CN116574031A - Passion fruit aroma compound, preparation method thereof and passion fruit aroma essence - Google Patents
Passion fruit aroma compound, preparation method thereof and passion fruit aroma essence Download PDFInfo
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- CN116574031A CN116574031A CN202310506694.5A CN202310506694A CN116574031A CN 116574031 A CN116574031 A CN 116574031A CN 202310506694 A CN202310506694 A CN 202310506694A CN 116574031 A CN116574031 A CN 116574031A
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- 244000288157 Passiflora edulis Species 0.000 title claims abstract description 77
- 235000000370 Passiflora edulis Nutrition 0.000 title claims abstract description 77
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 123
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 54
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 46
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 34
- 238000010438 heat treatment Methods 0.000 claims description 19
- 239000005997 Calcium carbide Substances 0.000 claims description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 18
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 18
- 229950009195 phenylpropanol Drugs 0.000 claims description 18
- 239000002994 raw material Substances 0.000 claims description 18
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 18
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 claims description 18
- 229960000583 acetic acid Drugs 0.000 claims description 17
- 239000012362 glacial acetic acid Substances 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 14
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N ethyl (2r)-2-methylbutanoate Chemical compound CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 11
- BJLRAKFWOUAROE-UHFFFAOYSA-N 2500-83-6 Chemical compound C12C=CCC2C2CC(OC(=O)C)C1C2 BJLRAKFWOUAROE-UHFFFAOYSA-N 0.000 claims description 7
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 claims description 7
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 claims description 7
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 claims description 7
- 229940117948 caryophyllene Drugs 0.000 claims description 7
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 6
- RLCMQWBYWOIEGD-UHFFFAOYSA-N 2-aminobenzoyl chloride Chemical compound NC1=CC=CC=C1C(Cl)=O RLCMQWBYWOIEGD-UHFFFAOYSA-N 0.000 claims description 6
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims description 6
- QZIAWMREHPRQEK-UHFFFAOYSA-N 5-bromo-3-(2-nitroethenyl)-1h-indole Chemical compound C1=C(Br)C=C2C(C=C[N+](=O)[O-])=CNC2=C1 QZIAWMREHPRQEK-UHFFFAOYSA-N 0.000 claims description 6
- 235000004936 Bromus mango Nutrition 0.000 claims description 6
- MMLZNXCSNIVHLE-UHFFFAOYSA-N CC(O)=O.O=C1CC=CO1 Chemical compound CC(O)=O.O=C1CC=CO1 MMLZNXCSNIVHLE-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 235000019501 Lemon oil Nutrition 0.000 claims description 6
- 235000014826 Mangifera indica Nutrition 0.000 claims description 6
- 235000009184 Spondias indica Nutrition 0.000 claims description 6
- 239000001813 ethyl (2R)-2-methylbutanoate Substances 0.000 claims description 6
- 229940090910 ethyl 2-methylbutyrate Drugs 0.000 claims description 6
- 239000010501 lemon oil Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000005303 weighing Methods 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 241000830535 Ligustrum lucidum Species 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 240000007228 Mangifera indica Species 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 235000013399 edible fruits Nutrition 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 6
- 235000009508 confectionery Nutrition 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 5
- 239000000654 additive Substances 0.000 abstract description 4
- 230000000996 additive effect Effects 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 4
- 230000014759 maintenance of location Effects 0.000 abstract description 4
- 235000013599 spices Nutrition 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 8
- 241001093152 Mangifera Species 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 4
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- -1 fatty acid ester Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZBFSYQBEXZGTAX-UHFFFAOYSA-N phenyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZBFSYQBEXZGTAX-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- 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
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
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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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
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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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
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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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention relates to the technical field of spices, in particular to a passion fruit aroma compound, a preparation method thereof and passion fruit aroma essence, wherein the passion fruit aroma compound has the following structural formula:the passion fruit aroma compound has remarkable passion fruit-like aroma and certain fruit sweet aroma, has obvious aroma and long aroma retention time, and has important market value in the field of daily chemical essence blending; preparing the passion fruit fragranceThe preparation method of the compound is simple and efficient, the operation control is convenient, the quality of the produced product is high, the cost is low, the industrial production is facilitated, and meanwhile, the prepared passion fruit aroma compound has obvious passion fruit-like aroma, and the defect that the conventional fruit essence is used as an essence additive can be effectively overcome; the essence prepared by using the passion fruit aroma compound has the aroma similar to passion fruit and certain fruit sweet aroma, and has good practicability.
