578-86-9
Liquiritigenin
CAS: 578-86-9
Molecular Formula: C15H12O4
578-86-9 - Names and Identifiers
| Name | Liquiritigenin |
| Synonyms | Liquiritigenin (2S)-Liquiritigenin 4',7-Dihydroxyflavanone 7,4''-DIHYDROXYFLAVANONE hplc (S)-7-Hydroxy-2-(p-hydroxyphenyl)chroman-4-one (2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one (S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (2S)-2α-(4-Hydroxyphenyl)-7-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one (2S)-2α-(4-Hydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (S)- 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (2S)- |
| CAS | 578-86-9 |
| InChI | InChI=1/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1 |
| InChIKey | FURUXTVZLHCCNA-AWEZNQCLSA-N |
578-86-9 - Physico-chemical Properties
| Molecular Formula | C15H12O4 |
| Molar Mass | 256.25 |
| Density | 1.386±0.06 g/cm3(Predicted) |
| Melting Point | 206-208°C |
| Boling Point | 529.5±50.0 °C(Predicted) |
| Flash Point | 207℃ |
| Vapor Presure | 7.94E-12mmHg at 25°C |
| BRN | 359378 |
| pKa | 7.71±0.40(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 1.661 |
| Physical and Chemical Properties | Derived from licorice. |
578-86-9 - Risk and Safety
| WGK Germany | 3 |
| HS Code | 29329990 |
578-86-9 - Reference Information
| Plant source: | Licorice |
| Glycyrrhiza uralensis extract | Glycyrrhizin (liquiritigenin), also known as glycyrrhizin, is a dihydroflavone monomer compound found in the leguminous plant Licorice (Glycyrrhiza uralensis Fisch), which is extracted from Glycyrrhiza uralensis and is a non-sugar natural sweetener. Glycyrrhizin has antispasmodic, anti-ulcer, antibacterial, hepatocyte monoamine oxidase inhibition. |
| Licorice | Licorice is a leguminous perennial medicinal plant, distributed throughout Europe and Asia. Since ancient times, China has widely used it in medicine and food processing. Glycyrrhiza uralensis is a wild plant that grows in deep sandy soil near water and is now mostly planted artificially. The better planting season is March. In October of the third or fourth year after planting, when the leaves fall off, the rhizomes can be dug out and cut off, washed and dried naturally in the air for 4-6 months, peeled or not peeled, and then bundled and transported to the processing plant. fig. 1 is a picture of licorice plants |
| the chemical composition of licorice | the chemical composition of licorice is extremely complex, the compounds isolated from licorice so far include glycyrrhizin, glycyrrhetinic acid, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, glycyrrhizin, 7-methyl coumarin, Umbelliferous lactone and other dozens of compounds, but these components and quantities usually vary with the type of licorice, planting area. A large number of studies have shown that glycyrrhizin and flavonoids are the most important physiologically active substances in licorice, which mainly exist in the epidermis of licorice root. There are not many reports on flavonoids in licorice. The existing research results all believe that it is another kind of important physiological active substance in licorice, which plays an important role in the physiological functions of licorice such as anti-ulcer and antispasmodic. Glycyrrhizin flavonoids include liquiritin (Liquiritigenin), isoglycyrrhizin (Isoliquiritigenin), liquiritin (Liquiritin), isoglycyrrhizin (Isoliquiritin), neoglycyrrhizin (Neoliquiritin), neoglycyrrhizin (Neoisoliquiritin), isoglycyrrhizin-4-β-glucose-β-genitoside (Licurazid), etc. licorice is also rich in licorice polysaccharide, which is an antiviral component of licorice. In recent years, some people have screened 7 kinds of viruses with licorice polysaccharide (GPS), and found that it has obvious inhibitory effect on 4 of them. The research on the separation and purification, structure analysis and physiological function of licorice polysaccharide needs to be further deepened. |
