(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one
Liquiritin
CAS: 551-15-5
Molecular Formula: C21H22O9
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Names and Identifiers
| Name | Liquiritin |
| Synonyms | Likviritin Liquiritin Liquiritoside Liquiritin(Sh) LIQUIRITIN(SH) Liquiritin 551-15-5 Liquiritin(Liquiritoside) 7-Hydroxyflavanone 4'-O-glucoside 4',7-Dihydroxyflavanone4'-(β-D-glucopyranoside) 4-[(2S)-7-hydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]phenyl beta-D-glucopyranoside (2S)-2,3-Dihydro-7-hydroxy-2-[4-(β-D-glucopyranosyloxy)phenyl]-4H-1-benzopyran-4-one (S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one |
| CAS | 551-15-5 |
| InChI | InChI=1/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1 |
| InChIKey | DEMKZLAVQYISIA-ZRWXNEIDSA-N |
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Physico-chemical Properties
| Molecular Formula | C21H22O9 |
| Molar Mass | 418.4 |
| Density | 1.529±0.06 g/cm3(Predicted) |
| Melting Point | 208 °C(Solv: ethanol (64-17-5)) |
| Boling Point | 746.8±60.0 °C(Predicted) |
| Flash Point | 265.9°C |
| Solubility | Soluble in methanol, insoluble in water. |
| Vapor Presure | 2.01E-23mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| pKa | 7.70±0.40(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.67 |
| MDL | MFCD00210526 |
| Physical and Chemical Properties | White crystal, soluble in methanol, almost insoluble in ether, derived from licorice. |
| In vitro study | Liquiritin can target the residues Ala-27, Val-29, Ala-25, and Asn-56 of AKR1C1. Liquiritin (50 μM; 6 hours) results in 85.00% of reduction in progesterone metabolism, which is mediated by Aldo-keto reductase family 1 member C1 (AKR1C1) enzymatic activity in HEC-1-B cells. Liquiritin (100 µM) increases glucose-6-phosphate dehydrogenase expression on B65 neuroblastoma cells. |
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Risk and Safety
| WGK Germany | 3 |
| HS Code | 29389090 |
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Nature
Open Data Verified Data
white crystalline powder, sweetness is about 200 times of sucrose. Sweet later, but stay sweet for a long time. A small amount of glycyrrhizin and sucrose sharing can be less than 20% sucrose and sweetness unchanged. Glycyrrhizin has no aroma but has the function of flavoring. Its aqueous solution is weakly acidic. Difficult to dissolve in cold water, soluble in hot water, insoluble in oil, the hot water solution after cooling is viscous jelly.
Last Update：2024-01-02 23:10:35
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Preparation Method
Open Data Verified Data
glycyrrhizin can be extracted from licorice.
- licorice powder was crushed by water extraction and passed through a 10-20 mesh sieve to obtain licorice powder. 5 to 7 times the mass of water is added to the licorice powder, and the mixture is heated to reflux at 85 to 100 ° C. 2. 5h extraction, filtration, filter residue plus 3 times the amount of water extraction once, combined filtrate. The filtrate was concentrated in vacuo using a thin film evaporator and filtered while hot when the volume of the filtrate was reduced by 4/5. After the filtrate was cooled, 95% ethanol of a capacity of 1/2 was added thereto, and the mixture was allowed to stand overnight, and precipitates such as vegetable proteins and polysaccharides were removed by filtration. The filtrate was adjusted to pH 3 with concentrated sulfuric acid to precipitate liquiritin, and then centrifuged to obtain crude liquiritin. The crude liquiritin is recrystallized with dilute ethanol at 60-70 ℃, filtered under reduced pressure, and the filter cake is vacuum heated at 70-80 ℃ for 40-60min, crushed and sieved to obtain a finished product. Liquiritin after acid precipitation can also be refined with acetone. The specific process is as follows: adding 3 times the amount of acetone in liquiritin precipitation, heating reflux extraction for 3H, pouring out the Acetone Extract; The residue is refluxed and extracted twice with acetone repeatedly, the extract is combined for 3 times, filtered, acetone was recovered to obtain liquiritin wet product. First dry th at 45 ℃, then warm up to 85~100 ℃, The product is obtained by crushing. In addition to purification using an organic solvent, purification using resin adsorption may also be used. The crude liquiritin was adsorbed by Dl01 resin column and HP20 resin column respectively, and then impurities were washed by water and low-concentration ethanol solution, and then the Dl01 resin and HP20 resin column were eluted by excess 50% and 60% ethanol, the eluate was collected, concentrated and crystallized to obtain the final product.
