Diosmin
Diosmin
CAS: 520-27-4
Molecular Formula: C28H32O15
Diosmin - Names and Identifiers
| Name | Diosmin |
| Synonyms | DIOSMIN Diosmin Diovenor DIOSIMIN BAROSMIN BAROSMIN hplc DIOSMETIN-7-RUTINOSIDE DIOSMETIN-7-O-RUTINOSIDE 3,5,7-Trihydroxy-4-methoxyflavone-7- rutinoside 3',5,7-trihydroxy-4'-methoxyflavone 7-rutinoside 3',5-Dihydroxy-4'-methoxy-7-(6-O-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)flavone 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxy-alpha-D-mannopyranosyl)-beta-D-glucopyranoside 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside |
| CAS | 520-27-4 |
| EINECS | 208-289-7 |
| InChI | InChI=1/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-/m1/s1 |
| InChIKey | GZSOSUNBTXMUFQ-YFAPSIMESA-N |
Diosmin - Physico-chemical Properties
| Molecular Formula | C28H32O15 |
| Molar Mass | 608.54 |
| Density | 1.68±0.1 g/cm3(Predicted) |
| Melting Point | 277-278°C |
| Boling Point | 926.8±65.0 °C(Predicted) |
| Specific Rotation(α) | (C=0.5, 0.1mol/L NaOH)-121 |
| Flash Point | 305.2°C |
| Water Solubility | Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C). |
| Solubility | Almost insoluble in water, soluble in dimethyl sulfoxide, almost insoluble in ethanol. Soluble in a dilute alkaline solution. |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | gray or yellowish hygroscopic powder |
| Color | Pale Beige to Brown |
| Maximum wavelength(λmax) | ['345nm(EtOH)(lit.)'] |
| Merck | 14,3297 |
| pKa | 6.10±0.40(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.711 |
| MDL | MFCD00009772 |
| Physical and Chemical Properties | It is soluble in dimethyl sulfoxide and strong alkaline solution, insoluble in water, methanol or ethanol, and slightly soluble in 0.1mol/L sodium hydroxide. |
| Use | For food, medicine, health care products, etc |
Diosmin - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29381000 |
Diosmin - Reference
| Reference Show more | 1. Liu Xuehui, Xie Hongqi, Zhang Si, etc. Separation of lignosulfonate from Australian Mint by high-speed countercurrent chromatography [J]. Chinese agricultural bulletin, 2016, 32(027):109-113. 2. Xing-Yan, L. I. U., et al. "Identification of active compound combination contributing to anti-allergic activity of Xiao-Cheng-Qi." Chinese journal of natural Medicine 16.7 (2018): 513-524.https:// do 3. Tang W, Li W, Yang Y, Lin X, Wang L, Li C, Yang R. Phenolic Compounds Profile and Antioxidant Capacity of Pitahaya Fruit Peel from Two Red-Skinned Species (Hylocereus polyrhizus and Hylocereus undatus). Foods. 2021; 10(6):1183. https://doi.org/10.3390/food 4. [IF=6.529] Xing-Yan Liu et al."The activity of Hou-Po-Da-Huang-Tang is improved through intestinal bacterial metabolism and Hou-Po-Da-Huang-Tang selectively stimulate the growth of intestinal bacteria associated with health."Biomed Pharmacother. 2017 Oct;94:794 5. [IF=3] Xing-Yan LIU et al."Identification of active compound combination contributing to anti-inflammatory activity of Xiao-Cheng-Qi Decoction via human intestinal bacterial metabolism."Chin J Nat Medicines. 2018 Jul;16:513 6. [IF=6.543] Wang Yue et al."Polymethoxyflavones in Citrus Regulate Lipopolysaccharide-Induced Oscillating Decay of Circadian Rhythm Genes by Inhibiting Nlrp3 Expression."Oxid Med Cell Longev. 2021;2021:8419415 7. [IF=4.35] Wanpei Tang et al."Phenolic Compounds Profile and Antioxidant Capacity of Pitahaya Fruit Peel from Two Red-Skinned Species (Hylocereus polyrhizus and Hylocereus undatus)."Foods. 2021 Jun;10(6):1183 8. [IF=5.34] Dong Shao et al."Identification of the active compounds and functional mechanisms of Jinshui Huanxian formula in pulmonary fibrosis by integrating serum pharmacochemistry with network pharmacology."PHYTOMEDICINE. 2022 Jul;102:154177 9. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
Diosmin - Standard
Authoritative Data Verified Data
This product is 7-[[6-0 (6-deoxy-a-L-manranosyl)-B-D-glucopyranosyl] oxy] -5-hydroxy-2-(3-hydroxy-4-methoxyphenylbenzopyran-4-one. The content of diosmin (C28H32015) shall not be less than 90.0% based on the dry product.
