CN104649964A - Compound used as umami agent - Google Patents
Compound used as umami agent Download PDFInfo
- Publication number
- CN104649964A CN104649964A CN201310588754.9A CN201310588754A CN104649964A CN 104649964 A CN104649964 A CN 104649964A CN 201310588754 A CN201310588754 A CN 201310588754A CN 104649964 A CN104649964 A CN 104649964A
- Authority
- CN
- China
- Prior art keywords
- delicate flavour
- compound
- product
- formula
- composition
- 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.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
Abstract
The invention relates to an organic compound used as an umami promoting agent, wherein the compound is characterized by being represented as the formula I.
Description
Technical field
The present invention relates to food chemistry field, specifically, the present invention relates to the compound that strengthens delicate flavour and savory flavor and comprise delicate flavour tastant composition and can purposes in consumable products.
Background technology
Delicate flavour is one of basic taste and is described to good to eat or like the local flavor of meat.It is the attribute of many foodstuff productss, particularly dainty product.Delicate flavour and savory flavor be caused by glutaminate, particularly monosodium glutamate (MSG) and these compounds may be used for thus changing can the delicate flavour of consumable products and savory flavor.But, think some human consumers by glutaminate, particularly MSG detrimentally affect and need thus not based on the compound of glutaminate to substitute this compound or to reduce dependency to it, thus change can the delicate flavour of consumable products and savory flavor.Known in this area can by adding naturally occurring purine nucleotides inosine monophosphate (IMP) and guanosine monophosphate (GMP) enhancing can the delicate flavour of consumable products and savory flavor.But these production of chemicals difficulty and expensive, thus limit their application in the industry.To for strengthening delicate flavour and savory flavor and the compound that there is not prior art defect exists demand.By providing the enhancing compound of in fact non-glutamic acid salt, can reduce changing composition and can the dependency of the delicate flavour of consumable products and the compound such as MSG of savory flavor.The compound that the invention still further relates to formula I hereafter strengthen comprise at least one delicate flavour tastant can purposes in the delicate flavour of consumable products and composition and savory flavor.The invention still further relates to the composition that strengthens and comprise at least one delicate flavour tastant and can the delicate flavour of consumable products and the method for savory flavor, can carry out in consumable products and composition by the compound of at least one formula I is joined.
The invention still further relates to the new compound of formula (I).
Term used herein " delicate flavour tastant " mean to cause delicate flavour any compound or
Composition, its limiting examples provides hereinafter.
Term used herein " delicate flavour and savory flavor toughener " means any compound or the composition that himself can cause, also can not cause delicate flavour or savory flavor, when in the composition for comprising at least one delicate flavour tastant, it causes overall delicate flavour and savory flavor sensation to increase.
Summary of the invention
In in first of the present invention, provide the delicate flavour of composition and the method for savory flavor that strengthen and comprise at least one delicate flavour tastant, undertaken by the compound of at least one formula (I) is joined in foregoing:
Compound of the present invention can comprise at least one chiral centre and can exist as stereoisomer mixture like this.If expect each steric isomer of preparation, then can prepare according to method well known in the art, such as preparation HPLC and GC or pass through stereoselective syntheses.
In the present invention, the compound of term formula I is used can to refer to racemic mixture or each isomer be separated.
Can the compound of formula I be joined in composition with the form be applicable to arbitrarily, such as respective pure form or form in a solvent or modified forms, such as first can capture them with trapping material, such as polymkeric substance, capsule, microcapsule, Nano capsule, liposome, precursor, membrane-forming agent, such as by using the sorbent material, ring oligosaccharide kind and composition thereof of carbon zeolites, or they can be combined with substrate stoichiometric, these substrates are suitable for the compound of release type (I) when external source sexual stimulus thing such as light, enzyme etc. apply.
In a more particular embodiment, composition of the present invention comprises at least one glutaminate particularly compound of MSG, at least one formula I and at least one purine nucleotides particularly inosine monophosphate (IMP) and guanosine monophosphate (GMP).
The compound of formula (I) can with at the most 99.9%, particularly 1.0-99% and more particularly the concentration of 5%-99% be used in composition.
