ジオスミン
バロスミン · 3',5-ジヒドロキシ-4'-メトキシ-7-(6-O-α-L-ラムノピラノシル-β-D-グルコピラノシルオキシ)フラボン · ベノサミン · ヘスペレジン · 7-[[6-O-(6-デオキシ-α-L-マンノピラノシル)-β-D-グルコピラノシル]オキシ]-2-(3-ヒドロキシ-4-メトキシフェニル)-5-ヒドロキシ-4H-1-ベンゾピラン-4-オン · 3',5-ジヒドロキシ-4'-メトキシ-7-[[6-O-(α-L-ラムノピラノシル)-β-D-グルコピラノシル]オキシ]フラボン · 7-[(6-O-α-L-ラムノピラノシル-β-D-グルコピラノシル)オキシ]-3',5-ジヒドロキシ-4'-メトキシフラボン · ジオスメチン7-ルチノシド
識別子と物理属性
| CAS No. | 520-27-4 |
|---|---|
| 分子式 | C28H32O15 |
| 平均分子量 | 608.5 g/mol |
| 単同位体質量 | 608.17412032 g/mol |
| SMILES | COc1ccc(-c2cc(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3o2)cc1O |
| InChIKey | GZSOSUNBTXMUFQ-YFAPSIMESA-N |
| PubChem CID | 5281613 |
| ChEMBL | CHEMBL231884 |
| ChEBI | CHEBI:4631 |
| EC No. | 208-289-7 |
| DTXSID | DTXSID4045892 |
| 現地名 | ジオスミン |
化学・物理的性質
| XLogP | -0.8 |
|---|---|
| 極性表面積 | 234 |
| 水素結合供与体数 | 8 |
| 水素結合受容体数 | 15 |
| 回転可能結合数 | 7 |
| 重原子数 | 43 |
| 形式電荷 | 0 |
| 複雑度 | 995 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| 脂質 | Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211] |
| 化粧品 | Antioxidant |
| LogP（分配係数） | 0.14 |
| 沸点 | 926.8±65.0926.8±65.0 °C(Predicted) |
| 融点 | 277-278277-278°C |
| Dissociation Constants | 6.10±0.40 |
| Collision Cross Section | 243.33 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]242.5 Ų [M+H]+ [CCS Type: TW |
| 密度 | 1.68±0.1 g/cm3(Predicted) |
| 蒸気圧 | 0Pa at 20℃ |
| 貯蔵条件 | Sealed in dry,2-8°C |
| 溶解度 | 水にほとんど溶けず、ジメチルスルホキシドに溶け、アルコールにほとんど溶けない。アルカリ金属水酸化物の希薄溶液に溶けます。DMSO (50 mg/ml)、水 (122 mg/ml、25°C)、エタノール (<1 mg/ml、25°C) に可溶。 |
| 外観・状態 | Solid |
| pKa（酸解離定数） | 6.10±0.40(Predicted) |
| 色 | ペールベージュからブラウン |
| Merck | 14,3297 |
| 主な用途 | 食品および飲料 |
| 化粧品成分の機能 | 抗酸化物質 |
| InChIKey | GZSOSUNBTXMUFQ-YFAPSIMESA-N |
| SMILES | COc1ccc(cc1O)C2=CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 |
| LogP（分配係数） | 0.14 at 20℃ |
| CAS データベース | 520-27-4(CAS DataBase Reference) |
化学的特性
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.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 90.8% (89 of 98) of all reports.Not ClassifiedAggregated GHS information provided per 98 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Status: Active Update: 13-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21071 |
| Hazard Classes and Categories | Not Classified |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29381000 |
| 危険文句（R） | 36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 26-36-36/37-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
ジオスミン(英: Diosmin)はジオスメチンの7位にルチノースが結合したフラボノイド配糖体。柑橘類の果実に含まれている。。ジオスミンは血管保護作用があるとされ、慢性静脈不全、痔、リンパ水腫、静脈瘤に使用される。
説明
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.
来歴
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 30years in EuropeDiosmin is a typical flavonoid. It could be prepared from natural resources or semisynthesized from the natural product hesperidin by dehydrogenation reaction.
使用
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.