CN109516904B

CN109516904B - Musk ether and composition, preparation method and application thereof

Info

Publication number: CN109516904B
Application number: CN201811441879.8A
Authority: CN
Inventors: 杜芝芝; 马永鹏; 李明祥; 王雨华; 裴盛基; 张红霞; 孙洪正; 李怡; 刘宏
Original assignee: Kunming Institute of Botany of CAS
Current assignee: Kunming Institute of Botany of CAS
Priority date: 2018-05-22
Filing date: 2018-11-29
Publication date: 2020-05-08
Anticipated expiration: 2038-11-29
Also published as: CN109516904A; CN108558620A

Abstract

The invention relates to the field of daily chemicals, in particular to the field of mosquito repellent products, essence and fragrance and cosmetics, and specifically relates to moschus ether and a composition, a preparation method and application thereof. In particular, the invention relates to a compound shown as the following structural formula, a preparation method of the compound, a composition for repelling mosquitoes and insects by taking the compound as an effective component, and application of the compound in preparing mosquito-repellent products and application of the compound as a perfume.

Description

Musk ether and composition, preparation method and application thereof

Technical Field

The invention relates to the field of daily chemicals, in particular to the field of mosquito repellent products, essence and fragrance and cosmetics, and specifically relates to moschus ether and a composition, a preparation method and application thereof.

Background

Muscat Menglaber (Adenosma buchneroides Bonati) is an annual herb plant of the genus Musk of the family Scrophulariaceae, and is a unique species in Yunnan of China. The plant has special fragrance, is a medicinal plant used by ni people (a branch of Hani nationality) in Xishuangbanna Menglan county, and is also called as Aiqing grass and flea grass by local people due to its special use and implication. The Aini women like the fragrance of the grass, and the grass can smell the fragrance at any time and has the functions of expelling insects and mosquitoes when being worn on ears of the women; the grass can be placed in quilt and under the sheet for preventing and treating flea. Although Menglan moschus occupies an important place in the life of people, the related studies are very few, and only those who have courage et al report the results of preliminary studies on its use as a novel perfume plant. At present, the Muscovitum Menglace is not well known, developed and utilized.

The stems, leaves and inflorescences of the Muscovitum Menglaber are aromatic and rich in essential oil. Essential oil is also called volatile oil and aromatic oil, and is a volatile and fat-soluble oily substance contained in aromatic plants. The essential oil has complicated chemical components, and can be divided into terpenoids, aromatic compounds, aliphatic compounds, sulfur-containing nitrogen-containing heterocyclic compounds, special compounds with macrocyclic lactone structure, etc. according to the structure. The essential oil has various physiological activities, including antibacterial, antiinflammatory, antivirus, analgesic, antitumor, mosquito repelling, penetration promoting, antioxidant, etc. The Muscovitum Menglaber is rich in essential oil, is an important secondary metabolite contained in the Muscovitum, and is lack of related research, development and utilization at present.

Disclosure of Invention

In order to develop and utilize the Muscovitum Menglace, the invention develops related researches against folk utilization of the plant. The invention discloses a mosquito-repellent incense containing moschus menbracteatum essential oil, which is prepared by carrying out activity tracing and separation on mosquito-repellent active substances of the essential oil, clarifying the basis of the mosquito-repellent active substances of the moschus menbracteatum essential oil, and discovering a new volatile diterpene ether compound with mosquito-repellent activity, namely moschus ether A, so that the invention provides the following steps:

musk ether A and preparation method thereof

In one aspect, the present application provides a compound Muscat ether A, represented by the following structural formula,

the application also provides a preparation method of the compound, which comprises the step of separating the compound from the Mengla hair musk oil.

In certain embodiments, the method comprises the steps of:

step 1: extracting from aerial parts of Muscovitum with distillation method to obtain essential oil;

step 2: the compounds of the invention are isolated from essential oils by chromatographic methods.

In certain embodiments, step 1 comprises:

step 1-1: weighing aerial parts of Muscovitum, and distilling in water (for example, distilling for 1-5 hr, for example, distilling for 3 hr);

step 1-2: collecting volatile oil from the upper layer of distillate, and drying with desiccant (such as anhydrous sodium sulfate) to obtain essential oil.

In certain embodiments, the aerial parts of the Musk Menglauca are dried and comminuted.

In certain embodiments, the aerial parts of menglans musk is the fresh stems and leaves or inflorescence of menglans musk.