Description
Technical Field
The invention relates to the technical field of spices, in particular to a passion fruit aroma compound, a preparation method thereof and passion fruit aroma essence.
Background
Passion fruit is a fruit produced in tropical fruit and integrates multiple fruit flavors, and is named passion fruit. Although the aroma components of passion fruit comprise a series of small molecular compounds such as fatty acid, fatty acid ester, aldehyde, ketone, olefin and the like, the characteristic aroma of passion fruit has strong identification degree, and the characteristic aroma is similar to the aroma presented by the compound tricyclodecenyl acetate, so that the tricyclodecenyl acetate is also commonly used for preparing passion fruit aroma type daily chemical essence. However, similar aroma compounds are rare, and a flavoring agent commonly uses furanone, strawberry acid, maltol, caryophyllene and thiopeach ketone to prepare the aroma of passion fruits, so that great difficulty is brought to flavoring operation. Therefore, the development of the compound with passion fruit characteristic aroma has important market value in the field of daily chemical essence blending.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide the passion fruit aroma compound which has obvious passion fruit-like aroma and certain fruit-sweet aroma, has obvious aroma and long aroma retention time and has important market value in the field of daily chemical essence blending.
The invention further aims to provide a preparation method of the passion fruit aroma compound, which is simple and efficient, convenient to operate and control, high in quality of produced products, low in cost and beneficial to industrial production, and meanwhile, the prepared passion fruit aroma compound has remarkable passion fruit-like aroma, and the defect that the conventional fruit essence is used as an essence additive can be effectively overcome.
The invention further aims to provide the passion fruit fragrance type essence, and the essence finally prepared by adding passion fruit fragrance compounds has fragrance similar to passion fruit samples and certain fruit sweet fragrance, so that the essence has good practicability.
The aim of the invention is achieved by the following technical scheme: an passion fruit aroma compound having the structural formula:
the compound provided by the invention has remarkable passion fruit-like aroma and certain fruit-sweet aroma, is obvious in aroma and long in aroma retention time, and has important market value in the field of daily chemical essence blending.
The invention also provides a preparation method of the passion fruit aroma compound, which comprises the following steps:
s1, taking anthranilic acid, thionyl chloride and toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to the temperature of- (0-2), adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to the room temperature, and continuously stirring for 3-6 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, adding phenylpropanol, a sodium carbonate solution, anhydrous magnesium sulfate and 10% calcium carbide by mass concentration into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 5-9 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 1-3 hours, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 10-16 hours, filtering to remove solids, recovering filtrate, adding the calcium carbide into the filtrate, heating to 75-85 ℃, refluxing for 10-14 hours, recovering room temperature, filtering to remove solids, and recovering the filtrate to obtain the toluene solution of the phenyl anthranilate for later use;
s3, taking n-hexanal and glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, decompressing to 500-600Pa, heating to 75-85 ℃, reacting for 10-14h, synchronously separating and reflecting the water generated by using a water separator in the reaction process, continuously heating to 100-120 ℃, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
The passion fruit aroma compound is prepared by adopting the method, has remarkable passion fruit-like aroma, and can effectively overcome the defect that the conventional fruit essence is used as an essence additive; the preparation method is simple and efficient, convenient to operate and control, high in quality of the produced product, low in cost and beneficial to industrial production.
Preferably, in step S1, the weight ratio of the anthranilic acid, thionyl chloride and toluene is 6.5-7.5:7.0-7.8:5.4-6.4.
Preferably, the weight ratio of the amount of phenylpropanol in step S2 to the amount of anthranilic acid in step S1 is 5.0-6.0:6.5-7.5.
