Product Name

  • Name

    Naringin

  • EINECS 233-566-4
  • CAS No. 10236-47-2
  • Article Data9
  • CAS DataBase
  • Density 1.66 g/cm3
  • Solubility Soluble in water, alcohol, acetone and warm acetic acid.
  • Melting Point 166 °C
  • Formula C27H32O14
  • Boiling Point 928.1 °C at 760 mmHg
  • Molecular Weight 580.543
  • Flash Point 308.5 °C
  • Transport Information
  • Appearance beige to yellowish powder
  • Safety 22-24/25-36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 10236-47-2 (Naringin)
  • Hazard Symbols IrritantXi
  • Synonyms Nvaringin;Momordica grosvenori Extract;schizandra extract;Naringin 98% (HPLC);PolymethoxyLatecl Flavones (Nobiletin);Naringoside;4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy- R-L-mannopyranosyl)-a-D-glucopyranosyl]- oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(2S)-;Naringenin 7-O-[beta-L-rhamnosyl-(1->2)-beta-D-glucoside];45-diOH-Flavone-7-rhgluc;Naringenin 7-O-neohesperidoside;7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;7-(2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone;
  • PSA 225.06000
  • LogP -1.16520

Synthetic route

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone
50376-43-7

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

naringin
10236-47-2

naringin

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 25℃; Kinetics; Equilibrium constant; Activation energy; Further Variations:; Solvents;
naringin
10236-47-2

naringin

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on
480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Conditions
ConditionsYield
With sulfuric acid In water at 121℃; for 2h;100%
naringin
10236-47-2

naringin

acetic anhydride
108-24-7

acetic anhydride

4',5-diacetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranoxyl-β-D-glucopyranosyl)oxy]flavan-4-one

4',5-diacetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranoxyl-β-D-glucopyranosyl)oxy]flavan-4-one

Conditions
ConditionsYield
With pyridine; dmap at 20℃; for 2h; Inert atmosphere;99%
With sodium acetate for 4h; Acetylation; Heating;
naringin
10236-47-2

naringin

[4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
18916-17-1

[4-[[2-O-(6-deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; potassium hydroxide In ethanol at 55℃; under 7500.75 - 15001.5 Torr; Temperature; Reagent/catalyst; Pressure; Autoclave;98%
With potassium hydroxide; hydrogen; palladium on activated charcoal at 30℃; under 2280 Torr; for 0.5h;
naringin
10236-47-2

naringin

triethylentetramine
112-24-3

triethylentetramine

N,N-1,1'-bis(naringin)triethylenetetraamine

N,N-1,1'-bis(naringin)triethylenetetraamine

Conditions
ConditionsYield
In methanol; ethanol at 50℃; for 1.5h;87%
naringin
10236-47-2

naringin

2,6-dihydroxy-4-(β-neohesperidosyloxy)acetophenone
23643-71-2

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

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;64%
naringin
10236-47-2

naringin

prunin
221362-75-0

prunin

Conditions
ConditionsYield
With sulfuric acid In water at 121℃; for 0.5h; High pressure;58%
naringin
10236-47-2

naringin

dimethyl sulfate
77-78-1

dimethyl sulfate

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
5128-44-9

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Conditions
ConditionsYield
Stage #1: naringin With pyridine; iodine Heating;
Stage #2: With sulfuric acid In ethanol Heating;
Stage #3: dimethyl sulfate With potassium carbonate In acetone at 45℃; for 0.5h; regioselective reaction;		44%
naringin
10236-47-2

naringin

A

D-Glucose
2280-44-6

D-Glucose

B

prunin
221362-75-0

prunin

C

2-O-α-L-rhamonopyranosyl-D-glucopyranose
2781-65-9

2-O-α-L-rhamonopyranosyl-D-glucopyranose

D

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on
480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Conditions
ConditionsYield
With water at 120℃; for 45h;A 16 mg
B 13 mg
C 30 mg
D 30 mg
...Expand
naringin
10236-47-2

naringin

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C33H42O19

C33H42O19

Conditions
ConditionsYield
With cyclodextrin glucanotransferase from alkanophilic Bacillus sp. AP A2-5a In water at 40℃; for 16h; other reagent;
naringin
10236-47-2

naringin

4'-rhamnoglucosyloxy-2',4,6'-trihydroxychalcone
50376-43-7

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

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 25℃; Kinetics; Equilibrium constant; Activation energy; Further Variations:; Solvents;
With sodium hydroxide In ethanol; water for 0.0833333h; Heating;
naringin
10236-47-2

naringin

1-[2,6-dihydroxy-4-O-(α-L-rhamnopyranosyl(1-> 2)-β-D-glucopyranosyl)-3-2H-phenyl]-3-(4-hydroxyphenyl)-[2,2,3,3]-2H4-propan-1-one

