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)-

Base Information

• Chemical Name: 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)-
• CAS No.: 10236-47-2
• Molecular Formula: C27H32O14
• Molecular Weight: 580.543
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID10860071
• Wikidata: Q104978210
• Mol file: 10236-47-2.mol

Synonyms:4',5,7-trihydroxyflavanone 7-rhamnoglucoside;aurantiin;Cyclorel;naringenin-7-hesperidoside;naringin;naringin dihydrochalcone;naringin sodium

Chemical Property of 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)-

Chemical Property:

• Appearance/Colour: beige to yellowish powder
• Vapor Pressure: 2.25Pa at 20℃
• Melting Point: 166 °C
• Refractive Index: -84 ° (C=2, EtOH)
• Boiling Point: 928.1 °C at 760 mmHg
• PKA: 7.17±0.40(Predicted)
• Flash Point: 308.5 °C
• PSA: 225.06000
• Density: 1.66 g/cm³
• LogP: -1.16520
• Storage Temp.: 0-6°C
• Water Solubility.: Soluble in water, alcohol, acetone and warm acetic acid.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 580.17920569
• Heavy Atom Count: 41
• Complexity: 884

Purity/Quality:

98% ^*data from raw suppliers

Naringin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
• Description: Naringin 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. It tastes bitter and is naturally existed in the skin and flesh of Rutaceae like grapefruit, mandarin orange, and orange. It is also one of the active ingredients in many traditional Chinese medi cines like Rhizoma Drynariae, Immature Bitter Orange, Fructus Aurantii, and Exocarpium Citri Grandis. The contents of naringin in different plants vary greatly with the category and origin, and the content of naringin is high in immature fruits . 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.
• Physical properties: Appearance: white to light yellow crystalline powder. Solubility: soluble in metha nol, ethanol, acetone, acetic acid, dilute alkali solution, and hot water and insoluble in nonpolar solvent like petroleum benzin, ether, benzene, and chloroform. Melting
• Uses: antihaemorrhagic, antiinflammatory Naringoside 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. Naringin has been used:as a bitter tastant to compare the behavioral response of the Drosophila larva and adult(2)to study its anti-inflammatory property and to determine its effect on nucleus pulposus (NP) cells(3)to determine its effect on bone metabolism like osteogenic differentiation, inhibition of osteoclast formation(4)
• Clinical Use: It was used for the treatment of bacterial infection, calm, and cancer prevention

Technology Process of 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)-

There total 9 articles about 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)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone (50376-43-7) → naringin (10236-47-2)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 25 ℃; Further Variations:; Solvents; Kinetics; Equilibrium constant; Activation energy;

Reference yield:

→ naringin (10236-47-2)

Guidance literature:

aus Naringin-chalcon in 50percentig. A., McIlvaine-Puffer-Lsg. (pH 7) (Siedetemp.);

Reference yield:

naringin → naringin (10236-47-2) + 4′,5,7‐trihydroxyflavanone‐7‐rhamnoglucoside (58001-41-5)

Guidance literature:

In methanol; formic acid; acetonitrile; at 20 ℃; Resolution of racemate;

DOI:10.1002/chir.23147

upstream raw materials:

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone

Downstream raw materials:

5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one

prunin

2,6-dihydroxy-4-(β-neohesperidosyloxy)acetophenone

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone

Refernces

• 1、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 2、 -. "Antimicrobial compositions of matter and a process for preparing antimicrobial compositions of matter from naturally occurring flavanoid glycosides". . . Retrieved 2008/06/13.