CN103314092B - Perfume composition - Google Patents
Perfume composition Download PDFInfo
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- CN103314092B CN103314092B CN201280005064.XA CN201280005064A CN103314092B CN 103314092 B CN103314092 B CN 103314092B CN 201280005064 A CN201280005064 A CN 201280005064A CN 103314092 B CN103314092 B CN 103314092B
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- nonadiene
- dimethyl
- flavor compositions
- fragrance
- alcohol
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- 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
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2026—Hydroxy compounds
Abstract
Provided are a perfume composition, which is obtained by mixing three kinds of compounds, 4,8-dimethyl-3,7-nonadiene-2-ol, 4,8-dimethyl-3,7-nonadiene-2-yl acetate, and 4,8-dimethyl-3,7-nonadiene-2-1, which are extremely effective for giving a sense of lemony citrus, a sense of natural spontaneity and a sense of fresh feeling, each in a specific proportion; and foods, beverages, perfumes and cosmetics that are formulated with the perfume composition. Provided is a perfume composition that is obtained by mixing three kinds of compounds, namely 4,8-dimethyl-3,7-nonadiene-2-ol, 4,8-dimethyl-3,7-nonadiene-2-yl acetate, and 4,8-dimethyl-3,7-nonadiene-2-1, in a specific proportion.
Description
Technical field
The present invention relates to the flavor compositions that can be used as food flavor, perfuming cosmetic spices etc., specifically, relate to flavor compositions, it is characterized in that, with specific ratio mixing 4,8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates, 4,3 kinds of compounds of 8-dimethyl-3,7-nonadiene-2-ketone form.
Background technology
Citral be lemon sample contained in lemon, bitter orange, grape fruit etc. there is stronger fraicheur fragrance component, be widely used as one of important perfume base of diet product or perfuming cosmetic etc.
On the other hand, known citral heating reduces or time dependent reduces, and generates peculiar smell (the peculiar smell foreign odor of not welcoming) (non-patent literature 1).Particularly in acid condition, containing the citral in the goods of citral manufacturing, circulation, between storage life in each stage in reduce, its structure changes due to reactions such as oxidation, cyclisation, hydration, isomerization, thus, cause fraicheur reduction and produce very strong deterioration smelly, the quality causing goods significantly reduces.
At present, about the smelly reason material of the various deteriorations generated by citral, the object produced for preventing it, carries out there are the various trials such as antioxidant (non-patent literature 2) such as adding arabo-ascorbic acid, but suppresses about the generation of its deteriorated smelly reason material, although there is effective method, but cannot suppress the decomposition of citral itself, as a result, the feeling of freshness of citral disappears, therefore, non-essence solves the problem keeping citral aroma characteristic originally.
On the other hand, there will be a known, by using, there is the similar aroma characteristic of citral, and the high lemon aldehydes edge material of stability replaces citral to carry out the structure change of Inhibitor, prevent the method for the generation of deteriorated smelly reason material.
Such as, as the lemon aldehydes edge body that stability is high, there will be a known 4,8-dimethyl-3,7-nonadiene-2-alcohol or 4,8-dimethyl-3,7-nonadiene-2-yl acetate or 4,8-dimethyl-3,7-nonadiene-2-ketone etc.But the aromatic of each material has the aromatic of the uniqueness that the heterogeneous aromatic close to the material of citral mixes, it is not wield fragrance material separately.
Up to now, disclose by adding 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,8-dimethyl-3, the mixture of 7-nonadiene-2-ketone, provides and has excellent olfactive characteristics, and have higher color stability flavor compositions (patent document 1), provide nature and the fresh flavor compositions (patent document 2) with stronger lemon sample fragrance; By combining 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,8-dimethyl-3,2 kinds of 7-nonadiene-2-yl acetate and the alcohol etc. that derived by terpene compound, there is provided fresh and flavour and the local flavor of stronger lemon sample can be given, and there is the flavor compositions (patent document 3) of higher ageing stability in acidic beverages.
Disclosing in the above-mentioned documents can by interpolation 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4, the mixture of 8-dimethyl-3,7-nonadiene-2-ketone or combination 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,2 kinds of 8-dimethyl-3,7-nonadiene-2-yl acetate and the alcohol etc. that derived by terpene compound manufacture has the similar aroma characteristic of citral, and has the flavor compositions of higher ageing stability.
