Product Name

  • Name

    Glabridin

  • EINECS 611-908-7
  • CAS No. 59870-68-7
  • Article Data7
  • CAS DataBase
  • Density 1.257 g/cm3
  • Solubility
  • Melting Point 154-155oC
  • Formula C20H20O4
  • Boiling Point 518.555 °C at 760 mmHg
  • Molecular Weight 324.376
  • Flash Point 267.413 °C
  • Transport Information
  • Appearance light yellow powder ,insoluble in water
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 59870-68-7 (Glabridin)
  • Hazard Symbols
  • Synonyms 1,3-Benzenediol,4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl)-, (R)-;
  • PSA 58.92000
  • LogP 4.00070

Synthetic route

2',4'-dimethylglabridin

2',4'-dimethylglabridin

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃; for 2h;84%
With boron tribromide In dichloromethane at -78℃; for 2h; Inert atmosphere;79%
2',4'-di(methoxymethyl)glabridin

2',4'-di(methoxymethyl)glabridin

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 5h;
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
2.1: sulfur; morpholine / 12 h / 130 °C
2.2: 12 h / Reflux
3.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
3.2: 0.33 h / 55 °C
3.3: 3 h / 80 °C
4.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
5.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
6.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
2.1: sulfur; morpholine / 12 h / 130 °C
2.2: 12 h / Reflux
3.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
3.2: 0.33 h / 55 °C
3.3: 3 h / 80 °C
4.1: acetic acid; hydrogen; 5%-palladium/activated carbon / ethanol; water / 12 h / 20 °C
5.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
6.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
2.1: sulfur; morpholine / 12 h / 130 °C
2.2: 12 h / Reflux
3.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
3.2: 0.33 h / 55 °C
3.3: 3 h / 80 °C
4.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
5.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
6.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
2.1: sulfur; morpholine / 12 h / 130 °C
2.2: 12 h / Reflux
3.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
3.2: 0.33 h / 55 °C
3.3: 3 h / 80 °C
4.1: hydrogen / N,N-dimethyl-formamide / 0.5 h / 22 °C / 760.05 Torr
5.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
6.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
2',4'-dimethoxyacetophenone
829-20-9

2',4'-dimethoxyacetophenone

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfur; morpholine / 12 h / 130 °C
1.2: 12 h / Reflux
2.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
2.2: 0.33 h / 55 °C
2.3: 3 h / 80 °C
3.1: acetic acid; hydrogen; 5%-palladium/activated carbon / ethanol; water / 12 h / 20 °C
4.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
5.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sulfur; morpholine / 12 h / 130 °C
1.2: 12 h / Reflux
2.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
2.2: 0.33 h / 55 °C
2.3: 3 h / 80 °C
3.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
4.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
5.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sulfur; morpholine / 12 h / 130 °C
1.2: 12 h / Reflux
2.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
2.2: 0.33 h / 55 °C
2.3: 3 h / 80 °C
3.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
4.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
5.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
6.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sulfur; morpholine / 12 h / 130 °C
1.2: 12 h / Reflux
2.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
2.2: 0.33 h / 55 °C
2.3: 3 h / 80 °C
3.1: hydrogen / N,N-dimethyl-formamide / 0.5 h / 22 °C / 760.05 Torr
4.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
5.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
6.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
recorcinol
108-46-3

recorcinol

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydroxide / water / 3 h / 0 - 70 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
3.1: sulfur; morpholine / 12 h / 130 °C
3.2: 12 h / Reflux
4.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
4.2: 0.33 h / 55 °C
4.3: 3 h / 80 °C
5.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
6.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide / water / 3 h / 0 - 70 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
3.1: sulfur; morpholine / 12 h / 130 °C
3.2: 12 h / Reflux
4.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
4.2: 0.33 h / 55 °C
4.3: 3 h / 80 °C
5.1: acetic acid; hydrogen; 5%-palladium/activated carbon / ethanol; water / 12 h / 20 °C
6.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
7.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydroxide / water / 3 h / 0 - 70 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
3.1: sulfur; morpholine / 12 h / 130 °C
3.2: 12 h / Reflux
4.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
4.2: 0.33 h / 55 °C
4.3: 3 h / 80 °C
5.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
6.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
7.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
8.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sodium hydroxide / water / 3 h / 0 - 70 °C
2.1: aluminum (III) chloride / dichloromethane / 1 h / 0 - 20 °C
3.1: sulfur; morpholine / 12 h / 130 °C
3.2: 12 h / Reflux
4.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
4.2: 0.33 h / 55 °C
4.3: 3 h / 80 °C
5.1: hydrogen / N,N-dimethyl-formamide / 0.5 h / 22 °C / 760.05 Torr
6.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
7.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
8.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
2,4-dimethoxyphenylacetic acid
6496-89-5

