| Identification | More | [Name]
Diosmin | [CAS]
520-27-4 | [Synonyms]
3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE 7-RUTINOSIDE
3,5,7-TRIHYDROXY-4-METHOXYFLAVONE 7-RUTINOSIDE
BAROSMIN
DIOSMETIN-7-O-RUTINOSIDE
DIOSMETIN-7-RUTINOSIDE
DIOSMIN
Diosmine EP4
DIOSMINE
Buchu resin
Daflon
Diosmil
Diovenor
DIOSIMIN
BAROSMIN hplc
Diosmin+ Hesperidin
DIOSMIN WITH HPLC
7-[[6-O-(6-Deoxy-a-L-mannopyranosyl)--D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Venosmine
3',5-Dihydroxy-4'-methoxy-7-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)flavone
7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3-hydroxy-4-methoxyphenyl)-5-hydroxy-4H-1-benzopyran-4-one | [EINECS(EC#)]
208-289-7 | [Molecular Formula]
C28H32O15 | [MDL Number]
MFCD00009772 | [Molecular Weight]
608.54 | [MOL File]
520-27-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
277-278°C | [Boiling point ]
926.8±65.0 °C(Predicted) | [density ]
1.68±0.1 g/cm3(Predicted) | [vapor pressure ]
0Pa at 20℃ | [storage temp. ]
2-8°C
| [solubility ]
Practically insoluble in water, soluble in dimethyl sulfoxide, practically insoluble in alcohol. It dissolves in dilute solutions of alkali hydroxides. | [form ]
neat | [pka]
6.10±0.40(Predicted) | [color ]
Pale Beige to Brown | [Water Solubility ]
Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C). | [Usage]
Naturally occurring flavonic glycoside; rhamnoglycoside of Diosmetin. Capillary protectant | [λmax]
345nm(EtOH)(lit.) | [Merck ]
13,3327 | [InChIKey]
GZSOSUNBTXMUFQ-YFAPSIMESA-N | [LogP]
0.14 at 20℃ | [CAS DataBase Reference]
520-27-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 . | [WGK Germany ]
3
| [HS Code ]
29329900 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
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. | [Physical properties]
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. | [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. | [Uses]
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. | [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. | [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. | [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]
Notclassified | [Pharmacology]
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. | [Side effects]
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. |
| Questions And Answer | Back Directory | [Pharmacological Effects]
Diosmin is also called Alvenor. It is a kind of drug for the treatment of hemorrhoid symptoms related to acute episodes, can also be used in the treatment of symptoms associated with venous lymphatic insufficiency (leg heavy, pain, morning acid swells discomfort).
The effects of diosmin are as below:
1, Has specific affinity to the venous system, enhance the tension system without affecting the artery of vein;
2, To the microcirculation system, decrease the blood viscosity, improve the velocity of reducing silt up;
3, Contract the lymphatic system, which can enhance lymphatic and lymph drainage speed, speed up the return relieve edema.
4, Commercially available diosmin uses micronization technology, increase the contact area after using medicine, absorb more and higher bioavailability. Suitable for all kinds of hemorrhoids and acute hemorrhoids, also can be used for the treatment of chronic venous insufficiency, such as varicose veins, leg ulcers, etc.
This information is edited by ChemicalBook Xiao Nan. |
|
|