CN104672148A - Compound used as food flavoring agent - Google Patents

Compound used as food flavoring agent Download PDF

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Publication number
CN104672148A
CN104672148A CN201310627397.2A CN201310627397A CN104672148A CN 104672148 A CN104672148 A CN 104672148A CN 201310627397 A CN201310627397 A CN 201310627397A CN 104672148 A CN104672148 A CN 104672148A
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China
Prior art keywords
formula
food
compound
described compound
product
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CN201310627397.2A
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Chinese (zh)
Inventor
罗凯
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Individual
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Abstract

The invention provides a compound used as a food flavoring agent. The compound is shown in a structural formula in the specification.

Description

A kind of compound being used as food spice agent
Technical field
The present invention relates to food chemistry field.More specifically relate to a kind of compound being used as food spice agent.
Background technology
The present invention relates to benzo pyrimidine compound and this new chemical substance is used in and be used as spices and essence.Spices and essence industry need constantly to provide new chemical substance, with the local flavor enabling foodstuff flavouring teacher and perfumer create to make new advances and odor type product.When finding new flavor compounds, find the new dulcet benzo pyrimidine compound of tool.These compounds can be used in many kinds of spices by foodstuff flavouring teacher.An embodiment of the invention relate to a kind of formula I by being added with effective amount and improve food, strengthen or the method for modification.The present invention one preferred embodiment relates to a kind of Compounds of structural formula I by being added with effective amount and improves food, strengthens or the method for modification.
Summary of the invention
An embodiment of the invention relate to a kind of formula I by being added with effective amount and improve food, strengthen or the method for modification.
Term used herein " food " comprises and is supplied to the solid of human or animal and the absorbed material of liquid, usually has but does not need to have nutritive value.So, food comprises meat, gravy, soup, ready-to-eat, Fructus Hordei Germinatus, comprises alcohol and other beverage of soft drink and carbonated drink (soda), soy-containing product, comprise milk and the milk-product of Yoghourt and ice-creams, comprise sweet basil, dill grass, parsley, wild marjoram, marjoram, Salvia japonica Thunb., Thymus vulgaris, Rosmarinus officinalis, peppermint, cilantro, tarragon, chervil medicinal herbs, comprise the seafood of fish, crustacean, mollusk etc., candy, vegetables, cereal, snack, dog grain and cat grain, and other veterinary products etc.
Formula I also may be used for appetizer application.The example of preferred food product comprises soup, gravy, meat dish, snack, marinate and sauce.In a preferred embodiment of the invention, formula I can be used for improving food, strengthening or modification.
Think that formula I has the flavor characteristic (flavornote) of tropical fruit, catty, peach and berry.This structural compounds sees in roasting sesame seed oil.May be used for brown spices (cola, whisky and chocolate), tropical fruit, berry and orange flavor (peach, piscidia, mango, shaddock, lemon, bitter orange, blueberry, blackberry, blueberry), flavouring (nut, fricassee, rusk, decoct the head of garlic, sauteeing onions).
Compound in the present invention be used for seasoning composition time, can with the seasoning material of routine or adjuvant combination.This type of purposes of this type of combined composition or seasoning adjuvant is known in the art, has carried out extensive description to it in document.Require that this type of Adjuvanting material and compounds of structure I are compatible in the sense of taste, can absorb and can accept, and nontoxic or harmless.Except these require, can conventional material be used, comprise other seasoning material, vehicle, stablizer, thickening material, tensio-active agent, conditioning agent and flavour enhanced dose widely.
