CN101845363B - Method for preparing flavoring essence by using crystallization method - Google Patents

Method for preparing flavoring essence by using crystallization method Download PDF

Info

Publication number
CN101845363B
CN101845363B CN 201010124479 CN201010124479A CN101845363B CN 101845363 B CN101845363 B CN 101845363B CN 201010124479 CN201010124479 CN 201010124479 CN 201010124479 A CN201010124479 A CN 201010124479A CN 101845363 B CN101845363 B CN 101845363B
Authority
CN
China
Prior art keywords
flavoring essence
reaction
gram
product
hours
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN 201010124479
Other languages
Chinese (zh)
Other versions
CN101845363A (en
Inventor
张敦铁
肜霖
王萍
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Tobacco Hunan Industrial Co Ltd
Wuhan Huanghelou Science and Technology Park Co Ltd
Original Assignee
China Tobacco Hunan Industrial Co Ltd
Wuhan Huanghelou Science and Technology Park Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by China Tobacco Hunan Industrial Co Ltd, Wuhan Huanghelou Science and Technology Park Co Ltd filed Critical China Tobacco Hunan Industrial Co Ltd
Priority to CN 201010124479 priority Critical patent/CN101845363B/en
Publication of CN101845363A publication Critical patent/CN101845363A/en
Application granted granted Critical
Publication of CN101845363B publication Critical patent/CN101845363B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Seasonings (AREA)

Abstract

The invention relates to a preparation method of novel response tobacco or edible flavoring essence, in particular to a method for preparing the flavoring essence by using a crystallization method. The method leads amino acid material to have Maillard reaction with saccharide material, and is characterized by carrying out the Maillard reaction in organic solvent, taking acid compound as catalyst to react, reducing the temperature after the reaction, crystallizing to separate the solid material under 15 DEG C, and after filtration, collecting the solid material to be used as the flavoring essence. The invention utilizes the crystallization method to prepare the Maillard reaction flavoring essence and has simple technology, the product does not need repeated column elution, and the yield reaches more than 60%, so the production cost is greatly reduced. The flavoring essence prepared by the invention has rich fragrance, comfortable taste, offensive taste covering and long time of fragrance in cigarettes, and has the effect of obviously improving the cigarette quality.

