Diosmin

Bezeichnung:Diosmin

CAS-Nr520-27-4

Englisch Name:Diosmin

CBNumberCB6443258

SummenformelC28H32O15

Molgewicht608.54

MOL-Datei520-27-4.mol

Synonyma

Diosmin

Diosmin physikalisch-chemischer Eigenschaften

Schmelzpunkt	277-278°C
Siedepunkt	926.8±65.0 °C(Predicted)
Dichte	1.68±0.1 g/cm3(Predicted)
Dampfdruck	0Pa at 20℃
storage temp.	Sealed in dry,2-8°C
Löslichkeit	Practically insoluble in water, soluble in dimethyl sulfoxide, practically insoluble in alcohol. It dissolves in dilute solutions of alkali hydroxides.
pka	6.10±0.40(Predicted)
Farbe	Pale Beige to Brown
Wasserlöslichkeit	Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C).
maximale Wellenlänge (λmax)	345nm(EtOH)(lit.)
Merck	14,3297
InChIKey	GZSOSUNBTXMUFQ-YFAPSIMESA-N
LogP	0.14 at 20℃
CAS Datenbank	520-27-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36-36/37-24/25
WGK Germany	3
HS Code	29381000

Gefahreninformationscode (GHS)

Diosmin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Diosmin was separated from the root of Scrophularia nodosa L. in 1925. The root of Scrophularia nodosa L. has the function of nourishing, reducing fever, relieving internal heat, and detoxicating. It was firstly recorded in the Shen Nong’s Classic of Materia Medica, as a class of middle-grade drug and is currently recorded in the Ch.P 2015, Volume I. The natural resource was abundant in China, mainly provided from Zhejiang, Sichuan, Hubei, Anhui, and Jiangsu provinces. In the clinical practice, Scrophularia nodosa L. was employed to eliminate pathogenic heat from the blood. In the clinical indication, diosmin was mainly applied to treat fever, polydipsia, maculitis, gingivitis, amygdalitis, laryngopharyngitis, acute lymphadenitis, etc. It also has the biological function of antiplatelet aggregation and antitumor. The chemical components include iridoids, phenylpropanoid glycoside, flavonoids, and fatty acids.
Chemische Eigenschaften
Diosmin is a natural flavonoid mainly present in the peel of some citrus fruits, such as oranges and lemons. Flavonoids are anti-inflammatory plant compounds that protect your body from free radicals and other unstable molecules. The most prevalent uses for Diosmin include hemorrhoids and leg sores caused by poor blood flow. Diosmin was first found in 1925 in the wort plant and has since been used as a natural treatment for hemorrhoids, varicose veins, venous insufficiency, leg ulcers, and other circulatory issues.
Physikalische Eigenschaften
Appearance: Grayish yellow or light yellow hygroscopic powder. Solubility: Practically insoluble in water, soluble in dimethyl sulfoxide, practically insoluble in alcohol. It dissolves in dilute solutions of alkali hydroxides. Melting point: 277–278°C.
Originator
Diosmil,Bellon,France,1971
History
Diosmin was firstly introduced as a medicine in 1969. It was launched in France in 1987 with the product name “Alvenor.” As the protecting agent for blood vessel and therapeutic agent for chronic venous disease, diosmin has been used for over 30?years in Europe
Diosmin is a typical flavonoid. It could be prepared from natural resources or semisynthesized from the natural product hesperidin by dehydrogenation reaction.
Verwenden
Diosmin is an agonist of the aryl hydrocarbon receptor (AhR) and exhibits anti-proliferative and anti-inflammatory. It is used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) and hemorrhoidal disease (HD). Diosmin also reduces capillary hyperpermeability and expression of endothelial adhesion molecules (ICAM1, VCAM1). It effectively inhibits the P-glycoprotein (Pgp)-mediated efflux in cells.
Application
Diosmin is a naturally occurring flavonic glycoside isolated from various plants. Diosmin is a capillary protectant and It is used for the improvement of capillary fragility or venous insufficiency, including chronic venous insufficiency (CVI) and hemorrhoids. Diosmin is widely available over-the-counter and demonstrates a favourable a favorable safety profile.
Indications
The clinical indications of diosmin are those symptoms related to venous-lymphatic dysfunction such as leg heaviness, pains, soreness, and swelling in the morning. Besides, the symptoms related to acute hemorrhoids could also be treated with diosmin.
Definition
ChEBI: Diosmin is a disaccharide derivative that consists of diosmetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and an anti-inflammatory agent. It is a glycosyloxyflavone, a rutinoside, a disaccharide derivative, a monomethoxyflavone and a dihydroxyflavanone. It derives from a diosmetin.
Manufacturing Process
A mixture of 72 g hesperidin, 288 ml acetic anhydride and 300 ml glacial acetic acid were boiled in reflux with 15 ml pyridine as the catalyst for 144 hours until during the control of the reaction the band disappeared at a wave length between 264 to 280 nm, and a new maximum appeared at 330 nm. Thereafter in a rotation evaporator the reaction mixture was concentrated by evaporation under vacuum conditions.