But, 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4, this 2 kinds the combination of 8-dimethyl-3,7-nonadiene-2-ketone compared with situation about being used alone, although close to the aromatic of citral, but can feel simultaneously feel the fragrance of a flower, cosmetics aromatic exist different, insufficient in the natural sense with associative perception.
In addition, by combining 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,8-dimethyl-3,7-nonadiene-2-yl acetate 2 kinds and the alcohol etc. that derived by terpene compound, although also become the aromatic close to citral, but start to feel the aromatic of bitter orange sample with deterioration, in being changed by aromatic originally or remember one of important aromatic as citral and the lemon sense of representational performance in insufficient, strongly expect further to improve.
Prior art document
Patent document
Patent document 1: special table 2003-517052 publication
Patent document 2: JP 2001-181670 publication
Patent document 3: European Patent application discloses No. 1417896 description
Non-patent literature
Non-patent literature 1:Peter Schieberle and Werner Grosch; J.Agric.Food Chem., 36,797-800 (1988)
Non-patent literature 2:Val E.Peacock and David W.Kuneman; J.Agric.Food Chem., 33,330-335 (1985)
summary of the invention
The problem that invention will solve
In recent years, with the hobby variation of consumer, the exploitation of various commodity is expected.Particularly this tendency of diet product perfuming cosmetic industry is strong, is strongly required the exploitation being imbued with diversified diet product, perfuming cosmetic meeting the hobby of consumer.For these requirements, in the spices of the raw material material as one of diet product, perfuming cosmetic, the new expectation do not had so far improves constantly.
For fragrance material, particularly not only require to have the effect of the performance excellence of the fragrance fragrance of more natural natural sense, there is the high fragrance fragrance of hobby property, in addition, not only give good fragrance fragrance, but also requirement can not produce foreign odor in time dependent ground, has higher stability.
Problem of the present invention is, the natural natural sense that can give the natural ambition meeting consumer and the high fragrance fragrance of hobby property are provided, particularly allow the aromatic remembering lemon sense, and the flavor compositions that stability is high, the generation of foreign odor is by the time reduced and the diet product, the perfuming cosmetic that have coordinated this flavor compositions.
For solving the means of problem
In order to solve above-mentioned problem, the present inventor etc. concentrate on studies, result, it is shocking, find by different 3 kind edge materials, the i.e. alcohol (4 of mixing functional group, 8-dimethyl-3,7-nonadiene-2-alcohol), ester (4,8-dimethyl-3,7-nonadiene-2-yl acetate) and ketone (4,8-dimethyl-3,7-nonadiene-3-ketone) 3 kinds, lemon sense is significantly improved.And then it is shocking, for this ratio of 3 kinds, specific ratio is very important, also concentrates on studies about this ratio.
Its result, find about 4, 8-dimethyl-3, 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate and 4, 8-dimethyl-3, the mixed proportion of 7-nonadiene-2-ketone is, relative to 4, 8-dimethyl-3, 1 of 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate is 0.02 ~ 0.4, 4, 8-dimethyl-3, 7-nonadiene-2-ketone is 0.04 ~ 0.8, preferably relative to 4, 8-dimethyl-3, 1 of 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate is 0.04 ~ 0.2, 4, 8-dimethyl-3, 7-nonadiene-2-ketone is 0.08 ~ 0.4.
By being in harmonious proportion with above-mentioned specific ratio the 3 kinds of compounds contained in spices, compared with the flavor compositions of the flavor compositions containing citral or patent document 1 ~ 3, find it is shocking can provide a kind of take care of in acid condition after also keep stronger lemon sense, feeling of freshness, produce foreign odor hardly, the flavor compositions of the fragrance of the citral sample with natural natural sense can be given and coordinated diet product, the perfuming cosmetic of this flavor compositions, so that complete the present invention.
Unexposedly up to now anyly mixing 4 can be passed through, 8-dimethyl-3, 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate and 4, 8-dimethyl-3, 3 kinds of 7-nonadiene-2-ketone manufacture and have high ageing stability, and there is the lemon sense of the citral sample stronger than prior art, the record of fraicheur flavor compositions, moreover, also not mentioned can be manufactured by the 3 kinds of compounds mixed with specific ratio in acid condition take care of after also keep stronger lemon sense, feeling of freshness, produce foreign odor hardly, the record of the flavor compositions of the fragrance of the citral sample with natural natural sense can be given.
