CN113403141A - Cool base with flower and fruit fragrance and preparation method thereof - Google Patents

Cool base with flower and fruit fragrance and preparation method thereof Download PDF

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Publication number
CN113403141A
CN113403141A CN202110629764.7A CN202110629764A CN113403141A CN 113403141 A CN113403141 A CN 113403141A CN 202110629764 A CN202110629764 A CN 202110629764A CN 113403141 A CN113403141 A CN 113403141A
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base
fenchone
flower
fragrance
cool
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CN113403141B (en
Inventor
易封萍
朱万璋
俞根发
吴恺文
张松幸
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Shanghai Rong Fang Flavor And Fragrance Co ltd
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Shanghai Institute of Technology
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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
    • 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
    • C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
    • 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
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
    • 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
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

The invention discloses a cool base with flower and fruit fragrance and a preparation method thereof. The cool fragrant base with flower and fruit fragrance comprises 50-95% of base fragrant base and 5-50% of fenchone glycol ketal ethanol solution in percentage by mass; the base essence base comprises, by mass, 2-6% of geraniol, 0-1% of cyclamen aldehyde, 10-35% of methyl dihydrojasmonate, 5-15% of malthate, 2-8% of limonene, 0-2% of citral, 0-0.5% of ethyl acetate, 3-5% of methyl hexyl cinnamaldehyde and the balance of solvent. The invention applies the novel cool spice fenchone glycol ketal into the fragrance base, prepares the fragrance base with flower and fruit fragrance and cool according to proper adding proportion, and the fragrance base has harmonious fragrance. The perfume has practical applicability, and can be used as a novel perfume in the perfume and essence industry.