Description

A kind of method of preparing flavoring essence by using crystallization method
Technical field
The present invention relates to the preparation method of a kind of novel reaction class cigarette use or food flavour spices, specifically a kind of method of preparing flavoring essence by using crystallization method.
Background technology
Mailland reaction (Maillard reaction) is the study hotspot in the fields such as food chemistry, Food technology, trophology, flavor chemistry in recent decades always, because mailland reaction is the main source of the various local flavors of processed food color and luster and strong fragrance.For example utilize mailland reaction can obtain food spice and the essence of egg perfume, milk, meat perfume (or spice).In addition, mailland reaction also has important impact to Nutritive value of food, both may because the digestibility that has consumed the nutritive ingredient in food or reduced food reduces Nutritive value of food, also may generate antioxidant in the course of processing and increased its nutritive value.Mechanism to mailland reaction is carried out deep research, be conducive in the process of Food storage and processing, control food color and luster, fragrance variation or its reaction is carried out towards being conducive to the direction that color and luster, fragrance generate, reduce the loss of nutritive value, increase the accumulation of beneficial products, thereby improve the quality of food.
The separation of New Characteristics intermediate and end product and evaluation in the mailland reaction process further disclose the mechanism of mailland reaction; How to control reaction conditions in the production of reaction fragrance matter and make the influence factor that generates more characteristic chicken flavor composition and flavouring stability in reaction; The dynamic process of the formation of research mailland reaction toffee element, carcinogenic heterocyclic nitrogen is processed for food-processing effective reference mark is provided; The mailland reaction product on the pathological research of chronic diabetes, cardiovascular disorder and cancer etc. with and be the main focus of research when present mailland reaction on the impact of food safety etc.
Mailland reaction is the reaction of a complexity, its product is varied, since it is found that its intermediate---after Armagh Du Li compound, people just attempt ining all sorts of ways obtaining this compound, because this compound cannot be avoided generating a series of not conceivable materials in reaction of higher order, this compound is a kind of precursor body of important fragrance matter simultaneously, and is of many uses in cigarette and food.Along with the enhancing of people to food safety and health care consciousness, find that this compounds can effectively reduce various free radicals in cigarette and food, make this material personal value also greatly improve.Japanese Patent 9239/71 has been introduced respectively 1-deoxidation-1-L-proline(Pro)-D-Fructose as the fragrance-enhancing tobacco agent.Adding can increase cigarette perfume (or spice), reduces the tobacco pungency, covers assorted gas, improves jealous effect in cigarette.
It is generally repeatedly to cross post wash-out and productive rate generally in 1% left and right that the preparation of 1-deoxidation according to the literature-1-L-proline(Pro)-D-Fructose and 1-deoxidation-these class midbody compounds such as 1-L-L-Ala-D-Fructose separates, need in this course a large amount of poisonous eluents, the most frequently used a kind of as trichloromethane, also need a large amount of hydrochloric acid, sodium hydroxide activation pillar, its process is complicated, cost is high, and environmental influence is larger, and productive rate is low.Therefore, provide a kind of productive rate high, the preparation method of the essence and flavoring agent that cost is low is very important.
Summary of the invention
Purpose of the present invention is exactly the defective for prior art, and a kind of method of preparing flavoring essence by using crystallization method is provided, and the method production technique is simple, and cost is low, and productive rate improves greatly.
Technical scheme of the present invention is achieved in that it is that amino acid material and glucide are carried out mailland reaction, it is characterized in that: mailland reaction is in organic solvent, react as catalyzer with acidic cpd, reacted rear cooling, at crystallization solids below 15 ℃, collect solids after filtering and be essence and flavoring agent.Described organic solvent is one or more in acetone, sherwood oil, methyl alcohol, glycerine, trichloromethane, benzene.Particular methanol is as solvent.Described acidic cpd is one or more in hydrochloric acid, acetic acid, citric acid, propanedioic acid, p-sulfonic acid base Phenylsulfonic acid.Preferred propanedioic acid is as catalyzer.
The present invention's technical scheme preferably is: when carrying out mailland reaction, added sulphite or hydrosulphite in reaction system.Described sulphite or hydrosulphite are S-WAT, sodium bisulfite, potassium sulfite or Potassium hydrogen sulfite.
The mailland reaction intermediate---the solubleness of Armagh Du Li compound in water is very big, and it is less to the solubleness in weak solvent at some polar phase, and under the condition of these solvents heating various reducing sugars and amino acid whose solubleness larger, utilize this characteristics, therefore select polar phase to weak solvent or mixed solvent.The characteristics of mailland reaction are very easily to carry out to reaction of higher order under alkaline condition simultaneously, generate the senior Maillard reaction products of product complexity.It is also conceivable that the material that adds some can stop plum rad reaction of higher order, as sulphite, hydrosulphite.
Because reaction is carried out under heating condition, therefore must control temperature and reflux is installed.