This type of conventional seasoning material comprises saturated fatty acid, unsaturated fatty acids and amino acid; Comprise the alcohols of primary alconol and secondary alcohol; Ester class; Comprise the carbonyl compound of aldehydes and ketone; Lactone; Comprise other cyclic organic material of the heterocyclic such as aryl compound, alicyclic compound and such as furans, pyridine, pyrazine; Sulfocompound, comprises thio-alcohol, sulfide, disulphide etc.; Protein; Lipid; Carbohydrate; So-called flavour enhancer, as msg powder type; Psicosoma, Calcium glutamate, guanosine hydrochlorate and inosinate; Atural spice material, as cocoa powder, vanilla and caramel; Volatile oil and extract, as olium anisi, cloves wet goods; And artificial seasoning material, as vanillin food grade,1000.000000ine mesh, vanirone etc.
Concrete preferred seasoning adjuvant includes, but are not limited to following material: olium anisi; Ethyl 2-methylbutyrate; Vanillin food grade,1000.000000ine mesh; Cis-3-heptenol; Cis-3-hexenol; Trans-2-heptenic aldehyde; Butyl valerate; 2,3-diethyl pyrazine; Methyl-cyclopentanone alcohol; Phenyl aldehyde; Valerian oil; 3,4-syringol; Pentyl acetate; Amyl cinnamate; Gamma-butyrolactone; Furfural; Trimethylpyrazine; Toluylic acid; Isovaleric aldehyde; Veltol plus; Vanirone; Valeric acid ethylester; Ethyl butyrate; Cocoa medicinal extract; Coffee medicinal extract; Spearmint oil; Oleum Menthae Rotundifoliae; Syzygium aromaticum stem oil; Methyl allylphenol; Oils, Elettaria cardamomum; Wintergreen oil; Phenylacrolein; 2 methyl valeric acid ethyl ester; γ-hexenolactone; 2，4-heptadienal; Methylthiazol base alcohol (4-methyl-5-beta-hydroxyethyl thiazole); 2-methyl butyl sulfhydryl; 4-sulfydryl-2-butanone; 3-sulfydryl-2 pentanone; 1-sulfydryl-2-propylene; Phenyl aldehyde; Furfural; Furfuryl alcohol; 2 mercaptopropionic acid; Alkyl pyrazine; Methylpyrazine; 2-ethyl-3-methylpyrazine; Tetramethylpyrazine; Polysulfide; Dipropyl disulfide; Benzyl methyl disulfide; Alkylthrophene; 2,3-thioxene; 5 methyl furfural; 2-acetofuran; 2,4-decadienal; Methyl catechol; Phenylacetic aldehyde; β-decalactone; D-limonene; Acetoin; Pentyl acetate; Voitol; Ethyl butyrate; Levulinic acid; Piperonylaldehyde; Ethyl acetate; Octanal; Valeral; Hexanal; Dimethyl diketone; Msg powder type; Monopotassium glutamate; Sulfur-containing amino acid, such as halfcystine; Hydrolyzed vegetable protein; 2-methyl furan-3-mercaptan; 2-methyl dihydrofuran-3-mercaptan; 2,5-dimethyl furan-3-mercaptan; Hydrolyzed fish protein; Tetramethylpyrazine; Propyl group propenyl two sulphur; Propyl group propenyl trithio; Diallyl disulfide; Garlicin; Dipropenyl two sulphur; Dipropenyl trithio; 4-methyl-2-[(methylthio group)-ethyl]-1,3-dithiolane; 4,5-dimethyl-2-(methylthiomethyl)-1,3-dithiolane; And 4-methyl-2-(methylthiomethyl)-1,3-dithiolane.The seasoning component of these and other sees US Patent No. 6110520 and US6333180, includes in by reference herein.
As described above, formula I or comprise its composition can with one or more vehicle or carrier combinations, add in specific product.Vehicle can be edible, or other suitable material, as ethanol, propylene glycol, water etc., as described above.Carrier comprises as Sudan Gum-arabic, carrageenin, xanthan gum, guar gum etc.
Formula I can be combined by conventional methods with carrier, as spraying dry, roller drying etc.Examples of such carriers also can comprise the material condensing benzo pyrimidine compound of the present invention, to provide packaged products as described above.When described carrier is emulsion, seasoning composition also can comprise emulsifying agent, as monoglyceride and triglyceride, or lipid acid etc.These carriers or vehicle can be utilized to prepare the required physical form of described composition.
The usage quantity of formula I should be enough to make product have required flavor characteristic.Usage quantity can change according to following factor: the further processing that ultimate food, the amount being present in the spices in food at first and type, food are subject to or treatment step, provincialism and other preference factor, product need through storage type (if any), ultimate consumer will give the edible pre-treatment such as such as baking, fry etc. of product.
