FRAGRANCE MIXTURE

Abstract

A fragrance mixture and its applications, in particular perfume oils, cosmetic agents, application agents or washing and cleaning agents, containing a sensory effective amount of (i) (E)-2-methyl-but-2-endicarboxylic acid diethyl ester, (ii) (Z)-2-methyl-but-2-endicarboxylic acid diethyl ester or (iii) 2-methylenebutanedicarboxylic acid diethyl ester and mixtures thereof and analogous esters derived from these compounds and mixtures.

Claims

1. A fragrance mixture comprising a sensory effective amount of one, two or all three compounds selected from the group consisting of: formula (i), formula (ii) and formula (iii): ##STR00015## wherein R.sup.1 each represents a linear, branched or cyclic alkyl radical having 1 to 10 carbon atoms, an araliphatic or aromatic radical, and wherein R.sup.2 each represents a linear, branched or cyclic alkyl radical having 1 to 10 carbon atoms, an araliphatic or aromatic radical.

2. A fragrance mixture according to claim 1, wherein R.sup.1 and R.sup.2 in the compounds of formula (i), formula (ii) and formula (iii) are each the same radical.

3. A fragrance mixture according to claim 1, wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of: linear or branched methyl, ethyl, propyl, and butyl alkyl radicals.

4. A fragrance mixture according to claim 1, wherein the compounds of formula (i), formula (ii) and formula (iii) are each as follows: (i) (E)-2-methyl-but-2-endicarboxylic acid diethyl ester, (ii) (Z)-2-methyl-but-2-endicarboxylic acid diethyl ester, and (iii) 2-Methylenebutanedicarboxylic acid diethyl ester.

5. A fragrance mixture according to claim 1, characterized in that it contains the compound of formula (i), relative to the sum of the compounds of formula (i), formula (ii) and formula (iii), in an amount of 50 to 100% by weight.

6. A fragrance mixture according to claim 1, characterized in that it contains the compounds selected from the group consisting of formula (i), formula (ii) and formula (iii) that together amount to 0.001 to 99.999 wt. % based on the fragrance mixture.

7. A fragrance mixture according to claim 1, characterized in that it contains one or more further fragrances selected from the group consisting of: (1) Hydrocarbons; (2) Aliphatic alcohols; (3) Aliphatic aldehydes and their acetals; (4) Aliphatic ketones and their oximes; (5) Aliphatic sulphur-containing compounds; (6) Aliphatic nitriles; (7) Esters of aliphatic carboxylic acids; (8) Acyclic terpene alcohols; (9) Acyclic terpene aldehydes and ketones; (10) Cyclic terpene alcohols; (11) Cyclic terpene aldehydes and ketones; (12) Cyclic alcohols; (13) Cycloaliphatic alcohols; (14) Cyclic and cycloaliphatic ethers; (15) Cyclic and macrocyclic ketones; (16) Cycloaliphatic aldehydes; (17) Cycloaliphatic ketones; (18) Esters of cyclic alcohols; (19) Esters of cycloaliphatic alcohols; (20) Esters of cycloaliphatic carboxylic acids; (21) Araliphatic alcohols; (22) Esters of araliphatic alcohols and aliphatic carboxylic acids; (23) Araliphatic ethers; (24) Aromatic and araliphatic aldehydes; (25) Aromatic and araliphatic ketones; (26) Aromatic and araliphatic carboxylic acids and their esters; (27) Nitrogen-containing aromatic compounds; (28) Phenols, phenyl ethers and phenyl esters; (29) Heterocyclic compounds; (30) Lactones; and their mixtures.

8. A perfume oil agent, cosmetic agent, application agent or washing and cleaning agent containing a fragrance mixture according to claim 1.

9. An agent according to claim 8, characterized in that it contains the fragrance mixture according to claim 1 in an amount of 0.05 to 5 wt. %, based on the agent.

10. An agent according to claim 8, characterized in that it is selected from the group consisting of: solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions, skin creams and lotions, face creams and lotions, sun protection creams and lotions, after-sun creams and lotions, hand creams and hand lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair sprays, hair gels, hair lotions, hair conditioners, permanent and semi-permanent hair dyes, hair deforming agents, hair tonics, hair creams and lotions, deodorants, underarm sprays, roll-ons, deodorant sticks, deodorant cremes and decorative cosmetic products as well as perfume extracts, eau de parfums, eau de toilettes, shaving lotions, eau de colognes, preshave products, splash-colognes, refreshing wipes, acidic, alkaline and neutral cleaning agents, floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid WC cleaners, powdered and foamed carpet cleaners, liquid washing agents, powdered washing agents, laundry pretreatment agents, bleaching agents, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants, air fresheners in liquid form, gel-like form or in a form applied on a solid carrier, aerosol sprays, furniture polishes, floor waxes, shoe polishes.

11. A process for the preparation of a mono- and/or diester of mesaconic acid comprising the following steps: (i) reacting itaconic acid with acetic anhydride to obtain itaconic acid anhydride; (ii) isomerization of itaconic acid anhydride to citraconic acid anhydride; (iii) esterification of citraconic acid anhydride with an aliphatic, araliphatic or aromatic alcohol having 1 to 10 carbon atoms or diol having 1 to 5 hydroxyl groups to give a mono- and/or diester of the citraconic acid; and (iv) rearrangement of the mono- and/or diester of the citraconic acid to a mono- and/or diester of mesaconic acid.