(1) the present invention is flavor compositions, it is characterized in that, contains relative to 4,1 of 8-dimethyl-3,7-nonadiene-2-alcohol, with 4,8-dimethyl-3,7-nonadiene-2-yl acetate 0.02 ~ 0.4,4,8-dimethyl-3, ratio mixing 4,8-dimethyl-3, the 7-nonadiene-2-alcohol, 4 of 7-nonadiene-2-ketone 0.04 ~ 0.8,8-dimethyl-3, the material of the compound of 3 kinds of 7-nonadiene-2-yl acetate, 4,8-dimethyl-3,7-nonadiene-2-ketone.
(2) and then, the present invention is diet product or perfuming cosmetic, it is characterized in that, has coordinated the flavor compositions of above-mentioned (1).
Invention effect
Flavor compositions of the present invention is by being matched with diet product, perfuming cosmetic, can manufacture compared with prior art, can nature be given and there is lemon sense, the feeling of freshness of the citral sample of natural sense, and compared with the flavor compositions containing citral with similar aroma characteristic, diet product, perfuming cosmetic that the generation of time dependent foreign odor is reduced.
detailed description of the invention
Below, the present invention is described in detail.
(1) flavor compositions
The present invention is flavor compositions, it is characterized in that, contains
Formula (1)
(in formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary proportion mixture)
4,8-dimethyl-3, the 7-nonadiene-2-alcohol represented,
Formula (2)
(in formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary ratio mixture, and Ac represents acetyl group)
Represent 4,8-dimethyl-3,7-nonadiene-2-yl acetates and
Formula (3)
(in formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary ratio mixture)
3 kinds of compounds of 4,8-dimethyl-3, the 7-nonadiene-2-ketone represented.
4,8-dimethyl-3, the 7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates and 4,8-dimethyl-3, the 7-nonadiene-2-ketone that use in the present invention all can synthesize by utilizing the method for known document.
4,8-dimethyl-3,7-nonadiene-2-alcohol such as following reaction equation represents, can make citral carry out grignard reaction to obtain (Agarwal et al. by utilizing chloromethyl magnesium (MeMgCl); Indian Perfum., 27,112-118 (1983)).
4,8-dimethyl-3,7-nonadiene-2-yl acetate, can by utilizing acetic anhydride (Ac such as following reaction equation represents
2o) and pyridine (Pyr.) make the acetylation of 4,8-dimethyl-3,7-nonadiene-2-alcohol obtain (Agarwal et al.; IndianPerfum., 27,112-118 (1983)).
4,8-dimethyl-3,7-nonadiene-2-ketone is such as following reaction equation represents, by utilizing pyridine-chromium trioxide complex compound (Pyr.-CrO
3) make 4,8-dimethyl-3,7-nonadiene-2-alcohol carry out Sa Leite oxidation obtain (Agarwal et al.; Indian Perfum., 27,112-118 (1983)).
But the synthetic method of 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,8-dimethyl-3,7-nonadiene-2-yl acetate and 4,8-dimethyl-3,7-nonadiene-2-ketone is not limited to these methods.
Using as 4 of active ingredient of the present invention, 8-dimethyl-3, 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate and 4, 8-dimethyl-3, when 7-nonadiene-2-ketone is used for flavor compositions, the mixed proportion of these 3 kinds of compounds, relative to 4, 8-dimethyl-3, 1 of 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate is 0.02 ~ 0.4, 4, 8-dimethyl-3, 7-nonadiene-2-ketone is 0.04 ~ 0.8, preferably relative to 4, 8-dimethyl-3, 1 of 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate is 0.04 ~ 0.2, 4, 8-dimethyl-3, 7-nonadiene-2-ketone is 0.08 ~ 0.4.
Although the total addition of 3 kinds of compounds is different from the kind of its object or flavor compositions, but 0.000000001 quality % (10ppt) ~ 10 quality % of flavor compositions entire amount generally speaking, can be illustrated, preferably in the scope of 0.000001 quality % (10ppb) ~ 5 quality %.
As other composition joined together in flavor compositions of the present invention, be not particularly limited, the various spices materials of existing use can be used according to purposes and object, specifically, can enumerate: the existing known spices materials such as aldehydes, alcohols, ester class.
In addition, the fitting method as flavor compositions is also not particularly limited, and can enumerate the method for such as a kind of spices material of each cooperation, such as cooperation is pre-mixed the existing known fitting methods such as the method for the material of some spices materials in addition.