Preferably, in step S2, the weight ratio of the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide is 5.0-6.0:13.0-13.8:1.4-2.4:0.3-0.7.
Preferably, the weight ratio of the n-hexanal, glacial acetic acid in the step S3 to the amount of the anthranilic acid in the step S1 is 4.0-4.8:0.28-0.34:6.5-7.5.
The invention also provides passion fruit essence which comprises the following raw materials in parts by weight: 1.0 to 14 parts of lemon oil, 1.8 to 2.2 parts of maltol acetate, 4.3 to 4.7 parts of tricyclodecenyl acetate, 1.4 to 1.8 parts of hexanal, 0.2 to 0.6 part of glossy privet aldehyde, 2.1 to 2.6 parts of leaf alcohol, 3.3 to 3.7 parts of tetrahydrolinalool, 3.0 to 3.5 parts of ethyl 2-methylbutyrate, (E) -3-phenylpropyl-2- (cyclohexylamino) benzoate, 6.1 to 6.6 parts of thiopeach ketone, 0.02 to 0.06 part of thiomenthone, 0.01 to 0.05 part of furanone acetate, 0.008 to 0.012 part of caryophyllene, 0.01 to 0.03 part of mangiferone, 0.08 to 0.12 part of mango ketone and 73 to 77 parts of ethanol.
Preferably, the passion fruit essence is prepared by the following steps:
1) Weighing raw materials according to parts by weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
The essence provided by the invention has the advantages that the essence prepared finally has fragrance similar to passion fruit and certain fruit and sweet fragrance by adding passion fruit fragrance compounds, and the practicability is very good.
The invention has the beneficial effects that: the compound provided by the invention has remarkable passion fruit-like aroma and a certain fruit-sweet aroma, is obvious in aroma and long in aroma retention time, and has important market value in the field of daily chemical essence blending.
The preparation method of the passion fruit aroma compound is simple and efficient, convenient to operate and control, high in quality of produced products, low in cost and beneficial to industrial production, and meanwhile, the prepared passion fruit aroma compound has remarkable passion fruit-like aroma, and the defect that the conventional fruit essence is used as an essence additive can be effectively overcome; the essence added with the passion fruit aroma compound has the aroma similar to passion fruit and certain fruit sweet aroma, and has good practicability.
Drawings
FIG. 1 is a gas chromatogram of 4 (E) -3-phenylpropyl-2- (hexylidene amino) benzoate obtained in example 4 according to the present invention.
Detailed Description
The present invention is further described below with reference to examples and fig. 1 for the understanding of those skilled in the art, and the description of the embodiments is not intended to limit the present invention.
Example 1
An passion fruit aroma compound having the structural formula:
the passion fruit aroma compound is prepared by the following steps:
s1, taking anthranilic acid, thionyl chloride and toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to the temperature of-2 ℃, adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to the room temperature, and continuously stirring for 3 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, adding phenylpropanol, a sodium carbonate solution, anhydrous magnesium sulfate and 10% calcium carbide by mass concentration into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 5 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 1 hour, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 10 hours, filtering to remove solids, recovering filtrate, adding calcium carbide into the filtrate, heating to 75 ℃, refluxing for 10 hours, recovering room temperature, filtering to remove solids, and recovering the filtrate to obtain the toluene solution of the phenyl propyl anthranilate for later use;
s3, taking n-hexanal and glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, decompressing to 500Pa, heating to 75 ℃, reacting for 10 hours, synchronously separating and reflecting the generated water by using a water separator in the reaction process, continuously heating to 100 ℃, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
In the step S1, the weight ratio of the anthranilic acid to the thionyl chloride to the toluene is 6.5:7.0:5.4.
The weight ratio of the amount of phenylpropanol used in step S2 to the amount of anthranilic acid used in step S1 is 5.0:6.5.
In the step S2, the weight ratio of the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide is 5.0:13.0:1.4:0.3.
The weight ratio of the n-hexanal, glacial acetic acid in the step S3 to the amount of the anthranilic acid in the step S1 is 4.0:0.28:6.5.