- after drying, liquorice flakes were soaked in ammonia water (25% ~ 28%), left for overnight, filtered, and diluted sulfuric acid (10%) was added to the filtrate until the precipitation was complete, the product was allowed to stand for 1-2H, filtered, washed with water, dried, and then recrystallized from 70%-80% ethanol to obtain a liquiritin content of more than 70%. The raffinate after extracting glycyrrhizin can also be used as the raw material of natural pigment and other important drugs. In order to improve the purity of liquiritin obtained by aqueous ammonia extraction, liquiritin can be further refined. The specific process is as follows: the liquiritin crude product is extracted with industrial alcohol at 40~50 ℃ for 2 times, and the alcohol extract is combined for 2 times. Under stirring, concentrated ammonia water is added to pH 7.2~7.5, concentrate to a thick paste, then mix to a paste with an appropriate amount of glacial acetic acid, dissolve by heating, and stand still. The precipitate obtained by Suction filtration is washed with glacial acetic acid, Recrystallization from 70% to 80% ethanol. Crystallization and then 10% ethanol to 0.25% concentration of the solution, and then with dilute hydrochloric acid to adjust the pH value of 6.0~6.5, and then into the cation exchange resin column for ammonium removal, ammonium removal liquid concentration, evaporation, the product was obtained by recrystallization of the evaporated matter from glacial acetic acid in 92% yield. It is said that this method uses the first conversion of liquiritin for easy purification of ammonium salt and then ion exchange method to remove ammonium, although more complex, but the product purity is high (98%), suitable for industrial scale production.
- supercritical CO2 extraction method in this method, under the condition of supercritical extraction, liquiritin was extracted from licorice with CO2 as extractant and water-ethanol as entrainer, and the optimum extraction temperature was 40 ℃, the pressure was 35MPa, the mass ratio of the extraction system to the material was 4~5, and the extraction time was 5H. In the extraction, CO2 does not react with the active ingredients of the extract, which is non-toxic, non-polluting, non-carcinogenic, low boiling point, and easy to remove from the product.
Last Update：2022-01-01 11:13:40
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Use
Open Data Verified Data
can be used as a sweetener, a flavoring agent, and a flavor enhancer.
Last Update：2022-01-01 11:13:40
(S)-7-Hydroxy-2-[4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-yloxy)phenyl]chroman-4-one - Reference Information
| traits | white powder |
| use | when used as a sweet improver or enhancer, it is generally mixed with other sweeteners. liquiritin has anti-ulcer and anti-AIDS effects. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: anti-ulcer, anti-HIV and other effects. |
| Biological activity | Liquiritin is a flavonoid isolated from licorice. It is an effective and competitive AKR1C1 inhibitor. The IC50 for AKR1C1,AKR1C2 and AKR1C3 are 0.62 μM,0.61 μM and 3.72 μM respectively. Liquiritin effectively inhibits AKR1C1 mediated progesterone metabolism in vivo. Liquiritin is an antioxidant with neuroprotective, anti-cancer and anti-inflammatory activities. |
| target | IC50: 0.62 μM (AKR1C1), 0.61 μM (AKR1C2) and 3.72 μM (AKR1C3) |
| in vitro study | Liquiritin can target the residues Ala-27, Val-29, Ala-25, and Asn-56 of AKR1C1. Liquiritin (50 μM; 6 hours) results in 85.00% of reduction in progesterone metabolism, which is mediated by Aldo-keto reductase family 1 member C1 (AKR1C1) enzymatic activity in HEC-1-B cells. Liquiritin (100 m) increases glucose-6-phosphate dehydrogenase expression on B65 neuroblastoma cells. |
| Chemical properties | White crystal, easily soluble in methanol, almost insoluble in ether, derived from licorice. |
Last Update：2024-04-09 21:54:55
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Product Name: Liquiritin Visit Supplier Webpage Request for quotationCAS: 551-15-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Liquiritin Visit Supplier Webpage Request for quotationCAS: 551-15-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: Liquiritin Request for quotationCAS: 551-15-5
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
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