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7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon

5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside

HCID 4441
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Grundinformationen

CAS
10236-47-2
Standard-SMILES
CC1OC(OC2C(Oc3cc(O)c4c(c3)OC(c3ccc(O)cc3)CC4=O)OC(CO)C(O)C2O)C(O)C(O)C1O
InChIKey
DFPMSGMNTNDNHN-UHFFFAOYSA-N
Summenformel
C27H32O14
Durchschnittliche Molmasse
580,539 g/mol
Monoisotopische Masse
580,1792057

Namen und Bezeichner

Bevorzugter Name
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside
IUPAC
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside
Lokaler Name
7-(2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavon
Englischer Name
Naringin
Summenformel
C27H32O14
Molmasse
580.54

Namen und Synonyme

FEMA 2769NARINGENIN-7-O-NEOHESPERIDOSIDENaringCabinda bark extractnaringoside(2S)-NaringinNARINGIN WITH HPLCCitrus grandis OsbeckNARINGENIN-7-RHAMNOGLUCOSIDE7-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Datenbank-Bezeichner

CAS
10236-47-2
PubChem CID
4441
DTXSID
DTXSID10860071

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
166 °C · 166 °C
Siedepunkt
559.35 °C · 559.35°C (rough estimate)
Dichte
1.3285 · 1.3285 (rough estimate)
Dampfdruck
2.25 Pa · 2.25Pa at 20℃
Brechungsindex
-84 ° · -84 ° (C=2, EtOH)
FEMA
2769 · 2769 | NARINGEN EXTRACT (CITRUS PARADISI MACF.)
storage temp.
2 · 2-8°C
Löslichkeit
1 mg/mL · DMSO : 1 mg/mL (1.72 mM; Need ultrasonic)H2O : 1 mg/mL (1.72 mM; ultrasonic and warming and heat to 80°C)
Aggregatzustand
crystalline
pka
7.17 · 7.17±0.40(Predicted)
Farbe
off-white
Biologische Quelle
citrus fruit
Wasserlöslichkeit
Soluble in water, alcohol, acetone and warm acetic acid.
Merck
14 · 14,6425
BRN
102012 · 102012
Major Application
cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Kosmetik-Inhaltsstoffe Funktionen
SKIN PROTECTING
InChIKey
DFPMSGMNTNDNHN-JJLSSNRUSA-N
SMILES
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc3cc(O)c4C(=O)CC(Oc4c3)c5ccc(O)cc5)[C@H](O)[C@H](O)[C@H]1O
LogP
-0.44 at · -0.44 at 20℃
CAS Datenbank
10236 · 10236-47-2(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

F
3
wgk
3
tsca
TSCA listed
hs_code
29389090
RTECS-Nr.
QN6340000
risk_code
22-36/37/38
hazard_code
Xn,Xi
safety_code
22-24/25-36-26
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungNaringin is also called naringoside, hesperidin, and isohesperidin. It is a pale yellow flavanone compound extracted from immature or nearly mature outer layer of C. paradisi Macfad which belongs to Citrus grandis (L.) Osbeck. In terms of traditional Chinese medicine, the flavor of grapefruit is sweet and sour, and the nature is cold; the flavors of its peel are sweet, pungent, and bitter, and the nature of its peel is warm. Both the pulp and the peel of grapefruit have the bio logical function including reducing phlegm, helping digestion, relieving abdominal distention, and fast diaphragm. And they are mainly used for the treatment of cough with asthma, sense of suppression in the chest, coldness and pain in abdomen, dys peptic retention, and hernia.

HistoryNaringin is mainly existed in the peel of grapefruit, lime, and their varieties; it has multiple biological activities and is widely applied in the fields of medicine, food, and cosmetics. In the 1930s, Harvey and Rygg obtained naringin through the method of isolation and extraction. They also established a colorimetric method for the determination of naringin, which laid the foundation for the following researches . Booth and other researchers conducted the systematic researches on the narin gin metabolites . In the 1960s, Hagen and other researchers established a fluores cence chromatography method for the determination naringin . In addition, the biological activity of naringin was evaluated. It was observed to improve ascites, experimental pulmonary edema, peritonitis, and oxygenation . At present, the extraction methods of naringin are hot water extraction, alkali extraction, and acid precipitation and organic solvent extraction. A series of pharmacological activity studies have been conducted and demonstrated its various biological activities .

VerwendenNaringoside is a metabolite of Naringin (N378980), a major flavonoid found in grapefruit juice. It has antioxidant, lipid lowering, and anticancer activities. It is also an inhibitor of cytochrome P450 enzymes, affecting drug metabolism and thus drug absorption in humans.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

beta-Phenylpropiophenone1-[4-[[2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-on

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 116627
HRID 116627als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

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EPA chemische Informationen
4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)- (10236-47-2)
7-[[2-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-on
Isosakuranin
Naringin dihydrochalcone
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Ergänzende Hinweise

DefinitionChEBI: A disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosi ic linkage.