The passion fruit essence comprises the following raw materials in parts by weight: lemon oil 1.0 part, maltol acetate 1.8 parts, tricyclodecenyl acetate 4.3 parts, hexanal 1.4 parts, ligustral 0.2 parts, leaf alcohol 2.1 parts, tetrahydrolinalool 3.3 parts, ethyl 2-methylbutyrate 3.0 parts, (E) -3-phenylpropyl-2- (hexylamino) benzoate 6.1 parts, thiopeach ketone 0.02 parts, thiomenthone 0.01 parts, furanone acetate 0.008 parts, caryophyllene 0.01 parts, mango ketone 0.08 parts and ethanol 73 parts.
The passion fruit essence is prepared through the following steps:
1) Weighing raw materials according to parts by weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
Example 2
An passion fruit aroma compound having the structural formula:
the passion fruit aroma compound is prepared by the following steps:
s1, taking anthranilic acid, thionyl chloride and toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to the temperature of-1 ℃, adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to the room temperature, and continuously stirring for 4 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, adding phenylpropanol, a sodium carbonate solution, anhydrous magnesium sulfate and 10% calcium carbide by mass concentration into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 7 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 2 hours, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 13 hours, filtering to remove solids, recovering filtrate, adding calcium carbide into the filtrate, heating to 80 ℃, refluxing for 12 hours, recovering room temperature, filtering to remove solids, and recovering the filtrate to obtain the toluene solution of the phenyl propyl anthranilate for later use;
s3, taking n-hexanal and glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, reducing the pressure to 550Pa, heating to 80 ℃, reacting for 12 hours, synchronously separating and reflecting the generated water by using a water separator in the reaction process, continuously heating to 110 ℃, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
In the step S1, the weight ratio of the anthranilic acid to the thionyl chloride to the toluene is 7.0:7.4:6.0.
The weight ratio of the amount of phenylpropanol in step S2 to the amount of anthranilic acid in step S1 was 5.5:7.0.
In the step S2, the weight ratio of the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide is 5.5:13.4:1.9:0.5.
The weight ratio of the n-hexanal, glacial acetic acid in the step S3 to the amount of the anthranilic acid in the step S1 is 4.4:0.32:7.0.
The passion fruit essence comprises the following raw materials in parts by weight: lemon oil 1.2 parts, maltol acetate 2.0 parts, tricyclodecenyl acetate 4.5 parts, hexanal 1.6 parts, ligustral 0.4 parts, leaf alcohol 2.4 parts, tetrahydrolinalool 3.5 parts, ethyl 2-methylbutyrate 3.3 parts, (E) -3-phenylpropyl-2- (hexylamino) benzoate 6.4 parts, thiopeach ketone 0.04 parts, thiomenthone 0.03 parts, furanone acetate 0.01 parts, caryophyllene 0.02 parts, mango ketone 0.1 parts and ethanol 75 parts.
The passion fruit essence is prepared through the following steps:
1) Weighing raw materials according to parts by weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
Example 3
An passion fruit aroma compound having the structural formula:
the passion fruit aroma compound is prepared by the following steps:
s1, taking anthranilic acid, thionyl chloride and toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to 0 ℃, adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to room temperature, and continuously stirring for 6 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, adding phenylpropanol, a sodium carbonate solution, anhydrous magnesium sulfate and 10% calcium carbide by mass concentration into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 9 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 3 hours, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 16 hours, filtering to remove solids, recovering filtrate, adding calcium carbide into the filtrate, heating to 85 ℃, refluxing for 14 hours, recovering room temperature, filtering to remove solids, and recovering the filtrate to obtain the toluene solution of the phenyl propyl anthranilate for later use;
s3, taking n-hexanal and glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, reducing the pressure to 600Pa, heating to 85 ℃, reacting for 14 hours, synchronously separating the water which is reflected to be generated by using a water separator in the reaction process, continuously heating to 120 ℃, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
In the step S1, the weight ratio of the anthranilic acid to the thionyl chloride to the toluene is 7.5:7.8:6.4.
The weight ratio of the amount of phenylpropanol used in step S2 to the amount of anthranilic acid used in step S1 was 6.0:7.5.