In certain embodiments, the yield of essential oil extraction in step 1 is 0.3% to 0.7% (e.g., 0.5%).

In certain embodiments, the chromatography process in step 2 is silica gel column chromatography.

In certain embodiments, step 2 comprises:

step 2-1: loading the essential oil obtained in the step 1 into a column by using 200-sand 300-mesh silica gel, loading the sample by using a wet method, and performing gradient elution by using a petroleum ether-ethyl acetate system as a mobile phase; mixing similar components after TLC thin-layer chromatography to obtain 5 fractions Fr.1-Fr.5;

step 2-2: loading fraction Fr.4 into a thin-layer silica gel H column, loading by a wet method, performing gradient elution by adopting a normal-phase reduced pressure silica gel column chromatography method and taking a petroleum ether-chloroform system as a mobile phase to obtain the compound.

Composition for repelling mosquitoes and mosquito repelling product

The present inventors found that the compound of the present invention has a mosquito repellent effect, and thus, the present application provides a composition for repelling mosquitoes, which contains the compound of the present invention as an effective ingredient.

The composition can be in any suitable form, for example, various forms such as liquid, solid, semi-solid, gas, and the like. The compounds of the invention can be formulated with conventional non-toxic, pharmaceutically or daily chemical acceptable carriers and/or excipients in the form of solutions, sprays, aerosols, emulsions, suspensions, ointments, gels, patches and other forms suitable for use.

Such carriers and/or excipients include, for example, water, ethanol, propylene glycol, jojoba oil, gelatin, gum arabic, tween 80, glyceryl stearate, glyceryl trioctanoate, cetyl alcohol, lanolin, urea, petrolatum, stearyl alcohol, beeswax, polyoxyethylene oleyl ether, and other carriers and/or excipients suitable for use in preparing formulations in liquid, solid, semi-solid, gaseous forms and the like. The composition may additionally contain stabilizers, thickeners, colorants and/or fragrances.

In the invention, the composition for repelling mosquitoes can be used as a single effective component of the compound, and can also comprise other compounds with the function of repelling mosquitoes.

The application also relates to the use of the compounds of the invention for the preparation of mosquito repellent products.

The application also relates to a mosquito repelling product which takes the compound as an effective mosquito repelling component. In certain embodiments, the mosquito-repellent products have the compounds of the present invention as the sole active ingredient for mosquito repellency. In certain embodiments, the mosquito-repellent product may comprise other compounds that have a mosquito-repellent effect.

The mosquito repelling product can be liquid, ointment, a pendant or a convenient patch. The mosquito repellent product of the present invention may be a cosmetic. In the present invention, cosmetics refer to daily chemical industry products that are spread on any part of the surface of the human body (e.g., skin, hair, nails, lips, etc.) by rubbing, spraying, or the like, to clean, eliminate unpleasant odors, protect skin, beautify, and decorate the skin. The mosquito repellent product in the invention can be a resident cosmetic or a leaching cosmetic.

The mosquito repellent product can be a mosquito repellent (such as oil-based preparations, alcohol-based preparations and water-based preparations), and can also be mosquito repellent patches, mosquito repellent creams, mosquito repellent ointments, mosquito repellent shampoo products, mosquito repellent air fresheners and the like.

In the composition for repelling mosquitoes or mosquito-repellent products of the present invention, moschus ether a may be added in an amount of 0.1% to 30% (e.g., 0.1% to 1%, 1% to 5%, 5% to 10%, 10% to 20%, or 20% to 30%) of the total mass percentage of the composition or product.

In certain embodiments, the mosquito-repellent product is a mosquito repellent, the mosquito repellent is an oil-based formulation, moschus ether a is an active ingredient, and vegetable oil is used as an adjuvant; the addition amount of moschus ether A is 0.1-30% of the total mass percent of the mosquito repellent. The mosquito repellent is clear colorless flowing liquid and has the special fragrance of moschus ether A.

In some embodiments, the mosquito repellent product is a mosquito repellent, the mosquito repellent is an alcohol-based preparation, moschus ether a is used as an active ingredient, ethanol and water are used as auxiliary materials, and the addition amount of the moschus ether a is 0.1-30% of the total mass percent of the mosquito repellent. The mosquito repellent is clear colorless flowing liquid and has the special fragrance of moschus ether A.