Last Update：2024-01-02 23:10:35
Diosmin - Trait
Authoritative Data Verified Data
- This product is a gray-yellow to yellow powder or crystalline powder; Odorless.
- This product is dissolved in dimethyl sulfoxide, insoluble in water, methanol or ethanol; In 0.lmol / L sodium hydroxide is very slightly dissolved in 0.1 mol / L hydrochloric acid solution is almost insoluble.
Last Update：2022-01-01 11:43:37
Diosmin - Differential diagnosis
Authoritative Data Verified Data
- (1) Take 2mg of this product, add 2ml of dimethyl sulfoxide to dissolve, add 2ml of methanol and a little magnesium powder, add a few drops of concentrated hydrochloric acid, and the solution gradually changes to red.
- (2) in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- (3) Take appropriate amount of this product, add 0. The appropriate amount of 1 mol/ L sodium hydroxide solution was dissolved and diluted by ultrasound to prepare a solution containing 10ug per 1 ml, which was determined by UV-Vis spectrophotometry (General rule 0401), there is maximum absorption at wavelengths of 267nm and 370nm and minimum absorption at wavelengths of 247nm and 324Nm.
- (4) The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 11:43:38
Diosmin - Exam
Authoritative Data Verified Data
sulfate
take 2.0g of this product, add water 80ml, shake, filter, take the filtrate 40ml, check according to law (General rule 0802), and standard potassium sulfate solution 1.0ml of the control solution should not be more concentrated (0.01%).
hesperidin
take the test solution under the item of related substances as the test solution; Take 25mg of hesperidin reference substance, weigh it accurately, put it in a 50ml measuring flask, add dimethyl sulfoxide to dissolve and dilute it to the scale, shake, precision take 5ml, 50ml flask, diluted with dimethyl sulfoxide to the scale, shake, as a reference solution. According to the chromatographic condition test under the content determination item, take 10 u1 of each of the reference solution and the test solution, inject the human liquid chromatograph respectively, record the chromatogram, and calculate the peak area according to the external standard method, containing hesperidin not more than 5.0%.
Related substances
take 25mg of this product, precision weighing, put it in 25ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake, as a test solution; Take about 10mg of diosmin reference substance, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, take 3ml of precision weighing, put it in 100ml measuring flask, dilute it to the scale with dimethyl sulfoxide, shake well, as a control solution. The appropriate amount of the reference solution was Diluted 20 times with dimethyl sulfoxide as a sensitivity solution. According to the chromatographic condition test under the content determination item, 10ul of the sensitivity solution is injected into the liquid chromatograph, and the signal-to-noise ratio of the peak height of the main component should be greater than 10; Then each Lul of the reference solution and the test solution is accurately measured, they were injected into the liquid chromatograph, and the chromatogram was recorded to 5 times of the retention time of the main peak. If there are impurity peaks in the chromatogram of the test solution, the content of a single impurity shall not be more than 3.0%, and the content of a single impurity in the range of 1.0%-3.0% shall not be more than 3, calculated based on the peak area except hesperidin, the total amount of impurities should not exceed 8.0%. The chromatographic peaks in the chromatogram of the test solution which are smaller than the main peak area of the sensitivity solution are ignored (0.15%).
