CN107334139A - Glutathione analog derivative is modified in hydrocarbylation - Google Patents
Glutathione analog derivative is modified in hydrocarbylation Download PDFInfo
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- CN107334139A CN107334139A CN201710658648.1A CN201710658648A CN107334139A CN 107334139 A CN107334139 A CN 107334139A CN 201710658648 A CN201710658648 A CN 201710658648A CN 107334139 A CN107334139 A CN 107334139A
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- glutathione
- hydrocarbylation
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- analog derivative
- aliphatic group
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- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/045—Organic compounds containing nitrogen as heteroatom
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- 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
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- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/055—Organic compounds containing sulfur as heteroatom
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- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
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- Seeds, Soups, And Other Foods (AREA)
Abstract
The invention belongs to food additives field, there is provided glutathione analog derivative is modified in the hydrocarbylation that below formula is (a)~(i), and wherein R is aliphatic group CnH2n+1Or substituted-phenyl Ph (CH2)n, n=0~15, Ph represent phenyl.Can react to obtain with corresponding aldehyde material by glutathione or from food it is isolated, make an addition in the numerous foods such as meat soup, beverage, soy sauce, vinegar or other edible materials, the basic taste of food or the lasting sense of enhancing and successional flavor attributes can be lifted, and has the function that to strengthen aroma strength or keeps fragrance stability.
Description
Technical field
The invention belongs to food additives field, and in particular to glutathione analog derivative is modified in hydrocarbylation, and it makes an addition to
In the numerous foods such as meat soup, beverage, soy sauce, vinegar and other edible materials, its lasting sense and successional flavour are not only assigned
Characteristic, also have the function that to keep fragrance stability.
Background technology
Glutathione is a kind of important food additives and dispensing, has certain anti-oxidation characteristics, can be used as antioxygen
Agent is added in food, and SO is replaced with glutathione as patent (CN105176741A) discloses one kind2As antioxidant
Suppress the method for applejack brown stain.Meanwhile addition glutathione can not only improve the nutritive value of Flour product in Flour product, also
The rheological behavior of dough can be changed, that shortens in Dough Making Process mixed rubs the time.The flavour of food includes tart flavour, sweet taste, hardship
Five kinds of taste, saline taste and delicate flavour basic tastes, in addition to mellow sense, profusely coordination sense, sense, continuation etc..Glutathione is in itself almost
Without delicate flavour, but when in the delicate flavour solution that 0.02%w/v glutathione is added to monosodium glutamate composition, the delicate flavour of delicate flavour solution
Obvious enhancing (the .Flavor Characteristics of such as Ueda Yoichi Glutathione have been obtained with mellow sense
In Raw and Cooked Foodstuffs.Bioscience Biotechnology＆Biochemistry, 1997,61
(12)：1977-1980.)
Lipid oxidation degraded is a kind of important reaction in food processing process, the small molecule carbonyl class in its catabolite
Compound can act on amino acid in food or the amino in polypeptide, sulfydryl, obtain the amino acid or polypeptide of lipidization modification.It is existing
There is patent (US20160227825A1) to disclose a kind of amino acid analogue and the lipidization modification to be formed production is acted on fatty aldehyde
Thing, the lipidization modified outcome are made an addition in food, not only the flavor attributes such as the delicate flavour of enhancing food, saline taste, coordination sense, simultaneously
Overcome the defects of fatty aldehydes aroma substance easily escapes in food；Patent (WO/2001/035768) discloses one kind by half Guang
The mercapto groups and c of propylhomoserin, beta-unsaturated aldehyde act on the lipidization modified outcome to be formed, and the lipidization modified outcome makes an addition to food
In product, for discharging aldehydes fragrance matter, the flavouring essence quality of food is lifted；Patent (CN101305281) discloses three kinds by first
The glutathione of base, pi-allyl and nitroso modification, it not only has the function that to strengthen the basic flavour of five kinds of food, moreover it is possible to assigns
Certain flavour satiety, mellow sense etc..