In some embodiments, the mosquito repellent product is a mosquito repellent, the mosquito repellent is a water-based preparation, moschus ether A is used as an effective component, gelatin, gum arabic and deionized water are used as auxiliary materials, and the addition amount of the moschus ether A is 0.1-30% of the total mass percent of the mosquito repellent. The mosquito repellent is clear colorless flowing liquid and has the special fragrance of moschus ether A.

In some embodiments, the mosquito repelling product is a mosquito repelling patch, the mosquito repelling patch takes moschus ether A as an active ingredient, is combined with a polymer gel matrix, and is prepared into the mosquito repelling patch by utilizing a microdrop coating and constant-speed slow-release control technology, wherein the addition amount of the moschus ether A is 0.1-30% of the total mass percent of the mosquito repelling patch.

The present application also relates to a method of repelling mosquitoes comprising administering an effective amount of a compound of the invention, or a composition of the invention for repelling mosquitoes, or a mosquito-repelling product of the invention.

In certain embodiments, the mosquito is an aedes mosquito, such as aedes albopictus.

Perfume essence

The moschus ether A compound has rich and pure costustoot flavor (wood) and amber flavor (amber), is similar to the flavors of purple perilla and wild chrysanthemum, has strong and non-irritant smell, lasting fragrance and good fragrance fixing effect, is pleasant, and is suitable for being used as perfume with oriental wood fragrance to be aftermixed.

Accordingly, the present application provides the use of the compounds of the present invention as perfumes. In the present invention, the perfume is also called as a fragrant raw material, which is a substance capable of being smelled or smelled, and is generally used as a raw material for preparing essence.

The application also provides a perfume containing the compound. In the invention, the essence is a mixture prepared by mixing two or more than two spices according to a certain proportion, and is also called as a blending spice. In certain embodiments, the compounds of the present invention are present in the fragrance in an amount of 0.001% to 20% by weight.

The essence of the invention can be oil-soluble essence. The flavour may comprise a solvent, for example one or more of ethanol, isopropanol, diethylene glycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate.

The present application also relates to products comprising said perfume, such as: fabric washing powders, lotions, and other fabric care products; detergents and household cleaning, washing and disinfecting products; air fresheners, indoor sprays, and cartridges; soaps, bath and shower gels, shampoos, conditioners and other personal cleansing products; cosmetics such as perfumes, creams, ointments, toilet water, skin moisturizers, skin and other lotions, talc, body deodorants, antiperspirants, and the like.

The application also relates to the following technical scheme:

1. muscat ether A shown in the following structural formula,

2. the composition with the mosquito repelling effect contains the moschus ether A compound in the scheme 1 and a carrier acceptable by daily chemical products.

3. The application of the moschus ether A compound in the scheme 1 in preparing daily chemical products with mosquito repelling effect.

4. The application of the moschus ether A compound in the scheme 1 in preparing the essence with the mosquito repelling effect.

5. The application of the moschus ether A compound in the scheme 1 in preparing different fragrance essences.

6. Weighing aerial parts, stems and leaves or inflorescences of Muscovitum Musk which are dried and crushed or freshly cut, placing the weighed aerial parts, stems and leaves or inflorescences of Muscovitum Muscovy in a 3L round bottom flask, adding 1.5L of distilled water, distilling the obtained product in the water for 3h to extract volatile components, taking out upper-layer volatile oil of distillate, and adding anhydrous sodium sulfate for drying to obtain light-yellow Muscovitum essential oil; loading Musca menglaber essential oil on a 200-D300-mesh silica gel column, loading by a wet method, performing gradient elution by using a petroleum ether-ethyl acetate system as a mobile phase, performing reduced pressure rotary evaporation to recover a solvent, and combining similar components after TLC (thin layer chromatography) analysis to obtain 5 fractions Fr.1-Fr.5; and (3) loading the fraction Fr.4 into a column by using thin-layer silica gel H, loading the sample by a wet method, and performing gradient elution by using a normal-phase reduced pressure silica gel column chromatography method and a petroleum ether-chloroform system as a mobile phase to obtain a compound moschus ether A.

7. A moschus ether A-containing mosquito repellent product is characterized in that moschus ether A in a scheme 1 is used as an effective component of the mosquito repellent product, auxiliary materials are used, and the addition amount of moschus ether A is 0.1-30% of the total mass percentage of the mosquito repellent product.

8. The moschus ether A-containing mosquito repellent is characterized in that moschus ether A in a scheme 1 is used as an effective component of the mosquito repellent, vegetable oil is used as an auxiliary material, the addition amount of moschus ether A is 0.1-30% of the total mass percent of the mosquito repellent, and the mosquito repellent is an oil-based preparation.

