3682-03-9

Usage

Uses

Used in Pharmaceutical Applications:
Naringenin-6-C-glucoside is used as a bone anabolic agent for promoting bone health and treating conditions related to bone loss. It mimics the action of estrogen on osteoblasts, which are the cells responsible for bone formation. This action leads to potent bone anabolic effects, making it a promising candidate for the development of therapies to combat osteoporosis and other bone-related disorders.
Used in Nutraceutical Applications:
Naringenin-6-C-glucoside is also used as an ingredient in the nutraceutical industry due to its potential health benefits. It can be incorporated into dietary supplements and functional foods to support bone health and overall well-being.
Used in Cosmetic Applications:
In the cosmetic industry, naringenin-6-C-glucoside may be used as an active ingredient in skincare products. Its antioxidant and anti-inflammatory properties could contribute to the development of products aimed at improving skin health and appearance.

InChI:InChI=1/C21H22O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-4,6,12,14,17,19-23,25-29H,5,7H2/t12-,14+,17+,19-,20+,21-/m0/s1

Upstream product

• 50-99-7 D-glucose 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 133-89-1 UDP-glucose 

Downstream Products

• 1248653-79-3 6-(C-β-D-glucopyranosyl)-8-(C-β-D-xylopyranosyl)naringenin 

Relevant academic research and scientific papers

Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica

A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5′-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides. One enzyme, one product: A novel C-glycosyltransferase from Mangifera indica is reported, which is a promiscuous catalyst that synthesizes bioactive C-glucosides from natural and unnatural acylphloroglucinol 2-O-gulcosides in one-pot reactions. High yields of C-glucosides were achieved even with a catalytic amount of uridine 5′-diphosphate. This study demonstrates for the first time the significant potential of a single-enzyme approach for the C-glycodiversification.

Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-β-d-(glucopyranosyl- xylopyranosyl)-4′,5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected d-glucose and d-xylose in aqueous solution as the key reactions

Vicenin-3 was synthesized from naringenin via a short five-step reaction, which included two regioselective direct C-glycosylations with d-glucose and d-xylose (yields: 22% and 30%, respectively) as the key reactions for a total yield of 4.4%. Vicenin-1 was also synthesized from phloroacetophenone via a 10-step reaction, including the same glycosylation described above, for a total yield of 2.7% with a vicenin-3 yield of 1.7%.