1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy
Naringin dihydrochalcone
CAS: 18916-17-1
Molecular Formula: C27H34O14
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Names and Identifiers
| Name | Naringin dihydrochalcone |
| Synonyms | Naringin DC Senior saccharin NARINGINDIHYDROHALCONE NAGINGINDIHYDROCHALCONE Naringin dihydrochalcone NARINGIN DIHYDROCHALCONE NARINGIN DIHYDOROCHALCONE 2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)- 1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-L-glucopyranoside 1-[4-[[2-O-(6-Deoxy-L-mannopyranosyl)-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone 1-[4-[[2-o-(6-deoxy-l-mannopyranosyl)-d-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone |
| CAS | 18916-17-1 |
| InChI | InChI=1/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m0/s1 |
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Physico-chemical Properties
| Molecular Formula | C27H34O14 |
| Molar Mass | 582.56 |
| Density | 1.63±0.1 g/cm3(Predicted) |
| Melting Point | 131-132°C |
| Boling Point | 916.8±65.0 °C(Predicted) |
| Flash Point | 302.7°C |
| JECFA Number | 2208 |
| Solubility | DMSO : ≥ 100 mg/mL (171.66 mM) |
| Vapor Presure | 0Pa at 20-50℃ |
| Appearance | White to off-white (Solid) |
| Color | White to Off-white |
| pKa | 6.85±0.40(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 1.696 |
| MDL | MFCD08436145 |
| Physical and Chemical Properties | From fructus aurantii immaturus |
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Risk and Safety
| HS Code | 29329990 |
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Reference
| Reference Show more | 1. [IF=3.638] Yunfeng Pu et al."Effect of harvest, drying and storage on the bitterness, moisture, sugars, free amino acids and phenolic compounds of jujube fruit (Zizyphus jujuba cv. Junzao)."J Sci Food Agr. 2018 Jan;98(2):628-634 2. [IF=10.182] Yucong Zou et al."Highly efficient bioconversion of flavonoid glycosides from citrus-processing wastes in solvent-buffer systems."Green Chem. 2020 May;22(10):3196-3207 |
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Nature
Open Data Verified Data
There are many kinds of dihydrochalcone, such as naringin chalcone, neohesperidin dihydrochalcone, and rhamnoside dihydrochalcone. Pomelo peel dihydrochalcone is white needle-like crystals, the relative density (d:5) is 0.8104, the melting point is 166~168 ℃, no hygroscopicity, slightly soluble in water. New Orange Peel dihydrochalcone is white needle-like crystal or powder, the relative density is 0.8075, the melting point is 152~154 ℃. Slightly soluble in water, 25 C saturated aqueous solution pH 6.25. A common feature of the structure of dihydrochalcone is that it has phenolic hydroxyl groups, so they are more soluble in aqueous alkali solutions. Dihydrochalcone has a strong fruit-like sweet taste, the sweetness range is 100~2000, the sweetness of the most sweet dihydrochalcone is 2000 times that of sucrose, and the sweet taste is fresh, the duration is long, can reduce the sensitivity of the human body to the odor in beverages or pharmaceuticals.
Last Update：2024-01-02 23:10:35
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Preparation Method
Open Data Verified Data
There are many kinds of dihydrochalcone, and the preparation method is illustrated by taking naringin dihydrochalcone as an example. The grapefruit peel was thoroughly mixed with a small amount of 50% cold methanol solution and filtered, and the filtrate was left in a refrigerator for several days to complete crystallization. The crystals were then dissolved in water for recrystallization. The recrystallized naringin crystals are dissolved in 10% cold potassium hydroxide solution, and then 10% palladium-hydrocarbon catalyst is added to continuously oscillate at room temperature and 20 7 kPa hydrogen pressure, until the hydrogenation reaction was stopped. The catalyst was filtered off, the filtrate was placed in a water bath, acidified with concentrated hydrochloric acid, and then placed in a refrigerator to complete crystallization. The naringin dihydrochalcone crystals were collected, washed with water, recrystallized in water, filtered and dried under vacuum to obtain crystals (melting point 1 70 ° C.). If recrystallization is carried out in acetone, crystals of another crystal form (melting point 2 1 2 C) can be obtained.
