3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone
CAS: 60-81-1
Molecular Formula: C21H24O10
3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside - Names and Identifiers
| Name | 2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone |
| Synonyms | Phlorizin Floridzin phloridzin phlorhizin phlorizine phloridzine phlorizoside Phlorizin dihydrate 4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- 1-Propanone, 1-[2-(β-D-glucopyranosyloxy)- 3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl hexopyranoside 3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside 3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl beta-D-allopyranoside 1-propanone,1-(2-(beta-d-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyp 2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone |
| CAS | 60-81-1 |
| EINECS | 200-487-1 |
| InChI | InChI=1/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1 |
3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside - Physico-chemical Properties
| Molecular Formula | C21H24O10 |
| Molar Mass | 436.41 |
| Density | 1.3178 (rough estimate) |
| Melting Point | 113-114°C(lit.) |
| Boling Point | 468.89°C (rough estimate) |
| Specific Rotation(α) | (C=3.2, 95% EtOH)-54 |
| Flash Point | 270.7°C |
| Solubility | Soluble in water and methanol, easily dissolved in ethanol and DMSO. |
| Vapor Presure | 6.15E-25mmHg at 25°C |
| Appearance | yellowish needle crystal |
| Color | Light Yellow to Tan |
| Merck | 14,7327 |
| pKa | 7.15±0.40(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | -54 ° (C=3.2, 95% Et |
| MDL | MFCD00006591 |
3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UC2080000 |
| FLUKA BRAND F CODES | 3-10-23 |
| HS Code | 29389090 |
3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | Phlorizin is the glucoside of phloretin, the chemical name is 1-(2-(beta-D-glucopyranosyloxy)-46-dihydroxyphenyl)-3-(4-hydroxyphenyl)-acetone, belonging to the dihydrochalone class of flavonoids. Phlorizin mainly exists in the root bark, stem, young leaves and apple fruits of apple trees, and is also present in a small amount in Compositae, rhododendron, legume, Fagaceae, Liliaceae and other plants. It has many important biological activities, such as reducing blood sugar, improving memory, anti-allergy, anti-cancer and so on. It has potential value in food, beauty and health care industry. |
| distribution of phlorizin | phlorizin mainly exists in Apple plants of Rosaceae, Compositae, rhododendron, legaceae, Fagaceae, liliaceae and other plants have also reported the presence of phlorizin, but the content is less. In recent years, in litchi pericarp, pear leaves, cynomorium songaricum and other plants are found in the presence of root bark glycosides, its content is less, but in sweet tea there are a lot of root bark glycosides. In general, Apple is the main source of phlorizin, can be used as a raw material for the extraction of phlorizin. Apple branches, leaves, bark and so on contain a lot of root bark. The distribution of phlorizin in apple fruit is concentrated in the seed and peel. |
| extraction method | (1) crushing of raw materials: the dried apple branches or leaves are crushed into 10~20 mesh or 20~30 mesh coarse powder;(2) extraction: put the crushed coarse powder raw material into a round bottom flask, add 70% methanol reflux extraction 3 times, each time to add liquid volume of 6, 4, 4BV, 1h each time, combined extract; (three extracts were brown to brown)(3) concentration: add antioxidant VC to the combined extract at 0.2% of the total weight of the extract, and extract methanol under reduced pressure at 60 ℃; (the concentrated solution is a comprehensive Brown turbid solution)(4) impurity removal: the recovered concentrated solution without alcohol is added to 0.5% by weight of polymerized alumina, adjusted to p H 7.5 with calcium hydroxide, placed in an Erlenmeyer flask, kept at 60 ℃ for 30min, and filtered with suction to obtain a clear solution; (After adding the polymerized alumina, the bottle bottom has a strong precipitate)(5) extraction: the extraction concentrate is cooled and extracted with 1 times the amount of ethyl acetate for 3 times to obtain ethyl acetate solution; (The solution is layered quickly)(6) concentration: the ethyl acetate extract is refluxed under reduced pressure and concentrated to 10: 1 to obtain a concentrated solution;(7) purification: the concentrated solution is treated with 40% methanol Dissolution, Suction filtration, filtrate 24H, Suction filtration to obtain crystalline, atmospheric pressure or vacuum drying of phlorizin. (Yellow powder) activated carbon is used to decolorize the crude product. The reason why activated carbon is selected is because its decolorization principle is physical adsorption, which will not cause harm to the biological activity of phlorizin. The activated carbon was dried in a vacuum drying cabinet. The activated carbon was then added to the aqueous crude product solution, stirred, and filtered to obtain a clear liquid. Natural crystals were placed, and finally white needle-like crystals appeared. Fig.1 extraction process of phlorizin |