residual solvent
take an appropriate amount of this product, weigh it accurately, add dimethyl sulfoxide to dissolve and dilute to make a solution containing 40mg per lml, as a test solution; Take methanol, pyridine and N, an appropriate amount of N-dimethylformamide was precisely weighed and diluted with dimethyl sulfoxide to prepare a solution containing 120UG, 8UG and 35.2ug per 1 ml, respectively, as a reference solution. According to the test for determination of residual solvents (General Principle 0861 third method), the capillary column with 6% cyanopropyl phenyl-94% dimethyl polysiloxane (or similar polarity) as stationary liquid is used as the chromatographic column, and the initial temperature is 70°C, it was maintained for 5 minutes; The inlet temperature was 250°C; The detector temperature was 250°C, and the temperature was raised to 230°C at a rate of 25°C per minute for 5 minutes. The lul of the reference solution and the test solution were respectively injected into the gas chromatograph, and the chromatogram was recorded. According to the external standard method, the residual amount of methanol, pyridine and N,N-dimethylformamide shall be in accordance with the provisions.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 5.0% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.5%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
Last Update：2022-01-01 11:43:39
Diosmin - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with octa-alkyl silane as filler (phenenex C18,4.6mm X 100mm , 3um or equivalent column); Water-methanol-glacial acetic acid-acetonitrile (66:28:6:2) as mobile phase, the detection wavelength was 275nm. Add about 10 mg of diosmin to 10ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, use as solution (1), and add about 10 mg of hesperidin to 10ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake the sentence, take lml and solution (l) 3ml in the same 100ml measuring flask, dilute to the scale with dimethyl sulfoxide, shake, as the system applicable solution, 10u1 injection liquid chromatography, record chromatogram, hesperidin peak and diosmin peak separation degree should be greater than 4.6.
assay
take about 20mg of this product, accurately weigh it, put it in a 100ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake it well, and use it as a test solution, A sample of 10u1 was injected into human liquid chromatograph, and the chromatogram was recorded. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:43:40
Diosmin - Category
Authoritative Data Verified Data
capillary protective drugs.
Last Update：2022-01-01 11:43:40
Diosmin - Storage
Authoritative Data Verified Data
sealed and stored in a dry place.
Last Update：2022-01-01 11:43:40
Diosmin - Diosmin Tablets
Authoritative Data Verified Data
This product contains diosmin (C28H32015) should be 90.0% ~ 110.0% of the label amount.
trait
This product is a film-coated tablet, which is pale yellow to brown yellow after removing the coating.
identification
- take an appropriate amount of the fine powder of this product (about 10mg of diosmin), add 10ml of dimethyl sulfoxide, shake, filter, and take 2ml of the filtrate. According to the Identification Test (1) of diosmin, similar reaction was noted.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of fine powder of this product and add 0. The appropriate amount of 1 mol / L sodium hydroxide solution was dissolved and diluted by ultrasound to make a solution containing 10ug of diosmin per 1 ml, filtered and determined by UV-Vis spectrophotometry (General 0401), there is maximum absorption at wavelengths of 267nm and 370nm and minimum absorption at wavelengths of 24:7nm and 324Nm.
examination
- hesperidin, take the solution (2) under the content determination item as the test solution; Take another 25mg hesperidin reference substance, weigh it accurately, and put it into a 50ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, take 5ml into a 50ml measuring flask, dilute to the scale with dimethyl sulfoxide, shake well, and use as a reference solution. According to the chromatographic condition test under the content determination item, take 10ul of the test solution and the reference solution, respectively inject the human liquid chromatograph, record the chromatogram, and calculate the peak area according to the external standard method, the hesperidin content should not exceed 5.0% of the labeled dose of diosmin.
- for related substances, take the solution (2) under the content determination item as the test solution; Take about 10mg of the reference substance of diosmin, weigh it accurately, and put it in a 10ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, take 3ml accurately, put it in a 100ml measuring flask, dilute it to the scale with dimethyl sulfoxide, shake well, and use it as a reference solution. An appropriate amount of the control solution was taken and diluted 20-fold with dimethyl sulfoxide as a sensitivity solution. According to the chromatographic condition test under the content determination item, the sensitivity solution 10 u1 is injected into the liquid chromatograph, and the signal-to-noise ratio of the main component peak height should be greater than 10; then, 10 u1 of the reference solution and 10 u1 of the test solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 5 times of the retention time of the main peak. If there are impurity peaks in the chromatogram of the test solution, the content of a single impurity shall not be more than 3.0%, and the content of a single impurity in the range of 1.0%-3.0% shall not be more than 3, calculated based on the peak area except hesperidin, the total amount of impurities should not exceed 8.0%. The chromatographic peaks in the chromatogram of the test solution which are smaller than the main peak area of the sensitivity solution are all negligible (0.15%).
