Process for obtaining a scented extract of fresh flowers and/or leaves using natural solvents

Abstract

The invention relates to methods for obtaining a scented extract from fresh flowers, flowering heads and/or leaves of a moist plant. The method includes picking the flowers, flowering tops and/or leaves of the plant and infusing them in at least one bath comprising an alcoholic solvent, at a temperature below 50 C., to obtain an alcoholic mixture. The alcoholic mixture is then filtered to recover an alcoholic floral infusion. The method also includes performing a supercritical CO.sub.2 extraction of the alcoholic floral infusion to obtain a scented extract. This scented extract has an alcohol titrate of at least 75%. The invention also relates to scented water or perfume, food flavoring, and cosmetic compositions that contain the scented extract as an ingredient.

Claims

1. A method for obtaining a scented extract from fresh flowers, flowering tops, and/or leaves of a moist jasmine or mimosa plant, the method comprising: picking flowers, flowering tops and/or leaves of a moist jasmine or mimosa plant; infusing within 12 hours after picking and without breaking said flowers, flowering tops, and/or leaves in at least one bath including an alcoholic solvent comprising ethanol, at a temperature below 50 C., to obtain an alcoholic mixture comprising a final weight/weight flower-leaf to alcohol ratio of 1:1 to 1:3; wherein said flowers, flowering tops, and/or leaves are passed multiple times through the at least one bath including the alcoholic solvent, and wherein the infusing is performed at a temperature of between 15 C. and 35 C. for a period of about ten minutes to about two hours; filtering said alcoholic mixture to recover an alcoholic floral infusion; and performing a supercritical CO.sub.2 extraction of the alcoholic floral infusion to obtain a scented extract in alcohol.

2. The method according to claim 1, wherein infusing includes circulating the alcoholic solvent.

3. The method according to claim 1, further comprising cooling the alcoholic floral infusion at a temperature of about 4 to 10 C. for a period of between 1 day and a number of months.

4. The method according to claim 1, wherein performing the supercritical CO.sub.2 extraction includes applying a pressure of between 130 and 200 bars and a temperature of between 35 and 55 C.

5. The method according to claim 1, further comprising concentrating the scented extract under vacuum by heating at a temperature below 60 C. to form a concentrated scented extract.

6. The method according to claim 5, wherein the scented extract or the concentrated scented extract comprises methyl jasmonate, maltol, and phenylacetaldehyde.

7. The method according to claim 1, further comprising applying the scented extract to the skin as a perfume, or diluting the scented extract further with alcohol to form a perfumed dilution alcohol and then applying the perfumed dilution alcohol to the skin as a perfume.

8. The method of claim 1, wherein the jasmine flowers, flowering tops and/or leaves are selected from the group consisting of Jasminum grandiflorum, Jasminum officinale, Jasminum odoratissimum, Jasminum sambac, Jasminum auriculatum, and Jasminum flexile.

9. The method according to claim 1, further comprising adding the scented extract as a perfumery ingredient to a perfume medium.

10. The method according to claim 1, further comprising adding the scented extract, as a food flavoring, to a food.

11. The method according to claim 1, further comprising adding the scented extract to a cosmetically medium to form a cosmetic composition.

12. The method of claim 11, wherein the cosmetic composition is a topical composition.

13. The method of claim 1, wherein the scented extract comprises at least 75% wt/wt alcohol.

14. A method for obtaining a concentrated scented extract from fresh flowers, flowering tops, and/or leaves of a moist jasmine or mimosa plant, the method comprising: picking flowers, flowering tops and/or leaves of a moist jasmine or mimosa plant; infusing within 12 hours after picking and without breaking said flowers, flowering tops, and/or leaves in at least one bath including an alcoholic solvent comprising ethanol, at a temperature below 50 C., to obtain an alcoholic mixture comprising a final weight/weight flower-leaf to alcohol ratio of 1:1 to 1:3; wherein said flowers, flowering tops, and/or leaves are passed multiple times through the at least one bath including the alcoholic solvent, and wherein the infusing is performed at a temperature of between 15 C. and 35 C. for a period of about ten minutes to about two hours; filtering said alcoholic mixture to recover an alcoholic floral infusion; performing a supercritical CO.sub.2 extraction of the alcoholic floral infusion to obtain a scented extract in alcohol; and concentrating, only after performing the supercritical CO.sub.2 extraction, the scented extract.