2,4-dimethoxyphenylacetic acid

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
1.2: 0.33 h / 55 °C
1.3: 3 h / 80 °C
2.1: acetic acid; hydrogen; 5%-palladium/activated carbon / ethanol; water / 12 h / 20 °C
3.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
4.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
1.2: 0.33 h / 55 °C
1.3: 3 h / 80 °C
2.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
3.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
4.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
1.2: 0.33 h / 55 °C
1.3: 3 h / 80 °C
2.1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
3.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
4.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
5.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / 0.17 h / 100 °C
1.2: 0.33 h / 55 °C
1.3: 3 h / 80 °C
2.1: hydrogen / N,N-dimethyl-formamide / 0.5 h / 22 °C / 760.05 Torr
3.1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
4.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
5.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one
1891-01-6

3-(2,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; hydrogen; 5%-palladium/activated carbon / ethanol; water / 12 h / 20 °C
2: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
3: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
2: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
3: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: acetic acid; hydrogen; platinum on carbon / 12 h / 100 °C
2: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
3: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
4: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogen / N,N-dimethyl-formamide / 0.5 h / 22 °C / 760.05 Torr
2: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
3: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
4: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
3-(2,4-dimethoxyphenyl)-chroman-7-ol

3-(2,4-dimethoxyphenyl)-chroman-7-ol

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
2: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
3-(2,4-dimethoxyphenyl)-7-hydroxychroman-4-one
51106-84-4

3-(2,4-dimethoxyphenyl)-7-hydroxychroman-4-one

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; phenylboronic acid / toluene / 12 h / Reflux; Inert atmosphere
2: lithium aluminium tetrahydride / diethyl ether / 6 h / Reflux
3: boron tribromide / dichloromethane / 2 h / -78 - 20 °C
View Scheme
7-hydroxy-2H-chromen-2-one
93-35-6

7-hydroxy-2H-chromen-2-one

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) choride dihydrate / acetonitrile / 10 h / 20 °C
2: bromine / N,N-dimethyl-formamide / 2 h / Cooling with ice
3: 1.5 h / 180 °C
4: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C
5: lithium borohydride / tetrahydrofuran / 20 °C
6: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 10 h / Cooling with ice
7: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one
27421-18-7

7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: bromine / N,N-dimethyl-formamide / 2 h / Cooling with ice
2: 1.5 h / 180 °C
3: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C
4: lithium borohydride / tetrahydrofuran / 20 °C
5: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 10 h / Cooling with ice
6: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
C14H11BrO3

C14H11BrO3

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.5 h / 180 °C
2: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C
3: lithium borohydride / tetrahydrofuran / 20 °C
4: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 10 h / Cooling with ice
5: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
C14H11BrO3

C14H11BrO3

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C
2: lithium borohydride / tetrahydrofuran / 20 °C
3: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 10 h / Cooling with ice
4: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
C22H20O5

C22H20O5

(±)-glabridin
59870-68-7

(±)-glabridin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium borohydride / tetrahydrofuran / 20 °C
2: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 10 h / Cooling with ice
3: boron tribromide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
(±)-glabridin
59870-68-7

(±)-glabridin

1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole
13182-81-5

1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole

C26H27N3O6

C26H27N3O6

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 10h;66%
(±)-glabridin
59870-68-7

(±)-glabridin

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-(8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl)-2,6-dihydroxybenzaldehyde

3-(8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl)-2,6-dihydroxybenzaldehyde

Conditions
ConditionsYield
With trichlorophosphate at 100℃; for 3h; Cooling with ice;

Glabridin Specification

The 1,3-Benzenediol, 4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-, (R)-, with the CAS registry number 59870-68-7, is also known as Glabridin. It belongs to the product categories of Miscellaneous Natural Products; Natural Plant Extract. This chemical's molecular formula is C20H20O4 and molecular weight is 324.37. What's more, both its IUPAC name and systematic name are the same which is called 4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol. It is a chemical compound that is found in the root extract of licorice. This chemical is used as an ingredient in cosmetics and is listed in International Nomenclature of Cosmetic Ingredients.The product is yellowish-brown powder. It is insoluble in water, but soluble in organic solvents such as propylene glycol.

Physical properties about 1,3-Benzenediol, 4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-, (R)- are: (1)ACD/LogP: 4.105; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.11; (4)ACD/LogD (pH 7.4): 4.10; (5)ACD/BCF (pH 5.5): 775.53; (6)ACD/BCF (pH 7.4): 768.44; (7)ACD/KOC (pH 5.5): 4073.43; (8)ACD/KOC (pH 7.4): 4036.21; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 58.92 Å2; (13)Index of Refraction: 1.623; (14)Molar Refractivity: 90.944 cm3; (15)Molar Volume: 257.93 cm3; (16)Polarizability: 36.053×10-24 cm3; (17)Surface Tension: 56.38 dyne/cm; (18)Density: 1.258 g/cm3; (19)Flash Point: 267.413 °C; (20)Enthalpy of Vaporization: 82.095 kJ/mol; (21)Boiling Point: 518.555 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O4c2c1\C=C/C(Oc1ccc2C[C@H](c3ccc(O)cc3O)C4)(C)C
(2) InChI: InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
(3) InChIKey: LBQIJVLKGVZRIW-ZDUSSCGKSA-N

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