| glycyrrhizin | glycyrrhizin (glycyrrhizin) is a pentacyclic triterpene saponin contained in the root and rhizome of glycyrrhiza uralensis. the content fluctuates greatly with different varieties and harvest seasons. for example, the rhizome of Chinese glycyrrhiza uralensis contains about 3.11% ~ 6.53%, Russian 2.2% and Afghan 5.11%. The molecular formula of glycyrrhizin is C42H62O16, the relative molecular mass is 822.92, the melting point is 220 ℃, it is hardly soluble in cold water and dilute ethanol, it is easily soluble in hot water, the aqueous solution is weakly acidic, and it is viscous after cooling. The molecular structure of glycyrrhizin is formed by the combination of glycyrrhetinic acid and glycyrrhetinic acid. Glycyrrhetinic acid is the saponin ligand of glycyrrhizin and one of the effective active components of glycyrrhizin. as the most important active ingredient of licorice, glycyrrhizin has the functions of detoxification, anti-dental caries and anti-inflammation. Glycyrrhizin has no hemolytic effect, because it can prevent hemolysin from approaching red blood cells by absorbing hemolysin on the surface of red blood cells. Glycyrrhetinic acid has hemolytic effect, and also has anti-inflammatory, anti-allergic, anti-peptic ulcer and other functions. In addition to the above physiological functions, glycyrrhizin also has a greater sweetness, a small amount of hay sugar and sucrose sharing can reduce the amount of sucrose. figure 2 shows the chemical structure of glycyrrhizin (1) and glycyrrhetinic acid (2) the extraction of glycyrrhizin from glycyrrhizin is only a matter of nearly 20 years. the United States, Japan and Russia have done a lot of research in this regard. At present, commercial products are lumpy, granular and viscous. |
| extraction method | the method of extracting liquorice from licorice is characterized by the following steps: (1) pulverizing licorice into 60 mesh powder, extracting with hydrochloric acid solution with a concentration of 1mol/L for 120 minutes under the conditions of 80 ℃ and solid-liquid mass ratio of 1:5~8, four layers of gauze are filtered, and the filtrate is cooled to room temperature, and 1mol/L sodium hydroxide solution is added to adjust to neutral to obtain the crude liquiritin extract; (2) The crude liquiritin extract is mixed with a resin column, use 5-8 times the column volume of deionized water, 5 times the column volume of 20% ~ 40% ethanol aqueous solution, 4 times the column volume of 70% ethanol aqueous solution for elution, collect the volume of the eluent of 70% ethanol aqueous solution, concentrate under reduced pressure to 30% sugar degree, add equal volume of deionized water, stir well, crystallide at 20 ℃ for 8 hours, absorb the supernatant, crystallization is dissolved by adding 4 times the volume of absolute ethanol, concentrated under reduced pressure to 30% sugar degree, adding equal volume of deionized water, stirring evenly, crystallization at 20 ℃ for 8 hours, filtering, crystallization is washed with deionized water until no alcohol taste, and dried under reduced pressure at 60 ℃ to obtain purified liquorice. |
| identification method | HPLC determination conditions of glycyrrhizin ▼ ▲ separation component chromatographic column stationary phase mobile phase flow rate (ml/min) detection wavelength (nm) column warm glycyrrhizin Hyporsil ODS2 C18 column (250mm × 4.6mm,5 μm) methanol-water (45: 55) is 276nm when 0.8 0~25min, 360nm 25 ℃ |
| pharmacological action | licorice has antispasmodic effect on smooth muscle, such as licorice extract, glycyrrhizin, isoglycyrrhizin and FM100 can obviously inhibit the movement of isolated intestinal tubes of animals, and can also relieve intestinal spasm caused by acetylcholine, barium chloride and histamine. 1. This product has the functions of anti-oxidation, anti-ulcer, anti-allergy, anti-mold, prevent skin aging, and effectively remove superoxide ions. 2. Glycyrrhizin is a good whitening cosmetic raw material, which can inhibit tyrosinase activity well. 3. Suitable for sweetening and seasoning canned food, seasoning, candy, biscuits and candied fruit (Cantonese cold fruit). 4. Glycyrrhizin has antispasmodic and depressive psychosis. |
| safety | licorice is a traditional seasoning and traditional Chinese medicine in our country. since ancient times, licorice has been used as an antidote and condiment, and no harm to human body has been found. normal usage is safe. |
| store | 4 ℃ sealed, refrigerated and protected from light. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: antispasmodic, anti-ulcer, antibacterial. It can inhibit monoamine oxidase, thereby treating depressive psychosis. |
Last Update：2024-04-09 20:52:54
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Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
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