Last Update：2022-01-01 11:13:49
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Use
Open Data Verified Data
It is used as a sweetener in food and medicine.
Last Update：2022-01-01 11:13:49
1-Propanone,1-[4-[[2-O-(6-deoxy-α-L-mannopy - Reference Information
| Plant source: | Fructus Aurantii Immaturus |
| FEMA | 4495 | NARINGIN DIHYDROCHALCONE |
| LogP | -0.703-1.01 at 22.6℃ and pH5-9 |
| introduction | as a new type of sweetener, grapefruit dihydrochalone is 500-700 times as sweet as sucrose, and has the characteristics of high sweetness, low calorific value, non-toxicity and safety, which can be applied to food, medicine and daily chemical industries. And because of its fresh taste, long-lasting aftertaste, and with a special fragrance, has an excellent effect of shielding bitter taste, naringenin dihydrochalone is especially suitable for dairy products, fats and oils, frozen foods, processed vegetables, jelly, Jam, alcohol-free beverages, chewing gum, toothpaste and oral medicine tablets. As a substitute for sugar, grapefruit dihydrochalone can also reduce the body's intake of sugar, which is undoubtedly a good news for patients who are obese and unsuitable for sugar. |
| overview | naringin is a natural and cheap flavanone glucoprum, which can be extracted from citrus pericarp, especially from grape sleeve. The content of pomelo peel in pomelo peel is about one, and pomelo peel accounts for more than the quality of the entire cypress. China is also a big country producing pomelo peel, so the use of naringin to synthesize dihydrochalcone has broad prospects. picture: naringin |
| synthesis | naringin is used as raw material to synthesize naringin dihydrochalone: the sweetness of naringin dihydrochalone is 100 times that of sucrose, and its structural formula R is hydrocarbon group, R' is hydrogen, R'' is new orange peel sugar group. Since the number of methoxy and hydrocarbyl groups on the ring directly affects the degree of sweetness of the compound, the sweetness of grapefruit side dihydrochalcone is relatively low. Naringin is first treated with alkali, and the concentration of alkali is generally 10%-25%. In order to ensure that all the meridians in the raw material can be neutralized by alkali, the molar ratio of alkali to flavanone is 3-4, U.S. Patent 2700047, which reports in more detail the effect of the amount of flavanone and alkali on the ring opening of chalcone, and points out that the molar ratio of alkali to flavanone can be completely converted into chalcone. picture: the synthetic route of naringone dihydrochalone there have been patent reports on the synthesis of naringone dihydrochalone abroad. The patented 4087588 uses a one-step method to synthesize naringin dihydrochalone, the specific steps are to dissolve 5g of naringin in 25Ml 10% sodium hydroxide, the catalyst is palladium carbon, and hydrogenation at room temperature and pressure. After the reaction, the catalyst is removed, and then the catalyst-free liquid is removed from the solution through an ion exchange column, and the white naringin dihydrochalone crystal is evaporated to obtain a melting point of 169-170 ℃. The specific method of naringin dihydrochalcone synthesis introduced in the patent 308782 is a two-step method. The first step is to dissolve 2g naringin in a solution of 40Ml 25%, add concentrated hydrochloric acid to cool, and precipitate bright yellow gelatinous chalcone. After vacuum drying, recrystallize with boiling water to obtain the intermediate product chalcone with a melting point of 201-202 ℃. In the second step, naringin chalcone is dissolved in 80mL of ethanol and hydrogenated at normal temperature and pressure. The catalyst is palladium and carbon. Finally, the vacuum dried product is recrystallized twice with water as a solvent to obtain needle-like white naringin dihydrochalcone crystals with a melting point of 168-169 ℃. |
