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520-27-4

Basic Information
CAS No.: 520-27-4
Name: Diosmin
Molecular Structure:
Molecular Structure of 520-27-4 (Diosmin)
Formula: C28H32O15
Molecular Weight: 608.54 g/mol
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;
EINECS: 208-289-7
Density: 1.68 g/cm3
Melting Point: 277-278 °C
Boiling Point: 926.8 °C at 760 mmHg
Flash Point: 305.2 °C
Solubility: Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C).
Appearance: Greyish-yellow or light yellow hygroscopic powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-36/37
Transport Information:
PSA: 238.20000
LogP: -1.08970
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%
520-27-4

diosmin

520-34-3

diosmetin

Conditions
ConditionsYield
With sulfuric acid; acetic acid In water for 12h; Reflux;88%
With sulfuric acid; water at 20℃; for 0.166667h;85%
With sulfuric acid; acetic acid In water at 95 - 105℃;85%
With sulfuric acid In methanol; water at 130℃; for 11h;
With sodium hydroxide at 100℃; for 0.666667h; Temperature; Large scale;100 kg
77-78-1

dimethyl sulfate

520-27-4

diosmin

10544-05-5

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one

Conditions
ConditionsYield
Stage #1: dimethyl sulfate; diosmin In acetone for 6h;
Stage #2: With sulfuric acid In ethanol for 4h; Reflux;
87%
520-27-4

diosmin

copper dichloride

[Cu(diosmin)2(H2O)2]*1.5H2O

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 60℃; for 3h; pH=5 - 8;80%
14210-25-4

5-Chloro-1-phenyltetrazole

520-27-4

diosmin

771480-96-7

3'-O-(1-phenyltetrazol-5-yl)diosmin

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 2h;40%
520-27-4

diosmin

107-07-3

2-chloro-ethanol

80604-69-9

hidrosmin

Conditions
ConditionsYield
With sodium hydroxide In water for 288h; Ambient temperature;34.9%
108-24-7

acetic anhydride

520-27-4

diosmin

diosmetin 7-rutinoside octaacetate

Conditions
ConditionsYield
With pyridine Ambient temperature;38 mg
520-27-4

diosmin

107-07-3

2-chloro-ethanol

80604-68-8

5-O-(beta-hydroxyethyl)diosmin

Conditions
ConditionsYield
With sodium hydroxide 1.) H2O, 45 deg C, 2.15 h, 2.) H2O, 85 deg C, 5.30 h; Yield given. Multistep reaction;
With triethylamine In methanol under 0.45 - 0.5 Torr; Reagent/catalyst; Large scale;
520-27-4

diosmin

50848-66-3

7,4'-dimethoxy-5-hydroxy-6-iodoflavone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 40 percent / KHCO3 / dimethylformamide / 2 h / 80 °C
2: 53 percent / HCOONH4 / Pd/C / methanol / 5 h / Heating
3: 70 percent / aq. HCl / 1.5 h / 50 - 55 °C
4: 95 percent / K2CO3 / dimethylformamide / 20 °C
5: 73 percent / benzyltrimethylammonium dichloroiodate; CaCO3 / CH2Cl2; methanol / 20 °C
View Scheme
520-27-4

diosmin

480-44-4

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 40 percent / KHCO3 / dimethylformamide / 2 h / 80 °C
2: 53 percent / HCOONH4 / Pd/C / methanol / 5 h / Heating
3: 70 percent / aq. HCl / 1.5 h / 50 - 55 °C
View Scheme
520-27-4

diosmin

5128-44-9

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 40 percent / KHCO3 / dimethylformamide / 2 h / 80 °C
2: 53 percent / HCOONH4 / Pd/C / methanol / 5 h / Heating
3: 70 percent / aq. HCl / 1.5 h / 50 - 55 °C
4: 95 percent / K2CO3 / dimethylformamide / 20 °C
View Scheme
520-27-4

diosmin

480-36-4

acacetin 7-O-rutinoside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 40 percent / KHCO3 / dimethylformamide / 2 h / 80 °C
2: 53 percent / HCOONH4 / Pd/C / methanol / 5 h / Heating
View Scheme
520-27-4

diosmin

5,7-Dihydroxy-2-[3-(2-hydroxy-ethoxy)-4-methoxy-phenyl]-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) 10percent NaOH, 2.) 10percent NaOH / 1.) H2O, 45 deg C, 2.15 h, 2.) H2O, 85 deg C, 5.30 h
2: 56.3 percent / 1N HCl / 1.33 h / Heating
View Scheme
520-27-4

diosmin

7-Hydroxy-5-(2-hydroxy-ethoxy)-2-[3-(2-hydroxy-ethoxy)-4-methoxy-phenyl]-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 34.9 percent / 10percent NaOH / H2O / 288 h / Ambient temperature
2: 47.4 percent / 1N HCl / 3 h / Heating
View Scheme
520-27-4

diosmin

172805-77-5

3',7-di-O-(β-hydroxyethyl)diosmetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 10percent NaOH, 2.) 10percent NaOH / 1.) H2O, 45 deg C, 2.15 h, 2.) H2O, 85 deg C, 5.30 h
2: 56.3 percent / 1N HCl / 1.33 h / Heating
3: 89.2 percent / 3percent NaOH / H2O / 70 h / 50 °C
View Scheme
520-27-4

diosmin

5,7-Bis-(2-hydroxy-ethoxy)-2-[3-(2-hydroxy-ethoxy)-4-methoxy-phenyl]-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 34.9 percent / 10percent NaOH / H2O / 288 h / Ambient temperature
2: 47.4 percent / 1N HCl / 3 h / Heating
3: 60.6 percent / 3percent NaOH / H2O / 4.3 h / 80 °C
View Scheme
520-27-4

diosmin

7585-39-9

β‐cyclodextrin

C28H32O15*C42H70O35

Conditions
ConditionsYield
In ethanol; water for 2h; Milling;
520-27-4

diosmin

diosmetinidin

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 160℃; for 10h;1.73 g

vanadyl(IV) chloride

520-27-4

diosmin

1310-73-2

sodium hydroxide

[VO(dios)(OH)3]Na5*6H2O

Conditions
ConditionsYield
pH=12;
Raw Materials
520-26-3
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    Diosmin

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Consensus Reports

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

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).