Description

Cool base with flower and fruit fragrance and preparation method thereof
Technical Field
The invention relates to a cool base with flower and fruit fragrance and a preparation method thereof, belonging to the technical field of spices.
Background
The perfume is a general term for volatile aromatic substances which can be used for preparing essence, and is divided into natural perfume and artificial perfume, and is used for manufacturing and perfuming light industrial products such as cosmetics and food. Fenchone is a colorless to pale yellow oily liquid with strong sweet, green and woody aroma with fresh and fruity aroma. Fenchone glycol ketal is a novel fragrance compound having the following chemical formula:
Figure BDA0003103225630000011
it has a special cool fragrance like camphor, has fruity, green and woody fragrance, and is considered to be a novel cool fragrance of great value. However, this new type of perfume has not been applied to actual perfumery.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the problem of development and utilization of fenchone glycol ketal as a perfume.
In order to solve the technical problem, the invention provides a cool fragrant base with flower and fruit fragrance, which comprises 50-95% of base fragrant base and 5-50% of fenchone glycol ketal ethanol solution in percentage by mass; the base essence base comprises, by mass, 2-6% of geraniol, 0-1% of cyclamen aldehyde, 10-35% of methyl dihydrojasmonate, 5-15% of malthate, 2-8% of limonene, 0-2% of citral, 0-0.5% of ethyl acetate, 3-5% of methyl hexyl cinnamaldehyde and the balance of solvent.
Preferably, the fenchone glycol ketal concentration in the ethanol solution of fenchone glycol ketal is 0.125-1 wt%.
Preferably, the solvent is at least one of ethanol, propylene glycol, glycerol, caprylic capric glyceride and triethyl citrate.
The invention also provides a preparation method of the cool fragrant base with flower and fruit fragrance, which comprises the following steps:
step 1): drawing up a basic perfume formula, and determining the sequence and the addition amount of the perfume;
step 2): adding spice and solvent into the same beaker in sequence, stirring and standing to obtain a basic essence base with flower and fruit fragrance;
step 3): dissolving fenchone ethylene glycol ketal in ethanol to prepare a fenchone ethylene glycol ketal ethanol solution; adding the prepared fenchone glycol ketal ethanol solution into the basic essence base obtained in the step 2), and obtaining the essence base with flower and fruit fragrance and cool feeling.
Preferably, the adding sequence of the perfume in the step 2) is determined according to the adding amount of the perfume in the formula, the adding is performed in the order of the adding amount from small to large, and finally the solvent is added.
Preferably, the stirring temperature in the step 2) is less than 30 ℃, the stirring speed is 300-500rpm, and the stirring time is 10-30 min; the standing time in the step 2) is 30-120min, and the standing temperature is less than 30 ℃.
Preferably, the concentration and the addition amount of the fenchone ethylene ketal ethanol solution in the step 3) are determined by the following method: firstly, using ethanol to dilute fenchone ethylene ketal according to a 2-fold dilution method gradient until the mass concentration is 1/2-1/210Inviting 10 professionally trained sensory evaluators to sniff the dilution to determine a threshold; then, the fenchone glycol ketal dilutions were added to the base at the threshold and 4 dilutions prior to the threshold in different proportions to prepare mixed solutions, and 10 trained sensory evaluators were invited to sniff the mixed solutions to determine the amount of fenchone glycol ketal in ethanol added to the base.
More preferably, the method for determining the threshold value is as follows: the three-point test method is adopted, and 9 persons in the sensory evaluator deem that the former dilution concentration is the threshold concentration when the fragrance cannot be smelled.
More preferably, the mixed solution comprises a mixed solution prepared by adding fenchone ethylene glycol ketal diluted solutions with the threshold value and 4 diluted concentrations before the threshold value into 1mL of the basic incense base respectively in the mass ratio of 1:1-1: 15.
More preferably, the mixture is aged by standing at a temperature lower than room temperature for 1-5 days before smelling.
Compared with the prior art, the invention has the beneficial effects that:
1. the novel cool flavor fenchone glycol ketal provided by the invention is used as a novel flavor, has special cool feeling and flower and fruit fragrance, but is not yet applied in practice, and the preparation method of the cool flavor base with flower and fruit fragrance provided by the invention has universality, so that the flavor is proved to have practical applicability and can be used as a novel flavor in the flavor and fragrance industry;
2. the cool incense base with flower and fruit fragrance has certain representativeness, has the characteristic flower and fruit fragrance and cool feeling after being properly blended, and can be applied as an experimental incense base with universality.
Detailed Description
In order to make the invention more comprehensible, preferred embodiments are described in detail below.
Example 1
A preparation method of a cool fragrant base with flower and fruit fragrance comprises the following steps:
step 1: the formula of the basic essence base is drawn up, wherein the basic essence base with flower and fruit fragrance comprises, by mass, 4.5% of geraniol, 0.05% of cyclamen, 23% of methyl dihydrojasmonate, 8.5% of malolacte, 2.3% of limonene, 0.5% of citral, 0.02% of ethyl acetate, 4.85% of methyl hexyl cinnamaldehyde and the balance of ethanol;
step 2: according to the formulated basic perfume formula, sequentially adding perfume into the same beaker according to the sequence of the mass fractions from small to large, finally adding a solvent, and stirring for 30min at the temperature of 25 ℃ and the rpm of 300; standing for 20min to obtain basic essence.