Formula I preferred dose scope is in the product from 0.001ppm to 10ppm, preferred 0.001ppm to 5ppm, more preferably 0.001ppm to 1ppm.Thus, flavor compositions can comprise the compound in one or more the present invention.
Therefore, term " significant quantity " and " q.s " are interpreted as enough amounts that quantitatively can change flavour of food products in the context of the present invention.
Embodiment
Below by embodiment, the invention will be further described.The method described in the embodiment of the present invention that it should be understood that is only used for the present invention is described, instead of limitation of the present invention, under concept thereof of the present invention, all belong to the scope of protection of present invention to the simple modifications of preparation method of the present invention.The all raw materials used in embodiment and solvent are all purchased from Sigma Biochemical and Organic Compounds for Research and Diagnostic Clinical Reagents company.
Embodiment 1: the preparation of formula I.
(1) 2-(4-(4-chlorobenzene the pyrimidine formyl radical) phenoxy group of 20 grams is got)-2 Methylpropionic acid isopropyl ester is dissolved in 12 milliliters of sulfur alcohols, then slowly instilled under 0 DEG C of condition by the boron trifluoride ether solution of 8.7 milliliters.Drip and finish, continue stirring 1 little of reaction end.Then use saturated sodium bicarbonate cancellation, and be extracted with ethyl acetate.Organic phase uses saturated sodium bicarbonate, water and saturated common salt water washing successively, dry, and concentrated, thick product obtains 12.6 grams through column chromatography (sherwood oil: ethyl acetate/50:1).
1H NMR (400MHz, CDCl 3) δ: 1.05 (t, J=7.6Hz, 6H), 1.20 (d, J=6.4Hz, 6H), 1.59 (s, 6H), 2.25-2.33 (m, 4H), 5.04-5.11 (m, 1H), 6.74 (d, J=8.8Hz, 2H), 7.24 (d, J=8.8Hz, 2H), 7.36 (d, J=8.8Hz, 2H), 7.46 (d, J=8.8Hz, 2H)。
(2) 11.26 grams of step obtained above (1) products are dissolved in 20 milliliters of methylene dichloride, slowly add 8 grams of two (2-methoxy ethyl) amine sulfur trifluorides in 0 DEG C under argon shield, then add the bromo-succinimide of 10.68 grams.Continue stirring 15 minutes at this temperature, reaction solution is poured in 100 milliliters of ice saturated sodium bicarbonate solutions, and with 25 milliliters of dichloromethane extraction three times.Organic phase is concentrated, washing, dry and obtain 9.0 grams of oily matter products through column chromatography (sherwood oil: ethyl acetate/50:1).
1H NMR (400MHz, CDCl 3) δ: 1.22 (d, J=6.4Hz, 6H), 1.63 (s, 6H), 5.10 (m, 1H), 6.86 (d, J=8.8Hz, 2H), 7.35 (d, J=8.8Hz, 2H), 7.39-7.46 (m, 4H); 19F NMR (376 MHz, CDCl3) δ: –86.3。
Embodiment 2: toxicity test.
[MTT test].
Carry out MTT test with the cytotoxicity detecting compound of the present invention.MTT is a kind of yellow water-soluble material, but when it is imported into viable cell, it is changed into the insoluble crystal of purple by the desaturase in plastosome.Can by measuring OD being dissolved in after in methyl-sulphoxide by MTT 550determine cytotoxicity.Experiment is carried out as follows.
CV-1 cell is inoculated into (5000 cells/well) in 96 orifice plates.By cell at 37 DEG C, 5%CO 2incubation case in cultivate 24 hours, then use the formula 1 of different concns and the compound treatment of formula 2.Then in cell, add MTT reagent and it is cultivated 24 hours again.Cultivate after 15 minutes, the purple crystals of generation is dissolved in methyl-sulphoxide.Optical density(OD) is measured to determine cytotoxicity with microplate reader.As a result, compound represented by formula 1 of the present invention and optical isomer (compound of formula 2) thereof is determined even if 100,000 times of EC 50cytotoxicity is not had under the concentration of value yet.
[mouse toxicity test].
