4192-90-9

Usage

Uses

Used in Food and Beverage Industry:
Prunindihydrochalcone is used as a natural sweetener for its low-calorie content and potential health benefits over traditional sugar. It is favored for its ability to provide sweetness without the negative health implications associated with excessive sugar consumption.
Used in Health and Nutrition Applications:
Prunindihydrochalcone is utilized as a dietary supplement or ingredient in health products due to its potential to offer sweetness without contributing excess calories, making it a suitable option for those seeking to manage their sugar intake or maintain a healthy diet.
Used in Product Formulation:
In the development of new food and beverage products, prunindihydrochalcone is used as an ingredient to formulate low-calorie or sugar-free options, catering to consumers' preferences for healthier alternatives to traditional sweeteners.

InChI:InChI=1/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1

Synthetic route

4'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-2',4”,6'-tribenzyloxychalcone → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; ethyl acetate at 20℃; for 19h;	93%

C29H32O14 (1133352-99-4) → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
With sodium methylate In methanol for 5h; Reflux;	50%

[4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone (18916-17-1) → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
With hydrogenchloride

naringin (10236-47-2) → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; aqueous KOH-solution 2: palladium/charcoal; ethanol / Hydrogenation 3: aqueous hydrochloric acid View Scheme

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone (50376-43-7) → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/charcoal; ethanol / Hydrogenation 2: aqueous hydrochloric acid View Scheme

UDP-glucose (133-89-1) + 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2) → phloretin-4-O-β-D-glucopyranoside + 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9) + phloridizin (60-81-1, 6426-09-1, 40816-73-7, 130549-93-8, 138665-98-2)

Conditions	Yield
With glycosyltransferase from Carthamus tinctorius (L.) (Honghua) recombinant In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	A 2.9 mg B 3.8 mg C 2 mg

naringin (10236-47-2) → 4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / water / 0.5 h / 121 °C / High pressure 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h 2.2: 8 h / 20 °C 3.1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 19 h / 20 °C View Scheme

4'-(β-D-glucopyranosyloxy)-2',4”,6'-trihydroxydihydrochalcone (4192-90-9) → 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2)

Conditions	Yield
With hydrogenchloride

Upstream product

• 18916-17-1 [4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone 
• 50376-43-7 4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone 
• 1133352-99-4 C₂₉H₃₂O₁₄ 
• 133-89-1 UDP-glucose 
• 60-82-2 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on 
• 10236-47-2 naringin 
• 10236-47-2 naringin 

Downstream Products

• 60-82-2 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on 

Relevant academic research and scientific papers

Synthesis of trilobatin from naringin via prunin as the key intermediate: Acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions

Trilobatin [4-(β-D-glucopyranosyloxy)-2,4”,6-trihydroxydihydrochalcone] was synthesized from commercially available naringin in three steps with an overall yield of 30%. The key step was the acid-catalyzed site-selective hydrolysis of terminal α-rhamnopyranosidic linkage in neohesperidose involved in naringin under controlled conditions, by applying a high-pressure steam sterilizer.

Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius

The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.

Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors

Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardioprotective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, Ki = 16.00 μM) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (Ki = 2.88 μM), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modifications could yield selective and potent hCNT3 inhibitors.