The content of the invention
The object of the invention modifies glutathione analog derivative to provide hydrocarbylation, and one-level chemical constitution is formula (a)~(i)
Middle a kind of or its edible salt or ester, wherein R are aliphatic group-CnH2n+1, n=0~15, or substituted-phenyl Ph- (CH2)n-,
N=0~15, aliphatic group can be straight chain fatty alkyl or branched aliphatic, and Ph represents phenyl.
Glutathione analog derivative is modified in hydrocarbylation of the present invention, and one-level chemical constitution is one in formula (a)~(i)
Kind or its edible salt or ester, preferable R are aliphatic group-CnH2n+1, n=0~13, or substituted-phenyl Ph- (CH2)n-, n
=0~5, aliphatic group can be straight chain fatty alkyl or branched aliphatic, and Ph represents phenyl.
Glutathione analog derivative is modified in hydrocarbylation of the present invention, and one-level chemical constitution is one in formula (a)~(i)
Kind or its edible salt or ester, most preferred R are aliphatic group-CnH2n+1, n=2~7, aliphatic group is straight chain aliphatic hydrocarbons
Base.
Glutathione analog derivative is modified in the hydrocarbylation that formula of the present invention is (a)~(i), can pass through glutathione
React to obtain with corresponding aldehyde material, as R is C in structure (g)4H9When, it can be obtained by glutathione and 2- heptene aldehyde reactions；
R is C in structure (e)5H11When, it can react to obtain by glutathione and 2,4- decadienals.In addition, formula is (a~c) compound
Also the dipeptides of Cysteine-Glycine can be used to be obtained with corresponding aldehyde reaction, as R is C in formula (a)4H9When, can be by half Guang
The dipeptides of propylhomoserin-glycine reacts to obtain with valeral.The product of reaction, then by certain means (such as column chromatography, efficient liquid phase
Chromatogram, thin-layer chromatography, gel chromatography etc.) after purification, that is, obtain corresponding hydrocarbylation modification glutathione derivative.
Glutathione analog derivative is modified in the hydrocarbylation that formula of the present invention is (a)~(i), and R is most preferably straight chain
Aliphatic group-CnH2n+1, n=2~7, the now corresponding aldehyde that can be reacted with glutathione is propionic aldehyde, butyraldehyde, valeral, hexanal, heptan
Aldehyde, octanal, 2- pentenals, 2- hexenoic aldehydes, 2- heptenals, 2- octenals, 2- nonenyl aldehydes, 2- decenals, 2,4 ,-heptadienal,
2,4- octadiene aldehyde, 2,4- nonadienals, 2,4- decadienals, 2,4- undecadienals, the olefine aldehydr of 2,4-, 12 carbon two etc. are straight
Chain fatty aldehyde.
In addition, glutathione analog derivative is modified in the hydrocarbylation that formula of the present invention is (a)~(i), also can be from day
Right product include meat (pork, beef) and its product (bacon, ham), protein zymolyte (such as pork protein zymolyte) or
In the numerous foods such as the thermal response product of protein zymolyte or edible material, take ultrafiltration, column chromatography, high performance liquid chromatography,
The means such as thin-layer chromatography, gel chromatography are isolated.
Formula of the present invention be (a)~(i) hydrocarbylation modify glutathione analog derivative, itself flavour compared with
It is weak, make an addition in the numerous foods such as meat soup, beverage, soy sauce, vinegar and other edible materials, the basic taste that can improve food such as carries
Delicate flavour, or lasting sense and the successional flavor attributes of enhancing food are risen, its specific addition is by the actual taste according to food
With technological requirement determine, typically between 1~10000mg/kg, addition manner can be directly addition, or with other any food
Or added after edible material combination.
Glutathione analog derivative is modified in the hydrocarbylation that formula of the present invention is (a)~(i), can be during edible
Or corresponding aldehydes flavor substance is discharged in food processing process, so as to strengthen the aroma strength of food, or make up in food
Original aldehydes flavor substance easily escapes defect, has the function that to keep food aroma stability.
