Hesperidin

HCID 10621

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

hesperidin520-26-3CirantinHesperidosideHesperetin 7-rutinosideCiratin(S)-(-)-HesperidinDIOSVEINDTXSID9044328Hesperetin 7-rhamnoglucosideCHEBI:28775E750O06Y6O
Weitere Namen anzeigen
HESPERIDINEVITAMIN PCitrus 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-oneHesperidenHESPERETIN-7-O-RUTINOSIDEHespiridin(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-oneHesperidHespeidin
(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-oneHesperetin 7 RhamnoglucosideDTXCID7024328Hesperetin 7-O-rutinosideNSC-441844H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydo-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)oxy)-4-chromanonNSC44184

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

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Cosmetics · 2 Einträge

Emollient

Personal care product -> emollient

LogP0.32
Food AdditivesFLAVOR ENHANCER -> FDA Substance added to food
Collision Cross Section · 2 Einträge

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)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

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 · 3 Einträge

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.

Other Safety InformationIMAP assessments - 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)-: Environment tier I assessment
Hazard Classes and CategoriesNot Classified

Sicherheitsdaten

F
3-10
wgk
3
tsca
TSCA listed
hs_code
29389090
RTECS-Nr.
MK6650000
risk_code
22-36/37/38

Chemie und Industrie

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationCosmetics -> Emollient
General Manufacturing Information4H-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)-, (2S)-: ACTIVE
Anwendungen · 3 Einträge

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.

Anbieter100 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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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