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler (phenmenex C18,4.6mm X 100mm,3um or performance equivalent column); water-methanol-glacial acetic acid-acetonitrile (66:28:6:2) was used as mobile phase, and the detection wavelength was 275nm. About 10 mg of diosmin was added to a 10ml measuring flask, dissolved with dimethyl sulfoxide and diluted to the scale. The solution was used as solution (1) by shaking, and about 10 mg of hesperidin was added to a 10ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, take 1 ml and 3ml of solution (l) in the same 100ml measuring flask, dilute to the scale with dimethyl sulfoxide, shake well, as the system applicable solution, take injection liquid chromatograph, record chromatogram, hesperidin peak and diosmin peak separation degree should be greater than 4.6.
- determination Method: Take 10 pieces of this product, remove the film coating, precisely weigh it, grind it finely, and precisely weigh an appropriate amount (about equivalent to Osmin lOOmg ), and place it in a 100ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake, filter, take the filtrate as solution (2), Take 5ml, put it in a 25ml measuring flask, dilute it to the scale with dimethyl sulfoxide, shake, as a test solution, take the injection of human liquid chromatography, record the chromatogram; Take the appropriate amount of diosmin reference, precise weighing, dimethyl sulfoxide was added to dissolve and quantitatively dilute to prepare a control solution containing about 0.2mg per 1 ml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as diosmin.
specification
0.45g
storage
sealed storage.
Last Update：2022-01-01 11:43:41
Diosmin - Reference Information
| Plant source: | Fructus Aurantii Immaturus |
| LogP | 0.14 at 20℃ |
| Pharmacological effects | Diosmin, also known as Aimilang, is a drug for the treatment of various symptoms related to acute hemorrhoid attacks, and can also be used to treat various symptoms related to venous lymphatic insufficiency (leg heaviness, pain, morning soreness and discomfort). the function characteristics of diosmin are as follows: 1. it has specific affinity for venous system, enhances venous tension without affecting arterial system; 2. it can reduce blood viscosity, increase flow rate and reduce stasis for microcirculation system; 3. it can enhance lymphatic vessel contraction and lymphatic drainage speed for lymphatic system, accelerate reflux and reduce edema. 4. the commercially available diosmin adopts micronization technology, which increases the contact area, absorbs more and has higher bioavailability after using the medicine. It is suitable for acute attacks of various hemorrhoids and hemorrhoids, and can also treat chronic venous insufficiency, such as varicose veins, lower limb ulcers, etc. |
| Application | Diosmin is one of the commonly used clinical vascular protective drugs. It is commonly used to treat a variety of peripheral vascular diseases. Clinical research results show that Diosmin can improve blood and lymph circulation and reduce edema. It is often used to treat the following 4 diseases in modern clinic. 1. Varicose veins of the lower extremities: Clinical studies have shown that diosmin can effectively improve the clinical symptoms of patients with varicose veins of the lower extremities, reduce pain and inconvenience, relieve venous stasis of the lower extremities, and improve venous return. 2. Acute or chronic hemorrhoids: Clinical studies have shown that for patients with chronic hemorrhoids, Diosmin can effectively improve the size of their hemorrhoids, reduce the number of bleeding and anal prolapse, and effectively prevent and treat their acute attacks; secondly, for acute For patients with hemorrhoids, the application of Diosmin on the basis of symptomatic treatment such as hemostasis can quickly control bleeding and reduce perianal pain, thereby effectively alleviating the pain of patients and improving the prognosis. 3. Lymphatic reflux disorder and lymphedema: Diosmin can effectively improve lymphatic reflux and reduce limb swelling. Clinical studies have shown that after taking diosmin, the swelling and pain of the limbs of patients with lymphedema are significantly reduced, which makes the lymphatic circulation smooth and improves the quality of life and health of patients. 4. Peripheral skin ulcers: Clinical studies have shown that on the basis of promoting skin healing treatment, the use of diosmin can effectively accelerate the prognosis of skin wounds or ulcers, reduce local inflammation, relieve skin pain, and effectively improve the prognosis of the disease. |
| adverse reactions | 1, nausea, vomiting, abdominal pain, dyspepsia, diarrhea, insomnia, dizziness, headache, lethargy, anxiety and other adverse reactions may occur. 2, there are a few mild gastrointestinal reactions and autonomic dysfunction and other adverse reactions, but generally mild do not need to stop the drug. 3. Hemorrhoids of pregnant and lactating women can be used safely. |