9. The moschus ether A-containing mosquito repellent is characterized in that moschus ether A in a scheme 1 is used as an effective component of the mosquito repellent, ethanol and water are used as auxiliary materials, the adding amount of moschus ether A is 0.1-30% of the total mass percent of the mosquito repellent, and the mosquito repellent is an alcohol-based preparation.

10. The mosquito repellent is characterized in that moschus ether A is used as an effective component of the mosquito repellent according to the scheme, gelatin, gum arabic and deionized water are added, the addition amount of moschus ether A is 0.1-30% of the total mass percent of the mosquito repellent, and the mosquito repellent is a water-based preparation.

11. The moschus ether A-containing mosquito repelling paste is characterized in that moschus ether A in a scheme 1 is used as an effective component of the mosquito repelling paste, the moschus ether A is combined with a polymer gel matrix, the mosquito repelling paste is prepared by utilizing a microdrop coating and constant-speed slow release control technology, the addition amount of moschus ether A is 0.1-30% of the total mass percent of a mosquito repelling agent, and the mosquito repelling agent is a convenient paste.

12. The fragrant product containing musk ether A is characterized in that the fragrant product only contains musk ether A perfume or a perfume composition containing musk ether A perfume, and the musk ether A in the fragrant product accounts for 0.001-20% by weight.

13. The application of the compound musk ether A in preparing essences with different fragrance tones is characterized in that the application is the application of the musk ether A in the following products: fabric washing powders, lotions, cleansers, disinfectants, air fresheners, room sprays, cartridges, soaps, bath and shower gels, shampoos, conditioners, perfumes, creams, ointments, toilet water, skin lotions, talc, body deodorants, antiperspirants.

Advantageous effects

The invention provides a new volatile diterpenoid ether compound with mosquito repelling activity, namely moschus ether A. The moschus ether A-containing mosquito repellent product has the characteristics of being green and environment-friendly. Musk A has pleasant fragrance, so mosquito repellent products with Musk A as effective component are easily accepted by consumers. Muscatol A has the characteristics of obvious mosquito-repellent effect, no stimulation to skin, naturalness, environmental protection and safety, and can be prepared into oil-based, alcohol-based and water-based mosquito repellents, mosquito repellent patches and other mosquito repellent products.

Embodiments of the present invention will be described in detail below with reference to the drawings and examples, but those skilled in the art will understand that the following drawings and examples are only for illustrating the present invention and are not to be construed as limiting the scope of the present invention. Various objects and advantageous aspects of the present invention will become apparent to those skilled in the art from the accompanying drawings and the following detailed description of the preferred embodiments.

Drawings

FIG. 1 shows the chemical structure and key of Musk Ether A of the present invention¹H-¹H COSY is related to HMBC.

Figure 2 shows the key ROESY correlation of the inventive compound Muscat ether A.

Detailed Description

Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.

Example 1

1. Preparation of Musk Ether A.

And (3) a separation process: weighing 0.5kg of dried and crushed Muscovitum overground part, placing the Muscovitum overground part into a 3L round-bottom flask, adding 1.5L of distilled water, distilling in the water for 3h to extract volatile components, taking out the volatile oil on the upper layer of the distillate, adding anhydrous sodium sulfate, drying, and distilling in cumulative water for 12 times to obtain 70.2g of the light yellow Muscovitum essential oil, wherein the yield of the dried product is 1.17%. Taking 60.0g of Musca menglaber essential oil, loading the Musca menglaber essential oil into a 300-mesh silica gel column by using 1.4kg of 200-mesh silica gel, loading the Musca menglaber essential oil into the column by using a wet method, taking a petroleum ether-ethyl acetate system (P/E100:0, 7.2L; 98:2, 10.8L; 95:5, 8.1L; 90:10, 7.2L; 80:20, 4.5L; 50:50, 9.9L; 25:75,6.3L) as a mobile phase, carrying out gradient elution, carrying out reduced pressure rotary evaporation to recover a solvent, combining similar components after TLC thin-layer chromatography analysis, and obtaining 5 fractions Fr.1-Fr.5; flow fractionation Fr.4(186mg) was subjected to normal-phase reduced pressure silica gel column chromatography (petroleum ether-chloroform P/C1: 0,400 mL; 7:1,300 mL; 3:1,120mL as mobile phase) to give Muscat ether A (151 mg).