12. A process for preparing a mono- and/or diester of the mesaconic acid according to claim 11, wherein in step (ii) a solvent system is used comprising a high boiling point solvent having a boiling point greater than 150 C. and further comprising a co-solvent having a boiling point between 90 and 120 C.

13. A process for the preparation of a mono- and/or diester of mesaconic acid comprising the following steps: (i) providing a solution containing at least one mono- and/or diester of citraconic acid, and optionally, a solvent; (ii) Adding iodine to the solution; (iii) heating the iodine-containing solution to about 170 to 200 C.; and (iv) optionally, distillative purification of the resulting product.

14. A process according to claim 11, characterized in that the mono- and/or diester of the mesaconic acid is an (E)-2-methyl-but-2-endicarboxylic acid ester.

15. A method for imparting, modifying or enhancing a fruity, pear-like scent note in a fragrance mixture, a perfume oil, cosmetic agent, application agent or washing and cleaning agent, comprising the following steps: (a1) providing one or more compounds of formula (i), formula (ii) and/or formula (iii) according to claim 1; and (a2) mixing a sensory effective amount of the one or more compounds of (a1) with a mixture of additional fragrances sufficient to afford a fruity, pear-like scent in the finished preparation, or (b1) providing one or more compounds of formula (i), formula (ii) and/or formula (iii) according to any claim 1; and (b2) mixing a sensory effective amount of the one or more compounds of (b1) with the perfume oil, cosmetic agent, application agent or washing and cleaning agent sufficient to afford a fruity, pear-like scent in the finished preparation.

16. (canceled)

17. A method of imparting, modifying or enhancing a fruity, pear-like scent in a fragrance mixture, a perfume oil, cosmetic agent, application agent or washing and cleaning agent, comprising adding one or more compounds in the group of formula (i), formula (ii) and formula (iii) according to claim 1 to a fragrance mixture, a perfume oil, cosmetic agent, application agent or washing and cleaning agent.

18. The method of claim 17, wherein the compounds of formula (i), formula (ii) and formula (iii) are each as follows: (i) (E)-2-methyl-but-2-endicarboxylic acid diethyl ester, (ii) (Z)-2-methyl-but-2-endicarboxylic acid diethyl ester, and (iii) 2-Methylenebutanedicarboxylic acid diethyl ester.

19. A fragrance mixture according to claim 6, characterized in that it contains the compounds selected from the group consisting of formula (i), formula (ii) and formula (iii) that together amount to 0.05 to 50 wt. % based on the fragrance mixture.

20. A process for preparing a mono- and/or diester of the mesaconic acid according to claim 12, wherein in step (ii) a solvent system is used comprising a polyalkylene glycol (PAG) having a boiling point greater than 150 C. and further comprising dioxane as a co-solvent.

21. A process according to claim 14, characterized in that the mono- and/or diester of the mesaconic acid is (E)-2-methyl-but-2-endicarboxylic acid diethyl ester.

Description

EXAMPLES

Example for Production Process 1: Preparation of mesaconic acid diethyl ester=(E)-2-methyl-but-2-ene-dicarboxylic acid diethyl ester

[0317] Stage 1: Itaconic Acid Anhydride

##STR00007##

[0318] 612 g (6.0 mol) of acetic anhydride were placed in a 2-litre three-necked flask with KPG stirrer, 15-Vigreux column and column head and 780 g (6.0 mol) of solid itaconic acid was added while stirring. The mixture was then slowly heated to 80 C. until the solid was dissolved and stirred for another 30 minutes at this temperature. Subsequently, approx. 680 g acetic acid was distilled off at a vacuum between 150 and 10 mbar and a sump temperature of 80 to 82 C. The acetic acid was then removed from the sample. Approx. 690 g of sump bottom product remained, the raw yield being 680 g. The raw product was used directly in stage 2.

[0319] A 5 g sample of the ester was purified by ball tube distillation and analyzed by gas chromatography and had a composition of 11 wt. % citraconic acid anhydride and 89 wt. % itaconic acid anhydride.

[0320] Stage 2: Citraconic Acid Anhydride

##STR00008##

[0321] In a 2-liter three-necked flask with KPG stirrer, 15 Vigreux column and column head, 100 g of a high-boiling solvent (Synalox 50-B) were placed in the flask and heated to 230 C. while stirring. Subsequently, 690 g of itaconic acid anhydride (crude product stage 1), dissolved in 100 g Synalox, were dosed at a vacuum of approx. 350 mbar within 4 hours. The isomerization product citraconic acid anhydride was continuously extracted with an R/D ratio of 1:1. At the end of the dosing process, the vacuum was increased to 10 mbar and a total of 630 g distillate was obtained, which corresponded to a yield of 94% over both stages. The GC purity was 99%.

[0322] Stage 3: Citric Acid Diethyl Ester

##STR00009##

[0323] In a 2-litre three-necked flask with KPG stirrer, 15 Vigreux column and column head, 780 g ethanol was added and 630 g (5.63 mol) citraconic acid anhydride was added while stirring at room temperature. Subsequently 30 g concentrated sulphuric acid were added within 5 min and heated for 2 hours under reflux. 530 g of a mixture of ethanol/water (80/20 wt. %) were then distilled off at normal pressure and a head temperature of 86 C. (R/D 1:3, duration approx. 80 min). One sample was purified by ball tube distillation and analyzed by gas chromatography, whereby 10 wt. %citraconic acid anhydride and 89 wt. %citracononic acid diethyl ester were found.

