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Preparation method of capsaicin and capsaicin prepared by using method
The invention relates to a capsaicin preparation method and capsaicin prepared by the method. The preparation method comprises the steps that: in the presence of an organic solvent and a catalyst, vanillylamine and carboxylic acid serve as reactants, after amidation reaction, capsaicin reaction liquid is obtained, and the catalyst comprises a boric acid ester compound. Compared with the prior art, the capsaicin preparation method provided by the invention has the following beneficial effects: 1) a large amount of water is not generated in the reaction process, violent reflux for water separation is not needed, the production cost is reduced, and the production safety is improved; 2) boric acid is replaced by the boric acid ester compound, so that the reaction time can be shortened, the reaction yield can be improved, and the product purity is very high; and 3) the boric acid ester compound can be recycled after proper treatment after the reaction, so that the production cost is saved, and green production is realized.
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(2021/06/26)

Preparation method of capsaicine and capsaicine prepared by method
The invention provides a preparation method of capsaicine and capsaicine prepared by the method. The preparation method comprises the following steps: in the presence of an organic solvent and a catalyst, by taking vanillylamine carboxylate and carboxylic acid as reactants, carrying out amidation reaction to obtain a capsaicine reaction liquid. Compared with the prior art, the capsaicine preparation method provided by the invention at least has one of the following beneficial effects: 1) vanillylamine is converted into vanillylamine carboxylate, so that the problem of oxidative discoloration of vanillylamine is avoided, and the problems of purification, drying and storage of intermediate products are solved; 2) the vanillylamine carboxylate can be directly used for the next amidation reaction, other substances are not introduced, and the amidation reaction, operation and post-treatment are not influenced; and 3) after the vanillylamine solid is salified and dissolved, the thorough separation of the Raney Ni catalyst is facilitated, and the catalyst separated by the method can be continuously used after being treated.
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(2021/04/07)

Novel method for preparing N-(4-hydroxy-3-methoxybenzyl) nonamine without catalyst
The invention belongs to the technical field of chemical synthesis, and discloses a novel catalyst-free method for preparing N-(4-hydroxy-3-methoxybenzyl) nonanolamine, which comprises the following steps: by taking 4-hydroxy-3-methoxybenzyl amine and n-nonanoic acid as raw materials and ethyl acetate as a solvent, adding a water absorbent into a high-pressure reaction kettle, heating to 75 DEG C, stirring and reacting for 14-16 hours to prepare N-(4-hydroxy-3-methoxybenzyl) nonyl amine; wherein the molar ratio of the 4-hydroxy-3-methoxybenzylamine to the n-nonanoic acid is 1: 1. The process is simple, the production cost is greatly reduced, the reaction conditions are simple, the operation is easy, the product yield is high, the purity is high, the solvent recovery rate is high, the method is green and environment-friendly, and the obtained N-(4-hydroxy-3-methoxybenzyl) nonamine product is stable in quality and suitable for industrial production.
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Paragraph 0018; 0020-0031

(2021/07/14)

Vanilla amide synthesis method
The invention discloses a vanilla amide synthesis method, which comprises the following step: by taking alcohol and vanilla amide as raw materials, or aldehyde and vanilla amide as raw materials, inorganic ferric salt and inorganic indium salt as a composite catalyst and oxygen as an oxidant, carrying out one-pot reaction in an organic solvent to generate vanilla amide. The synthesis raw materials adopted by the synthesis method are wide in source, a large amount of chemical reaction waste can be avoided in the whole reaction process, and the synthesis method is clean and environmentally friendly, has the advantages of mild and controllable reaction conditions, simple operation, convenience in product separation and purification, high product yield, wide universality of reaction substrates and the like, and is a method suitable for industrial production.
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Paragraph 0083-0086; 0099-0101

(2021/06/13)

Method for preparing azelaic acid vanilla amide (by machine translation)
3 - Methoxyl 3 - hydroxybenzylamine and n-nonanoic acid are subjected to dehydration reaction under the catalytic action of aryl boronic acid, and the reaction time is -4 - and after stirring, the organic solvent is 3 - removed.4 - The method further comprises the following steps 1 of cooling to room temperature under the catalysis of aryl boronic acid; stirring after 1.2 adding water to obtain a pale yellow transparent -4 - liquid; and carrying out 10% dehydration reaction under a catalytic 25 °C - 85 °C action of aryl boronic 20min - 5h acid to obtain a white solid powder of anisononanoic acid. The method is simple in process, low in cost, high in yield, high in atom economy, low in reaction condition, high in product purity and environmentally friendly. (by machine translation)
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Paragraph 0005; 0032-0051

(2020/11/22)

