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| CAS No.: | 520-27-4 |
|---|---|
| Name: | Diosmin |
| Molecular Structure: | |
|
|
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| Formula: | C28H32O15 |
| Molecular Weight: | 608.553 |
| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-36/37 |
| PSA: | 238.20000 |
| LogP: | -1.08970 |
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| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium hydroxide |
- 520-27-4
diosmin
| Conditions | Yield |
|---|---|
| With iodine; sodium methylate; potassium acetate; acetic anhydride; acetic acid 1.) reflux, 16 h; 2.) 25 min, 0 deg C; Yield given. Multistep reaction; |
- 520-27-4
diosmin
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide; chloroform; dibenzoyl peroxide Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge; |
- 520-27-4
diosmin
| Conditions | Yield |
|---|---|
| With sodium hydroxide In tetrahydrofuran at 20℃; for 4h; |
- 520-27-4
diosmin
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
- 520-27-4
diosmin
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
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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: 
Xi
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).