1-[2,6-dihydroxy-4-O-(α-L-rhamnopyranosyl(1-> 2)-β-D-glucopyranosyl)-3-2H-phenyl]-3-(4-hydroxyphenyl)-[2,2,3,3]-2H4-propan-1-one

Conditions
ConditionsYield
With deuteromethanol; sodium formate; palladium on activated charcoal for 0.5h; Heating;
naringin
10236-47-2

naringin

1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
111316-17-7

1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; aq. KOH / 5 percent Pd/C / 0.5 h / 30 °C / 2280 Torr
2: iPr2NH / dioxane; methanol / 1 h / 20 °C
3: aq. HCl / 0.5 h / 100 °C
View Scheme
naringin
10236-47-2

naringin

1-{4-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-hydroxy-6-methoxy-phenyl}-3-(4-hydroxy-phenyl)-propan-1-one

1-{4-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-hydroxy-6-methoxy-phenyl}-3-(4-hydroxy-phenyl)-propan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2; aq. KOH / 5 percent Pd/C / 0.5 h / 30 °C / 2280 Torr
2: iPr2NH / dioxane; methanol / 1 h / 20 °C
View Scheme
naringin
10236-47-2

naringin

1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one
39548-86-2

1‐(2‐(benzyloxy)‐4,6‐dihydroxyphenyl)ethan‐1‐one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
View Scheme
naringin
10236-47-2

naringin

2,6-dihydroxy-4-(carboxymethoxy)acetophenone

2,6-dihydroxy-4-(carboxymethoxy)acetophenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 2.83 g / 5percent aq.KOH / tetrahydrofuran / 2 h / 0 °C
6: 78 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 6 h / 2280 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 2.83 g / 5percent aq.KOH / tetrahydrofuran / 2 h / 0 °C
6: 78 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 6 h / 2280 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,6-dihydroxy-4-(carboxymethoxy)dihydrochalcone

2,6-dihydroxy-4-(carboxymethoxy)dihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 62 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 24 h / Ambient temperature
6: 72 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 2.25 h / 2280 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 62 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 24 h / Ambient temperature
6: 72 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 2.25 h / 2280 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2-acetylpholoroglucinol 1,3-bis(benzyl ether)
76799-38-7

2-acetylpholoroglucinol 1,3-bis(benzyl ether)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 3.80 g / 3percent aq. H2SO4 / ethanol / 22 h
View Scheme
naringin
10236-47-2

naringin

2-hydroxy-4-(carboxymethoxy)-6-(benzyloxy)acetophenone
76799-20-7

2-hydroxy-4-(carboxymethoxy)-6-(benzyloxy)acetophenone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 2.83 g / 5percent aq.KOH / tetrahydrofuran / 2 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 2.83 g / 5percent aq.KOH / tetrahydrofuran / 2 h / 0 °C
View Scheme
naringin
10236-47-2

naringin

2,3'6-trihydroxy-4-(carboxymethoxy)dihydrochalcone

2,3'6-trihydroxy-4-(carboxymethoxy)dihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 72 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 18 h
6: 81 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 18 h / 2280 Torr
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 72 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 18 h
6: 81 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 18 h / 2280 Torr
View Scheme
naringin
10236-47-2

naringin

2-hydroxy-4-(carbethoxymethoxy)-6-(benzyloxy)acetophenone
76799-13-8

2-hydroxy-4-(carbethoxymethoxy)-6-(benzyloxy)acetophenone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-chlorodihydrochalcone

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-chlorodihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 50 percent / 60percent aq. KOH / 1,2-dimethoxy-ethane / 120 h / Ambient temperature
6: 91 percent / H2 / Pd/C / ethyl acetate / 3 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 50 percent / 60percent aq. KOH / 1,2-dimethoxy-ethane / 120 h / Ambient temperature
6: 91 percent / H2 / Pd/C / ethyl acetate / 3 h / 760 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,3',4',6-tetrahydroxy-4-(carboxymethoxy)dihydrochalcone

2,3',4',6-tetrahydroxy-4-(carboxymethoxy)dihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 85 percent / 60percent aq. KOH / ethanol; tetrahydrofuran / 18 h / Ambient temperature
6: 70 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 18 h / 2280 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 85 percent / 60percent aq. KOH / ethanol; tetrahydrofuran / 18 h / Ambient temperature
6: 70 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 18 h / 2280 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-(methylamino)dihydroxychalcone

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-(methylamino)dihydroxychalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 44 percent / 60percent aq. KOH / dimethylformamide / 72 h / Ambient temperature
6: 50 percent / H2 / Pd/C / 18 h / 2280 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 44 percent / 60percent aq. KOH / dimethylformamide / 72 h / Ambient temperature
6: 50 percent / H2 / Pd/C / 18 h / 2280 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,6-dihydroxy-3'-amino-4-(carboxymethoxy)-4'-methoxydihydrochalcone

