5471-51-2
4-(4-hydroxyphenyl)-2-butanone
CAS: 5471-51-2
Molecular Formula: C10H12O2
5471-51-2 - Names and Identifiers
| Name | 4-(4-hydroxyphenyl)-2-butanone |
| Synonyms | RASBERRY KETONE Raspberry keton Raspberry Ketone RASPBERRY KETONE 4-Hydroxybenzylacetone Dobutamine EP Impurity B Raspberry ketone natural Raspberry ketone synthetic 4-p-Hydroxylphenyl)-2-butone Natural Raspberry Ketone 4-(4-hydroxyphenyl)butan-2-one 4-(4-hydroxyphenyl)-2-butanone 2-(4-Hydroxyphenyl)ethyl methyl ketone 4-(4-Hydroxyphenyl)-2-butanone 5471-51-2 |
| CAS | 5471-51-2 |
| EINECS | 226-806-4 |
| InChI | InChI=1/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3 |
| InChIKey | NJGBTKGETPDVIK-UHFFFAOYSA-N |
5471-51-2 - Physico-chemical Properties
| Molecular Formula | C10H12O2 |
| Molar Mass | 164.2 |
| Density | 1.0326 (rough estimate) |
| Melting Point | 81-85 °C (lit.) |
| Boling Point | 200°C |
| Flash Point | 122.9°C |
| JECFA Number | 728 |
| Water Solubility | Insoluble in water. |
| Solubility | Insoluble in water and petroleum, soluble in ethanol, ether and volatile oils. |
| Vapor Presure | 40Pa at 25℃ |
| Appearance | White powder |
| Color | Clear colorless |
| BRN | 776080 |
| pKa | 9.99±0.15(Predicted) |
| Storage Condition | under inert gas (argon) |
| Refractive Index | 1.5250 (estimate) |
| MDL | MFCD00002394 |
| Physical and Chemical Properties | White needle-like crystalline or granular solid. Raspberry aroma and fruit sweet taste. The melting point was 82-83 °c. Insoluble in water and petroleum, soluble in ethanol, ether and volatile oil. Natural products are present in raspberry (raspberry) and the like. |
| Use | For the preparation of food spices, with flavor and sweetening effect, can also be used in cosmetics and soap flavor |
5471-51-2 - Risk and Safety
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | EL8925000 |
| TSCA | Yes |
| HS Code | 29145011 |
| Hazard Note | Irritant |
5471-51-2 - Upstream Downstream Industry
| Raw Materials | Acetone 4-Hydroxybenzaldehyde Ethyl Alcohol |
5471-51-2 - Reference
| Reference Show more | 1. Yan Xihuan, Liu Fang, Yang Meixia, et al. Changes of raspberry ketone content in raspberry fruit and its regulation by methyl jasmonate [J]. Journal of Beijing Agricultural College, 2020, 035(003):1-7. 2. Ma Jianyong, Li, Li, Li, Chunmei. Analysis of nutritional components of raspberry with different maturity and effect of pectinase on juice yield of raspberry [J]. Science and Technology of food industry 2017 38(006):213-216. 3. Kuanhui, Feng Jianwen, Fan Qian, etc. Component Analysis and anti-lipid peroxidation activity of red raspberry polyphenols in vitro [J]. Food Science, 2018, 39(003):83-89. |
5471-51-2 - Reference Information
| update date: | 2022/11/12 10:05:38 |
| FEMA | 2588 | 4-(P-HYDROXYPHENYL)-2-BUTANONE |
| LogP | 0.935-1.33 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | raspberry ketone (also known as raspberry ketone) exists in natural raspberry juice with a content of about (0.1~0.2) × 10-6. it is an important fragrance component of potted essential oil and a kind of fragrance with elegant fruit aroma widely used at home and abroad. its chemical name is 4-p-hydroxyphenyl -2-butanone, it is a shiny granular or needle-like white crystal with a melting point of 83 ℃ and a boiling point of 161 ℃( 0.67 kPa). It is soluble in alcohols and oils and almost insoluble in water. Raspberry ketone has great economic value and has received extensive attention in recent years, and the demand has also increased year by year. |
| application | raspberry ketone is not only used in large quantities to prepare edible essence and daily essence, but also used in synthetic manufacturing of medicines, stimulants, cosmetics, cigarettes, dyes, etc. in addition, raspberry ketone and its acetyl compounds are fruit fly sex attractants and can be synthesized and used as pesticides. At the same time, because the molecular structure of raspberry ketone contains aromatic rings, hydroxyl groups and ketone groups, it has special chemical activity and is also an important fine chemical intermediate. With the further development of the spice industry and the organic synthesis industry, the research value of raspberry ketone has also increased steadily. In addition to being used as a spice, it has also been widely used in other fields. |