[0324] A further 230 g ethanol was then added and again heated for 1 hour under reflux at a head temperature of 84 C. Then 170 of a mixture of ethanol/water (90/10 wt. %) were distilled off (R/D 1:3, duration approx. 40 min). One sample was processed by ball tube distillation and analyzed by gas chromatography, finding 5 wt. % citraconic acid anhydride and 95 wt. % citracononic acid diethyl ester.

[0325] Again, 140 g ethanol were added, heated for 1 hour under reflux and a mixture of 110 g ethanol/water (90/10 wt. %) was distilled off at a head temperature of 82 C. (R/D 1:3, duration approx. 25 min). A sample was processed by ball tube distillation and analyzed by gas chromatography. This revealed 2 wt. % citraconic acid anhydride and 96 wt. % citracononic acid diethyl ester.

[0326] The reaction product was then cooled to room temperature and washed with 400 g water after 400 g MTBE had been added. The organic phase was then first washed three times with saturated sodium bicarbonate solution under strong carbon dioxide development and then with 400 g of a 5 wt. % saline solution. After phase separation, a total of 1,970 g of aqueous phase (waste water fraction I, pH 6) and 1,140 g of organic phase were present.

[0327] 10% of the organic phase was processed by distillation and analyzed by gas chromatography: Yield: 74 g (71% of theory); purity: 99% citracronic acid diethyl ester.

[0328] Stage 4: Mesaconic Acid Diethyl Ester

##STR00010##

[0329] In a 2 litre three-neck flask with KPG stirrer, 15 Vigreux column and column head, 1,100 g of citraconic acid diethyl ester in MTBE (raw product stage 3) were placed and the solvent was distilled off to a sump temperature of 150 C. at 50 to 80 mbar. In this way, about 320 g of MTBE was obtained, which could be used again (see below). Then it was cooled down to approx. 80 C., aerated and mixed with 8 g (31 mmol) iodine while stirring. It was heated to 190 C. for 1 hour. One sample was purified by ball tube distillation and analyzed by gas chromatography, 72.9 wt. % mesaconic acid diethyl ester, 1.1 wt. % itaconic acid diethyl ester and 25.9 wt. % citraconic acid diethyl ester were found.

[0330] Since the proportion of the mesaconic acid ester was still below 80 wt. %, reaction vessel was heated to 190 C. for another hour. One sample was purified by ball tube distillation and analyzed by gas chromatography, and 84.6 wt. % of mesaconic acid diethyl ester, 1.4 wt. %of itaconic acid diethyl ester and 13.8 wt. % of citraconic diethyl ester were found.

##STR00011##

Mesaconic acid diethyl ester=(E)-2-methyl-but-2-enedicarboxylic acid-diethyl ester

[0331] ##STR00012##

Citracononic acid diethyl ester=(Z)-2-methyl-but-2-ene-dicarboxylic acid diethyl ester

[0332] ##STR00013##

Itaconic acid diethyl ester=2-methylene-butanedicarboxylic acid diethyl ester

[0333] After cooling to about 40 to 45 C., 320 g of reused MTBE was added while stirring and it was washed four times with 300 g of a 40% w/w sodium hydrogen sulphite solution, one time with 300 g 5% w/w sodium bicarbonate solution and one time with 300 g 10% w/w sodium chloride solution, with phase separations occurring within 5 minutes. A total of about 1,800 g aqueous phase (waste water fraction II, pH 4) and about 1,000 g organic phase were obtained. The product was cleaned with a quantity of about 1,000 g using a 10 cm nudist column according to Table 1.

TABLE-US-00001 TABLE 1 Distillative Cleaning T(sump) T(head) Pressure R/ Quantity fraction [ C.] [ C.] [mbar] D [g] analysis 1 76-96 55-69 300 250 MTBE 2 96-97 82 300 8 intermediate 3 97-115 82 707 mesaconic acid ester (84.6%) 26 residue 29 cold trap

[0334] The product either turned pink during distillation or discoloured when left standing. To decolorize the ester, 14 g activated carbon was added to the ester while stirring, stirred for 30 minutes at room temperature and then filtered. The yield was 705 g (95% of the theory).

[0335] Rearrangement Step (ii) with Solvent System

[0336] An improved process using a solvent mixture is described below.

##STR00014##

[0337] The solvent mixture Synalox plus 1,4-dioxane is used in the production of citraconic acid anhydride from itaconic acid anhydride. This offers a good yield even with larger approaches. The following implementation was applied.

[0338] The itaconic acid anhydride was placed in dioxane or obtained as a residue from step (i) (3 mol), mixed with 390 g 1,4-dioxane and filled into the dropping funnel.

[0339] After this, step (ii) is carried out in accordance with the prescription set out below.