2,6-dihydroxy-3'-amino-4-(carboxymethoxy)-4'-methoxydihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 1.) 60percent aq. KOH / ethanol; 1,2-dimethoxy-ethane / 48 h / Ambient temperature
6: 59 percent / H2 / Pd/C / tetrahydrofuran; methanol / 1 h / 1520 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 1.) 60percent aq. KOH / ethanol; 1,2-dimethoxy-ethane / 48 h / Ambient temperature
6: 59 percent / H2 / Pd/C / tetrahydrofuran; methanol / 1 h / 1520 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2,6-dihydroxy-3',4'-(methylenedioxy)-4-(carboxymethoxy)dihydrochalcone

2,6-dihydroxy-3',4'-(methylenedioxy)-4-(carboxymethoxy)dihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 49 percent / 60percent aq. KOH / 1,2-dimethoxy-ethane / 80 h / Ambient temperature
6: 86 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 1 h / 2280 Torr
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 49 percent / 60percent aq. KOH / 1,2-dimethoxy-ethane / 80 h / Ambient temperature
6: 86 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 1 h / 2280 Torr
View Scheme
naringin
10236-47-2

naringin

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-n-propoxydihydrochalcone

2,3',6-trihydroxy-4-(carboxymethoxy)-4'-n-propoxydihydrochalcone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 45 percent / 60percent aq. KOH / ethanol; tetrahydrofuran / 18 h / Ambient temperature
6: 70 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 18 h / 2280 Torr / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 45 percent / 60percent aq. KOH / ethanol; tetrahydrofuran / 18 h / Ambient temperature
6: 70 percent / H2 / Pd/C / ethanol; tetrahydrofuran / 18 h / 2280 Torr / Ambient temperature
View Scheme
naringin
10236-47-2

naringin

2-hydroxy-4-(carboxymethoxy)-6-(benzyloxy)chalcone
76799-21-8

2-hydroxy-4-(carboxymethoxy)-6-(benzyloxy)chalcone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: K2CO3 / dimethylformamide / 168 h / Ambient temperature
3: 42 percent / 3percent aq. H2SO4 / ethanol / 46 h / Heating
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 62 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: 64 percent / 10percent aq. KOH / 4 h / Heating
2: 48.1 g / K2CO3 / dimethylformamide / 1.) RT, 21 h, 2.) 80 deg C, 6 h
3: 5.18 g / 3percent aq. H2SO4 / ethanol / 22 h
4: 76 percent / K2CO3 / dimethylformamide / 24 h / Ambient temperature
5: 62 percent / 60percent aq.KOH / ethanol; tetrahydrofuran / 24 h / Ambient temperature
View Scheme

Naringin Chemical Properties

IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms of Naringin (CAS NO.10236-47-2): 5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon ; Naringenin-7-beta-neohesperidoside ; Naringoside ; 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannapyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (S)- ; 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)- ; 7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
CAS NO: 10236-47-2
Molecular Formula: C27H32O14
Molecular Weight: 580.54
Molecular Structure:
H bond acceptors: 14
H bond donors: 8
Freely Rotating Bonds: 14
Polar Surface Area: 137.06 Å2
Index of Refraction: 1.708
Molar Refractivity: 135.63 cm3
Molar Volume: 347.8 cm3
Surface Tension: 101.2 dyne/cm
Density: 1.66 g/cm3
Flash Point: 308.5 °C
Enthalpy of Vaporization: 141.42 kJ/mol
Boiling Point: 928.1 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting Point: 166 °C
Alpha: -91 º (c=1, C2H5OH)
Storage temp: 0-6°C
Appearance: beige to yellowish powder
Product Categories of Naringin (CAS NO.10236-47-2): Flavanones;Biochemistry;Disaccharides;Flavonoids;Glycosides;Sugars;Natural Plant Extract

Naringin Uses

 Naringin (CAS NO.10236-47-2) has obvious anti-inflammation effect. Besides it can reduce blood viscosity and thrombosis. Naringin can also be used for analgesia, calm, and increase the secretion of bile of the experimental animals.

Naringin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.
rat LD50 intraperitoneal 2gm/kg (2000mg/kg)   Eksperimentalna Meditsina i Morfologiya. Vol. 19, Pg. 207, 1980.

Naringin Safety Profile

Safety information of Naringin (CAS NO.10236-47-2):
Hazard Codes: HarmfulXn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 22-24/25-36
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: QN6340000
F: 3

Naringin Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: Use agent most appropriate to extinguish fire. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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