Neosperidin dihydrochalcone CAS#: 20702-77-6; 凯望编码 (ChemWhat Code): 96296
Identification
| 英文名 | Neosperidin dihydrochalcone |
| IUPAC Name | 1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one |
| 分子结构 |  |
| CAS编号 | 20702-77-6 |
| EINECS Number | 243-978-6 |
| MDL Number | MFCD00017711 |
| Beilstein Registry Number | 105692 |
| 别名 | neohesperidinneohesperidin dihydrochalconeNHDCneohesperidine dihydrochalconeneosperidin dihydrochalcone |
| 分子式 | C28H36O15 |
| 分子量 | 612.581 |
| InChI | InChI=1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1 |
| InChI Key | ITVGXXMINPYUHD-CUVHLRMHSA-N |
| Canonical SMILES | COc1ccc(CCC(=O)c2c(O)cc(O[C@@H]3OC@HC@@HC@H[C@H]3O[C@@H]3OC@@HC@HC@@H[C@H]3O)cc2 |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| WO2018/200663 | SWEETNESS AND TASTE IMPROVEMENT OF STEVIOL GLYCOSIDE AND MOGROSIDE SWEETENERS WITH DIHYDROCHALCONES | 2018 |
| EP299533 | High potency sweetening agents | 1989 |
Physical Data
| Appearance | White to Yellowish Powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Description (Association (MCS)) | Solvent (Association (MCS)) | Temperature (Association (MCS)), °C | Partner (Association (MCS)) |
| Association with compound | aq. phosphate buffer | 24.84 | bovine serum albumin |
| Stability constant of the complex with … | 41.9 | β-cyclodextrin | |
| NMR spectrum of the complex | D2O | 25 | β-cyclodextrin |
| Further physical properties of the complex | β-cyclodextrin |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | CD3OD | 400 | |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | ||
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 25 | |
| Chemical shifts | 1H | D2O |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands, Spectrum | ||
| Spectrum | solid | 3800 – 2300 cm**(-1) |
| Description (Mass Spectrometry) |
| CID (collision-induced dissociation), spectrum |
| time-of-flight mass spectra (TOFMS), liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), fragmentation pattern, spectrum |
| tandem mass spectrometry, liquid chromatography mass spectrometry (LCMS), time-of-flight mass spectra (TOFMS), electrospray ionisation (ESI), spectrum |
| liquid chromatography mass spectrometry (LCMS), time-of-flight mass spectra (TOFMS), high resolution mass spectrometry (HRMS), spectrum |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm |
| Spectrum | aq. phosphate buffer | 228, 288 |
| 228, 288 |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: neohesperidin With water; sodium hydroxide at 50℃; for 5h; Stage #2: With hydrogenchloride; 10% Pd/C; ammonium formate In water at 70℃; for 10h; pH=6 – 7; Reagent/catalyst; Temperature; pH-value; | 97% |
| Multi-step reaction with 4 steps 1: orthoformic acid triethyl ester; indium(III) chloride / 3 h / 70 °C / Industrial scale 2: sodium hydroxide; water / Industrial scale 3: platinum on carbon / 5 h / 50 °C / 15001.5 Torr / Industrial scale 4: hydrogenchloride / water / pH 6 / Industrial scale | |
| Multi-step reaction with 4 steps 1: trimethyl orthoformate; decaborane / 6 h / 65 °C / Industrial scale 2: sodium carbonate; water / Industrial scale 3: hydrogen / 20 h / 35 °C / 3750.38 Torr / Industrial scale 4: citric acid / pH 7 / Industrial scale | |
| With sodium hydroxide | |
| Stage #1: neohesperidin With sodium hydroxide Stage #2: With Pd/C; hydrogen at 20℃; under 760.051 Torr; |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 612.585 |
| logP | 0.338 |
| HBA | 10 |
| HBD | 9 |
| Matching Lipinski Rules | 2 |
| Veber rules component | |
| Polar Surface Area (PSA) | 245.29 |
| Rotatable Bond (RotB) | 10 |
| Matching Veber Rules | 1 |
| Use Pattern |
| NHDC is a natural sweetener and flavoring extracted from citrus fruit and modified by hydrogenation. It is a dihydrochalcone derivative of the flavonoid family. |
| Food Industry High-intensity sweetener: Approximately 1500–1800 times sweeter than sucrose, significantly reducing sugar usage. Flavor Modifier: Masks bitterness in foods, beverages, and pharmaceuticals (especially caffeine, citric acid, quinine, and certain medications). Enhancer: Enhances flavors such as citrus, mint, and strawberry. Common Applications: Sugar-free chewing gum, carbonated beverages, juice drinks, dairy products, desserts, and functional foods. |
| Health Products and Pharmaceuticals Auxiliary Taste Masking: Added to some traditional Chinese medicine preparations or health supplements with a pronounced bitterness to improve taste and enhance compliance. Potential antioxidant and anti-inflammatory effects (still under research). |
| Feed Additive: Improves feed palatability and masks bitter or unpleasant flavors. Used in aquatic feed and livestock feed to boost feed intake. |
| Cosmetics and Oral Care Used as a flavoring and bitter-masking agent in toothpaste and mouthwash to improve taste. Combined with sweeteners, it enhances the long-lasting sweetness experience. |
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认证生产商 | |
| Ulcho Biochemical Ltd | http://www.ulcho.com/ |
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