15. A method for obtaining a scented extract from fresh flowers, flowering tops, and/or leaves of a moist jasmine or mimosa plant, the method consisting essentially of: picking flowers, flowering tops and/or leaves of a moist jasmine or mimosa plant; infusing within 12 hours after picking and without breaking said flowers, flowering tops, and/or leaves in at least one bath including an alcoholic solvent comprising ethanol, at a temperature below 50 C., to obtain an alcoholic mixture comprising a final weight/weight flower-leaf to alcohol ratio of 1:1 to 1:3; wherein said flowers, flowering tops, and/or leaves are passed multiple times through the same bath including the alcoholic solvent, and wherein the infusing is performed at a temperature of between 15 C. and 35 C. for a period of about ten minutes to about two hours; filtering said alcoholic mixture to recover an alcoholic floral infusion; and performing a supercritical CO.sub.2 extraction of the alcoholic floral infusion to obtain a scented extract in alcohol.

Description

(1) The invention and the advantages resulting therefrom will be easier to understand in view of the following description and non-limiting embodiments, with reference to the appended figures, wherein:

(2) FIG. 1 shows a floral diagram wherein the scent of a hexane jasmine flower extract is compared with that of an extract obtained according to the process according to the invention; and

(3) FIG. 2 shows a floral diagram wherein the scent of a hexane mimosa flower extract is compared with that of an extract obtained according to the process according to the invention.

(4) The process according to the invention is implemented so as to obtain a scented extract from fresh flowers, flowering tops, and/or leaves, particularly fragile, from a moist plant.

(5) A moist or fresh plant is a living organism forming part of the plant kingdom, which comprises at least 70% water by weight of its total weight, conventionally around 85% water, before or after loss to desiccation in particular associated with picking.

(6) As a non-limiting example of fragile fresh flowers, flowering tops and/or leaves according to the invention, it is possible to cite jasmine and in particular among more than 200 species, Jasminum grandiflorum, Jasminum officinale, Jasminum odoratissimum, Jasminum sambac, Jasminum auriculatum, Jasminum flexile, mimosa, rose, tuberose, genet, bitter orange, carnation, violet, verbena, linden, chamomile, basil leaf, coriander leaf, frangipani, tiar, gardenia, marigold, French marigold, narcissus, hyacinth, daffodil, lily, magnolia, lily of the valley, ylang-ylang, osmanthus, lilac, honeysuckle or geranium.

(7) In a first step of the process according to the invention, the important parts of the plant are picked, namely the flowers, flowering tops and/or leaves.

(8) Such freshly picked flowers, flowering tops and/or leaves are very fragile and can be preserved as is only for a short time, at most several hours, for example 12 hours, and will preferably be used within 3 hours after picking to prevent degradation and loss of a large part and sometimes all of their scented, and primarily fragrant, qualities.

(9) For example, jasmine flowers degrade 3 hours after being picked, and mimosa or tuberose flowers can be preserved as is for up to 12 hours.

(10) Then, according to the process according to the invention, said freshly picked flowers, flowering tops and/or leaves are infused in at least one bath containing an alcoholic solvent, at a temperature below 50 C., so as to obtain an alcoholic mixture.

(11) As an example of an alcoholic solvent according to the invention, a natural alcohol is used, chosen from methanol, ethanol, propanol 1, 2-propanol, butanol, isobutanol, pentanol, isoamylic alcohol and preferably ethanol which has a lower boiling point (except for methanol) and which is much less toxic than methanol in particular.

(12) According to the invention, the flowers, flowering tops and/or leaves are preferably infused in the alcoholic solvent at room temperature, i.e. at a temperature between 15 and 35 C.

(13) The duration of the infusion step according to the invention can be up to several hours, for example 12 hours, and will have an influence on the olfactory profile of the extract.

(14) Advantageously, the duration of the infusion according to the invention was optimized and is between around ten minutes to around two hours, a time necessary and sufficient for extracting the scented molecules collected in the primary scented alcohol extract according to the invention.

