5471-51-2 Usage
Chemical properties
It appears as white needle crystal or granular solid, exhibiting raspberry aroma and fruit aroma. The melting point temperature is 82~83 °C. It is insoluble in water and oil, being soluble in alcohol, ether and volatile oil.
The natural products exist in raspberry (raspberry) and so on.
Uses
Different sources of media describe the Uses of 5471-51-2 differently. You can refer to the following data:
1. 1. Raspberry Ketone is used in the preparation of food spices with sweetening effect, can also be used for cosmetics and soap flavor. 2. Raspberry Ketone is widely used in strawberry, raspberry, pineapple, peaches and other food flavors, usually used as a fixing agent in the fruity flavor. In daily flavor, it can be used in formulations such as jasmine, gardenia flowers and tuberose. As a modifier, it can be used in jasmine, gardenia, tuberose and other fragrant daily flavor. In food flavors, it is mostly used for strawberries, pineapple, peaches, plums, mayberry and other fragrance. In medicine, it is mostly used as intermediates.
2. 4-(4-Hydroxyphenyl)-2-butanone is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor.
3. The primary aroma compound of red raspberries, used in perfume compositions, shampoos, cosmetics and as a food additive.
Also an impurity in the synthesis of Dobutamine (D494445).
4. Intermediates of Liquid Crystals
Production method
3.5mol 15% sodium hydroxide is first added to the reactor, and 2 mol of acetone and 1mol of p-hydroxybenzaldehyde are added dropwise under stirring. The temperature is controlled between 20 and 30 DEG C, and the stirring reaction is continued for 20 hours. The solid sodium salt of 4-p-hydroxyphenylbutene-3-ketone-2 was obtained after filtering, further dissolved in water, and then acidified with hydrochloric acid to precipitate 4-p-hydroxyphenylbutene-3-ketone-2, further filter and dry for further application.
The autoclave was supplied with 100 g of the intermediate and 5 g of the nickel catalyst, and the atmosphere was replaced with hydrogen. The mixture was heated to 120-140 °C and reacted at a pressure of 0.98 MPa for 1.5 h. After cooling, the catalyst was filtered off, the raspberry ketone content was 89% and the hydrogenation yield was 92%. The crude product above is subject to vacuum distillation once with further recrystallization of 1-2 times getting white crystals with the melting point of 82 ° C.
Phenol route
94g phenol and 85% phosphoric acid mixed catalyst were added into the reactor, 70g methyl vinyl ketone was added dropwise in 40min, the temperature was maintained at 15-20 ℃, and the reaction was stirred for 4h. After completion of the reaction, the reaction mixture was washed with water until neutral, and 63 g of phenol was distilled off under reduced pressure to obtain 25 g of a product having a melting point of 81.5 to 82.5 ° C and a yield of 80%.
It is obtained through the condensation between hydroxybenzaldehyde and acetone and further hydrogenation.
It is obtained through the condensation between the ketone acid and phenol.
Description
4-(p-Hydroxyphenyl)-2-butanone has a sweet, fruity, raspberry
preserves odor. May be prepared by catalytic hydrogenation of phydroxy-benzylidene acetone in the presence of platinum black in
ether or methanol or in the presence of palladium absorbed on
charcoal.
Chemical Properties
Different sources of media describe the Chemical Properties of 5471-51-2 differently. You can refer to the following data:
1. 4-(p-Hydroxyphenyl)-2-butanone has a sweet, fruity, raspberry preserves–type odor.
2. 4-(4-Hydroxyphenyl)-2-butanone is a highly characteristic component of raspberry aroma. It
forms colorless crystals (mp 82–83°C) with a sweet, fruity odor strongly reminiscent
of raspberries.
Raspberry ketone is prepared by alkali-catalyzed condensation of the alkali
salt of 4-hydroxybenzaldehyde and acetone, followed by selective hydrogenation
of the double bond in the resulting 4-hydroxybenzalacetone. Other syntheses
start from phenol, which is converted into 4-(4-hydroxyphenyl)-2-butanone with
methyl vinyl ketone or with 4-hydroxy-2-butanone.
