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Cas Database |
| Name |
Glabridin |
EINECS | 611-908-7 |
| CAS No. | 59870-68-7 | Density | 1.257 g/cm3 |
| PSA | 58.92000 | LogP | 4.00070 |
| Solubility | N/A | 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 | N/A | Appearance | light yellow powder ,insoluble in water |
| Safety | 24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
1,3-Benzenediol,4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl)-, (R)-; |
Article Data | 7 |
Glabridin Synthetic route
- 59870-68-7
(±)-glabridin
Conditions
| Conditions | Yield |
|---|---|
| With boron tribromide In dichloromethane at -78 - 20℃; for 2h; | 84% |
| With boron tribromide In dichloromethane at -78℃; for 2h; Inert atmosphere; | 79% |
- 59870-68-7
(±)-glabridin
Conditions
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; isopropyl alcohol at 20℃; for 5h; |
- 151-10-0
1,3-Dimethoxybenzene
- 59870-68-7
(±)-glabridin
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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 |
- 59870-68-7
(±)-glabridin
Conditions
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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 |
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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Glabridin