2. Structural analysis of moschus ether a:

colorless oil;

(c 0.25,MeOH)；UV(MeOH)λ_max(nm) (log ε):203(4.86),219(4.37),277 (3.67). According to the excimer ion peak M/z325[ M + Na ] in ESI-MS spectrum]⁺And are combined with¹³C NMR and DEPT spectral analysis, and the molecular formula of the compound is deduced to be C₂₀H₃₀O₂. Height ofThe accurate relative molecular mass of an excimer ion peak given by resolution mass spectrum HREI-MS is M/z 325.2139[ M + Na [ ]]⁺(calculation value C)₂₀H₃₀O₂Na,325.2138), further confirming the molecular formula of the compound as C₂₀H₃₀O₂With 6 unsaturations. Characteristic peak v in infrared absorption spectrum IR_max3437,1631,1251cm^-1The presence of a hydroxyl group, a benzene ring and an ether group, respectively, is indicated. 3 aromatic proton signals [ delta ] in ABX coupling system_H6.76(1H,d,1.5),6.74(1H,dd,7.5,1.5),7.06(1H,d,7.5)]Indicating the presence of a 1',2',4' -trisubstituted benzene ring. Further, the method comprises¹³C NMR analysis revealed that the compound closely resembled the carvacrol signals except for the carvacrol C-1 'and C-2' signals (. delta.)_C120.8,153.6) to a lower field (delta), respectively_C125.0,156.0) presumably to form an ether group by substitution of the carvacrol 2' -OH with another moiety. Analysis of the residual carbon Signal (. delta.)_C72.0,80.2,117.6,147.1,25.0,33.5,21.9,34.5,21.5,21.5) and another fragment was found to be very similar to the carbon signal of (1R,2R) - (-) -3-p-menthen-l,2-diol, except for the latter C-2 and C-3 signals (delta)_C74.8,121.0) respectively move to delta in the low field direction_C80.2 and delta_C117.7, indicating that the latter 2-OH is a dehydration condensation with carvacrol 2' -OH to form an ether group, in good agreement with the above presumption. By HMBC correlation spectroscopy (FIG. 1), all signals were assigned (Table 1), especially H-2(δ)_H4.68)/C-2'(δ_C156.0) and proves that C-2 is connected with C-2' through ether bond. Although the absolute configuration of this compound was not determined by direct experimental means, no spatial correlation of H-2 with H-7 was observed in the ROESY correlation spectra (FIG. 2), indicating that H-2 and 1-CH₃On opposite sides, i.e., the C-1 and C-2 configurations are either (1R,2R) -or (1S,2S) -forms. In combination with literature data, it was found that p-menthen-l,2-diol of natural origin is all of the (1R,2R) -type, whereas the (1S,2S) -type is an artificially synthesized product. And the direction of optical rotation of the compound is caused by the chiral carbons of C-1 and C-2

(c 0.25,MeOH)]The same direction of optical rotation as that of (1R,2R) - (-) -3-p-menthen-l,2-diolThe optical rotation direction of the (1S,2S) -form is just opposite, and further, it can be confirmed that it is the (1R,2R) -form. Thus, the compound was identified as (1R,2R) - (-) -2- [2' - (1' -methyl-4' -isopropylpropyl) -phenoxyl]-1-methyl-4-isopopyl l-3-en-1-cyclohexanol, named Muscat A (adenosin A). The structural formula is as follows:

TABLE 1 spectroscopic data (chloroform-d) of Musk ether A Compound

Example 2

1. Moschus ether A mosquito repellent experiment

The moschus ether A is adopted as an effective component of a mosquito repelling product, In order to confirm the mosquito repelling effect of the moschus ether A, an In-cage mosquito repelling model (In-cage mosquito repelling bioassay) is adopted to perform a mosquito repelling test on the moschus ether A, and compared with positive control mosquito repelling amine DEET (N, N-diethyl-3-methylbenzamide), the specific method and the result (Table 2) are as follows:

① selecting about 500 (+ -10%) mosquitoes to be tested, placing in a mosquito cage (45cm × 37.5cm × 35cm) for 25 (+ -2.5) min, starting the test, ② precisely weighing 150mg of the tested object, placing in a penicillin bottle, dissolving with 2mL of absolute ethanol, shaking thoroughly, taking out half of the solution, placing in a bottle with 50cm²(5 cm. times.10 cm) gauze to make it be uniformly infiltrated into the above-mentioned all-cotton cloth to obtain 1.5mg/cm²The initial concentration of (a); diluting the rest 1mL with anhydrous ethanol to 2mL, and sequentially half-soaking and half-diluting to obtain a solution on gauze of 0.75, 0.375, 0.094, 0.047, 0.023, and 0.011mg/cm²And a series of dilution concentrations. The bottle seal is stored in an environment at-4 deg.C and is reactivated at the time of testing (typically<48h) The test can be started by removing the gauze from the bottle and placing it on cardboard for 3-5min, then wearing a glove of arm and then a plastic material of polyethylene on the hands of ③ volunteersGloves with a 4 x 8cm opening in the middle of the wrist to elbow to evaluate mosquito stopping and biting, the opening should allow the gas released from the skin surface to attract mosquitoes, in the test, gauze treated with the test article was applied to the open area ④ first with an intermediate concentration (e.g.,0.187 mg/cm)²) The test is carried out by sticking the gauze at the opening, if 0-4 bits/min exists, the concentration is considered to be effective, then testing the gauze with lower concentration until the gauze is ineffective, if more than or equal to 5 bits/min exists, the gauze is considered to be ineffective, then testing the gauze with higher concentration until the gauze is effective, finally, the critical concentration of the effective concentration and the ineffective concentration is the minimum effective dose MED, generally repeating the test for at least 3 times, calculating the average value and the standard deviation of the MED, only 10 continuous tests are allowed in each stage of the test in order to prevent the tested mosquitoes from being reduced in the sensitivity to the odor due to long-term exposure, 15min of recovery period is required in the middle, ⑤ more than 4 volunteers (male and female halves) are alternately participated in a group, each gauze is tested for 1min, the same concentration of the gauze cannot be used for the test once being used for more than 10min, so as to avoid the deviation caused by the volatilization of the object to be tested, referring to GB/T352009 (pesticide laboratory pesticide test room efficacy test and evaluation part 9: repellent), and after the test, the examinee is approved by the central policy of approving to control all the disease.

TABLE 2 Muscat ether A minimum effective dose MED (mean + sd mg/cm) to repel Aedes albopictus²)

Compound (I)	MED
		Musk Ether A	0.063 + -0.027 (Strong)
DEET	0.031 ± 0.014 (Strong)

The experimental result shows that moschus ether A is equivalent to MED of positive control mosquito repellent amine DEET, which shows that the moschus ether A has a remarkable mosquito repellent effect on mosquito repellent strength as DEET.

2. Moschus ether a was tested for cytotoxic activity using the MTT method.

① inoculating cells, preparing a single cell suspension from RMPI 1640 culture medium containing 10% fetal calf serum, inoculating and culturing the cells in advance for 12-24h, adding ② compound solution to be tested, dissolving the compound in DMSO, primary screening the extract at a concentration of 100 μ g/mL, primary screening the compound at a concentration of 40 μ M, secondary screening the compound at a concentration of 100, 20,4, 0.8, 0.16 μ g/mL, and a final volume of 200 μ L, wherein 3 duplicate wells are provided for each treatment, ③ developing color, suspending 100 μ L of culture supernatant of the cells after culturing at 37 ℃ for 48h, adding 20 μ L of MTS solution to each well, setting 3 blank duplicate wells (mixed solution of 20 μ L of MTS solution and 100 μ L of culture solution), continuing incubation for 4h, determining the light absorption value after the reaction is fully performed, selecting the colorimetric ④ colorimetric method, selecting the wavelength of 492nm, reading the light absorption coordinate values of a multi-function microplate reader (MUISKAN), reading the light absorption coordinate values, recording the results of the treated wells, and calculating the survival rate of the growth curve of the cells by using the Reanchovular growth curve (Reanchovnig method) as two points₅₀Values (table 3).

TABLE 3 cytotoxic Activity of Muscat A

NC-no toxicity at maximum concentration of 40. mu.M

The experimental result shows that the moschus ether A does not show cytotoxicity to human dermal fibroblast HDFa under the highest concentration of 40 mu M, and the cellular level shows that the moschus ether A has the safety advantage when being used for mosquito repellent products.

Example 3 preparation of moschus ether a-containing mosquito repellent air freshener

20 parts of moschus ether A is dissolved in 20 parts of absolute ethyl alcohol according to the mass ratio, 60 parts of distilled water and 0.5 part of Tween 80 solubilizer are added, and the mixture is fully stirred and uniformly mixed.