And step 3: preparing a 1 wt% solution of fenchone ethylene ketal in ethanol by diluting fenchone ethylene ketal in ethanol; adding the prepared fenchone glycol ketal ethanol solution into the basic incense base according to the mass ratio of 1:15, and aging for 1 day to obtain the cool incense base with flower and fruit fragrance; the resulting scent base was sniffed by 10 professionally trained sensory evaluators and their descriptions of the scent were recorded. Among sensory evaluators, 7 persons considered that fenchone glycol ketal characteristic aroma could be smelled, and compared with the base aroma in step 2, the fenchone glycol ketal characteristic aroma was clearly distinguished, and the aroma was harmonious.
Example 2
A preparation method of a cool fragrant base with flower and fruit fragrance comprises the following steps:
step 1: the formula of the basic perfume base is drawn up: a basic essence base with flower and fruit fragrance comprises, by mass, 3.5% of geraniol, 0.25% of cyclamen aldehyde, 20% of methyl dihydrojasmonate, 6.5% of fructone, 2% of limonene, 0.05% of citral, 0.05% of ethyl acetate, 3.5% of methyl hexyl cinnamaldehyde and the balance of propylene glycol.
Step 2: according to the formulated basic perfume formula, sequentially adding perfume into the same beaker according to the sequence of the mass fractions from small to large, finally adding a solvent, and stirring for 10min at 25 ℃ and 500 rpm; standing for 60min to obtain basic essence.
And step 3: preparing a 0.5 wt% solution of fenchone glycol ketal in ethanol by diluting fenchone glycol ketal; adding the prepared fenchone glycol ketal ethanol solution into the basic incense base according to the mass ratio of 1:7, and aging for 1 day to obtain the cool incense base with flower and fruit fragrance; the resulting scent base was sniffed by 10 professionally trained sensory evaluators and their descriptions of the scent were recorded. 8 of the sensory evaluators considered that the characteristic fragrance of fenchone glycol ketal could be smelled, was distinguishable from the base fragrance in step 2, had a distinct cool fragrance characteristic, and had a harmonious fragrance.
Example 3
Determination of the diluted concentration and addition proportion of fenchone glycol in the cool fragrant base formula with flower and fruit fragrance:
step 1: performing gradient dilution on fenchone ethylene ketal by using ethanol according to a 2-fold dilution method until the mass concentration is 1/2-1/210And inviting 10 specially trained sensory evaluators to smell the diluent, and determining a threshold value by adopting a three-point test method, wherein 9 of the sensory evaluators deem that the former diluent concentration is the threshold concentration when people cannot smell the aroma. The threshold value of fenchone glycol ketal in ethanol was determined to be 1/2 by sniffing with an organoleptic evaluator4(0.0625wt％)；
Step 2: the fenchone glycol ketal diluent comprises 5 groups of diluents with the concentration as the threshold value and 4 diluent concentrations before the threshold value, and the diluents are added into 1mL of the base incense base in the example 1 at a gradient addition ratio of 1:1-1:15, and 10 specially trained sensory evaluators are invited to smell the mixture to determine the addition ratio of the fenchone glycol ketal in the incense base, and the results are shown in Table 1.
TABLE 1 fragrance evaluation results of various fenchone glycol ketal dilution concentrations and addition ratios in the fragrance group
Figure BDA0003103225630000041
Figure BDA0003103225630000051
As can be seen from the results in Table 1, when the fenchone glycol ketal diluted solution is used for preparing a fragrance base, the appropriate concentration of the fenchone glycol ketal in ethanol is 0.125 to 1 wt%, and since the addition ratio can be in a wide range according to actual needs at this diluted concentration, when the fenchone glycol ketal diluted solution is added to the fragrance base in a mass ratio of 1:1 to 1:15, an appropriate and harmonious fragrance can be obtained. From the data in table 1, a suitable concentration of fenchone glycol ketal in the fragrance base is 0.0625 wt% which matches the threshold concentration determined in step 2.
Comparative example 1
A2-fold threshold concentration (i.e., 0.125 wt%) fenchone glycol ketal ethanol dilution was prepared according to example 3, step 2, and mixed with the fragrance base of example 1 at a mass ratio of 1:5 and aged for 1 day to obtain a fragrance base containing fenchone glycol ketal. 10 sensory evaluators were invited to sniff and their descriptions of the aroma were recorded. The characteristic fragrance of fenchone glycol ketal was not smelled in the 3 position and no characteristic fragrance was observed in the 7 position, which is considered to be a significant change from the base fragrance described in example 1.
Comparative example 2
A fenchone glycol ketal ethanol dilution of 4 times the threshold concentration (i.e., 0.25 wt%) was prepared according to example 3, step 2, and mixed with the fragrance base of example 1 at a mass ratio of 1:1 and aged for 1 day to obtain a fragrance base containing fenchone glycol ketal. 10 sensory evaluators were invited to sniff and their descriptions of the aroma were recorded. The 8-position of the sensory evaluation person considered that the amount of fenchone glycol ketal added was too high, and the fragrance characteristic of the fragrance base described in example 1 was masked, and the fragrance was not consistent.
The above-described embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention in any way and substantially, it should be noted that those skilled in the art may make several modifications and additions without departing from the scope of the present invention, which should also be construed as a protection scope of the present invention.