The residue was absorbed in 1,200 ml ethyl acetate, admixed with 20 ml ethanol and boiled for one hour under reflux action. The solution was filtered and compressed to dryness. The residue was dried in a vacuum drying cabinet. The yield amounted to 107.5 g.
35.8 g thereof were then dissolved in 280 ml glacial acetic acid and
ominated with a solution of 6.05 g
omine in 30 ml glacial acetic acid. Thereafter the mixture compressed to dryness by means of the rotation evaporator, there being obtained a residue of 41.8 g. Such was dissolved in 150 ml methanol, admixed with a solution of 36 g sodium hydroxide in 180 ml water and stirred for one hour at 50°C.
The diosmin was precipitated out by adding 120 ml glacial acetic acid and stirring at 70°C for 30 minutes. The precipitate was filtrated in a suction filter or strainer, washed with methanol, water and again methanol and dried at 60°C in the drying cabinet. Raw yield: 17.0 g corresponding to 71% yield.
omine content 0.51%.
10 g of the thus-obtained diosmin was dissolved in a solution of 24 g sodium hydroxide in 120 ml water, admixed with 100 ml methanol and 100 ml pyridine and stirred for one hour at 50°C. The diosmin was precipitated by the addition of 100 ml glacial acetic acid and stirred for 30 minutes at 70°C, filtered and washed with methanol and water and again methanol.
After drying at 60°C there was obtained a pure yield of 9.2 g diosmin (65% based upon the employed hesperidin) having a
omine content of 0.07%.
Therapeutic Function
Bioflavonoid
Flammability and Explosibility
Not classified
Pharmakologie
Diosmin is a micronized, purified, flavonoid-structure drug. It is helpful for lymphatic return and stimulating microcirculation, treating hemorrhoids and venous dysfunction by increasing the venous tension.
1. Increasing the venous tension. Diosmin could strengthen the tensile force of the venous wall even under high temperature. Diosmin’s action in venous constriction is stronger than other drugs like rutin. Even under the acidic toxicity in the body, it could still raise the venous tension. Diosmin has special affinity to the venous other than the arterial system.
2. Improving the microcirculation. Diosmin could effectively reduce adhesion and migration of leukocyte and vascular endothelial cells. It could also release inflammatory substances such as histamine, bradykinin, alexin, leukotriene, prostaglandin, and surplus free radicals. Hence, the penetration of capillary blood vessel was reduced, and the tension was enhanced. Besides, diosmin could decrease blood viscosity, accelerate erythrocyte flow rate, and finally reduce the chances of microcirculatory stasis
3. Stimulating the lymphatic return. Diosmin could effectively increase the speed of lymphatic drainage and the lymphatic contraction, accelerating the circumfluence of interstitial fluid, improving lymphatic return, and relieving edema.
Clinical Use
Diosmin was mainly used to treat diseases like chronic venous dysfunction, haemorrhoids, lymphedema, phlebeurysm, etc.
Nebenwirkungen
Diosmin can cause some side effects such as nausea, stomach pain, diarrhea, insomnia, dizziness, headache, drowsiness, skin redness and hives, muscle pain, blood problems, and altered heart rate.
There may be a few of minor gastrointestinal reactions and adverse reactions such as plant nerve function disorder, but generally mild and don't have to stop the drug.
Pregnant women and nursing mothers with hemorrhoids are safe to use this product.
Mode of action
1. Enhance the vein tension, even not exceptional under high temperature condition. It has a stronger effect causing the constriction of vein than other drugs such as rutin, still can enhance the tension of the vein when the body was acidosis. Diosmin has specific affinity for vein without affecting the arterial system.
2. Improve microcirculation. Diosmin can obviously reduce the white blood cells and vascular endothelial cell adhesion, migration, disintegrating the release of inflammatory substances, such as histamine, slow excitation peptide, complement, leukotriene, prostaglandins, and too many free radicals, reducing the permeability of capillaries and enhance its tension. Diosmin can lower blood viscosity, enhance the function of red blood cell velocity, thus reduce the microcirculation clogged.
3. Promote lymphatic circumfluence. Diosmin can increase the speed of lymphatic drainage.

Diosmin Upstream-Materialien And Downstream Produkte

Diosmin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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