1-(2,6-dihydroxy-4-methoxyphenyl)ethanone
Phloretin
CAS: 60-82-2
Molecular Formula: C15H14O5
1-(2,6-dihydroxy-4-methoxyphenyl)ethanone - Names and Identifiers
| Name | Phloretin |
| Synonyms | Floretin Phloretin PHLORETIN(RG) Dihydronaringenin 1-(2,6-dihydroxy-4-methoxyphenyl)ethanone 1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6- β-(4-hydroxyphenyl)-2,4,6-trihydroxypropiophenone 2,4,6-Trihydroxy-B-(4-Hydroxyphenyl)Propiophenone 2',4',6'-TRIHYDROXY-3-(4-HYDROXYPHENYL)PROPIOPHENONE 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone |
| CAS | 60-82-2 |
| EINECS | 200-488-7 |
| InChI | InChI=1/C9H10O4/c1-5(10)9-7(11)3-6(13-2)4-8(9)12/h3-4,11-12H,1-2H3 |
| InChIKey | VGEREEWJJVICBM-UHFFFAOYSA-N |
1-(2,6-dihydroxy-4-methoxyphenyl)ethanone - Physico-chemical Properties
| Molecular Formula | C15H14O5 |
| Molar Mass | 274.27 |
| Density | 1.1827 (rough estimate) |
| Melting Point | ~260 °C |
| Boling Point | 337.26°C (rough estimate) |
| Flash Point | 146.3°C |
| JECFA Number | 2022 |
| Water Solubility | soluble |
| Solubility | Soluble in methanol, ethanol and acetone, almost insoluble in water. |
| Vapor Presure | 1.4E-05mmHg at 25°C |
| Appearance | Pale red powder |
| Color | White to beige |
| Merck | 14,7326 |
| BRN | 1887240 |
| pKa | 7.16±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to heat and light |
| Refractive Index | 1.573-1.575 |
| MDL | MFCD00002288 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from Apple, pear and other fruit peel and root bark. |
| Use | Used as pharmaceutical, cosmetic additives, food additives, etc |
| In vitro study | Phloretin is a dihydrochalcone found in the bark of pears (Western pear), apples, cherries and other fruits. Phloretin inhibits the active transport of glucose into cells through SGLT1 and SGLT2, although the inhibitory effect is weaker than that of its carbohydrate ligand phlorizin. Oral Phlorizin is completely converted to phloretin by hydrolases in the small intestine. An important role of this process is the inhibition of glucose absorption by the small intestine and the inhibition of renal glucose reabsorption. Phloretin also inhibits various urea transporters. When combined with a high-protein diet, it causes a decrease in urea and has a diuretic effect. |
1-(2,6-dihydroxy-4-methoxyphenyl)ethanone - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S37/39 - Wear suitable gloves and eye/face protection 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 |
| FLUKA BRAND F CODES | 3-10 |
| HS Code | 29145090 |
| Hazard Class | IRRITANT |
1-(2,6-dihydroxy-4-methoxyphenyl)ethanone - Reference
| Reference Show more | 1. Zhang Guowen, Song Xin, Zeng Yu. Effect of phloretin on the activity and conformation of tyrosinase [J]. Journal of Nanchang University: Natural Science Edition, 2018(6):557-562. 2. Ran Yu, Guo Yanli, Wang Lifeng, etc. Transport mechanism of hannomaloside in MDCK monolayer cell model [J]. Chinese Journal of Experimental prescriptions, 2019, 25 (15):155-160. 3. Zheng Yan, Zhang Chunling, Liu Hui, et al. Determination of phenolic compounds in kiwifruit juice by UPLC [J]. Journal of Pomology 2018 035(008):1006-1015. 4. Lin, Suyun, et al. "Medical flavons as xanthine oxidase inhibitors: Structure-affinity and structure-activity relationships." Journal of agricultural and food chemistry 63.35 (2015): 7784-7794. 