Capsaicin preparation method and the preparation method of the capsaicin (by machine translation)
The present invention provides a capsaicin preparation method and the preparation method of the capsaicin. The capsaicin preparation method comprises: to vanilla amine free base and carboxylic acid as raw materials, the use of SiO2 - H3 BO3 Catalyst, in the acylation reaction is carried out in a solvent, to obtain the capsaicin reaction solution. The present invention provides capsaicin preparation method, compared with the prior art, has the following advantages: 1) with carboxylic acid as the raw material, to avoid the preparation of the acyl chloride and a large number of strong corrosive organic waste liquid generation; 2) SiO for2 - H3 BO3 Catalyst instead of boric acid as catalyst, can realize the repeated use of the catalyst, and the cost is reduced, significantly reduces the production of waste water containing boron; 3) can effectively shorten the reaction time, reduce energy consumption. (by machine translation)
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(2019/10/17)

Novel method for preparing synthetic capsaicin
The invention relates to a novel method for preparing synthetic capsaicin. The novel method comprises the following step of by taking vanillin amine and n-nonanoic acid as raw materials and taking toluene as a solvent, performing dewatering reaction under the catalytic action of boric acid to prepare the synthetic capsaicin, wherein the molar ratio of the vanillin amine and the n-nonanoic acid is1 to 1, the molar ratio of the vanillin amine and the boric acid is 1 to (0.05-0.20), the dosage of the toluene is as follows: adding 8-10mL toluene per 1g vanillin amine, a temperature of the dewatering reaction is 120-130 DEG C, and the reaction time is 8-10h. The novel method also comprises the following steps of cooling to room temperature after the dewatering reaction is finished, washing with water, drying with anhydrous sodium sulfate, performing decompression recovery on the toluene by using a rotary evaporator, and stirring residual liquid for crystallization to obtain the synthetic capsaicin. The novel method provided by the invention is simple in technology, low in cost, high in yield, low in reaction condition and high in product purity, is environmentally friendly and solves the problems of non environmental protection, low yield, complex aftertreatment and the like of a method for synthesizing capsaicin in the prior art.
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Paragraph 0027; 0028; 0029; 0030; 0031; 0032; 0033-0040

(2018/03/25)

A capsaicin preparation method
The invention discloses a preparation method of capsaicine. The method takes vanillin as a raw material, and comprises the steps of: carrying out reaction in an ammonia-gas-containing methanol solution; carrying out hydrogenation reduction by sodium borohydride; carrying out hydrochlorination on the vanillin amine collected from the reaction product; adding the intermediate vanillin amine hydrochloride into a dimethyl formamide (DMF) solvent, and dissolving; and adding nonoic acid, triethylamine and a condensing agent HBTU into the solution, and carrying out condensation reaction to obtain the target product capsaicine. The detection proves that the purity reaches up to more than 98%, and the total yield is 72.1%-81.1%. The preparation method is mild in reaction conditions, high in controllability of the operation process, low in cost and good in purity; a thin layer chromatography (TLC) detection method is used for controlling the reaction process, so that the obtained target product capsaicine is stable in quality and suitable for industrial production.
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Paragraph 0029; 0031; 0032; 0034

(2017/08/25)

SYNTHESIS OF AMIDES AND AMINES FROM ALDEHYDES OR KETONES BY HETEROGENEOUS METAL CATALYSIS
This invention concerns the first mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalystand amine donor. The initial heterogeneous metal- catalyzed reaction between the carbonyl and the amine donor components is followed up with the addition of a suitable acylating agent component in one-pot. Hence, the present invention provides a novel catalytic one-pot three-component synthesis of amides. Moreover, the integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis ofamides from aldehyde and ketone substrates, respectively. The process can be applied to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. It can also be applied for asymmetric synthesis. In the present invention, a novel co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Moreover, implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.
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(2016/07/05)

Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis
Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.
Palo-Nieto, Carlos,Afewerki, Samson,Anderson, Mattias,Tai, Cheuk-Wai,Berglund, Per,Córdova, Armando
p. 3932 - 3940
(2016/07/06)

A novel method for the synthesis of capsaicin (by machine translation)
The invention is in the field of organic synthesis, in particular relates to a novel method for the synthesis of capsaicin, in the method for synthesizing the salts of hydrochloric acid and element amine Xianglan pelargonyl chloride as raw materials, to toxicity is relatively small of the mixed solution of methylene chloride and water as the solvent, the crude product obtained by the reaction, after cooling crystallization purification, solid synthetic capsaicin can be obtained. The characteristic feature of the invention is: the operation is simple, the controllability is strong, only needs to use the conventional reaction for synthesizing device can complete, easy commercial production; to dichloromethane as solvent, compared with the toxicity of benzene, toluene and other organic solvent to be small, the danger to workers of the at the time of production small; produced in the process of producing salt-containing waste water and organic waste liquid can be recycled, the whole process zero discharge of waste liquid, no pollution to the environment; in the raw material of the sodium bicarbonate to remove the hydrochloric acid component and increase the reaction temperature to 38 the [...] 45 °C, synthetic speed is faster, the extraction rate is higher, can reach 90% or more; the use of cooling crystallization method of purifying the product, the capsaicin can reach pure rate to 99% or more. (by machine translation)
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Paragraph 0040; 0041; 0042