TABLE-US-00002 Duration Total rec. time Temp. Head Dest. Implementation [h:min] [h:min] Fr. [ C.] [ C.] [g] Remarks Place 300 g Synalox 0:15 0:15 20-230 on top and heat up Dos. Itaconic 2:35 2:50 2 230-235 57-135 686 Vacuum acid anhydride (350-20 mbar) in dioxane
The product is then evaporated in a rotation evaporator (60-70 C./100-20 mbar) and 296 g (GC purity=96.6%) of the citraconic acid anhydride is obtained with a yield of 85%.

[0340] Production of Further Esters

[0341] In analogy to the above-mentioned process examples for (E)-2-methyl-but-2-enedicarboxylic acid diethyl esters, further esters were produced. In particular, the methyl, propyl and n-butyl esters of mesaconic acid were synthesized and analyzed. This resulted in a total of four compounds variants:

[0342] (E)-2-methyl-but-2-endicarboxylic acid dimethyl ester,

[0343] (E)-2-methyl-but-2-endicarboxylic acid diethyl ester,

[0344] (E)-2-methyl-but-2-endicarboxylic acid dipropyl ester,

[0345] (E)-2-methyl-but-2-endicarboxylic acid dibutyl ester.

[0346] Spectroscopic Data:

(E)-2-methyl-but-2-endicarboxylic acid dimethyl ester

[0347] .sup.1H-NMR (400 MHz, CDCl.sub.3): =2.31 (d, J=1.6 Hz, 3H), 3.78 (s, 3H), 3.28 (s, 3H), 6.80 (q, J=1.6 Hz, 1H).

[0348] .sup.13C NMR (CDCl3, 101 MHz): =167.6 (CO), 166.3 (CO), 143.7 (C), 126.5 (CH), 52.6 (CH.sub.3), 51.7 (CH.sub.3), 14.3 (CH.sub.3).

[0349] MS (70 eV): 158, 143, 127, 113, 99.

(E)-2-methyl-but-2-ene-dicarboxylic acid diethyl ester

[0350] .sup.1H-NMR (400 MHz, CDCl.sub.3): =1.32 ppm (t, J=7.1 Hz, 3H), 1.33 ppm (t, J=7.1 Hz, 3H), 2.29 (d, J=1.6 Hz, 3H), 4.23 (q, J=7.1 Hz, 2H), 4.26 (q, J=7.1 Hz, 2H), 6.78 (q, 1.6 Hz, 1H).

[0351] .sup.13C NMR (CDCl.sub.3, 101 MHz): =167.16 (CO), 165.97 (CO), 143.76 (C), 126.66 (CH), 61.57 (CH.sub.2), 60.62 (CH.sub.2), 14.27 (CH.sub.3), 14.20 (CH.sub.3), 14.13 (CH.sub.3).

[0352] MS (70 eV): 186, 157, 141, 113, 99.

(E)-2-methyl-but-2-endicarboxylic acid dipropyl ester

[0353] .sup.1H-NMR (400 MHz, CDCl.sub.3): =0.98 (t, J=7.4 Hz, 3H), 0.98 (t, J=7.4 Hz, 3H), 1.79-1.64 (m, 4H), 2.29 (d, J=1.6 Hz, 3H), 4.13 (t, J=6.5 Hz, 2H), 4.16 (t, J=6.5 Hz, 2H), 6.79 (q, J=1.6 Hz, 1H).

[0354] .sup.13C NMR (CDCl.sub.3, 100 MHz): =167.3 (C), 166.1 (C), 143.7 (C), 126.7 (CH), 67.2 (CH.sub.2), 66.3 (CH.sub.2), 21.9 (CH.sub.2), 21.6 (CH.sub.2), 14.3 (CH.sub.3), 10.4 (CH.sub.3), 10.4 (CH.sub.3).

[0355] MS (70 eV): 214, 199 185, 155, 131, 96.

(E)-2-methyl-but-2-endicarboxylic acid dibutyl ester

[0356] .sup.1H-NMR (400 MHz, CDCl.sub.3): =0.95 (t, J=7.3 Hz, 3H), 0.96 (t, J=7.3 Hz, 3H), 1.47-1.36 (m, 4H), 1.72-1.61 (m, 4H), 2.29 (d, J=1.6 Hz, 3H), 4.18 (t, J=6.7 Hz, 2H), 4.20 (t, J=6.6 Hz, 2H), 6.77 (q, J=1.6 Hz, 1H).

[0357] .sup.13C NMR (CDCl.sub.3, 100 MHz): =167.3 (C), 166.1 (C), 143.7 (C), 126.7 (CH), 65.5 (CH.sub.2), 64.6 (CH.sub.2), 30.5 (CH.sub.2), 30.6 (CH.sub.2), 19.19 (CH.sub.2), 19.18 (CH.sub.2), 14.3 (CH.sub.3), 13.7 (CH.sub.3).

[0358] MS (70 eV): 242, 227, 213, 169, 131, 68.

[0359] Table 2 below shows the results of the GC profile and fragrance test for the esters produced. The abbreviations DD and TN stand for the terms dry down and top note.