(2) application of flavor compositions
Flavor compositions of the present invention by making an addition to the tea beverage of (a) green tea, black tea, oolong tea etc., as the beverage class of fruit nectar, drinks, milk beverage class, soda class and so on; B () is as the frozen food class of ice cream, ice cream class, rock sugar class and so on; C () is as the fermented dairy product of yogurt class, cheese class and so on; D () is as the hobby category of Chinese and Western snack categories, baking snack categories, jam, rubber carbohydrate, Bread and Pastries, cocoa, coffee, tea, cigarette and so on; E () such as cloth class D, jellies, Bava reveals the Dessert of this class, mousse class and so on; F () is as the soup class of Japanese soup class, Western-style soup class and so on; (g) flavoring; H () various instant beverage and foodstuff, various fast food classes etc., can provide and impart nature and the diet product with the fragrance fragrance of the citral sample of natural sense.
In addition, flavor compositions of the present invention can be widely used in shampoo class, hair cream class, pomade class, other Hair grooming cosmetics, face powder, lipstick, other cosmetics, washing cleaning agent, sterilization cleaning agent class, space deodorant other the perfuming cosmetic such as various health hygienic material types, pharmaceuticals all.
The addition of flavor compositions of the present invention in diet product or perfuming cosmetic is also different from the kind of diet product, perfuming cosmetic, but generally speaking, if with 4 in diet product or perfuming cosmetic, 8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetate and 4,8-dimethyl-3, the total concentration of 3 kinds of compounds of 7-nonadiene-2-ketone is that the mode of 0.000000000001 quality % (0.01ppt) ~ 0.05 quality % is added, then can give nature to diet product, perfuming cosmetic and have the fragrance fragrance of the citral sample of natural sense.
Embodiment
Then, illustrate that embodiment is described further particularly to the present invention, but the present invention does not limit these embodiments therewith.
(synthesis example of spices)
The synthesis of (1) 4,8-dimethyl-3,7-nonadiene-2-alcohol
Under nitrogen flowing, in oxolane 200ml, add methyl-magnesium-chloride (3M tetrahydrofuran solution) 100ml, after being cooled to-5 DEG C, at-10 DEG C ~ 0 DEG C, drip citral 43.5g through 30 minutes.
React after 1 hour at-10 DEG C ~ 0 DEG C, reaction solution is joined in 10% aqueous ammonium chloride solution 500ml at 0 ~ 10 DEG C, extracts with heptane 90g.After heptane layer saturated sodium bicarbonate water, brine It, with anhydrous sodium sulfate drying, with rotary evaporator distillation removing heptane, obtain thick oily 53g.
By by thick oily simple distillation, obtain 4,8-dimethyl-3,7-nonadiene-2-alcohol 45g of GC purity 99.0%.(boiling point: 59 ~ 63 DEG C/70Pa)
The synthesis of (2) 4,8-dimethyl-3,7-nonadiene-2-yl acetates
In 4,8-dimethyl-3,7-nonadiene-2-alcohol 25g, add sodium acetate 5g, after being warming up to 65 DEG C, drip acetic anhydride 59g at 60 ~ 70 DEG C through 10 minutes.
After 3 hours 60 ~ 70 DEG C of reactions, reaction solution is cooled to 40 DEG C, joins in water 150g at 0 ~ 10 DEG C, extract with heptane 50g.After heptane layer water, 5% anhydrous V Soda solution washing, with anhydrous sodium sulfate drying, with rotary evaporator distillation removing heptane, obtain thick oily 31g.
By by thick oily simple distillation, obtain 4,8-dimethyl-3,7-nonadiene-2-yl acetate 30g of GC purity 99.1%.(boiling point: 71 DEG C/80Pa)
The synthesis of (3) 4,8-dimethyl-3,7-nonadiene-2-ketone
In 4,8-dimethyl-3,7-nonadiene-2-alcohol 2g, add acetonitrile 130g, N-methylmorpholine-N-oxide 2.9g, molecular sieve 4A4.6g, after being cooled to-10 DEG C, adding tetrapropyl height ruthenic acid ammonium 125mg, be returned to room temperature and stir 2 hours.
Reaction solution is joined in 5% sodium thiosulfate solution, extract with heptane 50g.After heptane layer 3% aqueous hydrochloric acid solution, brine It, with anhydrous sodium sulfate drying, with rotary evaporator distillation removing heptane, obtain thick oily 2.1g.