In the step S2, the weight ratio of the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide is 6.0:13.8:2.4:0.7.
The weight ratio of the n-hexanal, glacial acetic acid in the step S3 to the amount of the anthranilic acid in the step S1 is 4.8:0.34:7.5.
The passion fruit essence comprises the following raw materials in parts by weight: 14 parts of lemon oil, 2.2 parts of maltol acetate, 4.7 parts of tricyclodecenyl acetate, 1.8 parts of hexanal, 0.6 part of glossy privet aldehyde, 2.6 parts of leaf alcohol, 3.7 parts of tetrahydrolinalool, 3.5 parts of ethyl 2-methylbutyrate, (E) -3-phenylpropyl-2- (hexylamino) benzoate, 0.06 part of thiopeach ketone, 0.05 part of thiomenthone, 0.012 part of furanone acetate, 0.03 part of caryophyllene, 0.12 part of mango ketone and 77 parts of ethanol.
The passion fruit essence is prepared through the following steps:
1) Weighing raw materials according to parts by weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
Example 4
An passion fruit aroma compound having the structural formula:
the passion fruit aroma compound is prepared by the following steps:
s1, taking 6.85kg of anthranilic acid, 3.6L of thionyl chloride and 8.5L of toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to 0 ℃, adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to room temperature, and continuing stirring for 5 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, taking 5.5L of phenylpropanol, 12L of sodium carbonate solution, 1.8kg of anhydrous magnesium sulfate and 0.5kg of 10% calcium carbide in mass concentration, adding the phenylpropanol into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 7 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 1.5 hours, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 12 hours, filtering to remove solids, recovering filtrate, adding calcium carbide into the filtrate, heating to 80 ℃, refluxing for 12 hours, recovering room temperature, filtering to remove solids, recovering filtrate, and obtaining the toluene solution of the phenyl propyl anthranilate for standby;
s3, taking 5L of n-hexanal and 0.3L of glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, decompressing to 550Pa, heating to 80 ℃, reacting for 12 hours, synchronously separating and reflecting the generated water by using a water separator in the reaction process, continuously heating to 110 ℃, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
The passion fruit essence comprises the following raw materials in parts by weight: lemon oil 1.2mL, maltol acetate 2mL, tricyclodecenyl acetate 4.5mL, hexanal 1.5mL, ligustral 0.3mL, leaf alcohol 2.3mL, tetrahydrolinalool 3.5mL, ethyl 2-methylbutyrate 3.2mL, (E) -3-phenylpropyl-2- (hexylideneamino) benzoate 6.3mL, thiopeach ketone 0.04mL, thiomenthone 0.03mL, furanone acetate 0.01mL, caryophyllene 0.02mL, mango ketone 0.1mL, and ethanol 75mL.
The passion fruit essence is prepared through the following steps:
1) Weighing the raw materials according to the weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
The mass spectrum of the obtained 4-methoxybenzyl (E) -3-phenylpropyl-2- (hexylidene amino) benzoate is shown in figure 1, and the mass spectrum analysis data are as follows:
MS(ESI,m/z)360.2(M+Na + ) The method comprises the steps of carrying out a first treatment on the surface of the Theoretical calculation data of high-resolution electrospray ionization mass spectrum is [ C ] 22 H 27 NNaO 2 ] + (M+Na + ) 360.1934, the actual measured value is 360.1953.
Aroma evaluation:
the perfumer inviting the 5 th 5 year or more experience was evaluated as follows for the fragrance of (E) -3-phenylpropyl-2- (hexylamino) benzoate: wherein, 5 perfumers consider that the compound presents a passion-like aroma.
The above embodiments are preferred embodiments of the present invention, and besides, the present invention may be implemented in other ways, and any obvious substitution is within the scope of the present invention without departing from the concept of the present invention.
