529-55-5

Basic information

• Product Name: NARINGENIN-7-O-GLUCOSIDE
• Synonyms: 4',5-DIHYDROXY-7-GLUCOSYLOXYFLAVANONE;NARINGENIN-7-O-GLUCOSIDE;NARINGENIN-7-GLUCOSIDE;PRUNIN;(S)-7-(beta-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;NARINGENIN-7-GLUCOSIDE hplc;NARINGENIN-7-O-GLUCOSIDE WITH HPLC;(2S)-2α-(4-Hydroxyphenyl)-5-hydroxy-7-(β-D-glucopyranosyloxy)-2,3-dihydro-4H-1-benzopyran-4-one
• CAS NO: 529-55-5
• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.39
• EINECS: 208-464-8
• Product Categories: Flavanones
• Mol File: 529-55-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 222-224°C
• Boiling Point: 802.4°Cat760mmHg
• Flash Point: 284.6°C
• Appearance: /
• Density: 1.597g/cm³
• Storage Temp.: ?20°C
• PKA: 7.18±0.40(Predicted)
• CAS DataBase Reference: NARINGENIN-7-O-GLUCOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NARINGENIN-7-O-GLUCOSIDE(529-55-5)
• EPA Substance Registry System: NARINGENIN-7-O-GLUCOSIDE(529-55-5)

Safety Data

• Hazard Codes: N
• Statements: 22-50
• Safety Statements: 22-45-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 529-55-5(Hazardous Substances Data)

Usage

Description

Naringenin-7-O-glucoside, also known as Prunin, is a naturally occurring flavonoid derived from various plant sources, including citrus fruits. It possesses bioactive properties and is known for its potential health benefits.
Data of describe:
Naringenin-7-O-glucoside is a naturally occurring flavonoid found in citrus fruits, known for its bioactive properties and potential health benefits.

Uses

Used in Pharmaceutical Applications:
Naringenin-7-O-glucoside is used as a bioactive compound for its tyrosine phosphatase 1B inhibition and stimulation of glucose uptake in insulin-resistant HepG2 cells. This makes it a promising candidate for the development of drugs targeting type 2 diabetes and related metabolic disorders.
Used in Functional Foods and Nutraceuticals:
Naringenin-7-O-glucoside is used as an ingredient in functional foods and nutraceuticals for its potential health benefits, including its antioxidant and anti-inflammatory properties. It may contribute to the development of products aimed at promoting overall health and well-being.
Used in Cosmetics:
In the cosmetics industry, Naringenin-7-O-glucoside is used as an active ingredient for its antioxidant and anti-inflammatory properties. It may be incorporated into skincare products to help protect the skin from environmental stressors and promote a healthy, youthful appearance.
Used in Agricultural Applications:
Naringenin-7-O-glucoside may also be used in agricultural applications, particularly in the development of plant-derived products with enhanced nutritional and health-promoting properties. Its bioactive properties could be harnessed to improve the quality and value of crops and derived products.

Upstream product

• 10236-47-2 naringin 
• 64-18-6 formic acid 
• 108-93-0 cyclohexanol 
• 94392-49-1 naringenin 7-O-(6-O-((E)-p-coumaroyl)-β-D-glucopyranoside) 
• 480-41-1 naringenin 
• 133-89-1 UDP-glucose 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Downstream Products

• 252324-55-3 prunin 6''-O-acetate 
• 1256627-50-5 prunin 6''-O-butyrate 
• 1256627-51-6 prunin 6''-O-decanoate 
• 1256627-53-8 prunin 6''-O-laurate 
• 1256627-52-7 prunin 6''-O-stearate 
• 492-62-6 alpha-D-glucopyranose 
• 480-41-1 naringenin 
• 491-69-0 (2S)-poncirenin 

Relevant articles and documents

Covalent Immobilization of Naringinase over Two-Dimensional 2D Zeolites and its Applications in a Continuous Process to Produce Citrus Flavonoids and for Debittering of Juices

The crude naringinase from Penicillium decumbens and a purified naringinase with high α-L-rhamnosidase activity could be covalently immobilized on two-dimensional zeolite ITQ-2 after surface modification with glutaraldehyde. The influence of pH and temperature on the enzyme activity (in free and immobilized forms) as well as the thermal stability were determined using the specific substrate: p-nitrophenyl-alpha-L-rhamnopyranoside (Rha-pNP). The crude and purified naringinase supported on ITQ-2 were applied in the hydrolysis of naringin, giving the flavonoids naringenin and prunin respectively with a conversion '90 percent and excellent selectivity. The supported enzymes showed long term stability, being possible to perform up to 25 consecutive cycles without loss of activity, showing its high potential to produce the valuable citrus flavonoids prunin and naringenin. We have also succeeded in the application of the immobilized crude naringinase on ITQ-2 for debittering grapefruit juices in a continuous process that was maintained operating for 300 h, with excellent results.

Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca

In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3′. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3′ positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.

Preparation of Prunin and derivative thereof and application of Prunin derivative in drugs for relieving cough and reducing phlegm

The invention relates to preparation of a Prunin derivative and application thereof in drugs for relieving a cough and reducing phlegm. The Prunin derivative is obtained by introducing glycosyl or aliphatic chains or an amine group or an ether group, and the water solubility, the dissolving-out speed and the bioavailability are significantly improved. The Prunin derivative has better cough relieving and phlegm reducing effects, the curative effects on various coughs and asthma caused by acute bronchitis, chronic bronchitis, colds and the like are significant, and no toxic or side effect exists; compared with traditional cough medicine Nin Jiom Pei Pa Koa, the curative effect is more significant, and the Prunin derivative is an ideal drug for relieving the cough and reducing the phlegm, andhas a wide market prospect. The formula is defined in the description.