Utilized by thick oil silica gel column chromatography (hexane: ethyl acetate=19:1) carry out refining and carry out simple distillation, obtain 4,8-dimethyl-3,7-nonadiene-2-ketone 1.3g of GC purity 99.7% thus.(boiling point: 67 DEG C/70Pa)
(embodiment 1 and comparative example 1 ~ 4) (lemon flavor)
Common method is utilized to obtain flavor compositions No.1 of the present invention according to following prescription.In addition, as comparative example 1 ~ 4, be changed flavor compositions No.2 ~ 5 of mixing ratio of 4,8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates, 4,8-dimethyl-3,7-nonadiene-2-ketone.
[table 1]
Table 1 flavor compositions (No.1 ~ 5)
The mixing ratio of 4,8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates and 4,8-dimethyl-3,7-nonadiene-2-ketone in the flavor compositions obtained (No.1 ~ 5) is shown in table 2.
[table 2]
Active ingredient mixing ratio in table 2 flavor compositions (No.1 ~ 5)
That is, in flavor compositions No.1 be following flavor compositions: of the present invention, 4,8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates and 4, the mixed proportion of 8-dimethyl-3,7-nonadiene-2-ketone is relative to 4,1,4 of 8-dimethyl-3,7-nonadiene-2-alcohol, 8-dimethyl-3,7-nonadiene-2-yl acetate is 0.02 ~ 0.4,4,8-dimethyl-3,7-nonadiene-2-ketone is in the scope of 0.04 ~ 0.8.
On the other hand, flavor compositions No.2 is 4, 8-dimethyl-3, the flavor compositions that the mixing ratio of 7-nonadiene-2-yl acetate is lower than mixing ratio of the present invention, flavor compositions No.3 is 4, 8-dimethyl-3, the flavor compositions that the mixing ratio of 7-nonadiene-2-yl acetate is higher than mixing ratio of the present invention, flavor compositions No.4 is 4, 8-dimethyl-3, the flavor compositions that the mixing ratio of 7-nonadiene-2-ketone is lower than mixing ratio of the present invention, flavor compositions No.5 is 4, 8-dimethyl-3, the flavor compositions that the mixing ratio of 7-nonadiene-2-ketone is higher than mixing ratio of the present invention.
(comparative example 5 ~ 8)
According to the invention of patent document 1 and 2, utilize the prescription of following expression, obtain flavor compositions No.6 (comparative example 5), according to the invention of patent document 3, coordinate 2, 4, 8-trimethyl-7-nonene-2-alcohol replaces 4 of embodiment 1, 8-dimethyl-3, 7-nonadiene-2-ketone, obtain flavor compositions No.7 (comparative example 6), citral is coordinated to replace 4 of embodiment 1, 8-dimethyl-3, 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate, 4, 8-dimethyl-3, 7-nonadiene-2-ketone, obtain flavor compositions No.8 (comparative example 7), ethanol is coordinated to replace 4 of embodiment 1, 8-dimethyl-3, 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate, 4, 8-dimethyl-37-nonadiene-2-ketone, obtain flavor compositions No.9 (comparative example 8).
[table 3]
Table 3 flavor compositions (No.6 ~ 9)
The mean value of the result of being carried out the fragrance fragrance of the flavor compositions (No.1 ~ 9) of the embodiment 1 and comparative example 1 ~ 8 obtained by 10 professional evaluation groups based on following metewand is shown in table 4, the explanation obtained when evaluating is shown in table 5.
Fragrance fragrance metewand; Very strong feels: 5
Feel by force: 4
Feel: 3
Feel: 2 slightly weakly
Feel: 1 very weakly
[table 4]
The mean value of the fragrance fragrance evaluation result of the flavor compositions (No.1 ~ 9) of table 4 embodiment 1 and comparative example 1 ~ 8
[table 5]
The fragrance fragrance evaluation explanation of the flavor compositions (No.1 ~ 9) of table 5 embodiment 1 and comparative example 1 ~ 8
< result >
The flavor compositions No.1 of the embodiments of the invention 1 and flavor compositions No.8 of comparative example 7 has the fragrance having stronger lemon sense, feeling of freshness, natural natural sense.
On the other hand, 4, 8-dimethyl-3, 7-nonadiene-2-alcohol and 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate and 4, 8-dimethyl-3, the mixed proportion of 7-nonadiene-2-ketone, relative to 4, 8-dimethyl-3, 1 of 7-nonadiene-2-alcohol, 4, 8-dimethyl-3, 7-nonadiene-2-yl acetate is 0.02 ~ 0.4, 4, 8-dimethyl-3, 7-nonadiene-2-ketone becomes following evaluation result at the flavor compositions (No.2 ~ No.7 and No.9) of the extraneous comparative example 1 ~ 6 and 8 of 0.04 ~ 0.8: all feel the fragrance of chlorine sample sense, metal sense, the fragrance that pungent etc. are different compared with embodiment 1, or lack lemon sense, natural sense.