| Preparation | 1) Using p-hydroxybenzaldehyde and acetone as raw materials under base catalysis by Claisen -Schmidt condensation, 4-p-hydroxyphenyl-3-butene-2-one (yield 88.4%) was synthesized by orthogonal test optimization process, and raspberry ketone (yield 84.0%) was synthesized by hydrogenation under palladium-carbon catalysis; using NaOH solution as Claisen -Schmidt condensation catalyst, p-hydroxyphenyl -3-butene-2-one was synthesized. Then 5% Pd /C and nickel formate were used as catalysts for the second reaction, and the yields of raspberry ketone were 72.55% and 65.7%, respectively. The condensation reaction conditions of p-hydroxybenzaldehyde and acetone were studied by orthogonal test, and the preferred process conditions were obtained as follows: the molar ratio of material n (p-hydroxybenzaldehyde) ∶n (acetone) ∶n( NaOH) = 1.0 ∶ 25 ∶ 25 (reaction at 30 ℃ for 5 h), and raspberry ketone (yield 61.8%) was obtained by conventional hydrogenation reduction, vacuum distillation and mixed solvent recrystallization. Using p-hydroxybenzaldehyde and acetone as raw materials, claisen-Schmid condensation reaction was catalyzed by NaOH, and then raspberry ketone was prepared by hydrogenation reduction with nickel formate as catalyst and isopropanol as solvent (yield 42.0%). |
| use | GB 2760-96 specifies edible spices that are allowed to be used. Mainly used to prepare raspberry, grape, strawberry and other flavors. It is used to prepare food spices, which has the effect of enhancing fragrance and sweetening. It can also be used in cosmetics and soap flavors. Raspberry ketone is a food spice allowed by my country's "Health Standards for the Use of Food Additives". It is mostly used to prepare pineapple, peach, strawberry, plum and other fruit flavors. The amount used in chewing gum is 40~320 mg/kg; 54 mg/kg in baked food; 44 mg/kg in candy; 34 mg/kg in cold drinks; 16 mg/kg in soft drinks; 5.0~50 mg/kg in pudding. It is widely used in edible flavors such as strawberries, Rubus, pineapples, peaches, etc. It is usually used as a fixative in fruit-flavour flavors. It can be used in jasmine, mast flower, tuberose and other formulas in daily chemical essence. As a modifier, it is used in jasmine, gardenia, tuberose and other floral daily flavors. It is mostly used in edible flavors such as strawberries, pineapples, peaches, plums, and hanging fish. Uses: As a modifier, it is used in jasmine, tuberose and other daily spices, and is mostly used in strawberries, pineapples, peaches, plums and other spices in edible spices. Used in medicine as Rankdoxamine intermediates, etc. Telephone 15827146163 |
| production method | hydrogenation route: first add 3.5mol 15% of sodium hydroxide to the reactor, add a mixture of 2mol of acetone and 1mol of p-hydroxybenzaldehyde dropwise under stirring, control the temperature at 20~30 ℃, continue stirring for 20h after dropping. Filter to obtain the solid sodium salt of 4-p-hydroxyphenylbutene-3-keto-2, add water to dissolve, and then acidify with hydrochloric acid to precipitate 4-p-hydroxyphenylbutene-3-keto-2, filter and dry for use. 100g of the intermediate and 5g of nickel catalyst were added into the autoclave, the air was replaced by hydrogen, and then heated to 120~140 ℃, and reacted at 0.98MPa for 1.5h. After cooling, the catalyst was filtered, the raspberry ketone content was 89%, and the hydrogenation yield was 92%. Distill the crude product under reduced pressure once, recrystallize for 1~2 times to obtain white crystals with a melting point of 82 ℃. In the phenol route, 94g of phenol and a proper amount of 85% phosphoric acid mixed catalyst are added into the reactor, 70g of methyl vinyl ketone is added dropwise within 40min, the temperature is kept at 15~20 ℃, and then stirred for 4h after adding. After the reaction is over, the reactants are washed with water until neutral, 63g of phenol is recovered by distillation under reduced pressure to obtain 25g of product with a melting point of 81.5~82.5 ℃ and an yield of 80%. It is formed by condensation of p-hydroxybenzaldehyde and acetone and hydrogenation. It is formed by condensation of butanoic acid and phenol. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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