TABLE-US-00003 TABLE 2 GC profile: Compound structure DB Wax Fragrance: methyl (E)-2-methyl-but-2- 86% DD: Nothing endicarboxylic acid TN: anise, anethol, dimethyl ester fruity, pineapple, (Z)-2-methyl-but-2- 11% green. endicarboxylic acid dimethyl ester 2-Methylene- 3% butanedicarboxylic acid dimethyl ester ethyl (E)-2-methyl-but-2- 85% DD: buttery, sugary ene-dicarboxylic TN: fruity, green, acid diethyl ester pear (Z)-2-methyl-but-2- 13.8%.sup. ene-dicarboxylic acid diethyl ester 2-Methylene- 1.4% butanedicarboxylic acid diethyl ester propyl (E)-2-methyl-but-2- 82% DD: same as ethyl; endicarboxylic acid TN: fruity, sugary, dipropyl ester linear, violet, (Z)-2-methyl-but-2- 9% endicarboxylic acid dipropyl ester 2-Methylene- 6% butanedicarboxylic acid dipropyl ester n-butyl (E)-2-methyl-but-2- 88% DD: same as ethyl; endicarboxylic acid TN: greener than dibutyl ester others, but weak. (Z)-2-methyl-but-2- 3% green, fruity endicarboxylic acid dibutyl ester 2-Methylene- 8% butanedicarboxylic acid dibutyl ester

APPLICATION EXAMPLES

Example 1: Shower Gel

[0360]

TABLE-US-00004 Material Manufacturer INCI name wt. % Deionized water Water 76.3 Plantacare PS 10 Cognis sodium laureth 20.0 Germany GmbH sulfates, lauryl glucosides Dragocid Liquid Symrise phenoxyethanol, 0.5 methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben Sodium chloride sodium chloride 1.4 Citric acid citric acid 1.3 monohydrate crystalline Perfume oil A1 Symrise Perfume 0.5 or A2 from this (Fragrance) example 1

[0361] Perfume Composition for a Shower Gel

TABLE-US-00005 A2 A1 Example Compar- according ative to example invention HEXENAL TRANS-2 10% DPG 5 5 HEXENOL BETA GAMMA CIS, TRANS-3 1 1 HEXENOL TRANS-2 10% DPG 1 1 HEXENYLACETATE CIS, TRANS-3 6 6 10% DPG HEXENYLISOBUTYRATE CIS-3 5 5 10% DPG VERTOCITRAL 10% DPG 7 7 STYROLYL ACETATE 10% DPG 5 5 ITAL. CITRIC OIL 10 10 BUTYLACETATE 10 10 HEXYLACETATE 30 30 ISOAMYLACETATE 11 11 JASMAPRUNATE 40 40 PRENYL ACETATE 3 3 ALDEHYDE C14 SOG 4 4 PYROPRUNATE 10 10 FRAMBINON 10% DPG 5 5 MALTOL 1% DPG 2 2 DIMETHYLBENZYLCARBINYLBUTYRATE 15 15 PURE GERANYLACETATE 220 220 DAMASCENONE 2 2 ISODAMASCON 5 5 HEDIONE 100 100 AGRUMEX HC 14 14 AMBRETTOLIDE 1 1 ETHYLENE BRASSYLATE 3 3 GLOBALIDE 5 5 MESACONIC ACID DIETHYL ESTER 80 DIPROPYLENE GLYCOL 480 400 1000 1000

[0362] Mesaconic acid diethyl ester can be easily and stably incorporated into any perfume composition and adds a natural, fruity and radiant note.

Example 2: Body Lotion

[0363]

TABLE-US-00006 Component wt. % wt. % paraffin oil 5.00 5.00 isopropyl palmitate 5.00 5.00 cetyl alcohol 2.00 2.00 beeswax 2.00 2.00 Ceteareth-20 2.00 2.00 PEG-20 glyceryl stearate 1.50 1.50 glycerin 3.00 3.00 phenoxyethanol 0.50 Parabens (mixture of 0.50 methyl-, ethyl-, propyl-, butyl-, isobutylparabens) Perfume oil B1 or B2 0.50 0.50 water Ad 100 Ad 100

[0364] Perfume Oils for this Body Lotion

TABLE-US-00007 Perfume Perfume oil B1 oil B2 Fragrances comparative inventive NONADIENAL TRANS, CIS-2,6 5% 2.0 2.0 TEC 20% DPG ETHYL ACETOACETATE 3.0 3.0 FARENAL 10% DPG 5.0 5.0 VERTOCITRAL 3.0 3.0 CYCLOGALBANAT 10% DPG 2.0 2.0 STYRALYL ACETATE 3.0 3.0 MELONAL 0.5 0.5 DIHYDRO MYRCENOL 15.0 15.0 LINALYL ACETATE 20.0 20.0 LEMON OIL TERPENES FLAVOR WONF 8.0 8.0 EUCALYPTOL NAT. 10% DPG 0.5 0.5 HEXYL ACETATE 1.5 1.5 ISOAMYL ACETATE 10% DPG 4.0 4.0 PRENYL ACETATE 10% DPG 4.0 4.0 ALDEHYDE C14 SO-CALLED 2.0 2.0 ETHYL METHYL BUTYRATE-2 1.0 1.0 ALLYL CYCLOHEXYL PROPIONATE 2.0 2.0 ALDEHYDE C16 SO-CALLED 1.0 1.0 FRAGOLANE 0.5 0.5 MAJANTOL 25.0 25.0 LINALOOL 40.0 40.0 DIMETHYL BENZYL CARBINOL 10.0 10.0 TERPINEOL PURE 10.0 10.0 PHENIRAT 30.0 30.0 CITRONELLOL 950 15.0 15.0 GERANIOL 60 10.0 10.0 CITRONELLYL ACETATE EXTRA 2.0 2.0 HEDIONE 90.0 90.0 HEXYL CINNAMIC ALDEHYDE ALPHA 35.0 35.0 HEXYL SALICYLATE 160.0 160.0 METHYL OCTIN CARBONATE 10% DPG 2.0 2.0 CALONE 1951 10% DPG 1.0 1.0 GALAXOLIDE 50% IN IPM 20.0 20.0 ANETHOLE SUPRA 21.5 CELSIUS 2.0 2.0 AGRUMEX HC 15.0 15.0 ORYCLON SPECIAL 40.0 40.0 MESACONIC ACID DIETHYL ESTER 15.0 DIPROPYLENE GLYCOL 415.0 400.0 1.000.0 1.000.0