Claims (10)

1. The cool fragrant base with flower and fruit fragrance is characterized by comprising 50-95% of base fragrant base and 5-50% of fenchone glycol ketal ethanol solution in percentage by mass; the base essence base comprises, by mass, 2-6% of geraniol, 0-1% of cyclamen aldehyde, 10-35% of methyl dihydrojasmonate, 5-15% of malthate, 2-8% of limonene, 0-2% of citral, 0-0.5% of ethyl acetate, 3-5% of methyl hexyl cinnamaldehyde and the balance of solvent.
2. The cool aroma base with flower-fruit aroma according to claim 1, wherein the concentration of fenchone glycol ketal in the ethanol solution of fenchone glycol ketal is 0.125-1 wt%.
3. The cool aroma base with flower and fruit aroma according to claim 1, wherein said solvent is at least one of ethanol, propylene glycol, glycerin, caprylic/capric glyceride and triethyl citrate.
4. The preparation method of the cool feeling flavor base with flower and fruit flavor as claimed in any one of claims 1 to 3, characterized by comprising the following steps:
step 1): drawing up a basic perfume formula, and determining the sequence and the addition amount of the perfume;
step 2): adding spice and solvent into the same beaker in sequence, stirring and standing to obtain a basic essence base with flower and fruit fragrance;
step 3): dissolving fenchone ethylene glycol ketal in ethanol to prepare a fenchone ethylene glycol ketal ethanol solution; adding the prepared fenchone glycol ketal ethanol solution into the basic essence base obtained in the step 2), and obtaining the essence base with flower and fruit fragrance and cool feeling.
5. The method for preparing a cool base with flower and fruit fragrance according to claim 4, wherein the adding order of the spices in the step 2) is determined according to the adding amount of the spices in the formula, the spices are added in the order of small adding amount to large adding amount, and finally the solvent is added.
6. The method for preparing cool incense base with flower and fruit aroma as claimed in claim 4, wherein the stirring temperature in step 2) is less than 30 ℃, the stirring speed is 300-500rpm, and the stirring time is 10-30 min; the standing time is 30-120min, and the standing temperature is less than 30 ℃.
7. The method for preparing a floral aroma base with flower and fruit aroma according to claim 4, wherein the concentration and the addition amount of the fenchone glycol ketal in ethanol in the step 3) are determined by the following method: firstly, using ethanol to dilute fenchone ethylene ketal according to a 2-fold dilution method gradient until the mass concentration is 1/2-1/210Inviting 10 professionally trained sensory evaluators to sniff the dilution to determine a threshold; then, the fenchone glycol ketal dilutions were added to the base at the threshold and 4 dilutions prior to the threshold in different proportions to prepare mixed solutions, and 10 trained sensory evaluators were invited to sniff the mixed solutions to determine the amount of fenchone glycol ketal in ethanol added to the base.
8. The method for preparing cool fragrant base with flower and fruit fragrance according to claim 7, wherein the threshold is determined by: the three-point test method is adopted, and 9 persons in the sensory evaluator deem that the former dilution concentration is the threshold concentration when the fragrance cannot be smelled.
9. The method according to claim 7, wherein the mixed solution comprises 1mL of the basic flavoring solution, and the fenchone glycol ketal dilutions with the threshold value and the first 4 dilution concentrations are added in the ratio of 1:1-1: 15.
10. The method for preparing a cool base with flower and fruit fragrance according to claim 7, wherein the mixed solution is aged by standing at a temperature lower than room temperature for 1-5 days before smelling.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB191126694A (en) * 1910-12-15 1912-05-02 Kurt Rulke A Process for the Manufacture of Solutions or Emulsions of Fenchone, and the Products Produced thereby.
JP2003137758A (en) * 2001-10-29 2003-05-14 Kiyomitsu Kawasaki Masking composition for hair cosmetic and hair cosmetic containing the same and method for masking hair cosmetic
US20070148283A1 (en) * 2005-12-23 2007-06-28 Cadbury Adams Usa Llc Compositions providing a sensation substantially similar to that provided by menthol
US20110117147A1 (en) * 2008-04-01 2011-05-19 Kenya Ishida Cooling sensation agent composition and sensory stimulation agent composition
CN106281680A (en) * 2016-08-27 2017-01-04 山东中烟工业有限责任公司 A kind of quick-fried pearl of Herba Menthae cigarette cool taste Mint Essence and preparation method and application
CN109342600A (en) * 2018-10-23 2019-02-15 陕西中医药大学 A kind of discrimination method in the fennel seeds place of production

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB191126694A (en) * 1910-12-15 1912-05-02 Kurt Rulke A Process for the Manufacture of Solutions or Emulsions of Fenchone, and the Products Produced thereby.
JP2003137758A (en) * 2001-10-29 2003-05-14 Kiyomitsu Kawasaki Masking composition for hair cosmetic and hair cosmetic containing the same and method for masking hair cosmetic
US20070148283A1 (en) * 2005-12-23 2007-06-28 Cadbury Adams Usa Llc Compositions providing a sensation substantially similar to that provided by menthol
US20110117147A1 (en) * 2008-04-01 2011-05-19 Kenya Ishida Cooling sensation agent composition and sensory stimulation agent composition
CN106281680A (en) * 2016-08-27 2017-01-04 山东中烟工业有限责任公司 A kind of quick-fried pearl of Herba Menthae cigarette cool taste Mint Essence and preparation method and application
CN109342600A (en) * 2018-10-23 2019-02-15 陕西中医药大学 A kind of discrimination method in the fennel seeds place of production

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
WILLIAM G. DAUBEN等: "Organic Reactions at High Pressure. Conversion of Cyclic Alkanones and Enones to 1,3-Dioxolanes1", 《J. ORG. CHEM》, vol. 51, 31 December 1986 (1986-12-31), pages 4964 - 4970 *
俞根发等: "食用香料化学课程思政教学初探", 《大学化学》, vol. 36, no. 3, 20 November 2020 (2020-11-20), pages 2008062 *
刘树文等: "《合成香料技术手册（第1版）》", 31 July 2000, 中国轻工业出版社, pages: 355 - 357 *

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