| synthesis method | The precursor substance for synthesis of Phlorizin is malonyl-CoA (Malonyl-CoA) and p-coumaroyl-CoA (p-coumaroyl-CoA). First, p-coumaroyl-CoA generates 4-hydrogenated cinnamoyl-CoA via the NADPH pathway; Then, malonyl-CoA and 4-hydrocinnamyl-CoA produce Phloretin under the action of theastone synthase; Finally, Phloretin is glycosylated to Phloretin. (2015-12-02) |
| biological activity | 1. Hypoglycemic effect diabetes is a major disease threatening human health, and the typical symptom of diabetes is hyperglycemia. At present, the main drugs for the treatment of diabetes are traditional sulfonylureas, Biguanides and some new hypoglycemic drugs such as rosiglitazone, pioglitazone and so on. Its mechanism of action is mostly to promote the secretion of insulin or increase the sensitivity of insulin. A large number of studies have shown that phlorizin has the effect of reducing fasting blood glucose. The mechanism of phlorizin lowering blood glucose is that it competitively inhibits the transport of glucose molecules by glucose transporters (SGLTs and GLUTs). 2. Antioxidant effect phlorizin has obvious protective effect on the oxidative damage of Drosophila melanogaster caused by high fat diet, and can significantly prolong the life span of Drosophila melanogaster by enhancing the activity of SOD and CAT. The physiological correlation between phlorizin and plant is closely related to the physiological phenomena of plant growth, development and stress resistance. It can resist a variety of pathogenic bacteria, such as apple scab, fire blight and so on. However, it has an inhibitory effect on the growth of some plants. Low concentration of phlorizin can promote the growth of Malus hupehensis seedlings, but the high concentration will cause the continuous cropping obstacles. Phlorizin can promote the regeneration of papaya embryo, especially the root growth. Therefore, when it is used as a plant growth regulator, its dosage is an important consideration. Other active phlorizin in addition to hypoglycemic, antioxidant and other biological activities, its anti-inflammatory, anti-cancer and other effects. |
| Application | phlorizin can reduce blood sugar, with anti-tumor, anti-allergic, antioxidant activity, beauty and health care products industry have potential use value. Food phlorizin has been approved as a food additive. It is the characteristic phenolic compounds in Apple, due to the type, origin and other issues, the content of phlorizin in different apples is different, therefore, its content can be used as an indicator to distinguish the origin and quality of apple juice. Phlorizin can promote the absorption and utilization of genistein (genistein, genistein, inhibit the growth and metastasis of tumor cells), the development of functional foods rich in phlorizin and genistein has broad market prospects in cancer prevention and treatment. It is a very high degree of sweetness of natural sweeteners, can be used as a Sugar Sugar substitute food for diabetics. The product produced by the oxidation of polyphenol oxidase can be converted into a bright yellow dye, which has strong water solubility and can be used in the food processing industry to replace artificial dyes and avoid the toxic effect of artificial synthetic pigments. It has potential application value both as a food additive and functional food development and utilization. 2. Medicine because Phlorizin is easily hydrolyzed in the human body to produce phloretin, and the absorption rate of phlorizin in the small intestine is low, phlorizin and other compounds are often designed as high molecular polymers for drug development. The antioxidant activity and anti-aging function of cosmetics phlorizin have been confirmed by modern scientific research. Phloretin, a hydrolysis product of phlorizin, can competitively inhibit tyrosinase activity and interfere with melanin synthesis, and its whitening effect is superior to many whitening products on the market. However, it should be noted that phlorizin increases the expression of tyrosinase gene by activating cAMP signaling pathway, which leads to the production of melanin. |
Last Update：2024-04-09 19:05:13
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Mobile: 86+15671228036
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Product Name: Phlorizin Visit Supplier Webpage Request for quotationCAS: 60-81-1
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