[0365] The addition of mesaconic acid diethyl ester (MSDEE) to the fragrance composition results in a fresher, fruity note. In addition, the top note becomes more radiant and the end note more nourishing.

Example 3: Fabric Softener

[0366]

TABLE-US-00008 Material Manufacturer Chemical name Function wt. % Deionized water solvents 72.4 water Rewoquat Evonic dialkyl ester cationic 16.6 WE 18 Goldschmidt ammonium surfactant Ltd. ethosulfate Mergal K9N Honeywell 5-chloro-2- preservative 0.10 Austria GmbH methyl-3-(2H)- isothiazolones and 2-methyl- 3-(2H)- isothiazolone Dow Corning Dow Corning polydimethyl defoamer 0.30 1520 Antifoam GmbH. Germany siloxane Magnesium magnesium consistency 10.00 chloride 1% chloride enhancer solution solution Perfume oil Symrise perfume 0.60 C1 or C2 (fragrance)

[0367] Perfume Oils for this Fabric Softener

TABLE-US-00009 Perfume Perfume oil C1 oil C2 Fragrances comparative inventive ALDEHYDE C10 0.5 0.5 ALDEHYDE C11 ISO 2.0 2.0 ALDEHYDES C11 UNDECYLENIC 12.0 12.0 ALDEHYDE C12 MNA 6.0 6.0 FARENAL 1.0 1.0 VERTOCITRAL 8.0 8.0 ALLYL AMYL GLYCOLATE 1.0 1.0 STYRALYL ACETATE 1.5 1.5 DIHYDRO MYRCENOL 65.0 65.0 AGRUNITRIL 1.0 1.0 PEONILE 15.0 15.0 METHYL ANTHRANILATE 10.0 10.0 NEROLIONE 10% DPG 1.5 1.5 ROSEMARY OIL BM 7.0 7.0 SAGE OFFICINALE OIL DALM. 3.0 3.0 ISOBORNYL ACETATE 40.0 40.0 PRENYL ACETATE 0.5 0.5 ISOAMYL BUTYRATE 0.5 0.5 ALDEHYDE C14 SO-CALLED 5.0 5.0 MANZANATE 0.5 0.5 MUGETANOL 5.0 5.0 DIMETHYL BENZYL CARBINYL 2.5 2.5 ACETATE ROSE OXIDE D 3.0 3.0 ANTHER 0.5 0.5 PHENYLETHYL ALCOHOL 35.0 35.0 CITRONELLOL 950 15.0 15.0 GERANIOL 60 10.0 10.0 ISODAMASCON 2.0 2.0 ROSACETATE 35.0 35.0 CRESYL METHYL ETHER PARA 0.5 0.5 BENZYL ACETATE 20.0 20.0 HEXYL CINNAMIC ALDEHYDE ALPHA 40.0 40.0 METHYL BENZOATE 1.0 1.0 AMYL SALICYLATE N/ISO 10.0 10.0 BENZYL SALICYLATE 70.0 70.0 MYSORE ACETATE 15.0 15.0 PARMANYL 0.5 0.5 EUGENOL 10.0 10.0 ETHYL VANILLIN 0.5 0.5 COUMARIN 3.0 3.0 AGRUMEX HC 45.0 45.0 ARBAFLORATE 25.0 25.0 AMBERWOOD F 5.0 5.0 ISO E SUPER 170.0 170.0 PATCHOULI OIL DECOL. 2.5 2.5 SANDRANOL 10.0 10.0 ISOBUTYL QUINOLINE 1.0 1.0 EVERNYL 0.5 0.5 AMBROXIDE 1.0 1.0 GALAXOLIDE 50% IN IPM 120.0 120.0 INDOFLOR CRYST. 0.5 0.5 MESACONIC ACID DIETHYL ESTER 60.0 DIPROPYLENE GLYCOL 220.0 160.0 1,000.0 1,000.0

[0368] The addition of mesaconic acid diethyl ester (MSDEE) to the fragrance composition results in a more natural, round, transparent and fruity note.