Embodiment
Embodiment 1
1.844g glutathione and 0.769g octanals are added in 20mL pH 5.5 phosphate buffer, at 70 DEG C
80min is reacted in oil bath pan.Reaction product is separated using automatic liquid phase chromatographic separator and cation exchange resin column,
1BV (bed volume) 1mol/L hydrochloric acid solution activated resin is first used, is then eluted with 2BV 0.3mol/L ammonia spirits, elution
When ammonia spirit flow velocity be 1mL/min, according to ultraviolet detection spectral peak collect target product.Repeated multiple times loading, collection liquid merging,
Freeze-drying, obtain the heptane glutathione derivative that formula is (a), about 0.328g.
Weigh 0.010g, be added in 100mL orange beverage, using former orange beverage as control, select 7 it is experienced
Valuation officer carries out sensory evaluation, and the conclusion that all valuation officers obtain is：Formula is added for the heptane glutathione of (a) to spread out
Biology, mellow in taste, continuation enhancing, and citrus gives off a strong fragrance.
Embodiment 2
By 1.844g glutathione and 0.841g 2- nonenyl aldehydes be added to 20mL pH be 5.5 phosphate buffers in,
20min is reacted in 90 DEG C of oil bath pans.Reaction product is entered using automatic liquid phase chromatographic separator and anti-phase large pore resin absorption column
Row separation, mobile phase are 50% ethanol/water solution, flow velocity 1mL/min, target product are collected according to ultraviolet detection spectral peak.
Repeated multiple times loading, collection liquid merges, freeze-drying, obtains the aldehyde C-9 glutathione derivative that formula is (d), about
0.344g。
0.013g is weighed, is added to during 100mL cucumber squeeze the juice, is squeezed the juice with former cucumber as control, 9 is selected and experienced comments
Valency person is judged, and 9 valuation officers think：Add the aldehyde C-9 glutathione derivative that formula is (d), Fresh Cucumber Juice mouthfeel alcohol
It is thick, full, and cucumber fragrance protrudes.
Embodiment 3
By 1.844g glutathione and 0.457g 2,4- decadienals be added to 20mL pH be 6 phosphate buffer
In, react 5min in 100 DEG C of oil bath pans.Reaction product is carried out using automatic liquid phase chromatographic separator and polyamide resin column
Separation, first eluted with 1BV pure water after loading, then eluted with 2BV 0.03mol/L ammonia spirits, ammoniacal liquor during elution
Flow velocity be 1.5mL/min, according to ultraviolet detection spectral peak collect target product.Repeated multiple times loading, collection liquid merges, freezing is dry
It is dry, that is, obtain the heptene glutathione derivative shown in structural formula (h), about 0.159g.
Chicken soup is obtained after whole chicken is stewed into 1h.The heptene glutathione shown in 0.050g structural formulas (h) is weighed to spread out
Biology is added in 100mL chicken soup, using jungle fowl meat soup as control.Select 7 experienced valuation officers and carry out sensory evaluation, it is right
Its flavour and smell are described.7 valuation officers think：After formula is added as the heptene glutathione derivative of (h), chicken
Soup taste is full, and chicken fat gives off a strong fragrance.
Embodiment 4
The pH that 1.844g glutathione and 0.463g 2- decenals are added to 20mL is in 6.8 phosphate buffer,
15min is reacted in 90 DEG C of oil bath pans.Reaction product is handled by ProElut C18 solid-phase extraction columns, extraction column activation loading
First eluted with 1BV 30% methanol/water solution, then eluted with 1BV pure methanol afterwards.Collection liquid adds diluted sodium hydroxide solution
Neutralize, after freeze-drying, that is, obtain the sodium salt of the heptane glutathione derivative shown in structural formula (g), about 0.348g.
The meat gruel of pork adds water, boils 1h, pork soup is obtained after filtering.Weigh the heptane that 0.070g formulas are (g)
The sodium salt of glutathione derivative, it is added in 100mL pork soup, using former pork soup as control.Select 9 experienced evaluations
Member carries out sensory evaluation, and its flavour and smell are described.9 valuation officers think：Formula is the heptane gluathione of (g)
After the sodium salt of peptide derivant, the enhancing of meat soup delicate flavour, mellow in taste, have and given off a strong fragrance compared with strong continuity, fat perfume (or spice).
