4192-90-9

Basic information

• Product Name: PRUNINDIHYDROCHALCONE
• Synonyms: PRUNINDIHYDROCHALCONE;1-[4-(β-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone;Phloretin 4'-glucoside;p-Phloridzin;p-Phlorizin;Trilobatin;TRILOBATIN(SH);Trilobatin, 98%, from leaf of strigose hydrangea
• CAS NO: 4192-90-9
• Molecular Formula: C₂₁H₂₄O₁₀
• Molecular Weight: 436.40926
• Mol File: 4192-90-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 170-173 °C
• Boiling Point: 787.9°Cat760mmHg
• Flash Point: 277.1°C
• Appearance: /
• Density: 1.555g/cm³
• Vapor Pressure: 3.71E-26mmHg at 25°C
• Refractive Index: 1.686
• PKA: 6.85±0.40(Predicted)
• CAS DataBase Reference: PRUNINDIHYDROCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: PRUNINDIHYDROCHALCONE(4192-90-9)
• EPA Substance Registry System: PRUNINDIHYDROCHALCONE(4192-90-9)

Safety Data

• Hazardous Substances Data: 4192-90-9(Hazardous Substances Data)

Usage

General Description

Prunindihydrochalcone is a chemical compound found in the leaves of Prunus Mume (also known as Chinese Plum or Japanese Apricot) and is known for its potential sweetening properties. It is a type of dihydrochalcone, which is a class of natural sweeteners that are derived from plants. Prunindihydrochalcone has been studied for its potential as a low-calorie sweetener and has been found to have a sweet taste without the potential negative health effects associated with traditional sugar. It is also being researched for its potential use in the food and beverage industry as a natural and safe alternative to artificial 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

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

Downstream Products

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

Relevant articles and documents

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.

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.