(embodiment 2) (lemon beverage (pH=3))
According to following prescription, obtain lemon beverage 1 (pH=3) of the present invention according to common method.
[table 6]
Table 6 lemon beverage 1(pH=3)
(comparative example 9 ~ 11)
Coordinate flavor compositions No.6 ~ 8 to replace the flavor compositions No.1 of embodiment 2 respectively, obtain lemon beverage (pH=3) 2 ~ 4.
(test example 1)
The lemon beverage obtained (pH=3) 1 ~ 4 is filled in respectively the transparent polyester bottle container of 350mL, 70 DEG C of sterilizations after 10 minutes, 50 DEG C of keepings 10 days.The mean value of the result of the evaluation of the fragrance fragrance of the lemon beverage (pH=3) after the professional evaluation group by 10 is carried out keeping based on following metewand is shown in table 7, the explanation obtained when evaluating is shown in table 8.
Fragrance fragrance metewand; Very strong feels: 5
Feel by force: 4
Feel: 3
Feel: 2 slightly weakly
Feel: 1 very weakly
[table 7]
The mean value of the fragrance fragrance evaluation result of the lemon beverage (pH=3) after table 7 keeping
| Implementation content | Lemon sense | Natural sense | Feeling of freshness | Deterioration is smelly |
| Lemon beverage 1 | 3.3 | 3.3 | 2.4 | 1.2 |
| Lemon beverage 2 | 2.4 | 2.1 | 1.9 | 1.7 |
| Lemon beverage 3 | 2.6 | 2.9 | 1.9 | 1.7 |
| Lemon beverage 4 | 1.2 | 1.2 | 1.7 | 2.9 |
[table 8]
The fragrance fragrance evaluation explanation of the lemon beverage (pH=3) after table 8 keeping
| Implementation content | Explanation |
| Lemon beverage 1 | Have lemon sense, natural sense, foreign odor is few |
| Lemon beverage 2 | Slightly there is lemon sense, but lack natural sense, slightly feel foreign odor |
| Lemon beverage 3 | Slightly there is lemon sense, natural sense, but slightly feel foreign odor |
| Lemon beverage 4 | There is foreign odor, lack lemon sense, natural sense and feeling of freshness |
< result >
Lemon beverage 1 of the present invention also has the fresh fragrance having lemon sense, natural sense after 10 days 50 DEG C of keepings, compared with lemon beverage 2 ~ 4, the sensation of foreign odor reduces.
(embodiment 3) (grape fruit local flavor)
According to following prescription, common method is utilized to obtain flavor compositions No.10 of the present invention.
[table 9]
Table 9 flavor compositions No.10
(comparative example 12)
Coordinate ethanol to replace 4,8-dimethyl-3,7-nonadiene-2-alcohol of embodiment 3 and 4,8-dimethyl-3,7-nonadiene-2-yl acetate and 4,8-dimethyl-37-nonadiene-2-ketone, obtain flavor compositions No.11.
(embodiment 4, comparative example 13)
According to following prescription, common method is utilized to obtain grape fruit beverage 1 of the present invention and the grape fruit beverage 2 as comparison other.
[table 10] grape fruit beverage (1,2)
(test example 2)
By 10 professional evaluation groups to grape fruit beverage 1 of the present invention and the 2 comparative evaluation fragrance fragrance as comparison other.The fragrance fragrance evaluation result that it is average is shown in table 11.
[table 11]
Table 11 grape fruit beverage 1,2 fragrance fragrance evaluation result
| Implementation content | Fragrance fragrance is evaluated |
| Grape fruit beverage 1 | Compared with the control, natural sense, feeling of freshness increase |
| Grape fruit beverage 2 | Contrast |
(embodiment 5) (citrus flavors)
According to following prescription, common method is utilized to obtain flavor compositions No.12 of the present invention.
[table 12]
Table 12 flavor compositions No.12
(comparative example 14)
Coordinate ethanol to replace 4,8-dimethyl-3,7-nonadiene-2-alcohol of embodiment 5 and 4,8-dimethyl-3,7-nonadiene-2-yl acetate and 4,8-dimethyl-37-nonadiene-2-ketone, obtain flavor compositions No.13.