Claims (5)
1. glutathione analog derivative is modified in hydrocarbylation, it is characterised in that：
One-level chemical constitution is a kind of or its edible salt or ester in formula (a)~(i),
Wherein R is aliphatic group-CnH2n+1N=0~15, or substituted-phenyl Ph- (CH2)n-, n=0~15, aliphatic group can be straight
Chain fatty alkyl or branched aliphatic, Ph represent phenyl.
。
2. modify glutathione analog derivative according to hydrocarbylation described in claim 1, it is characterised in that：
One-level chemical constitution is a kind of or its edible salt or ester in formula (a)~(i), wherein
R is preferably aliphatic group-CnH2n+1, n=0~13, or substituted-phenyl Ph- (CH2)n-, n=0~5, aliphatic group can be
Straight chain fatty alkyl or branched aliphatic, Ph represent phenyl.
3. modify glutathione analog derivative according to hydrocarbylation described in claim 1, it is characterised in that：
One-level chemical constitution is a kind of or its edible salt or ester in formula (a)~(i), wherein
R is most preferably aliphatic group-CnH2n+1, n=2~7, aliphatic group is straight chain fatty alkyl.
A kind of 4. edible mixture, containing the hydrocarbylation modification glutathione analog derivative having the right described in 1-3 or its edible
Salt or ester.
5. any one compound described in claim 1-3 changes the purposes of food taste characteristic or food aroma characteristic.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710658648.1A CN107334139A (en) | 2017-08-04 | 2017-08-04 | Glutathione analog derivative is modified in hydrocarbylation |
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| CN201710658648.1A CN107334139A (en) | 2017-08-04 | 2017-08-04 | Glutathione analog derivative is modified in hydrocarbylation |
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| CN107334139A true CN107334139A (en) | 2017-11-10 |
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| CN201710658648.1A Pending CN107334139A (en) | 2017-08-04 | 2017-08-04 | Glutathione analog derivative is modified in hydrocarbylation |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001035768A1 (en) * | 1999-11-15 | 2001-05-25 | J.Manheimer, Inc. | Flavor freshness enhancers |
| CN101305281A (en) * | 2005-11-09 | 2008-11-12 | 味之素株式会社 | KOKUMI-imparting agent |
| JP2011094044A (en) * | 2009-10-30 | 2011-05-12 | Ogawa & Co Ltd | Persistent scent imparting agent |
| WO2011081715A1 (en) * | 2009-12-28 | 2011-07-07 | Perricone Nicholas V | Topical acyl glutathione psoriasis formulations |
| CN102940224A (en) * | 2011-05-31 | 2013-02-27 | 西姆莱斯有限公司 | Cinnamamides as savory flavorings |
| WO2015048991A1 (en) * | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| US20150342231A1 (en) * | 2013-01-22 | 2015-12-03 | Mars, Incorporated | Flavor composition and edible compositions containing same |
| CN105176741A (en) * | 2015-09-29 | 2015-12-23 | 江南大学 | Method for preparing cider with glutathione used as antioxidant |
-
2017
- 2017-08-04 CN CN201710658648.1A patent/CN107334139A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001035768A1 (en) * | 1999-11-15 | 2001-05-25 | J.Manheimer, Inc. | Flavor freshness enhancers |
| CN101305281A (en) * | 2005-11-09 | 2008-11-12 | 味之素株式会社 | KOKUMI-imparting agent |
| JP2011094044A (en) * | 2009-10-30 | 2011-05-12 | Ogawa & Co Ltd | Persistent scent imparting agent |
| WO2011081715A1 (en) * | 2009-12-28 | 2011-07-07 | Perricone Nicholas V | Topical acyl glutathione psoriasis formulations |
| CN102940224A (en) * | 2011-05-31 | 2013-02-27 | 西姆莱斯有限公司 | Cinnamamides as savory flavorings |
| US20150342231A1 (en) * | 2013-01-22 | 2015-12-03 | Mars, Incorporated | Flavor composition and edible compositions containing same |
| WO2015048991A1 (en) * | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| CN105176741A (en) * | 2015-09-29 | 2015-12-23 | 江南大学 | Method for preparing cider with glutathione used as antioxidant |
Non-Patent Citations (10)
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