Change the various place of production, the kind of amino acid material and kind and amount and the proportionings of adding glucide of containing, amount and the kind of change solvent, thus obtain tobacco aromatics using wide in variety, to satisfy the production of cigarettes needs.
Above-mentioned all compounds are added in reactor, stir into uniform reaction system.Open the water coolant of reflux, be heated to 40~70 ℃, it adds thermal recovery heat transfer oil electric heating or steam heating.
In order to make the reaction system thermally equivalent, in heating, must stir, stir and use the adjustable speed agitator, its rotating speed should be between 100~1000 rev/mins.
Make the temperature of reaction reach predetermined temperature by heating.And different, general control is at 40~70 ℃ according to different reaction systems for its temperature of reaction, and reaction is carried out under normal pressure.Reaction times, and different, general control was at 1-5 hour according to different reaction systems.
After reaction finishes, reaction product is put into storage tank, the solids of refrigeration crystallization filter product-cigarette of the present invention with or food spices.
The present invention prepares the mailland reaction essence and flavoring agent with crystallization process, and its technique is simple, and product does not need repeatedly to cross the post wash-out, and productive rate reaches more than 60%, greatly reduces production cost.The essence and flavoring agent that the present invention makes has fragrance abundant in cigarette, and comfortable taste is covered assorted gas, and fragrance remaining time is long, obviously improves the effect of the quality of cigarette.
Embodiment
Further illustrate content of the present invention below in conjunction with example, but these implement not limit protection scope of the present invention.
Embodiment 1
Take 50 gram glucose, 5 gram L-Ala are put into three-necked flask, add 100 gram methyl alcohol, 20 gram glycerine, add again acetic acid 3 grams as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, with glass rod scrape flask walls place 10 ℃ lower 12 hours, find to have a large amount of Precipitations, crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 67%.Products obtained therefrom is slightly yellow, very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.
Embodiment 2
Take 50 gram glucose, 5 gram proline(Pro) are put into three-necked flask, add 100 gram methyl alcohol, then add propanedioic acid 2 grams as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity are 200 rev/mins, then stop heating, place 15 ℃ lower 12 hours, discovery has a large amount of Precipitations, and crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 55%.Products obtained therefrom is white slightly, and is very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, slightly stimulate, significantly improve cigarette quality.
Embodiment 3
Take 50 gram glucose, 7 gram α-amino-isovaleric acids are put into three-necked flask, add 100 gram methyl alcohol, then add propanedioic acid 2 grams as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity are 200 rev/mins, then stop heating, place 0 ℃ lower 12 hours, discovery has mass crystallization to separate out, and crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 60%.Products obtained therefrom is white slightly, and is very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.
Embodiment 4
Take 50 gram glucose, 7 gram α-amino-isovaleric acids are put into three-necked flask, add the sherwood oil of 60~90 ℃ of 80 grams, 20 gram glycerine, add again phenmethyl sulfonic acid 2 grams as catalyzer, connect reflux condensing tube, be heated to 60 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, places 10 ℃ lower 12 hours, discovery has mass crystallization to separate out, crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 54%.Products obtained therefrom is white slightly, and is very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.
Embodiment 5
Take 50 gram ribose, 3 gram α-amino-isovaleric acids, 5 gram proline(Pro) and put into three-necked flask, add 80 gram methyl alcohol, 20 gram glycerine, add again each 1 gram of phenmethyl sulfonic acid and propanedioic acid as catalyzer, connect reflux condensing tube, be heated to 60 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, places 5 ℃ lower 12 hours, discovery has mass crystallization to separate out, crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 48%.Products obtained therefrom is white slightly, and is very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.
Embodiment 6
Take 50 gram glucose, 5 gram Methionins are put into three-necked flask, add 100 gram acetone, 20 gram glycerine and 2 gram S-WATs, add again 3 gram acetic acid and 1 gram citric acid as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, with glass rod scrape flask walls place 0 ℃ lower 12 hours, find to have a large amount of Precipitations, crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 67%.Products obtained therefrom is slightly yellow, very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.
Embodiment 7
Take 50 gram glucose, 5 gram Gelucystines are put into three-necked flask, add 100 gram acetone, 20 gram glycerine and 1 gram sodium bisulfite, add again 3 gram acetic acid and 1 gram hydrochloric acid as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, with glass rod scrape flask walls place 0 ℃ lower 12 hours, find to have a large amount of Precipitations, crossing leaching solid recrystallization gained solid is product of the present invention, and productive rate reaches 67%.Products obtained therefrom is slightly yellow, very easily water-soluble.This product is joined in blank cigarette with 0.5 ‰ amount smoke panel test, find that this product can significantly increase flue gas concentration, increase aroma quality, cover assorted gas, significantly improve cigarette quality.

