ヘスペリジン
ヘスペリジン · (S)-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-ジヒドロ-5-ヒドロキシ-2-(3-ヒドロキシ-4-メトキシフェニル)-4H-1-ベンゾピラン-4-オン · (S)-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]-3',5-ジヒドロキシ-4'-メトキシフラバノン · シランチン · 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]-2α-(3-ヒドロキシ-4-メトキシフェニル)-5-ヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン · (2S)-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-ジヒドロ-5-ヒドロキシ-2-(3-ヒドロキシ-4-メトキシフェニル)-4H-1-ベンゾピラン-4-オン · (S)-3',5-ジヒドロキシ-4'-メトキシ-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]フラバノン · アトリプリシドB
識別子と物理属性
| CAS No. | 520-26-3 |
|---|---|
| 分子式 | C28H34O15 |
| 平均分子量 | 610.6 g/mol |
| 単同位体質量 | 610.18977037 g/mol |
| SMILES | COc1ccc(C2CC(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2)cc1O |
| InChIKey | QUQPHWDTPGMPEX-UHFFFAOYSA-N |
| PubChem CID | 3594 |
| ChEMBL | CHEMBL1535112 |
| DTXSID | DTXSID50859444 |
| 現地名 | ヘスペリジン |
化学・物理的性質
| XLogP | -1.1 |
|---|---|
| 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 | 940 |
| 融点 | 250-255 °C (dec.)(lit.) |
| 比旋光度 | -76 º (c=2,pyridine) |
| 沸点 | 576.16°C (rough estimate) |
| 密度 | 1.3290 (rough estimate) |
| 屈折率 | 1.5940 (estimate) |
| 貯蔵条件 | Sealed in dry,2-8°C |
| 溶解度 | DMSO（微量）、ピリジン（微量、超音波処理）水に不溶。 DMSOなどの有機溶媒に可溶。 |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 7.15±0.40(Predicted) |
| 色 | ライト・ブラウン |
| 由来生物 | Citrus sinensis (L.) Osbeck |
| Merck | 14,4671 |
| BRN | 75140 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 主な用途 | 食品および飲料 |
| 化粧品成分の機能 | 皮膚コンディショニング剤 - 保湿剤 |
| InChIKey | QUQPHWDTPGMPEX-QJBIFVCTSA-N |
| SMILES | COc1ccc(cc1O)[C@@H]2CC(=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） | 0.3 at 25℃ |
| CAS データベース | 520-26-3(CAS DataBase Reference) |
| EPAの化学物質情報 | Hesperidin (520-26-3) |
化学的特性
light brown powder
安全性と法規制
| F | 3-10 |
|---|---|
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | MK6650000 |
| 税関コード | 29389090 |
| 危険文句（R） | 22-36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 22-24/25-36/37/39-27-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
ヘスペリジン．フラバノンのルチノース配糖体．かんきつ類のほとんどすべて，とくに未熟な外果皮に含まれる．白色の微小針状晶．融点258～262 ℃．[α]20D－76°(ピリジン)．希アルカリ水溶液，アニリン，ピリジン，熱酢酸に可溶，メタノールに微溶，エーテル，ベンゼンに不溶．いわゆるビオフラボノイドとしてビタミンPとよばれるものの一つで，毛細血管強化薬に用いられる．
用途
ビタミンPの一つで、毛細血管の保護に用いられる。
説明
Hesperidin exists mainly in the peel of lemon, orange, and Seville orange flower, which belong to facilitating medicine. These Chinese medicines are warm and fragrant with the function of eliminating depression and knots. They cure abdominal distension, belching swallow acid pain, nausea and vomiting, diarrhea or constipation caused by the spleen, and stomach qi zhi; and they also cure depression, hernia, breast pain, and menoxenia caused by liver qi; moreover, they cure chest pain, cough, and asthma, which are caused by lung qi. Modern research has shown that li qi medicines have an extensive effect, such as regulatory effect on the digestive system, and they control the bronchial smooth muscle, the uterus smooth muscle, and the cardiovascular system. The base of the effect of li qi medicines in inverse, anti-nausea, antidiarrheal, and analgesia pharmacological effects is its effect in inhibiting gastric bowel movement; its exciting gastrointestinal movement is the foundation to eliminate swelling; its effect in relaxation of the bronchial smooth muscle is the foundation of pharmacological effects in antinausea. The intravenous injection to treat shock effect is the new development of li qi medicine.
来歴
Hesperidin is the glycoside in the form of hesperidin and rubiose and is a derivative of dihydroflavonoids. It widely exists in legume, birch, lip flower, butterfly flower, Rutaceae, and citrus plants. Hesperidin is an important composition of citrus pulp and peel; most of hesperidin exists in citrus processing waste such as skin and fruit bag. Mature skin and tissue have the highest content of hesperidin (30–50% in endocarp; 30–50% in orange collaterals, nuclear, and pulp; and 10–20% in exo_x005fcarp); the content of hesperidin is relatively low in juice and orange bag, which is about 1–5%. The crude extracts of hesperidin was first discovered in 1827 by Lebreton. Then the Hungarian scholar Albert Szent-Gyorgi discovered that the flavonoids have a protective microvascular effect in 1936, which is similar to that of vitamin P. Preparation of vitamin P was made in 1938. It was not until 1949 that it was discovered that vitamin P was made up of two flavonoids, luteolin and hesperidin, which are believed to be vitamin active. This substance, which was later named as vitamin P, was designed to reduce blood vessel permeability and brittleness, as well as alleviate bad blood and vitamin C deficiency. It was later discovered that the substance had an antioxidant effect, so the name of vitamin P was abandoned. Due to the widespread distribution of hesperidin in plant medicine, the research and development have been widely followed.
製法・合成法
純化方法
Dissolve hesperidine in dilute aqueous alkali and precipitate it by adjusting the pH to 6-7. [Beilstein 18 III/IV 3219, 18/5 V 218.]