5. Xing-Yan, L. I. U., et al. "Identification of active compound combination contributing to anti-inflammatory activity of Xiao-Cheng-Qi Decoction via human intestinal bacterial metabolism." Chinese journal of natural medicines 16.7 (2018): 513-524.https://do 6. Pei Pu, Xin Zheng, Linna Jiao, Lang Chen, Han Yang, Yonghong Zhang, Guizhao Liang Six flavonoids inhibit the antigenicity of β-lactoglobulin by noncovalent interactions: A spectroscopic and molecular docking study, Food Chemistry, Volume 339, 2021, 128106 7. Tiantian Tang, Xinfang Xie, Xue Ren, Wenjun Wang, Xuanming Tang, Jie Zhang, Zhidong Wang, A difference of enzymatic browning unrelated to PPO from physiology targeted metabolomics and gene expression analysis in Fuji apples, Postharvest Biology and Techno 8. [IF=6.953] Lin Han et al."Inhibitory effect of phloretin on α-glucosidase: Kinetics, interaction mechanism and molecular docking."Int J Biol Macromol. 2017 Feb;95:520 9. [IF=6.529] Xing-Yan Liu et al."The activity of Hou-Po-Da-Huang-Tang is improved through intestinal bacterial metabolism and Hou-Po-Da-Huang-Tang selectively stimulate the growth of intestinal bacteria associated with health."Biomed Pharmacother. 2017 Oct;94:794 10. [IF=5.279] Suyun Lin et al."Dietary Flavonoids as Xanthine Oxidase Inhibitors: Structure-Affinity and Structure-Activity Relationships."J Agr Food Chem. 2015;63(35):7784-7794 11. [IF=4.729] Kun Zhou et al."Genome-wide identification of glycosyltransferases converting phloretin to phloridzin in Malus species."Plant Sci. 2017 Dec;265:131 12. [IF=3.571] Qing Yang et al."Activation of Nrf2 by Phloretin Attenuates Palmitic Acid-Induced Endothelial Cell Oxidative Stress via AMPK-Dependent Signaling."J Agr Food Chem. 2019;67(1):120-131 13. [IF=3] Xing-Yan LIU et al."Identification of active compound combination contributing to anti-inflammatory activity of Xiao-Cheng-Qi Decoction via human intestinal bacterial metabolism."Chin J Nat Medicines. 2018 Jul;16:513 14. [IF=7.514] Pei Pu et al."Six flavonoids inhibit the antigenicity of β-lactoglobulin by noncovalent interactions: A spectroscopic and molecular docking study."Food Chem. 2021 Mar;339:128106 15. [IF=7.514] Jing Zhao et al."A sensitive and practical ELISA for analyzing naringenin in pummelo and herb samples."Food Chem. 2021 Nov;362:130223 16. [IF=7.514] Hongcai Li et al."Study on the nutritional characteristics and antioxidant activity of dealcoholized sequentially fermented apple juice with Saccharomyces cerevisiae and Lactobacillus plantarum fermentation."Food Chem. 2021 Nov;363:130351 17. [IF=5.81] Mu Jianfei et al."Determination of Polyphenols in Ilex kudingcha and Insect Tea (Leaves Altered by Animals) by Ultra-high-performance Liquid Chromatography-Triple Quadrupole Mass Spectrometry (UHPLC-QqQ-MS) and Comparison of Their Anti-Aging Effects."Fro 18. [IF=5.64] Zhang Yuxiang et al."Structure-Dependent Inhibition of Stenotrophomonas maltophilia by Polyphenol and Its Impact on Cell Membrane."Front Microbiol. 2019 Nov;0:2646 19. [IF=5.537] Tiantian Tang et al."A difference of enzymatic browning unrelated to PPO from physiology, targeted metabolomics and gene expression analysis in Fuji apples."Postharvest Biol Tec. 2020 Dec;170:111323 20. [IF=4.952] Si Tan et al."The effects of drying methods on chemical profiles and antioxidant activities of two cultivars of Psidium guajava fruits."Lwt Food Sci Technol. 2020 Jan;118:108723 21. [IF=4.24] Mengzhen Han et al."Effect of mixed Lactobacillus on the physicochemical properties of cloudy apple juice with the addition of polyphenols-concentrated solution."Food Biosci. 2021 Jun;41:101049 22. [IF=4.171] Lin Han et al."Activation of AMPK/Sirt3 pathway by phloretin reduces mitochondrial ROS in vascular endothelium by increasing the activity of MnSOD via deacetylation."Food Funct. 2020 Apr;11(4):3073-3083 23. [IF=2.391] Tan Si et al."Effects of three drying methods on polyphenol composition and antioxidant activities of Litchi chinensis Sonn.."Food Sci Biotechnol. 2020 Mar;29(3):351-358 24. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 25. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
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