(embodiment 6, comparative example 15)
According to following prescription, common method is utilized to obtain orange beverage 1 of the present invention and the orange beverage 2 as comparison other.
[table 13]
Table 13 orange beverage (1,2)
(test example 3)
By 10 professional evaluation groups to orange beverage 1 of the present invention and the 2 comparative evaluation fragrance fragrance as comparison other.The fragrance fragrance evaluation result that it is average is shown in table 14.
[table 14]
Table 14 orange beverage 1,2 fragrance fragrance evaluation result
| Implementation content | Fragrance fragrance is evaluated |
| Orange beverage 1 | Compared with the control, the fluffy sense at natural sense, top increases |
| Orange beverage 2 | Contrast |
(embodiment 7)
According to following prescription, common method is utilized to prepare flavor compositions No.14 of the present invention.
[table 15]
Table 15 flavor compositions No.14
(comparative example 16)
Citrene is coordinated to replace 4,8-dimethyl-3, the 7-nonadiene-2-alcohol and 4 of embodiment 7,8-dimethyl-3,7-nonadiene-2-yl acetate and 4,8-dimethyl-3,7-nonadiene-2-ketone, in addition, prepares flavor compositions No.15 by same prescription and method.
(embodiment 8, comparative example 17)
According to following prescription, common method is utilized to obtain shampoo 1 of the present invention and the shampoo 2 as comparison other.
[table 16]
Table 16 shampoo 1,2 fragrance evaluation result
［ test example 4 ］
By 10 professional evaluation groups to shampoo 1 of the present invention and the shampoo 2 comparative evaluation fragrance as comparison other.The fragrance evaluation result that it is average is shown in table 17.
[table 17]
Table 17 shampoo 1,2 fragrance evaluation result
| Implementation content | Fragrance is evaluated |
| Shampoo 1 | Compared with the control, there is natural sense, fresh fragrance emission and intensity enhancing |
| Shampoo 2 | Contrast |
Utilizability in industry
By with the specific ratio in the present invention by 4,8-dimethyl-3,7-nonadiene-2-alcohol and 4,8-dimethyl-3,3 kinds of compounds of 7-nonadiene-2-yl acetate and 4,8-dimethyl-3,7-nonadiene-2-ketone make an addition to flavor compositions, can manufacture compared with the flavor compositions containing citral with similar aroma characteristic, the perfuming cosmetic of the flavor compositions that the generation of foreign odor is by the time reduced, fruit drink, diet product and shampoo etc.
In addition, lemon sense, the feeling of freshness of natural natural sense and citral sample can be given to these goods.
Claims (4)
1. flavor compositions, it is characterized in that, material containing following 3 kinds of compounds: relative to 4,8-dimethyl-3,1 of 7-nonadiene-2-alcohol, with 4,8-dimethyl-3,7-nonadiene-2-yl acetate 0.02 ~ 0.4,4,4, the 8-dimethyl-3 that the ratio hybrid (1) of 8-dimethyl-3,7-nonadiene-2-ketone 0.04 ~ 0.8 represents, 7-nonadiene-2-alcohol, formula (2) represent 4,4, the 8-dimethyl-3 that 8-dimethyl-3,7-nonadiene-2-yl acetate and formula (3) represent, 7-nonadiene-2-ketone
In formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary ratio mixture,
In formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary ratio mixture, and Ac represents acetyl group,
In formula, the key table of wave-like line shows cis or trans or cis and trans arbitrary ratio mixture.
2. diet product, is characterized in that, have coordinated flavor compositions according to claim 1.
3. perfuming cosmetic, is characterized in that, has coordinated flavor compositions according to claim 1.
