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59870-68-7

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

2',4'-dimethylglabridin

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

59870-68-7

(±)-glabridin

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

1,3-Dimethoxybenzene

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
829-20-9

2',4'-dimethoxyacetophenone

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
108-46-3

recorcinol

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
6496-89-5

2,4-dimethoxyphenylacetic acid

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
1891-01-6

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

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

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
51106-84-4

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

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
93-35-6

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

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
Raw Materials
6496-89-5
829-20-9
151-10-0
108-46-3
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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