| taboo | is forbidden for people who are allergic to any ingredient in this product. |
| precautions | acute attack of hemorrhoids: treatment with this medicine cannot replace the special treatment required to deal with other anal diseases. This treatment must be short-term. If symptoms cannot be eliminated quickly, anorectal examination should be carried out and the treatment plan should be re-examined. this product contains flavonoids, which are effective glycosides in plants. the content is 450mg of diosmin effective flavonoids and 50mg of hesperidin per tablet. the total flavonoid glycosides are 500mg (also known as Daflon). Generally, flavonoids have certain biological activity, but they are less toxic and allergic reactions are rare. If they are allergic, they should be banned. |
| medication for pregnant and lactating women | medication for pregnant women: animal experiments have not shown any teratogenic effect. Further, no harmful effects on humans have been reported so far. Delivery: There is still a lack of detailed research data. Medication for lactating women: Although there is no information about the secretion of drugs with breast milk, breastfeeding is not recommended during treatment. |
| preparation | currently, diosmin is mainly made of hesperidin extracted from natural plants through semi-synthesis. China Patent CN104250276-A has published an industrialized production of Diosmin. The specific steps are as follows: add hesperidin (glycoside) to the mixed solvent of pyridine and dimethyl sulfoxide, and then add potassium iodide and sulfuric acid for dehydrogenation reaction to obtain the reaction intermediate product; add sodium hydroxide to the reaction intermediate product The methanol solution is reacted; then acid is added to adjust the pH value, and the crystal is left to deosmin. The purity of diosmin produced by this method is generally lower than 95%, which is not suitable for sale as a drug and needs further separation and purification. CN201810382522.0 proposes a high-purity teosmin preparation method. In order to achieve the above objective, the technical scheme of the present invention is: the crude diosmin product of the present invention is purified and prepared by a column chromatography method, and the packing in the chromatographic column is a polymer chromatography packing. Polymer chromatographic packing refers to the use of styrene, methacrylate and styrene and methacrylate copolymers as the matrix, through the particle size, morphology, particle size distribution, specific surface area, pore size structure and surface functional groups Such as precise control, the particle size is less than 100um, and the pore size is lower than the chromatographic packing. The polymer chromatographic packing is a chromatographic packing PSN 30-300. The method specifically includes the following steps: 1) Prepare a sample solution: take the crude diosmin product, add it to an alkaline solvent and fully stir it, dissolve it and filter it to obtain the crude diosmin solution for standby; 2) Chromatographic separation process: After the polymer chromatographic packing is filled in the chromatographic column, rinse with deionized water, and after balancing, the crude diosmin solution obtained in step 1) is injected into the chromatographic column with a pump for sample loading, after loading the sample, rinse with deionized water, and then use the first eluent and the second eluent to elute, collect each eluent and perform purity testing, and combine the deosmin eluent with a purity greater than 99%. Then precipitate diosmin with acid, filter and clean, and finally dry to obtain high-purity diosmin products. |
| use | used in food, medicine, health care products, etc. mechanism of action 1. enhance venous tension diosmin enhances venous wall tension, even at high temperature is no exception. it causes venous contraction stronger than rutin and other drugs, and can still enhance venous tension in acidosis. Diosmin has a specific affinity for veins without affecting the arterial system. 2. Improving microcirculation. Diosmin can significantly reduce the adhesion, migration, disintegration and release of inflammatory substances, such as histamine, bradykinin, complement, leukotriene, prostaglandin and excessive free radicals Etc., thereby reducing the permeability of capillaries and enhancing their tension. Diosmin also has the function of reducing blood viscosity and enhancing red blood cell flow rate, thereby reducing microcirculation stasis. 3. promoting lymphatic reflux diosmin increases lymphatic drainage speed a flavonoid found in citrus fruits and an agonist of aromatics receptor (AhR). |
Last Update：2024-04-09 21:04:16
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