基本情報
- CAS
520-26-3- 標準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- 分子式
- C28H34O15
- 平均分子量
- 610.6 g/mol
- 単同位体質量
- 610.18977037
名称と識別子
- 優先名称
- Hesperetin-7-Rutinoside
- IUPAC
- 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
- 現地名
- ヘスペリジン
- 英語名
- Hesperidin
- 分子式
- C28H34O15
- 分子量
- 610.56
名称と別名
名称をさらに表示
データベース識別子
- CAS
520-26-3- PubChem CID
- 3594
- DTXSID
DTXSID50859444- ChEMBL
CHEMBL1535112
物性
構造計算による物性
- XLogP
- -1.1
- 極性表面積
- 234 Ų
- 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
物理化学的性質
- 融点
- 250 · 250-255 °C (dec.)(lit.)
- 比旋光度
- -76 · -76 º (c=2,pyridine)
- 沸点
- 576.16 °C · 576.16°C (rough estimate)
- 比重(密度)
- 1.329 · 1.3290 (rough estimate)
- 屈折率
- 1.594 · 1.5940 (estimate)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- DMSO(微量)、ピリジン(微量、超音波処理)
- 外見
- 粉
- 酸解離定数(Pka)
- 7.15 · 7.15±0.40(Predicted)
- 色
- ライト・ブラウン
- 由来生物
- Citrus sinensis (L.) Osbeck
- 水溶解度
- 水に不溶。 DMSOなどの有機溶媒に可溶。
- Merck
- 14 · 14,4671
- BRN
- 75140 · 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
- 0.3 at · 0.3 at 25℃
- CAS データベース
- 520 · 520-26-3(CAS DataBase Reference)
- EPAの化学物質情報
- Hesperidin (520-26-3)
化学的性質
化学的特性light brown powder
安全と法規制
安全データ
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MK6650000
- hs_code
- 29389090
- risk_code
- 22-36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25-36/37/39-27-26
- ストレージクラス
- 11 - Combustible Solids
化学と産業
応用分野
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.
使用Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.
調製方法
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー101 社
補足説明
定義本品は、レモンやスイートオレンジ等に存在する主要なフラボノイドであり、次の化学式で表される。
定義ChEBI: A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
関連反応
化合物ノート
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