Example 4 preparation of moschus ether A-containing mosquito repellent

Dissolving moschus ether A10 parts and citronella essential oil 10 parts in anhydrous ethanol 20 parts according to the mass ratio, adding 60 parts of distilled water and Tween 80 solubilizer 0.5 part, and fully stirring and uniformly mixing.

Example 5 moschus ether A-containing mosquito repellent cream

The formula is as follows: 16% of glyceryl stearate, 5.0% of glyceryl tricaprylate, 1.0% of cetyl alcohol, 5.0% of lanolin, 5.0% of propylene glycol, 5.0% of moschus ether A and 62% of deionized water.

Example 6 mosquito repellent cream containing moschus ether a.

The formula is as follows: 5.0% of moschus ether A, 20% of urea, 40% of vaseline, 4.5% of stearyl alcohol, 20% of beeswax, 0.5% of polyoxyethylene oleyl alcohol ether and 10.5% of deionized water.

Example 7 shampoo containing moschus ether a.

The formula is as follows: distilled water about 65%, sodium laureth sulfate 12%, sodium lauryl sulfate 3%, dodecyl betaine 2%, coco diethanol amide 4%, isopropyl palmitate 2%, siloxane 0.6%, glycerin 2%, pearling agent 4%, methyl paraben 0.3%, polygonum multiflorum root extract 5%, proper amount of citric acid, proper amount of pigment, and moschus ether A0.03%.

The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention, and are not intended to limit the scope of the present invention, and any modifications, equivalent substitutions, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.

Claims

1. A compound which is (1R,2R) - (-) -2- [2' - (1' -methyl-4' -isopropyl) -phenoxy ] -1-methyl-4-isopropyl-3-en-1-cyclohexanol.

2. A process for the preparation of a compound according to claim 1, comprising isolating said compound from the essence of menglace musk deer.

3. The method of claim 2, comprising the steps of:

step 2: the compound was isolated from the essential oil by chromatographic methods.

4. A composition for repelling mosquitoes containing the compound of claim 1 as an active ingredient.

5. The composition of claim 4, comprising a carrier and/or excipient.

6. The composition of claim 5, wherein said carrier and/or excipient is selected from the group consisting of water, ethanol, propylene glycol, jojoba oil, gelatin, gum arabic, tween 80, glyceryl stearate, glyceryl tricaprylate, cetyl alcohol, lanolin, urea, petrolatum, stearyl alcohol, beeswax, polyoxyethylene oleyl ether.

7. A composition according to claim 4, which comprises stabilisers, thickeners, colourants and/or perfumes.

8. The composition of claim 4, wherein the compound of claim 1 is added in an amount of 0.1% to 30% by weight of the total composition.

9. Use of a compound of claim 1 for the preparation of a mosquito repellent product.

10. A mosquito-repellent product containing the compound of claim 1 as an active ingredient for mosquito repellency.

11. The mosquito-repellent product of claim 10, which is a liquid, an ointment, a pendant, or a convenient patch.

12. The mosquito-repellent product of claim 10, which is a cosmetic.

13. The mosquito-repellent product of claim 10, which is a mosquito repellent.

14. The mosquito-repellent product of claim 13, wherein the mosquito repellent is selected from the group consisting of oil-based formulations, alcohol-based formulations, and water-based formulations.

15. The mosquito-repellent product of claim 10, selected from the group consisting of mosquito repellent patches, mosquito repellent creams, mosquito repellent shampoos, mosquito repellent air fresheners.

16. The mosquito-repellent product of claim 10, wherein the compound of claim 1 is added in an amount of 0.1% to 30% of the total mass of the product.

17. A method of repelling mosquitoes comprising administering an effective amount of a compound of claim 1, a composition for repelling mosquitoes of any one of claims 4-8, or a mosquito-repelling product of any one of claims 10-16.

18. Use of a compound according to claim 1 as a fragrance.

19. A perfume comprising the compound of claim 1.

20. A perfume according to claim 19 wherein the compound is present in the perfume in an amount of from 0.001% to 20% by weight.

21. The fragrance of claim 19 comprising a solvent.

22. The fragrance of claim 21, the solvent being selected from the group consisting of: one or more of ethanol, isopropanol, diethylene glycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate and isopropyl myristate.

23. A product comprising the flavour of any of claims 19-22.