds from Reynoutria japonica. Arch Pharm Res. 2012 Sep;35 (9) :1583-9.|[3]Wang C, et al., Neuroprotective effects of emodin-8-O-beta-D-glucoside in vivo and in vitro. Eur J Pharmacol. 2007 Dec 22;577 (1-3) :58-63.|[4]Zhang K, et al., Discovery of Natural Products Alleviating Renal Fibrosis with a Viscosity-Responsive Molecular Probe. Anal Chem. 2024 Apr 23;96 (16) :6356-6365.|[5]Vaziri-Amjad S, et al., Natural anthraquinones as promising MAPK3 inhibitors for complementary cancer therapy[J]. Journal of Chemistry, 2023, 2023 (1) : 6683470.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Emodin-8-glucoside

Emodin 8-glucoside is a dihydroxyanthraquinone.

CAS Number23313-21-5
PubChem CID99649
IUPAC Name1,6-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Molecular FormulaC21H20O10
Molecular Weight432.4
XLogP0.9
Topological Polar Surface Area174
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Heavy Atom Count31
Formal Charge0
Complexity700
SMILES
CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChI
InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1
InChIKey
HSWIRQIYASIOBE-JNHRPPPUSA-N
Chemical Structure
2D Structure
2D structure of Emodin-8-glucoside
CAS: 23313-21-5
CID: 99649
Formula: C21H20O10
MW: 432.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight432.4
XLogP30.9
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count3
Exact Mass432.10564683
Monoisotopic Mass432.10564683
Topological Polar Surface Area174 Ų
Heavy Atom Count31
Formal Charge0
Complexity700
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes