Product Name

  • Name

    Diosmin

  • EINECS 208-289-7
  • CAS No. 520-27-4
  • Article Data16
  • CAS DataBase
  • Density 1.68 g/cm3
  • 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
  • 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;
  • PSA 238.20000
  • LogP -1.08970

Synthetic route

hesperidin
520-26-3

hesperidin

diosmin
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
(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
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

diosmin
520-27-4

diosmin

Conditions
ConditionsYield
With sodium hydroxide
hesperidin octaacetate

hesperidin octaacetate

diosmin
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-<O2,O3,O4-triacetyl-O6-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy>-chroman-4-one

(S)-5-acetoxy-2-<3-acetoxy-4-methoxy-phenyl>-7-<O2,O3,O4-triacetyl-O6-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy>-chroman-4-one

diosmin
520-27-4

diosmin

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

5-hydroxyheptaacetyldiosmin

diosmin
520-27-4

diosmin

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 20℃; for 4h;
C30H34O16

C30H34O16

diosmin
520-27-4

diosmin

Conditions
ConditionsYield
With water; sodium hydroxide for 1.5h;
(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
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

diosmin
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

C30H36O16

diosmin
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
acetic anhydride
108-24-7

acetic anhydride

diosmin
520-27-4

diosmin

3',5-diacetoxy-7-[hexa-O-acetyl-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-4'-methoxyflavone
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
diosmin
520-27-4

diosmin

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

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
520-27-4

diosmin

diosmetin
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
dimethyl sulfate
77-78-1

dimethyl sulfate

diosmin
520-27-4

diosmin

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one
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%
water
7732-18-5

water

diosmin
520-27-4

diosmin

copper dichloride

copper dichloride

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

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

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 60℃; for 3h; pH=5 - 8;80%
...Expand
5-Chloro-1-phenyltetrazole
14210-25-4

5-Chloro-1-phenyltetrazole

diosmin
520-27-4

diosmin

3'-O-(1-phenyltetrazol-5-yl)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%
diosmin
520-27-4

diosmin

2-chloro-ethanol
107-07-3

2-chloro-ethanol

hidrosmin
80604-69-9

hidrosmin

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

acetic anhydride

diosmin
520-27-4

diosmin

diosmetin 7-rutinoside octaacetate

diosmetin 7-rutinoside octaacetate

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

diosmin

2-chloro-ethanol
107-07-3

2-chloro-ethanol

5-O-(beta-hydroxyethyl)diosmin
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;
diosmin
520-27-4

diosmin

7,4'-dimethoxy-5-hydroxy-6-iodoflavone
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
diosmin
520-27-4

diosmin

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one
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
diosmin
520-27-4

diosmin

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
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
diosmin
520-27-4

diosmin

acacetin 7-O-rutinoside
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
diosmin
520-27-4

diosmin

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

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
diosmin
520-27-4

diosmin

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

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
diosmin
520-27-4

diosmin

3',7-di-O-(β-hydroxyethyl)diosmetin
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
diosmin
520-27-4

diosmin

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

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
diosmin
520-27-4

diosmin

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C28H32O15*C42H70O35

C28H32O15*C42H70O35

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

diosmin

diosmetinidin

diosmetinidin

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 160℃; for 10h;1.73 g
vanadyl(IV) chloride

vanadyl(IV) chloride

water
7732-18-5

water

diosmin
520-27-4

diosmin

sodium hydroxide
1310-73-2

sodium hydroxide

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

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

Conditions
ConditionsYield
pH=12;
...Expand

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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