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Diosmin

CAT: 0804-HY-N0178-03Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0178-03Size:100 mg
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Description
Diosmin is a flavonoid found in a variety of citrus fruits and also an agonist of the aryl hydrocarbon receptor (AhR) .
CAS Number
520-27-4
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Aryl Hydrocarbon Receptor
Type
Natural Products
Related Pathways
Immunology/Inflammation
Applications
Cancer-programmed cell death
Field of Research
Cancer; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Diosmin.html
Concentration
10mM
Purity
99.51
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C1C=C(C2=CC=C(OC)C(O)=C2)OC3=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O)O)O4)O)O)O)=CC(O)=C13
Molecular Formula
C28H32O15
Molecular Weight
608.54
Precautions
H302, H315, H319, H335
References & Citations
[1]Ciolino HP, et al. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affectcytochrome P450 1A1 activity. Cancer Res. 1998 Jul 1;58 (13) :2754-60.|[2]Tong N, et al. Diosmin protects rat retina from ischemia/reperfusion injury. J Ocul Pharmacol Ther. 2012 Oct;28 (5) :459-66.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Launched

Chemical Information

Diosmin

Diosmin is a disaccharide derivative that consists of diosmetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and an anti-inflammatory agent. It is a monomethoxyflavone, a rutinoside, a dihydroxyflavanone, a glycosyloxyflavone and a disaccharide derivative. It is functionally related to a diosmetin.

CAS Number520-27-4
PubChem CID5281613
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Molecular FormulaC28H32O15
Molecular Weight608.5
XLogP-0.8
Topological Polar Surface Area234
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count15
Rotatable Bond Count7
Heavy Atom Count43
Formal Charge0
Complexity995
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
InChI
InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey
GZSOSUNBTXMUFQ-YFAPSIMESA-N
Chemical Structure
2D Structure
2D structure of Diosmin
CAS: 520-27-4
CID: 5281613
Formula: C28H32O15
MW: 608.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight608.5
XLogP3-0.8
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count15
Rotatable Bond Count7
Exact Mass608.17412031
Monoisotopic Mass608.17412031
Topological Polar Surface Area234 Ų
Heavy Atom Count43
Formal Charge0
Complexity995
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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