Mouse is used to carry out acute toxicity and reproductive toxicity test to evaluate the toxicity of formula I of the present invention.The compound of formula 1 is carried out Orally administered with the ICR mouse of the dosage of 50mg/kg, 300mg/kg and 2000mg/kg to 6 week age, then observes toxicity 14 days.As a result, even use maximum concentration 2000mg/kg, do not observe yet due to formula 1 compound use the death caused, and do not observe the noticeable change of body weight and feed food-intake yet.Autopsy findings display does not have abnormal sign.Use the reproductive toxicity test result of C57BL/6 mouse also consistent with the above results, do not observe the toxicity caused by the compound of formula 1.After to the Orally administered described compound of the female mice of pregnancy, the weight that checked embryo increases and the speed of growth.As a result, do not observe and use due to described compound the significant difference caused, and do not observe the change of bone development and disease-related event.
Embodiment 3: Application Example.
The threshold value of formula I in water is 0.5ppb, has the flavor characteristic of tropical fruit, catty, peach, berry.
Formula I in rolled oats.
Commercially available conventional instant groats constituent comprises whole grain roll extrusion rolled oats, calcium carbonate, salt, guar gum, caramel colorant, reduced iron, niacinamide, vitamin A, palmitate (ester), Vit B6, hydrochloride, riboflavin, thiamine mononitrate and folic acid.
When dosage is 2ppb, the peach local flavor given out when described compound with the addition of similar combustion of sulfur.When dosage is 0.5ppb, the flavor characteristic given out when described compound with the addition of slight similar combustion of sulfur, has joint action of potentiation to cereal flavor characteristic.
Formula I in orange carbonated drink.
Soda Ash Light 99.2min., high-fructose corn syrup, citric acid, potassium benzoate, Sudan Gum-arabic, natural perfume, ester gum, Huang 6, brominated vegetable oil, red 40.
When dosage is 3ppb, described compound makes the similar orangeade of the taste of orange carbonated drink.It makes the mouthfeel of carbonated drink more natural, and reduces acidity.
Formula I in beef broth.
Beef broth and the following material being less than 1%: salt, MSG, hydrolysed corn albumen, hydrolytic soya bean protein, hydrolyzed wheat protein, glucose, onion powder, autolysing yeast extract, caramel colorant, partly hydrolysed soya protein, natural perfume, thiamine hydrochloride, inosine acid disodium, Sodium guanylate.
When dosage is 5ppb, described compound enhances baking flavor characteristic.When the level higher than 5ppb, described benzo pyrimidine compound creates tropical flavor characteristic.
Formula I in mixed pulp tartaric acid cheese.
Pasteurize A level fermenting defatted milk, high-fructose corn syrup, modified corn starch, skimmed milk, Jew's gelatin, W-Gum, tricalcium phosphate, natural perfume, be fresh-keeping and that add potassium sorbate, Sucralose (Splenda board), acesulfame potassium, carry out pigment process with annatto extract, Vitamin D3 500,000 I.U/GM.
When dosage is 6ppb, described compound enhances fruit-like flavour feature.When the level higher than 6ppb, described benzo pyrimidine compound creates peach flavor characteristic.

Claims (6)

1. be used as a compound for food spice agent, it is characterized in that it is with shown in following structural formula:
。
2. a composition, is characterized in that containing auxiliary agent acceptable on formula I and food.
3. use a method for formula I, it is characterized in that described compound mixes in the food being selected from lower group: meat, sauce, gravy, soup, ready-to-eat, malt beverage, alcoholic beverage, soy-containing product, milk products, milk-product, medicinal herbs, fish, crustacean, mollusk, candy, vegetables, cereal, soft drink, snack, dog grain, cat grain and composition thereof.
4. method as claimed in claim 3, it is characterized in that, the weight level of described compound is from about 0.001ppm to about 10ppm.
5. method as claimed in claim 3, it is characterized in that, the weight level of described compound is from about 0.001ppm to about 5ppm.
6. method as claimed in claim 3, it is characterized in that, the weight level of described compound is from about 0.001ppm to about 1ppm.
CN201310627397.2A 2013-12-02 2013-12-02 Compound used as food flavoring agent Pending CN104672148A (en)

Priority Applications (1)

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Application publication date: 20150603