Example 4: Soap

[0369]

TABLE-US-00010 Material Manufacturer Chemical name Function wt. % Deionized water solvents 2.0 water Soap Bases various sodium surfactants 95.8 Mix tallowates/ palmitates Titanium Kronos Titan titanium dioxide Dyestuff/ 1.0 Dioxide GmbH. brightener Germany Perfume oil Symrise Perfume 1.2 D1 or D2 (Fragrance)

[0370] Perfume Oils for this Soap

TABLE-US-00011 Perfume oil D1 Perfume oil D2 Fragrances (comparative) (as invented) ALDEHYDE C 8 10.0 10.0 ALDEHYDE C10 14.0 14.0 ALDEHYDE C11 UNDECYLIC 5.0 5.0 ALDEHYDE C12 MNA 4.0 4.0 ISOAMYL ALCOHOL 6.0 6.0 VERTOCITRAL 4.0 4.0 ALLYL AMYL GLYCOLATE 4.0 4.0 DIHYDRO MYRCENOL 120.0 120.0 CITRAL 95 30.0 30.0 AGRUNITRIL 80.0 80.0 CITRONITRILE 40.0 40.0 CITRYLAL 4.0 4.0 ORANGE OIL TERPENES 250.0 250.0 METHYL ANTHRANILATE 1.5 1.5 TERPINEOL HEAD FRACTION 10.0 10.0 EUCALYPTOL NAT. 10.0 10.0 THYMOL CRYST 6.0 6.0 BORNYL ACETATE L CRYST. 82.5 82.5 CAMPHOR DL 20.0 20.0 JASMAPRUNATE 5.0 5.0 ALDEHYDE C14 SO-CALLED 2.0 2.0 MANZANATE 0.5 0.5 ALLYL HEPTOATE 2.5 2.5 ROSE OXIDE L 0.5 0.5 DAMASCONE ALPHA 0.5 0.5 HEDIONE 10.0 10.0 AMYL SALICYLATE N/ISO 60.0 60.0 HEXYL SALICYLATE 35.0 35.0 COUMARIN 2.5 2.5 AGRUMEX HC 30.0 30.0 ORYCLON SPECIAL 55.0 55.0 PATCHOULI OIL DECOL. 2.0 2.0 SANDRANOL 1.5 1.5 TONALIDE 2.0 2.0 MESACONIC ACID DIETHYL ESTER 40.0 DIPROPYLENE GLYCOL 130.0 90.0 1,000.0 1,000.0

[0371] The addition of mesaconic acid diethyl ester (MSDEE) results in more natural, transparent, pear-like and fruity notes. Furthermore, mesaconic acid diethyl ester gives the composition more strength and fullness.

Example 5: Pearl-Lustre Shampoo

[0372]

TABLE-US-00012 wt. Material Manufacturer INCI name % Deionized water water 71.5 Plantacare PS 10 BASF Personal Care sodium laureth sulfates, 20.0 & Nutrition GmbH Lauryl Glucosides Euperlan PK 771 BASF Personal Care glycol distearates, sodium 6.0 & Nutrition GmbH lauryl sulfates, cocamides MEA, Laureth-10 Dragocid Liquid Symrise AG phenoxyethanol, 0.5 methylparaben, ethylparaben, butylparaben, propylparaben, isobutylparaben sodium chloride sodium chloride 1.4 Citric acid citric acid 0.1 monohydrate crystalline Perfume oil G1 Symrise AG Perfume (Fragrance) 0.5 or G2

[0373] Perfume Oils for this Pearlescent Shampoo:

TABLE-US-00013 Perfume oil G1 Perfume oil G2 Fragrances (comparative) (as invented) FARENAL 3.0 3.0 FLORAZON 0.5 0.5 HEXENYL ACETATE CIS-3 3.0 3.0 VERTOCITRAL 1.0 1.0 DYNASCONE 10% DPG 2.0 2.0 CYCLOGALBANAT 2.0 2.0 STYRALYL ACETATE 1.5 1.5 DIHYDRO MYRCENOL 6.0 6.0 OXANTHIA 50% IN TEC 10.0 10.0 10% DPG LEMON OIL ITAL. 10.0 10.0 ORANGE OIL BRASIL 50.0 50.0 HEXYL ACETATE 2.0 2.0 ISOAMYL ACETATE 0.5 0.5 PRENYL ACETATE 0.5 0.5 ETHYL BUTYRATE 10% DPG 2.0 2.0 ALDEHYDE C14 SO-CALLED 25.0 25.0 DECALACTONE GAMMA 5.0 5.0 ETHYL METHYL BUTYRATE-2 1.0 1.0 ALLYL CAPROATE 1.5 1.5 ALLYL CYCLOHEXYL 3.0 3.0 PROPIONATE ALLYL HEPTOATE 2.5 2.5 MELOZONE 2.0 2.0 CALONE 1951 0.5 0.5 MUGETANOL 10.0 10.0 LINALOOL 25.0 25.0 DIMETHYL BENZYL 6.0 6.0 CARBINYL ACETATE DIMETHYL BENZYL 4.0 4.0 CARBINYL BUTYRATE PHENYLETHYL ACETATE 1.5 1.5 PHENYLETHYL ALCOHOL 15.0 15.0 CITRONELLOL 950 10.0 10.0 GERANIOL SUPER 5.0 5.0 GERANYL ACETATE PURE 15.0 15.0 ISODAMASCON 2.0 2.0 BENZYL ACETATE 15.0 15.0 HEDIONE 90.0 90.0 HEXYL CINNAMIC 35.0 35.0 ALDEHYDE ALPHA JASMONE CIS 0.5 0.5 BENZYL SALICYLATE 80.0 80.0 HEXENYL SALICYLATE CIS-3 30.0 30.0 ISORALDEINE 70 35.0 35.0 ARBAFLORATE 15.0 15.0 ISO E SUPER 15.0 15.0 ISOBORNYL CYCLOHEXANOL 30.0 30.0 BRAHMANOL 10.0 10.0 AMBROXIDE 1.5 1.5 GLOBALIDE 5.0 5.0 GALAXOLIDE 50% IN DPG 120.0 120.0 MESACONIC ACID 65.0 DIETHYL ESTER DIPROPYLENE GLYCOL 290.0 225.0 1,000.0 1,000.0

[0374] With a dosage of 0.5% of the perfume oil in the shampoo, the following results are obtained: the addition of mesaconic acid diethyl ester (MSDEE) to perfume oil G2 strengthens the radiant fruity character. In addition, the diffusivity is increased.