In another aspect of the present invention, provide strengthen or change comprise at least one delicate flavour tastant can the delicate flavour of consumable products and the method for savory flavor, comprise the compound of formula I joined described can step in consumable products.
Used hereinly consumable products can to mean to intend to be placed in oral cavity and swallow or use any products then discarded in the oral cavity.Be applicable to can consumable products including, but not limited to foodstuff products, drink product, healthcare product and dental care product, comprise mouth wass.
In another aspect of the present invention, what provide the compound that comprises at least one delicate flavour tastant and formula I can consumable products.
In a specific embodiment, can consumable products be food or drink product.
The example of foodstuff products such as, including, but not limited to seasonings, sauce, sauce, seasonings etc., savoury product, cereal product, rice product, pasta products, won ton, cassava product, sago product, baked goods, cracker product, pastry product, bread product, confectionary product, dessert product, honey product, molasses product, yeast product, mustard product, vinegar product, processed food prod, ripe fruit and vegetable products, meat and meat products, meat analog/surrogate, jelly, fruit flavouring substance, egg-products, cheese product, breast substitute, soybean prod, edible oil and fatty prod.
Savoury product example comprises, but be not limited to saliferous snacks (potato flakes, chrisps, nut, fried tortilla, pretzel, cheese snacks, grain snacks, potato-snacks, instant food product popcorn, can the corn grain that splits of Microwave Burst, pork rind, nut, crispbread, crisp fritter snacks, breakfast cereals, meat, meat jelly, alkali meat (ham, bacon), lunch/breakfast meat (hot dog, the cold sliced meat eaten, sausage), tomato products, oleomargarine, peanut butter, soup (clear soup, canned soup, cream soup, instant soup, UHT), canned vegetables, spaghetti seasonings.
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; Fiddlehead is common commercial products.
Embodiment 1: the preparation of formula I
Get dry fiddlehead and be ground into meal 1000g, add 60% ethanol 8000ml and extract 7 hours, collect extracting solution, filter, get filtrate recycling ethanol extremely without alcohol taste, add water and make the solution of every 1ml containing 0.5g crude drug, with macroporous resin column (D class macroporous resin, resin volume 3000ml, the resin height of bed is about 8 with diameter ratio) and alumina adsorption, gradient elution is carried out with the ethanol of different concns, alcohol concn was adjusted to 95% by 5% in 6 hours, flow velocity 4.5BV/h, discard containing the elutriant of alcohol concn beyond 30% to 70%, collect and contain alcohol concn more than 30% to the elutriant of less than 70%, less than 65 DEG C decompression and solvent recoveries are also concentrated into the clear cream that relative density is 1.13 (60 DEG C), ethyl acetate and Diethyl ether recrystallization (volume ratio: 3:1) obtain formula I.
1h NMR (solvent: deuterochloroform): δ: 6.04 (d, 1H), 6.32-6.44 (m, 1H), 6.62-6.67 (m, 2H), 7.25-7.28 (m, 4H), 7.34-7.49 (m, 6H), 7.61-7.65 (m, 6H), 7.88 (d, 1H).
Embodiment 2: biological activity test:
The delicate flavour of formula I as described in example 1 above strengthens the sensory analysis of threshold value.
Water for perceptual evaluation is purchased from table water (NongFuShanQuan).
" model meat soup " comprises one hydration Pidolidone one sodium (MSG) (1.9g), Star Dri 5 (6.375g), sodium-chlor (2.9g) and yeast extract (2.1g) in 1000mL water.
Prepare the ACN fraction from fiddlehead, formula I as described in Example 1.
By 25mg above formula I be dissolved in 0.2mL ethanol, then 20.0mL model meat soup is joined in sample.Then use model meat soup according to 1: 1 (v/v) gradient dilution sample, until the group of solution obtains the dilution factor of 8 to compound.
By one group of trained professionals evaluate's sample.Next following perceptual evaluation program is carried out to the sample of contained I.
In the mode avoiding any mixing, one of sample solution of 1mL is applied in the left part of each group member's tongue, and the 1mL model meat soup as blank value/neutral reference substance is applied in the right part of tongue.Require that group member compares the taste on its tongue two halves.After 5-30 second, require that group member is to its oral cavity friction-top tongue.Then inquire group member whether they can distinguish sample and blank (model meat soup).
