Hesperidin
HESPERIDINE · VITAMIN P · Citrus Sinensis Extract · (s)-7-[[6-o-(6-deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one · Hesperiden · HESPERETIN-7-O-RUTINOSIDE · Hespiridin · (S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Identifikatoren & physikalische Daten
| CAS No. | 520-26-3 |
|---|---|
| Summenformel | C28H34O15 |
| Durchschnittliche Molmasse | 610,6 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | Hesperidin |
Chemische & physikalische Eigenschaften
| XLogP | -1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 234 |
| H-Brücken-Donoren | 8 |
| H-Brücken-Akzeptoren | 15 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 43 |
| Formalladung | 0 |
| Komplexität | 940 |
| Schmelzpunkt | 250-255 °C (dec.)(lit.) |
| Siedepunkt | 576.16°C (rough estimate) |
| Dichte | 1.3290 (rough estimate) |
| Brechungsindex | 1.5940 (estimate) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Löslichkeit | DMSO (Slightly), Pyridine (Slightly, Sonicated)Insoluble in water. Soluble in organic solvents such as DMSO. |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 7.15±0.40(Predicted) |
| Farbe | light brown |
| Biologische Quelle | Citrus sinensis (L.) Osbeck |
| Merck | 14,4671 |
| BRN | 75140 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - EMOLLIENT |
| 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 (Verteilungskoeffizient) | 0.3 at 25℃ |
| CAS Datenbank | 520-26-3(CAS DataBase Reference) |
| EPA chemische Informationen | Hesperidin (520-26-3) |
Sicherheit & Vorschriften
| F | 3-10 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29389090 |
| RTECS-Nr. | MK6650000 |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-36/37/39-27-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
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.
History
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.
Verwenden
Hesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.