Claims (1)

1. the method for a preparing flavoring essence by using crystallization method, it is that 50 gram glucose, 7 gram α-amino-isovaleric acids are put into three-necked flask, adds 100 gram methyl alcohol, then adds propanedioic acid 2 grams as catalyzer, connect reflux condensing tube, be heated to 65 ℃ with oil bath, constant temperature 4 hours, stirring velocity is 200 rev/mins, then stop heating, place 0 ℃ lower 12 hours, cross leaching solid recrystallization, the gained solid is product of the present invention.
CN 201010124479 2010-02-26 2010-02-26 Method for preparing flavoring essence by using crystallization method Expired - Fee Related CN101845363B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201010124479 CN101845363B (en) 2010-02-26 2010-02-26 Method for preparing flavoring essence by using crystallization method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201010124479 CN101845363B (en) 2010-02-26 2010-02-26 Method for preparing flavoring essence by using crystallization method

Publications (2)

Publication Number Publication Date
CN101845363A CN101845363A (en) 2010-09-29
CN101845363B true CN101845363B (en) 2013-05-15

Family

ID=42770181

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201010124479 Expired - Fee Related CN101845363B (en) 2010-02-26 2010-02-26 Method for preparing flavoring essence by using crystallization method

Country Status (1)

Country Link
CN (1) CN101845363B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103349356B (en) * 2013-06-19 2016-10-05 河南中烟工业有限责任公司 Cigarette flavouring humectant 1-L-leucine-1-deoxidation-D-Fructose and preparation method thereof
CN106520368B (en) * 2016-11-18 2019-11-08 湖北中烟工业有限责任公司 A kind of application of formula for preparing Amadori reaction flavor and preparation method thereof and the fragrance
US20230024978A1 (en) * 2019-12-17 2023-01-26 Givaudan Sa Taste modifying ingredients

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
刘梅森 等.美拉德反应在肉类香精中的作用.《中国调味品》.2004,第35页.
反应型牛肉香精的研制及其香味活性化合物的分析;夏玲君;《中国优秀硕士学位论文全文数据库》;20071024;第7页 *
夏玲君.反应型牛肉香精的研制及其香味活性化合物的分析.《中国优秀硕士学位论文全文数据库》.2007,第7页.
美拉德反应在肉类香精中的作用;刘梅森 等;《中国调味品》;20040831;第35页 *

Also Published As

Publication number Publication date
CN101845363A (en) 2010-09-29

Similar Documents

Publication Publication Date Title
CN106520368B (en) A kind of application of formula for preparing Amadori reaction flavor and preparation method thereof and the fragrance
CN103783660B (en) The supercritical extraction method of flavor matter and application thereof in a kind of tobacco leaf fragment
FI58489C (en) ETH SOETNINGSMEDEL INNEHAOLLANDE 1- (2-HYDROXI-4-CARBOXIMETOXYFENYL) -3- (3-HYDROXI-4-METHOXYPHENYL) PROPAN-1-ON OCH / ELLER DESS ALKALI METAL SALTER
CN101845363B (en) Method for preparing flavoring essence by using crystallization method
CN104152265A (en) Sugar cane juice Maillard reaction product, preparation method thereof and application thereof to cigarettes
CN105542959A (en) Method for preparing electronic cigarette liquid flavor
CN105585470B (en) A method of 2- hydroxy-3-methyl -2- cyclopentene-1-ones are prepared by fructose
CN103865646A (en) Preparation method of modified fruit concentrate Maillard reaction product, and application of product in tobacco perfuming
CN110846133A (en) Cigarette caramel spice under negative pressure condition and preparation method thereof
SU685660A1 (en) 2,6,-trimethyl-1-cyclohexene-1-vinylalkanoates exhibiting organoleptic effect
US3843804A (en) Novel flavoring compositions and processes
CN115005488B (en) Atomizing agent for cigarettes and electronic cigarette liquid
CN106720915A (en) The processing method of dragon fruit
CN114516797B (en) Methyl cyclopentenolone menthol carbonate spice and synthetic method and application thereof
CN107787190A (en) The ketone of (5R) (β D glucopyranoses epoxide) 1,5 dihydro 2H pyrroles 2 as umami molecules
EP3370523A1 (en) Compounds, compositions and methods for coloring edible materials
CN109369743A (en) A kind of method of easy synthesis cedar wood alcohol glucoside
CN111116371B (en) Novel moss fen-flavor compound 4-methoxy ethyl olivetolate, preparation method and application thereof
JP6673564B2 (en) Composition
JPS5941701B2 (en) How to flavor food
CN108516998B (en) Preparation method and application of effective components of aroma releasing agent for burnt sweet type cigarettes
MX2008013193A (en) Flavorant compounds.
JP3001530B1 (en) Tobacco flavor enhancer and tobacco products containing it
CN117770450B (en) High-purity capsaicin composition, and preparation method and application thereof
CN114380693B (en) Methyl cyclopentenol ketogeraniol carbonate spice and synthetic method and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20130515

Termination date: 20140226