(2016/10/24)

EFFICIENT SYNTHESIS OF AMINES AND AMIDES FROM ALCOHOLS AND ALDEHYDES BY USING CASCADE CATALYSIS
The present invention relates generally to an eco-friendly methodology for the conversion of alcohols and aldehydes to amines and amides using an integrated enzyme cascade system with metal-and organocatalysis. More specifically, the present invention relates to synthesis of capsaicinoids starting from vanillin alcohol and using a combination of an enzyme cascade system and catalysts. Furthermore, the method also relates to synthesis of capsaicinoids derivatives starting from vanillin alcohol derivatives and using a combination of an enzyme cascade system and catalysts.
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(2015/11/24)

Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot
The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.
Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando
p. 2113 - 2118
(2014/07/07)

The SAR analysis of TRPV1 agonists with the α-methylated B-region
A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding α-methylated analogues were investigated. Whereas the α-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The analysis indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding.
Cho, Yongsung,Kim, Myeong Seop,Kim, Ho Shin,Ann, Jihyae,Lee, Jeewoo,Lee, Jiyoun,Pearce, Larry V.,Pavlyukovets, Vladimir A.,Morgan, Matthew A.,Blumberg, Peter M.
scheme or table
p. 5227 - 5231
(2012/09/07)

Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestlvum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.
Barbero, Gerardo F.,Molinillo, Jose M. G.,Varela, Rosa M.,Palma, Miguel,MacIas, Francisco A.,Barroso, Carmelo G.
experimental part
p. 3342 - 3349
(2011/07/30)

NOVEL COMPOUNDS AND USES THEREOF
The invention relates to compounds represented by the general formula (I): and pharmaceutically acceptable salts thereof, wherein n is an integer from 1 to 5; p is an integer from 0 to 4; R1 is selected from the group consisting of a hydroxyl group, an alkoxy group, a thiol group, and a thioether group; R2 and R3 are independently a methylene group or a nucleophile, with the proviso that at least one of R2 and R3 is a nucleophile group; Z is an oxygen (O) atom or sulfur (S) atom; T is hydrogen or an optionally substituted aliphatic group; with the proviso that when n = 2, R1 is not -OCH3 on the carbon-3 position of the phenyl group and R1 is not -OH on the carbon-4 position of the phenyl group.
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Page/Page column 45-46; 50

(2010/12/29)

Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists
The synthesis of a range of caged TRPV1 agonists and antagonists is reported. The photolysis characteristics of these compounds, when irradiated with a 355 nm laser, have been studied and in all cases the desired compound was produced. Photolysis of a caged TRPV1 agonist in cultured trigeminal neurons produced responses that were consistent with the activation of TRPV1 receptors.
Van Ryssen, Michael P.,Avlonitis, Nicolaos,Giniatullin, Rashid,McDougall, Craig,Carr, James L.,Stanton-Humphreys, Megan N.,Borgstroem, Emma L. A.,Brown, C. Tom A.,Fayuk, Dmitriy,Surin, Alexander,Niittykoski, Minna,Khiroug, Leonard,Conway, Stuart J.
body text
p. 4695 - 4707
(2009/12/08)

In vitro photo-release of a TRPV1 agonist
Intracellular photolysis of a novel 'caged' capsaicin analogue results in in vitro activation of the capsaicin receptor TRPV1.
Carr, James L.,Wease, Kerrie N.,Van Ryssen, Michael P.,Paterson, Suzanne,Agate, Ben,Gallagher, Katherine A.,Brown, C. Tom A.,Scott, Roderick H.,Conway, Stuart J.
p. 208 - 212
(2007/10/03)

Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity
As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.
Janusz, John M.,Buckwalter, Brian L.,Young, Patricia A.,LaHann, Thomas R.,Farmer, Ralph W.,et al.
p. 2595 - 2604
(2007/10/02)

Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic 'A-region'
A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring 45Ca2+ uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic 'A-region' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.
Walpole,Wrigglesworth,Bevan,Campbell,Dray,James,Perkins,Reid,Winter
p. 2362 - 2372
(2007/10/02)