18829-56-6Relevant academic research and scientific papers
Effect of oxidized arachidonic acid and hexanal on the mouse taste perception of bitterness and umami
Yamaguchi, Susumu,Fujiwara, Hidenori,Tashima, Ikukazu,Iwanaga, Daigo,Ushio, Hideki
, p. 1884 - 1890 (2010)
The oxidization of fatty acids generates many volatile compounds forming an aroma, but little is known whether mammals use gustatory sense to detect the oxidized products as a taste or only use olfactory sense to detect as an aroma. We examined in this study the effect of aqueous extracts of the compounds from autoxidized arachidonic acid (AA) ethyl ester or hexanal which is the predominant component generated from oxidized AA by the anosmic mouse licking performance to a tastant. The addition of the water extract from oxidized AA or hexanal to a quinine hydrochloride (QHC1) solution decreased the anosmic mice licking frequency at several concentrations of QHC1. Hexanal also reduced the licking frequency of anosmic mice conditioned to avoid MSG at several concentrations of monosodium glutamate (MSG). These results suggest that hexanal would affect mouse taste perception to QHC1 and MSG via the gustatory sensation.
Further Study on the One-Pot Synthesis of (E)-2-Nonenal from Castor Oil
Kula, Jozef,Sikora, Magdalena,Dabrowski, Robert
, p. 545 - 546 (1994)
A one-step procedure is described for the synthesis of (E)-2-nonenal from commercial castor oil by ozonolysis in methanol, followed by reduction of the ozonide products with dimethyl sulfide and exposure of the resulting intermediate product to dilute sulfuric acid.The developed process allows the production of the aldehyde with a yield of 80percent at a purity of 95percent.The method has advantages over all those reported earlier, because of inexpensive raw material and reducing agent, recycling of the solvent and its unusual simplicity.KEY WORDS: Castor oil, 2-nonenal, ozonolysis.
A convenient strategy for the synthesis of β,γ-unsaturated aldehydes and acids. A construction of skipped dienes
Saha, Goutam,Basu, Manas K.,Kim, Seongjin,Jung, Young-Ju,Adiyaman, Yurdanur,Adiyaman, Mustafa,Powell, William S.,FitzGerald, Garret A.,Rokach, Joshua
, p. 7179 - 7183 (1999)
A novel strategy is described for the synthesis of β,γ-unsaturated aldehydes which are the useful-synthons for the synthesis of arachidonic acid and other eicosanoid products. These β,γ-unsaturated aldehydes have been used in the total synthesis of arachidonic acid.
Reduction of 1,1-difluoro-1-alken-3-ols with lithium tetrahydroaluminate. Application to the synthesis of 1,1-difluoro-2-alkenes and 2-alkenals
Telliera, Frederique,Sauvetre, Raymond
, p. 181 - 185 (1996)
The reduction of 1,1-difluoro-1-alken-3-ols with lithium tetrahydroaluminate is described. The 1-fluoro-1-alken-3-ols obtained can be transformed to enals or difluoromethylated allylic derivatives.
Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors
Kon, Yoshihiro,Nakashima, Takuya,Yada, Akira,Fujitani, Tadahiro,Onozawa, Shun-Ya,Kobayashi, Shū,Sato, Kazuhiko
supporting information, p. 1115 - 1121 (2021/02/16)
The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.
Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System
Zhu, Quan,Luo, Yunsong,Guo, Yongyan,Zhang, Yushun,Tao, Yunhai
, p. 5463 - 5476 (2021/05/05)
A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.
Method for preparing olefine aldehyde through catalytic oxidation of enol ether
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Paragraph 0082-0087, (2021/06/23)
The invention relates to the technical field of olefine aldehyde preparation, and provides a method for preparing olefine aldehyde through catalytic oxidation of enol ether. According to the invention, a palladium catalyst, a copper salt, a solvent and enol ether are mixed and subjected to a catalytic oxidation reaction to obtain olefine aldehyde. According to the method, the copper salt is used as the oxidizing agent, the mixed solvent of water and acetonitrile is used as the reaction solvent, and the volume ratio of water to acetonitrile in the mixed solvent is controlled to be (3-7): (3-7), so that the catalytic oxidation reaction can be smoothly carried out in the mixed solvent with a specific ratio, and the generation of palladium black precipitate can be avoided. The method provided by the invention has the advantages of simple steps, low reagent cost, no need of dangerous reagents, wide substrate adaptability and small catalyst dosage. Furthermore, octadecane mercaptan is added to promote the catalytic oxidation reaction, and when the dosage of the palladium catalyst is extremely low, the olefine aldehyde yield can be greatly increased by adding octadecane mercaptan.
Method for reducing carboxylic acid compound into aldehyde
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Paragraph 0021-0031, (2020/02/27)
The invention discloses a method for reducing a carboxylic acid compound into aldehyde. In a nitrogen atmosphere, in an organic solvent, a ligand/Cu catalyst, the carboxylic acid compound, an anhydride compound and hydrosilane are added by a one-pot method, a reaction is performed under the condition of the temperature of 20-120 DEG C for 2-20 h, after the reaction is completed, quenching and column chromatography separation are performed to obtain the product. The carboxylic acid compound can be successfully converted into aldehyde through one-pot reaction, especially unsaturated carboxylic acid can be reduced, and the reaction yield is generally relatively high. Compared with the prior art, the method has the outstanding advantages that the cheap copper salt is used as a catalyst, so that the experiment cost is greatly reduced. Meanwhile, the used method enlarges the application range of the reaction substrate, improves the compatibility of functional groups, and provides a new synthesis way for reducing the carboxylic acid compound into aldehyde.
Porous organic polymer supported rhodium as a heterogeneous catalyst for hydroformylation of alkynes to α,β-unsaturated aldehydes
Liang, Zuyu,Chen, Jianbin,Chen, Xin,Zhang, Kai,Lv, Jinhe,Zhao, Haowen,Zhang, Guoying,Xie, Congxia,Zong, Lingbo,Jia, Xiaofei
supporting information, p. 13721 - 13724 (2019/11/19)
A new porous organic polymer supported rhodium catalyst (Rh/POL-BINAPa&PPh3) has been developed for the hydroformylation of various alkynes to afford the corresponding α,β-unsaturated aldehydes with high chem- and stereoselectivity, excellent catalytic activity and good reusability (10 cycles). The heterogeneous catalyst exhibited more catalytic activity than the comparable homogeneous Rh/BINAPa/PPh3 system.
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
supporting information, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