Then as described in document, carry out delicate flavour by geometric mean and strengthen threshold calculations (ASU:L00.90-9,1999).So-called " delicate flavour enhancing threshold value " means mean concns during compound enhancing model meat soup delicate flavour.For each group member, following formula is used for determining that average delicate flavour strengthens threshold value:
Wherein c
ethe concentration (in ppm) of the most weak concentration being accredited as delicate flavour reinforced effects, C
e-1be the concentration (in ppm) increasing progressively sample solution, E is the mean value that delicate flavour strengthens threshold value.
In order to the delicate flavour calculating group strengthens the mean value of threshold value, use following formula:
Wherein n is group member's quantity, E
iit is the result of the delicate flavour enhancing threshold value that each group member as above calculates.
Can observe, compound of the present invention shows delicate flavour and strengthens threshold value when 1.5ppm.
Claims (6)
1. be used as a compound for tasty agents, it is characterized in that its structure is with shown in formula I:
。
2. a composition, comprises the compound of the formula I defined at least one delicate flavour tastant and at least one claim 1.
3. composition according to claim 2, is characterized in that also comprising monosodium glutamate (MSG).
4. composition according to claim 2, is characterized in that also comprising inosine monophosphate (IMP) and guanosine monophosphate (GMP).
5. the composition according to claim 3-4, wherein said composition is foodstuff products or drink product.
6. the composition according to claim 3-4, wherein said composition is seasonings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310588754.9A CN104649964A (en) | 2013-11-21 | 2013-11-21 | Compound used as umami agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310588754.9A CN104649964A (en) | 2013-11-21 | 2013-11-21 | Compound used as umami agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104649964A true CN104649964A (en) | 2015-05-27 |
Family
ID=53241669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310588754.9A Pending CN104649964A (en) | 2013-11-21 | 2013-11-21 | Compound used as umami agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104649964A (en) |
-
2013
- 2013-11-21 CN CN201310588754.9A patent/CN104649964A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5547699A (en) | Marine micro-algae food material containing docosahexaenoic acid, food containing the same and manufacturing method therefor | |
| KR102098155B1 (en) | Sweetness and/or milk flavor enhancer | |
| CN101528060A (en) | Substituted bicyclo[4.1.0]heptane-7-carboxylic acid amides and derivatives thereof as food flavor substances | |
| EP2620060B1 (en) | Method for producing thermally reacted seasoning | |
| CN104853617B (en) | Application of the nitrogenous derivative of cinnamic acid as flavoring agent | |
| WO2021193429A1 (en) | Masking agent | |
| KR20170129102A (en) | A sweetener composition comprising erythritol | |
| RU2614776C2 (en) | Compounds, compositions and methods for reducing or eliminating bitter taste | |
| JP2008212131A (en) | Reproducing method of cooking residues and reproduced material | |
| JPWO2013140901A1 (en) | Yeast extract heat reaction seasoning | |
| JP7156270B2 (en) | Composition for imparting a burnt oil flavor | |
| Ana et al. | Organoleptic test patisserie product based on consumer preference | |
| JP3439564B2 (en) | Pungency enhancer and pungency enhancement method | |
| CN103783583A (en) | Korean spicy wrapped peanut | |
| CN104649964A (en) | Compound used as umami agent | |
| CN104207179A (en) | Donkey meat hamburger | |
| JP2015128406A (en) | Butter alternative fat | |
| TW201422159A (en) | Oil-contained food, rapeseed oil, and method for enhancing taste of oil-contained food | |
| JP2009073761A (en) | Leptin production promoter | |
| JP7172992B2 (en) | A composition for imparting a charcoal-like pungent flavor | |
| CN104650073A (en) | Compound used as umami agent | |
| CN105410877A (en) | Sweet potato sauce and making method thereof | |
| JP2017523183A5 (en) | ||
| JP2006314235A (en) | Salty-taste reinforcing method, method for reducing saltiness of food and drink, reduced-salt food and drink, and method for producing the food and drink | |
| JPH099871A (en) | Confectionery |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150527 |
|
| WD01 | Invention patent application deemed withdrawn after publication |