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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 | Hazard Symbols | Xi | |
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 |
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 |
(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
Conditions | Yield |
---|---|
With sodium hydroxide |
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; |
diosmin
Conditions | Yield |
---|---|
With N-Bromosuccinimide; chloroform; dibenzoyl peroxide Erwaermen des Reaktionsprodukts mit wss.-aethanol. Natronlauge; |
diosmin
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 20℃; for 4h; |
diosmin
Conditions | Yield |
---|---|
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
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 |
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 |
acetic anhydride
diosmin
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 |
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% |
Diosmin (CAS NO.520-27-4) is reported in EPA TSCA Inventory.
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).