(15) In the infusion, the flowers, flowering tops and/or leaves are steeped in the alcoholic solvent and can be gently stirred.

(16) Advantageously, the infusion is produced by circulating the solvent in a closed circuit, i.e. the solvent is circulated over the flowers, flowering tops and/or leaves so as to create movement in the extractor, without breaking in particular the petals, and avoiding areas of saturation of the solvent at the periphery of the petals. The stirring thus provides less saturated solvent, which in turn will perform the extraction.

(17) Alternatively, it is possible to produce infusions in a plurality of concomitant or sequential baths, depending on the quantity of flowers and/or leaves to be treated.

(18) It is possible, for example, to produce a single bath, then perform a rinsing with the new extraction solvent, a plurality of baths with the same flowers and/or leaves, or even a plurality of passes of flowers and/or leaves over the same bath because of the low ethanol saturation, for a final weight/weight flower-leaf/alcoholic solvent ratio of 1:1 to 1:10, preferably 1:1 to 1:3.

(19) For example, the flowers and/or leaves are advantageously passed multiple times through the same alcohol bath in order to saturate it, for example up to 5 passes, enabling the primary alcoholic extract to be concentrated. This is more economical in terms of volumes to be transported and subsequently treated with supercritical CO.sub.2.

(20) Then, according to the process according to the invention, the flowers, flowering tops and/or leaves are drained, without being crushed, and the alcoholic mixture thus obtained is filtered so as to recover an alcoholic floral infusion capable of being kept cool at a temperature of around 4 to 10 C. for a period of one day to a number of months.

(21) Such an alcoholic floral infusion according to the invention is a product that is possibly colored, with an especially high water and sugar content, and titrated with at least 45% alcohol.

(22) This infusion step according to the invention is essential because it makes it possible to preserve, for several weeks, at between 4 and 10 C. in the form of an alcoholic floral infusion, an extract of fresh fragile flowers and/or leaves that would not stay fresh, and without altering the scented qualities. Indeed such fresh flowers and/or leaves must be used quickly after being picked to prevent drying and loss of all of their scented and primarily fragrant qualities.

(23) To this effect, advantageously, the process according to the invention also comprises a step wherein the alcoholic floral infusion is kept fresh at a temperature of around 4 to 10 C. for a period of between 1 day and several months, for example 12 or even 24 months.

(24) Thus, the process according to the invention is easy to implement and limits the time constraints. Moreover, the process according to the invention makes it possible to guard against complex logistics associated with the bulk of the extraction equipment and the fact that the plants containing it are often not located near the harvesting sites. Instead, the alcoholic floral infusion obtained according to the invention can easily be transported to sites where it will undergo the refining necessary for obtaining a scented extract smelling of fresh flowers and/or leaves according to the invention.

(25) To this end, according to the process according to the invention, a supercritical CO.sub.2 extraction of the alcoholic floral infusion is performed in order to obtain said scented extract.

(26) Advantageously, this scented extract obtained according to the invention is titrated with at least 75% alcohol.

(27) The supercritical CO.sub.2 extraction process is known. In the supercritical state, namely more than 74 bars and 31 C., the CO.sub.2 has very specific properties and can be used as a natural extraction solvent. The fluid obtained is characterized by a high diffusivity (on the order of that of gases), which makes it suitable for diffusion, and a high density, which makes it highly suitable for transport and extraction.

(28) The supercritical CO.sub.2 extraction step according to the invention can be performed in static mode or in dynamic mode.

(29) According to the invention, CO.sub.2 is preferably used at a pressure of between 130 and 200 bars and at a temperature of between 35 and 55 C., even more preferably at 150 bars and 45 C., at counter-current, and is particularly suitable for obtaining a clear, limpid and stable scented extract of fresh flowers and/or leaves largely free of sugars, colorants, water and titrated with at least 75% alcohol.

(30) Advantageously, the process according to the invention also comprises a step wherein the scented extract obtained after extraction with supercritical CO.sub.2 is concentrated as is, under vacuum by gentle heating below 60 C., or on a substrate such as natural oil, Shea butter, natural glycerin or a natural fragrant molecule such as natural benzyl acetate.