Claims (10)
1. A passion fruit aroma compound characterized by: has the following structural formula:
2. a preparation method of passion fruit aroma compound is characterized in that: the method comprises the following steps:
s1, taking anthranilic acid, thionyl chloride and toluene, adding the anthranilic acid and the toluene into a reaction kettle, uniformly mixing, cooling to the temperature of- (0-2), adding the thionyl chloride into the reaction kettle, then returning the temperature of the reaction kettle to the room temperature, and continuously stirring for 3-6 hours to obtain a toluene solution of the anthranilic chloride for later use;
s2, adding phenylpropanol, a sodium carbonate solution, anhydrous magnesium sulfate and 8-12% calcium carbide by mass concentration into the toluene solution of the anthranilyl chloride obtained in the step S1, uniformly mixing, continuously reacting for 5-9 hours, adding the sodium carbonate solution into a reaction system, continuously reacting for 1-3 hours, standing for layering, collecting an upper organic phase, adding the anhydrous magnesium sulfate into the organic phase, stirring for 10-16 hours, filtering to remove solids, recovering filtrate, adding the calcium carbide into the filtrate, heating and refluxing for 10-14 hours, recovering room temperature, filtering to remove solids, recovering the filtrate to obtain the toluene solution of the phenyl propyl anthranilate for later use;
s3, taking n-hexanal and glacial acetic acid, adding the n-hexanal into the toluene solution of the phenyl propyl anthranilate obtained in the step S2, uniformly mixing, adding the glacial acetic acid, reducing the pressure, heating, reacting for 10-14h, continuously heating, distilling to remove the solvent, and cooling to room temperature to obtain the bright yellow liquid, namely the passion fruit aroma compound.
3. A passion fruit aroma compound as claimed in claim 2 wherein: in the step S1, the weight ratio of the anthranilic acid to the thionyl chloride to the toluene is 6.5-7.5:7.0-7.8:5.4-6.4.
4. A passion fruit aroma compound as claimed in claim 2 wherein: the weight ratio of the dosage of the phenylpropanol in the step S2 to the dosage of the anthranilic acid in the step S1 is 5.0-6.0:6.5-7.5.
5. A passion fruit aroma compound as claimed in claim 3 wherein: in the step S2, the weight ratio of the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide is 5.0-6.0:13.0-13.8:1.4-2.4:0.3-0.7 when the phenylpropanol, the sodium carbonate solution, the anhydrous magnesium sulfate and the calcium carbide are mixed.
6. A passion fruit aroma compound as claimed in claim 2 wherein: in the step S2, the temperature is raised to 75-85 ℃ during temperature rising and reflux.
7. A passion fruit aroma compound as claimed in claim 2 wherein: the weight ratio of the n-hexanal to the glacial acetic acid in the step S3 to the dosage of the anthranilic acid in the step S1 is 4.0-4.8:0.28-0.34:6.5-7.5.
8. A passion fruit aroma compound as claimed in claim 2 wherein: in the step S3, the pressure is reduced to 500-600Pa and the temperature is increased to 75-85 ℃; and continuously heating to 100-120 ℃.
9. An passion fruit essence is characterized in that: the material comprises the following raw materials in parts by weight: 1.0 to 14 parts of lemon oil, 1.8 to 2.2 parts of maltol acetate, 4.3 to 4.7 parts of tricyclodecenyl acetate, 1.4 to 1.8 parts of hexanal, 0.2 to 0.6 part of glossy privet aldehyde, 2.1 to 2.6 parts of leaf alcohol, 3.3 to 3.7 parts of tetrahydrolinalool, 3.0 to 3.5 parts of ethyl 2-methylbutyrate, (E) -3-phenylpropyl-2- (cyclohexylamino) benzoate, 6.1 to 6.6 parts of thiopeach ketone, 0.02 to 0.06 part of thiomenthone, 0.01 to 0.05 part of furanone acetate, 0.008 to 0.012 part of caryophyllene, 0.01 to 0.03 part of mangiferone, 0.08 to 0.12 part of mango ketone and 73 to 77 parts of ethanol.
10. The passion fruit flavored essence of claim 9 wherein: the passion fruit essence is prepared through the following steps:
1) Weighing raw materials according to parts by weight for standby;
2) Adding the raw materials into a reaction device, mixing, and repeatedly oscillating and shaking to obtain the passion fruit essence.
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