| application | application in pharmaceutical industry: dihydrochalcone compounds have a variety of physiological and pharmacological activities. by studying their structure-activity relationship and modifying them, new drugs with important value can be developed. Studies have found that dihydrochalcone compounds have a certain effect on the treatment of diabetes. In addition, dihydrochalcone compounds have an antioxidant pharmacophore, 2,6 dihydroxyacetophenone structure, which is achieved by eliminating peroxides and scavenging hydroxyl radicals. Application of food industry: Dihydrochalcone is one of the most attractive and mature natural sweeteners. According to research, the young fruits and pericarps of citrus in the aromatic family contain dihydroflavonoids, which have no sweet taste, but they can be converted into dihydrochalcone glycosides under appropriate conditions. The sweetness is higher than that of commonly used sweeteners such as saccharin, cyclamate or aspartame, which is usually equivalent to 1000 times the sweetness of sucrose 100 and 35 times that of saccharin. Dihydrochalcone sweeteners have a refreshing taste, a long-lasting aftertaste, and have an excellent effect of shielding withering. At present, the new orange peel camp has been widely used as a sweetener or flavoring agent in the food industry. When used alone as an artificial sweetener, the added concentration is 15-20 mg, and when used in combination with other sweeteners, especially when combined with saccharin, it can produce excellent synergistic effect. In addition, dihydrochalcone sweeteners can also be used in alcoholic and non-alcoholic beverages, appetizers, tomato sauce and mayonnaise. |
| references | [1] Tang dongmei. extraction and purification of limonin and naringin from fragrant pomelo and synthesis of dihydrochalcone [D]. central south university, 2011. [2] ouyang zhenyu. extraction of some effective components from pomelo peel and synthesis of dihydrochalcone [d]. Nanchang university, 2008. |
| Production method | There are many types of dihydrochalcone. Now take naringin dihydrochalcone as an example to illustrate the preparation method. The grapefruit peel is fully mixed with a small amount of 50% cold methanol solution and filtered. The filtrate is placed in the refrigerator for several days to make it crystallize completely. The crystals are then dissolved in water for recrystallization. The recrystallized naringin crystals are dissolved in a 10% cold potassium hydroxide solution, and then a 105 palladium-hydrocarbon catalyst is added, and it continues to oscillate at room temperature and a hydrogen pressure of 207KPa until the hydrogenation reaction stops. Filter the catalyst, place the filtrate in a water bath, acidify it with concentrated hydrochloric acid, and then place it in the refrigerator to crystallize completely. Collect naringin dihydrochalone crystals, recrystallize them in water after washing, filter, and dry them in vacuum to obtain crystals (melting point 170 ℃). If recrystallization is carried out in acetone, another crystal form (melting point 212°C) can be obtained. |
Last Update：2024-04-09 18:58:34
Supplier List
Spot supply
Product Name: Naringin dihydrochalcone Request for quotationCAS: 18916-17-1
Tel: +86-18162425036
Email: 3866263148@qq.com
Mobile: 18162425036
QQ: 3866263148
Wechat: 18162425036
Multiple Specifications
Product Name: Neohesperidin-dihydrochalcone Impurity 4 (Neohesperidin-dihydrochalcone EP Impurity D)(Naringin Dihydrochalcone) Request for quotationCAS: 18916-17-1
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Naringin dihydrochalcone Visit Supplier Webpage Request for quotationCAS: 18916-17-1
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Naringin dihydrochalcone Request for quotationCAS: 18916-17-1
Tel: +86-18162425036
Email: 3866263148@qq.com
Mobile: 18162425036
QQ: 3866263148
Wechat: 18162425036
Multiple Specifications
Product Name: Neohesperidin-dihydrochalcone Impurity 4 (Neohesperidin-dihydrochalcone EP Impurity D)(Naringin Dihydrochalcone) Request for quotationCAS: 18916-17-1
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Naringin dihydrochalcone Visit Supplier Webpage Request for quotationCAS: 18916-17-1
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History