(31) In addition, the process according to the invention gives yields at least similar to those obtained with the traditional processes for obtaining an essential oil or an absolute from these same flowers, and greater than those obtained by extraction directly on the flowers with supercritical CO.sub.2.

(32) As an example, according to the process according to the invention, mass yields equivalent to 2 kg of flowers per kg of extract are obtained.

(33) Moreover, when such an extract obtained according to the process according to the invention is concentrated, yields are obtained with the flower on the order of 0.1% to 0.2%, i.e. 0.5 to 1 tonne of flowers per kg of extract, equivalent to those obtained for the absolute.

(34) As an example, the table below shows, with measurements performed in gas chromatography by the applicant, the composition of an extract obtained according to the process according to the invention, using 750 kg of Jasminum grandiflorum flowers picked in the Maritime Alps from August to October 2010. Two hours after being picked, these flowers were infused, gently stirred, in natural ethanol at 25 C. for 20 minutes, with the flower/ethanol ratio being 1:1 by weight. Then, the flowers were drained, without being too crushed, and rinsed. The alcoholic floral infusion was then filtered and packaged for 2 to 3 months pending the supercritical CO.sub.2 extraction. Finally a supercritical CO.sub.2 extraction of the alcoholic floral infusion was performed at 45 C. and 150 bars for 20 minutes. The scented extract thus obtained according to the invention was then partially concentrated under vacuum at low temperature (35 C.). To this effect, in the table below, the composition of the scented extract according to the invention thus obtained was compared with that of a traditional absolute obtained by hexane extraction from the same flower harvest and diluted to 10% in alcohol.

(35) TABLE-US-00001 Concentrate of a jasmine extract obtained Jasmine hexane according to the Molecules identified absolute invention cis-3-hexenol 0.06 trans-2-hexenol 0.05 diethyl oxalate 0.16 phenylacetaldehyde 0.25 benzyl alcohol 1.8 3.17 methyl benzoate 0.25 maltol 0.22 1.19 p-cresol + linalol 3.16 4.45 phenylethyl alcohol 0.21 benzyl acetate 11.48 11.12 ethyl benzoate 0.11 methyl salicylate 0.05 terpineol 0.07 benzoic acid 0.39 0.37 phenylethyl acetate 0.06 geraniol 0.07 indole 0.38 methyl anthranilate 0.17 eugenol 2.12 0.51 vanillin + cis jasmone 1.95 2.16 isoeugenol + geranyl 0.13 0.15 acetone jasmine lactone 0.85 0.23 c15 alkane 0.17 c, t farnesene 0.08 t, t farnesene 1.87 2.53 benzoate c-3-hexanyl + 1.23 1.97 lactone methyl 0.57 0.48 acetylanthranilate methoxy-6-eugenol 0.14 0.2 t methyl jasmonate 0.69 0.47 c methyl jasmonate 0.22 0.75 coniferyl aldehyde 0.16 coniferyl alcohol 0.43 benzyl benzoate 10.12 9.35 trimethylpenadecanone-2 1.82 1.6 benzyl salicylate 0.62 0.32 methyl palmitate 0.87 0.9 isophytol 9.81 10.8 ethyl palmitate + C16 0.87 0.42 acid geranyllinalol 3.71 5.63 methyl linolenate 1.95 1.8 phytol 13.58 15.31 ethyl linolenate + 2.02 0.58 isophytyl acetate phytyl acetate 4.68 3.59 C23 alkane 0.27 phenylethyl linolenate 0.72 squalene 1.82 1.52 epoxydihydrosqualene 3.41

(36) This table shows, on the basis of the results obtained, differences in composition between a jasmine flower extract obtained according to the process according to the invention and a hexane absolute of these same flowers.

(37) More specifically, the jasmine flower extract obtained according to the process according to the invention comprises, in particular, in significant amounts, more methyl jasmonate and maltol than the hexane absolute does, and contains phenylacetaldehyde, whereas the hexane absolute does not contain it.

