Hesperidin
Grundinformationen
- CAS
520-26-3- Standard-SMILES
COc1ccc([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)cc1O- InChIKey
QUQPHWDTPGMPEX-QJBIFVCTSA-N- Summenformel
- C28H34O15
- Durchschnittliche Molmasse
- 610,6 g/mol
- Monoisotopische Masse
- 610,18977039
Überblick
Hesperidin is 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. It has a role as a mutagen. It is a member of 4'-methoxyflavanones, a rutinoside, a monomethoxyflavanone, a dihydroxyflavanone, a member of 3'-hydroxyflavanones, a disaccharide derivative and a flavanone glycoside. It is functionally related to a hesperetin.
Namen und Bezeichner
- Bevorzugter Name
- Hesperidin
- IUPAC
- (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
- Lokaler Name
- Hesperidin
- Englischer Name
- Hesperidin
- Summenformel
- C28H34O15
- Molmasse
- 610.56
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
520-26-3- PubChem CID
- 10621
- DTXSID
DTXSID9044328- ChEMBL
CHEMBL449317- ChEBI
CHEBI:28775- UNII
- E750O06Y6O
- EC Number
- 208-288-1
- Nikkaji
- J4.480F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,1
- Polarare Oberfläche (TPSA)
- 234 Ų
- H-Brücken-Donoren
- 8
- H-Brücken-Akzeptoren
- 15
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 43
- Formalladung
- 0
- Komplexität
- 940
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Cosmetics
Emollient
Personal care product -> emollient
Collision Cross Section
240.84 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
227 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 250 · 250-255 °C (dec.)(lit.)
- Siedepunkt
- 576.16 °C · 576.16°C (rough estimate)
- Dichte
- 1.329 · 1.3290 (rough estimate)
- Brechungsindex
- 1.594 · 1.5940 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- DMSO (Slightly), Pyridine (Slightly, Sonicated)
- Aggregatzustand
- Powder
- pka
- 7.15 · 7.15±0.40(Predicted)
- Farbe
- light brown
- Biologische Quelle
- Citrus sinensis (L.) Osbeck
- Wasserlöslichkeit
- Insoluble in water. Soluble in organic solvents such as DMSO.
- Merck
- 14 · 14,4671
- BRN
- 75140 · 75140
- Stabilität
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- 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
- 0.3 at · 0.3 at 25℃
- CAS Datenbank
- 520 · 520-26-3(CAS DataBase Reference)
- EPA chemische Informationen
- Hesperidin (520-26-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (42 of 42) of all reports.
Not Classified
Aggregated GHS information provided per 42 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
Status: Active Update: 28-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14278
4H-1-Benzopyran-4-one, 7-6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyloxy-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheitsdaten
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29389090
- RTECS-Nr.
- MK6650000
- risk_code
- 22-36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25-36/37/39-27-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
Anwendungen
BeschreibungHesperidin 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.
HistoryHesperidin 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.
VerwendenHesperidin is a flavoring agent that is a bioflavonoid found in citrus pulp. it has minor use as a flavorant.
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Ergänzende Hinweise
DefinitionChEBI: 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.
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