4. pair diet product or perfuming cosmetic give the method for the fragrance fragrance of citral sample, it is characterized in that, with 4 in diet product or perfuming cosmetic, 8-dimethyl-3,7-nonadiene-2-alcohol, 4,8-dimethyl-3,7-nonadiene-2-yl acetates and 4, the total concentration of 3 kinds of compounds of 8-dimethyl-3,7-nonadiene-2-ketone is that the mode of 0.000000000001 quality % (0.01ppt) ~ 0.05 quality % adds flavor compositions according to claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011017800A JP5027937B2 (en) | 2011-01-31 | 2011-01-31 | Fragrance composition |
| JP2011-017800 | 2011-01-31 | ||
| PCT/JP2012/051759 WO2012105430A1 (en) | 2011-01-31 | 2012-01-27 | Perfume composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103314092A CN103314092A (en) | 2013-09-18 |
| CN103314092B true CN103314092B (en) | 2015-03-25 |
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| CN201280005064.XA Active CN103314092B (en) | 2011-01-31 | 2012-01-27 | Perfume composition |
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| Country | Link |
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| JP (1) | JP5027937B2 (en) |
| KR (1) | KR101711246B1 (en) |
| CN (1) | CN103314092B (en) |
| MY (1) | MY162942A (en) |
| SG (1) | SG192194A1 (en) |
| WO (1) | WO2012105430A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014114733A1 (en) * | 2013-01-25 | 2014-07-31 | Basf Se | Use of 4,8-dimethyl-3,7-nonadien-2-ol as perfume |
| JP6600116B1 (en) * | 2019-07-19 | 2019-10-30 | 高砂香料工業株式会社 | Fragrance composition |
| JP7258449B2 (en) * | 2021-03-19 | 2023-04-17 | 長谷川香料株式会社 | Compound and flavor imparting composition using the same |
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| CN1387407A (en) * | 1999-12-16 | 2002-12-25 | 哈尔曼及赖默股份有限公司 | Aromas and aromas compositions contg. 4,8-dimethy-3,7-nonadien-2-one, and method for production thereof |
| EP1417896A1 (en) * | 2002-11-08 | 2004-05-12 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Fruit, berry, cranberry and hedonically-stable citrus flavored compositions and process for preparing same |
| CN101495000A (en) * | 2006-07-28 | 2009-07-29 | 吉万奥丹股份有限公司 | Organic compounds and methods |
| CN101522052A (en) * | 2006-10-13 | 2009-09-02 | 小川香料株式会社 | Perfume composition |
| CN101743296A (en) * | 2007-07-13 | 2010-06-16 | 小川香料株式会社 | Degradation inhibitor for flavor or aroma |
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| US5707961A (en) * | 1995-05-16 | 1998-01-13 | Givaudan-Roure (International) Sa | Odorant compounds and compositions |
| DE19961598A1 (en) * | 1999-12-21 | 2001-07-05 | Haarmann & Reimer Gmbh | Perfume composition containing 4,8-dimethyl-3,7-nonadien-2-one |
| JP2006020526A (en) * | 2004-07-06 | 2006-01-26 | Kiyomitsu Kawasaki | Coffee flavor composition, and food and drink containing the same |
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2011
- 2011-01-31 JP JP2011017800A patent/JP5027937B2/en active Active
-
2012
- 2012-01-27 MY MYPI2013701304A patent/MY162942A/en unknown
- 2012-01-27 WO PCT/JP2012/051759 patent/WO2012105430A1/en active Application Filing
- 2012-01-27 KR KR1020137022891A patent/KR101711246B1/en active IP Right Grant
- 2012-01-27 CN CN201280005064.XA patent/CN103314092B/en active Active
- 2012-01-27 SG SG2013057500A patent/SG192194A1/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1387407A (en) * | 1999-12-16 | 2002-12-25 | 哈尔曼及赖默股份有限公司 | Aromas and aromas compositions contg. 4,8-dimethy-3,7-nonadien-2-one, and method for production thereof |
| EP1417896A1 (en) * | 2002-11-08 | 2004-05-12 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Fruit, berry, cranberry and hedonically-stable citrus flavored compositions and process for preparing same |
| CN101495000A (en) * | 2006-07-28 | 2009-07-29 | 吉万奥丹股份有限公司 | Organic compounds and methods |
| CN101522052A (en) * | 2006-10-13 | 2009-09-02 | 小川香料株式会社 | Perfume composition |
| CN101743296A (en) * | 2007-07-13 | 2010-06-16 | 小川香料株式会社 | Degradation inhibitor for flavor or aroma |
| CN101784509A (en) * | 2007-08-21 | 2010-07-21 | 奇华顿股份有限公司 | Cyclopropanation process |
Also Published As
| Publication number | Publication date |
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| KR20140007419A (en) | 2014-01-17 |
| CN103314092A (en) | 2013-09-18 |
| MY162942A (en) | 2017-07-31 |
| SG192194A1 (en) | 2013-09-30 |
| JP5027937B2 (en) | 2012-09-19 |
| JP2012158647A (en) | 2012-08-23 |
| KR101711246B1 (en) | 2017-02-28 |
| WO2012105430A1 (en) | 2012-08-09 |
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