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Diosmin

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Name

Diosmin

EINECS 208-289-7
CAS No. 520-27-4 Density 1.68 g/cm3
PSA 238.20000 LogP -1.08970
Solubility Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C). Melting Point 277-278 °C
Formula C28H32O15 Boiling Point 926.8 °C at 760 mmHg
Molecular Weight 608.553 Flash Point 305.2 °C
Transport Information N/A Appearance Greyish-yellow or light yellow hygroscopic powder
Safety 26-36-36/37 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 520-27-4 (Diosmin) Hazard Symbols IrritantXi
Synonyms

4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.- D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-;5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxymethyl]oxan-2-yl]oxy-chromen-4-one;4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy- R-L-mannopyranosyl)-a-D-glucopyranosyl]- oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-;Diosmetin 7-O-rutinoside;4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-;Diosmine [INN-French];Diosminum [INN-Latin];Diosmine;Venosmine;Diosmin Inn;

Article Data 16

Diosmin Synthetic route

520-26-3

hesperidin

520-27-4

diosmin

Conditions
ConditionsYield
With iodine In pyridine at 90℃; for 10h;89%
With morpholine; iodine at 40 - 70℃; Temperature; Reagent/catalyst; Large scale; Green chemistry;85.7%
With ethanol; iodine; sodium acetate
69081-76-1

(2R,3Ξ)-5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-3-bromo-7-[O2,O3,O4-triacetyl-O6-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chroman-4-one

520-27-4

diosmin

Conditions
ConditionsYield
With sodium hydroxide

hesperidin octaacetate

520-27-4

diosmin

Conditions
ConditionsYield
With iodine; sodium methylate; potassium acetate; acetic anhydride; acetic acid 1.) reflux, 16 h; 2.) 25 min, 0 deg C; Yield given. Multistep reaction;
(S)-5-acetoxy-2-<3-acetoxy-4-methoxy-phenyl>-7--chroman-4-one

(S)-5-acetoxy-2-<3-acetoxy-4-methoxy-phenyl>-7--chroman-4-one

520-27-4

diosmin

Conditions
ConditionsYield
With N-Bromosuccinimide; chloroform; dibenzoyl peroxide Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge;

5-hydroxyheptaacetyldiosmin

520-27-4

diosmin

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 20℃; for 4h;

C30H34O16

520-27-4

diosmin

Conditions
ConditionsYield
With water; sodium hydroxide for 1.5h;
64726-90-5

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

520-27-4

diosmin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium acetate / 115 - 120 °C
2: sodium iodide / water / Reflux
3: dihydrogen peroxide; sulfuric acid / Reflux
4: water; sodium hydroxide / 1.5 h
View Scheme

C30H36O16

520-27-4

diosmin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium iodide / water / Reflux
2: dihydrogen peroxide; sulfuric acid / Reflux
3: water; sodium hydroxide / 1.5 h
View Scheme
108-24-7

acetic anhydride

520-27-4

diosmin

6195-54-6

3',5-diacetoxy-7-[hexa-O-acetyl-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-4'-methoxyflavone

Conditions
ConditionsYield
With pyridine at 20℃; for 48h;95%
With sodium fluoride at 130℃; for 0.583333h; Microwave irradiation;62%
With pyridine at 90℃; for 9h;6.78 g
520-27-4

diosmin

diosmin 2'',2''',3'',3''',4'',4'''-O-hexasulfate

Conditions
ConditionsYield
Stage #1: diosmin With triethylamine sulfurtrioxide In N,N-dimethyl acetamide at 65℃; for 23h;
Stage #2: With triethylamine In N,N-dimethyl acetamide; acetone at 4℃; for 24h;
Stage #3: With sodium acetate In water
91%

Diosmin Consensus Reports

 Diosmin (CAS NO.520-27-4) is reported in EPA TSCA Inventory.

Diosmin Specification

1. Introduction of Diosmin

Diosmin is one kind of light yellow powder. This chemical belongs to the Product Categories of Tetra-substituted Flavones;plant extract;Active pharmaceutical ingredients;Aromatics;Intermediates & Fine Chemicals;Oligosaccharides;Pharmaceuticals.

2. Properties of Diosmin

Diosmin has the following property datas: (1)Melting point: 277-278 °C; (2)Storage temp.: 2-8 °C; (3)Merck: 13,3327; (4)Density: 1.68 g/cm3; (5)Flash Point: 305.2 °C; (6)Index of Refraction: 1.711; (7)Surface Tension: 101.2 dyne/cm; (8)Enthalpy of Vaporization: 141.22 kJ/mol; (9)Boiling Point: 926.8 °C at 760 mmHg.

3. Structure Descriptors of Diosmin

You could convert the following datas into the molecular structure:
(1).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 
(2).InChIKey: InChIKey=GZSOSUNBTXMUFQ-YFAPSIMESA-N 
(3).Smiles: c12c(oc(c3cc(c(OC)cc3)O)cc1=O)cc(O[C@@H]1O[C@@H]([C@@H](O)[C@@H]([C@H]1O)O)CO[C@H]1[C@@H]([C@@H]([C@@H](O)[C@@H](O1)C)O)O)cc2O

4. Safety Information of Diosmin

Hazard Codes: IrritantXi
WGK Germany: 3
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-36/37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves.

5. Use of Diosmin

Diosmin is a semisynthetic phlebotropic drug which is a member of the flavonoid family. It is an oral phlebotropic drug used in the treatment of venous disease, chronic venous insufficiency (CVI) and hemorrhoidal disease (HD), in acute or chronic hemorrhoids, in place of rubber-band ligation, in combination with fiber supplement, or as an adjuvant therapy to hemorrhoidectomy, in order to reduce secondary bleeding. Diosmin (CAS NO.520-27-4) is also used with hesperidin to control internal symptoms of hemorrhoids (piles).

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