(38) Also, the jasmine flower extract obtained according to the process according to the invention comprises, in a significant amount, less eugenol than the hexane absolute does, and does not comprise geraniol or indole in this production.

(39) In addition, if it is compared with the compounds identified in the extract disclosed in document EP0309339, the extract obtained according to the process according to the invention does not contain, for example, geraniol or phenyl-2-ethanol.

(40) Thus, such differences in composition between the extracts are characterized by substantially different scents.

(41) Indeed, as shown in FIG. 1, the applicant performed a scent test using 8 professionals in order to compare the scents of the 2 jasmine flower extracts mentioned in the table above.

(42) This floral diagram shows, on the basis of the results obtained, differences in scent between the 2 extracts characterized by the differences in composition mentioned in the table above.

(43) The extract obtained according to the process according to the invention has fine floral scents due, in particular, to the jasmonates as well as a sweet, fruity honey scent due, in particular, to the maltol. Also, very vegetal notes are observed, of tea hay, characteristics of the scent of the local country, jasmine flowers and bushes with the extract obtained according to the process according to the invention, which is not the case with the hexane extract. However, the absence of indole and waxes in this extract according to the invention makes it possible to limit the powerful animal and fatty floral scent characteristic of these compounds, found only in the hexane extract.

(44) As an example, the extract obtained according to the process according to the invention using jasmine flowers is in the form of a very pale yellow to yellow, limpid, mobile, transparent liquid, and has a native fresh flower scent. After concentration, a concentrate is obtained that is in the form of a very powerful brown-green liquid or paste with jasmine, vegetal, fruity, honey notes.

(45) Similarly, the table below shows, with measurements performed in gas chromatography by the applicant, the composition of an extract obtained according to the process according to the invention using 2 kg of mimosa flowering branches picked in the Tanneron Massif in March 2010. Four hours after being picked, these mimosa flowering branches were infused in 6 kg of natural ethanol circulating at 25 C. for 2 hours, with the mimosa flowering branch/ethanol ratio being 1:3 by weight. The alcoholic floral infusion was then filtered and packaged pending the supercritical CO.sub.2 extraction for 3 weeks. Finally, a supercritical CO.sub.2 extraction of the alcoholic floral infusion was performed at 45 C. and 150 bars for 20 minutes. The scented extract thus obtained according to the invention was then concentrated under vacuum, iced and filtered, for a soluble concentrate yield of the flower of 0.40% in this trial. To this effect, the composition of the scented extract according to the invention thus obtained is compared in the table below with that of a traditional absolute obtained by hexane extraction from the same harvest of mimosa flowering branches and diluted to 10% in alcohol.

(46) TABLE-US-00002 Concentrate of a Mimosa branch extract Hexane obtained Molecules identified absolute according to GC analysis/non- Kovats of Mimosa the polar index branches invention volatile.sup.a/heavy.sup.b 0.12 0.68 content cis-3-hexenol 839 0.03 diethyloxalate 940 0.08 benzyl alcohol 1010 0.09 0.29 ethyl heptanoate 1080 0.05 nd phenylethyl alcohol 1096 0.17 0.1 2,3-dihydro-3,5- 1115 0.06 dihydroxy-6- methylpyran-4-one [28564-83-21] ethyl benzoate 1146 0.04 nd benzoic acid 1152 0.04 0.47 octanoic acid 1170 0.18 5-hydroxymethyl 1176 0.09 furfural 2,3- 1194 0.16 dihydrobenzofuran anisaldehyde 1224 0.02 0.09 anisic alcohol 1267 0.03 0.13 methyl anisate 1327 0.03 0.08 DEA ald C9 1371 0.04 0.05 ethyl anisate 1424 0.07 C15 alkane 1500 0.05 0.28 C16 alkene 1584 0.03 0.17 C16 alkane 1600 0.14 heptadecadiene 0.04 0.63 heptadec-8-ene 1684 2.05 12.6 C17 alkane 1700 0.38 2.2 benzyl benzoate 1726 0.04 0.04 C18 alkane 1800 0.07 0.24 6,10,14 1830 0.08 0.23 trimethylpentadecan- 2-one C19 alkene 1894 0.05 0.11 heptadecenal 0.2 C19 alkane 1900 1.79 6.91 heptadecanal 1897 0.41 ethyl palmitate 1976 0.96 0.96 C20 alkane 2000 0.72 0.16 alpha-kaurene 2006 0.09 C21 alkane 2100 0.51 1.82 ethyl linolenate 2153 0.72 0.35 C23 alkane 2300 0.24 2.83 C24 alkane 2400 0.21 C25 alkane 2500 0.02 0.69 Lupenone 52.08 29.35 Lupeol 7.03 3.95 .sup.avolatile compounds of which the Kovats index is below 2500 .sup.bbackground compounds based on the Kovats index equal to 2500.

