Product Details
Appearance:light yellow powder ,insoluble in water
59870-68-7 Properties
- Molecular Formula:C20H20O4
- Molecular Weight:324.376
- Appearance/Colour:light yellow powder ,insoluble in water
- Vapor Pressure:2.26E-11mmHg at 25°C
- Melting Point:154-155oC
- Refractive Index:1.622
- Boiling Point:518.555 °C at 760 mmHg
- PKA:9.66±0.40(Predicted)
- Flash Point:267.413 °C
- PSA：58.92000
- Density:1.257 g/cm3
- LogP:4.00070
59870-68-7 Usage
Chemical Properties
White to tan powder
Uses
Glabridin is a compound extracted from Licorice (root) shows properties that are cytotoxic, antimicrobial, estrogenic and anti-proliferative.
Definition
ChEBI: A member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4' and a 2,2-dimethyl-2H-pyran group across positions 7 and 8 respectively.
Biochem/physiol Actions
Glabridin is a bio-available isoflavan isolated from licorice (Glycyrrhiza glabra L.) root extract. Glabridin has been reported to posses varies biological activities including strong antioxidant activity, antioxidant against LDL oxidation, anti-Helicobacter pylori properties, estrogen-like activity and antinephritic and radical scavenging activities. Also it appears to inhibit serotonin re-uptake, melanogenesis, inflammation and cytochrome P450 3A4, 2B6, and 2C9.
InChI:InChI=1/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
59870-68-7 Relevant articles
Method for synthesizing glabridin
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Paragraph 0031; 0044-0045, (2021/11/14)
The invention relates to a method for synthesizing glabridin. According to the method, 2, 4-dimethoxy bromobenzene and diethyl malonate are used as starting raw materials, a key intermediate compound III is prepared through a cuprous iodide catalytic coupling reaction, a reduction reaction and a bromination reaction, methyl-protected glabridin is prepared through nucleophilic substitution and a Friedel-Crafts reaction, and glabridin is obtained after methyl is removed. According to the method for synthesizing glabridin, raw materials are cheap and easy to obtain, and the total yield is high.
Method for synthesizing optically pure glabridin
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, (2021/11/19)
The invention relates to a method for synthesizing optically pure glabridin. According to the method, chiral carbon of optically pure glabridin is constructed through biological enzyme catalysis, optically pure glabridin is prepared in combination with an organic synthesis method, and the key steps are that a chiral intermediate compound III is generated by using a lipase catalysis compound II, and an important intermediate compound IV is obtained through a bromination reaction. According to the method for synthesizing optically pure glabridin, raw materials are cheap and easy to obtain, and the total yield is high.
Method for asymmetrically synthesizing glabridin with optical purity
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, (2020/07/15)
The invention discloses a method for asymmetrically synthesizing glabridin with optical purity, belonging to the field of organic synthesis. According to the invention, 7-hydroxychroman-4-one is usedas a raw material and is subjected to seven successive reactions including a protecting group protection reaction, an enol esterification reaction, an asymmetric addition reaction, a carbonyl reduction reaction, a phenolic hydroxyl protecting group removal reaction, a cyclization reaction and a demethylation reaction so as to finally prepare glabridin with optical purity. The optically pure glabridin is obtained by asymmetrically introducing a chiral center by using a palladium catalyst and an organophosphorus ligand; reaction conditions are mild; operation is convenient; and the method is suitable for industrial application. The raw material is easy to obtain and low in cost, and the product is good in yield and high in stereoselectivity.
A synthesis method of glabridin (by machine translation)
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Paragraph 0024; 0043; 0044, (2019/02/04)
The invention discloses a glabridin synthesis method, the method to the cheap and easy 7 - hydroxy coumarin as raw materials with 2 - methyl - 3 - [...] - 1 - ol reaction to construct a alkyne ether, then the resulting α, β - unsaturated compounds of the introduction bromine atom at α, by the rearrangement, Szuki coupling as the core reaction to construct a key intermediate (IV), reduction of the conjugated double bond double-hydroxy compound, Mitsunobu cheng mi, removing methyl seven-step reaction, the final to 20% of the total yield of the fast, efficient synthesis of light glycyrrhiza. The invention than in the previous method has the following advantages: cheap raw material, the total route is short, the total yield is high, can be fast and efficient synthetic light glycyrrhiza. (by machine translation)
59870-68-7 Process route
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2',4'-dimethylglabridin
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- 59870-68-7
(±)-glabridin
| Conditions | Yield |
|---|---|
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2',4'-dimethylglabridin; With boron tribromide; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;
With methanol; In dichloromethane; for 0.5h; Inert atmosphere;
|
100% |
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With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 2h;
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84% |
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With boron tribromide; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;
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79% |
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2',4'-di(methoxymethyl)glabridin
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- 59870-68-7
(±)-glabridin
| Conditions | Yield |
|---|---|
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With hydrogenchloride; In water; isopropyl alcohol; at 20 ℃; for 5h;
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59870-68-7 Upstream products
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1,3-Dimethoxybenzene
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829-20-9
2',4'-dimethoxyacetophenone
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recorcinol
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6496-89-5
2,4-dimethoxyphenylacetic acid
59870-68-7 Downstream products
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59870-70-1
(R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene
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1217305-76-4
5'-formylglabridin
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68978-03-0
hispaglabridin A