3. white to slightly yellow powder or needles
Occurrence
Reported found European cranberry, raspberry, blackberry, loganberry and sea buckthorn (Hippophae rhamnoides L.).
Definition
ChEBI: A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at position 4 by a hydroxy group. It is found in a variety of fruits including raspberries, blackberries and cranberries, and is used in perfumery and cosmetics.
Taste threshold values
Taste characteristics at 40 ppm: fruity, jamy, berry, raspberry, and blueberry with seedy, cotton candy nuances
Synthesis Reference(s)
The Journal of Organic Chemistry, 41, p. 1206, 1976 DOI: 10.1021/jo00869a026Synthetic Communications, 19, p. 1109, 1989 DOI: 10.1080/00397918908051034
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
Check Digit Verification of cas no
The CAS Registry Mumber 5471-51-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,7 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 5471-51:
(6*5)+(5*4)+(4*7)+(3*1)+(2*5)+(1*1)=92
92 % 10 = 2
So 5471-51-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
5471-51-2Relevant articles and documents
Neurotrophic and anti-neuroinflammatory constituents from the aerial parts of Coriandrum sativum
Cha, Joon Min,Yoon, DaHye,Kim, Sun Yeou,Kim, Chung Sub,Lee, Kang Ro
, (2020)
In the course of our continuing search for biologically active compounds from medicinal sources, we investigated the MeOH extract of the aerial parts of Coriandrum sativum Linn. An extended phytochemical investigation of the aerial parts of C. sativum led to the isolation and identification of seven compounds (1–7) including two new isocoumarin glycosides (1–2) and a new phenolic glycoside (5). The chemical structures of the new compounds (1, 2, and 5) were elucidated by analysis of 1D and 2D NMR (1H and 13C NMR, COSY, HSQC, and HMBC) and HRESIMS data as well as by using chemical methods. All the isolates were evaluated not only for their potential neurotrophic activity by means of induction of nerve growth factor (NGF) in C6 glioma cells but also for production of nitric oxide (NO) levels in lipopolysaccharide (LPS)-activated murine microglia BV-2 cells to assess their anti-neuroinflammatory activity. Compounds 1–3 and 7 were stimulants of NGF release, with levels of NGF stimulated at 127.23 ± 1.89%, 128.22 ± 5.45%, 121.23 ± 6.66%, and 120.94 ± 3.97%, respectively. Furthermore, the aglycones of 1 and 2 (1a and 2a) showed more potent NGF secretion activity and anti-neuroinflammatory effect than did their glycosides (1a: 130.81 ± 5.45% and 2a: 134.44 ± 5.45%).
Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides
Colas, Kilian,Kohlhepp, Stefanie V.,Mendoza, Abraham,V. D. dos Santos, A. Catarina
supporting information, (2022/02/02)
The synthesis of ketones through addition of organometallic reagents to aliphatic carboxylic acids is a straightforward strategy that is limited to organolithium reagents. More desirable Grignard reagents can be activated and controlled with a bulky aniline-derived turbo-Hauser base. This operationally simple procedure allows the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones alike from functionalized alkyl, aryl and heteroaryl Grignard reagents.
Synthetic method of high-purity raspberry ketone
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Paragraph 0043-0049, (2021/11/21)
The invention belongs to the technical field of perfumes and fine chemical engineering. The invention specifically relates to a synthesis method of high-purity raspberry ketone. To the synthesis method, 2 and 6 - di-tert-butyl phenol are used as raw materials, and the butanone or a-hydroxybutanone is subjected to alkylation reaction under the catalysis condition of the acid catalyst 4 - to generate 2 and 6 - b di-tert-butyl -4 -hydroxybenzyl acetone. To the invention, 2, 6 -position occupying-protected phenol 2 and 6 - di-tert-butyl phenol are used as raw materials, and the butanone or 4 -hydroxybutanone alkylation reaction can 100% position in the para position, and the obtained 2 and 6 - di-tert-butyl -4 -hydroxybenzyl acetone. Yield. A tert-butyl process is performed, so that high-yield and high-purity raspberry ketone is obtained. The method is simple in process, short in reaction time, high in product purity, recyclable in reaction byproducts, recyclable in catalyst, low in cost and suitable for industrial production.
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