(47) This table shows, on the basis of the results obtained, a notable variation in the chemical balance between the most volatile compounds (the most scented) and the heaviest compounds to the advantage of the mimosa flowering branch extract (0.68) obtained according to the process according to the invention with respect to the classic extract (hexane then ethanol) (0.12). Composition differences are thus observed between this extract obtained in the process according to the invention and the absolute, and in particular the mimosa flowering branch extract obtained according to the process according to the invention comprises, in a significant amount, more heptadec-8-ene than the hexane absolute, and comprises two times less lupenone and lupeol in this production.

(48) Thus, such composition differences between the extracts are characterized by substantially different scents.

(49) Indeed, as shown in FIG. 2, the applicant performed a scent test with 8 professionals in order to compare the scents of the 2 mimosa flowering branch extracts mentioned in the table above.

(50) This floral diagram shows, on the basis of the results obtained, differences in scent between the 2 extracts characterized by the composition differences mentioned in the table above.

(51) The extract obtained according to the process according to the invention has fine floral scents characteristic of methyl anisate, very vegetal, powdery and faithful to the scent of mimosa. By contrast, the hexane absolute has a powerful green, fatty (cis-3-hexenol) floral note, powerful head note with a weaker and less persistent background note.

(52) As an example, the extract obtained according to the process according to the invention based on mimosa flowering branches is in the form of a mobile alcoholic liquid titrated at more than 85% by weight of alcohol, transparent yellow and with a very light, gentle honey scent, characteristic of fresh mimosa flowers. After concentration, a concentrate is advantageously obtained that can be iced and filtered, and then becomes pasty, darker, olive green, its odor intensifying with floral, honey and vegetal notes.

(53) The process according to the invention thus makes it possible to obtain a scented fresh flower and/or leaf extract using natural solvents, not obtained from petrochemistry, and which complies with the Cosmebio charter that defines the basic principles of ecological and organic cosmetics according to specifications certified by Ecocert. The process according to the invention makes it possible to obtain scented extracts that are faithful to the scent of natural fresh flowers, and that are different from the traditional perfumery standards.

(54) In addition, according to another aspect, the invention relates to an extract prepared by the process according to the invention.

(55) Such extracts are very difficult to characterize as such because they vary, for the same species, according to different factors such as the flowers used, the harvest site, or the harvest year.

(56) According to a third aspect of the invention, the extracts thus obtained according to the process according to the invention can be used as is as a perfume, or a perfumed dilution alcohol, or a perfumery ingredient. Such extracts can advantageously replace the neutral dilution alcohol of a scented water or a perfume. They can also be used in concentrated form.

(57) Indeed, the extract obtained after supercritical CO.sub.2 extraction is a natural alcohol delicately performed with the plant matter such as the jasmine flower, a limpid liquid that can be used as is. The extract has not been degraded by heating, and the scent is very faithful to that of the plant. In addition, the extract according to the invention is stable during storage, whereas the absolute, for example the jasmine absolute, deposits wax over time (sediment), influencing its appearance and even its scent.

(58) The extract according to the invention can also be used as a food flavoring or in the composition of a cosmetic product.

(59) As an example of a cosmetic composition, compositions intended for topical use in particular on the skin, such as a gel, a cream, a milk, a lotion, an oil, a shampoo or a soap can be cited.

(60) Of course, the invention is not limited to the embodiments and the examples presented above, and a person skilled in the art, performing routine operations, may be led to produce other embodiments not explicitly described, which fall within the broad scope of the invention.