Example 6: Transparent Deodorant Sticks (Formulation A, B) or Deodorant Cream Sticks (Formulation C, D)

[0375]

TABLE-US-00014 Component (in wt. %) A B C D aluminium zirconium 25.00 20.00 25.00 20.00 tetrachlorohydrate-glycine complex dimethicone (10 Cst) 5.00 5.00 cyclopentasiloxane 0.50 1.00 0.50 petroleum jelly 5.00 4.70 5.00 5.00 ozokerite 1.00 1.50 stearyl alcohol 12.00 12.00 2-butyloctanoic acid 0.50 0.50 wax 1.25 1.25 PPG-14 butyl ether 9.00 9.00 Hardened rapeseed oil 5.00 5.00 silicon dioxide 1.00 farnesol 0.25 0.25 paraffin oil 0.50 0.50 hydrogenated castor wax oil 3.50 3.50 talc 4.00 4.00 behenyl alcohol 0.20 0.20 d-panthenyl triacetate 1.00 1.00 preserving agent q.s. q.s. q.s. q.s. perfume oil H1 or H2 1.50 1.15 perfume oil G2 from example 5 0.90 0.75 water Ad 100 Ad 100 Ad 100 Ad 100

[0376] Perfume Oils for Transparent Deodorant Sticks or Deodorant Cream Sticks

TABLE-US-00015 Perfume oil H1 Perfume oil H2 Fragrances (comparative) (as invented) ALDEHYDE C10 0.5 0.5 ALDEHYDE C12 MNA 10% DPG 2.0 2.0 MINTONAT 40.0 40.0 MELOZONE 0.5 0.5 VERTOCITRAL 6.0 6.0 DIHYDRO MYRCENOL 120.0 120.0 TETRAHYDRO MYRCENOL 10.0 10.0 AGRUNITRIL 1.0 1.0 ORANGE OIL BRASIL 10.0 10.0 TAMARINE TYPE BASE 10.0 10.0 HEXYL ACETATE 6.0 6.0 ALDEHYDE C14 SO-CALLED 1.0 1.0 TETRAHYDRO LINALOOL 40.0 40.0 DIMETHYL BENZYL 5.0 5.0 CARBINYL BUTYRATE ORANGE FLOWER ETHER 5.0 5.0 PHENYLETHYL ACETATE 6.5 6.5 PHENYLETHYL ALCOHOL 15.0 15.0 GERANIOL SUPER 30.0 30.0 ROSAPHEN 25.0 25.0 ISODAMASCON 0.5 0.5 HEDIONE 300.0 300.0 UNDECAVERTOL 0.5 0.5 ALLYL IONONE 2.5 2.5 IONONE BETA 10.0 10.0 EUGENOL 4.0 4.0 ISO E SUPER 30.0 30.0 BRAHMANOL 2.0 2.0 AMBROXIDE 2.0 2.0 GLOBALIDE 12.0 12.0 GLOBANONE 8.0 8.0 MACROLIDE SUPRA 45.0 45.0 MESACONIC ACID DIETHYL ESTER 50.0 DIPROPYLENE GLYCOL 300.0 250.0 1,000.0 1,000.0

Example 7: Hair Conditioner with UV Protection

[0377]

TABLE-US-00016 Component INCI Name wt. % wt. % Lanette O cetearyl alcohol 4.00 4.00 Dragoxat 89 ethylhexyl isononanoates 4.00 4.00 Emulsiphos potassium cetyl phosphates, 0.50 0.50 hydrogenated palm glycerides Natrosol 250 HR hydroxyethyl cellulose 0.25 0.25 Neo Heliopan phenylbenzimidazole sulfonic 2.00 2.00 Hydro acid L-arginine arginine 1.20 1.20 benzophenone-4 benzophenone-4 0.50 0.50 Neo Heliopan AP disodium phenyl 0.50 1.00 dibenzimidazole tetrasulfonate Edeta BD disodium EDTA 0.05 0.05 Dragocide Liquid phenoxyethanol (and) 0.80 0.80 methylparaben (and) butyparaben (and) ethyparaben (and) propylparaben Dow Corning 949 amodimethicone, cetrimonium 2.00 2.00 Cationic Emulsion chloride, trideceth-12 Dow Corning 5200 laurylmethicone copolyol 0.50 0.50 Perfume oil B2 perfume 0.95 from example 2 Perfume oil H2 perfume 1.25 from example 6 water water (Aqua) Ad 100 Ad 100

Example 8: Sunscreen Milk (W/O)

[0378]

TABLE-US-00017 part raw materials INCI designation wt. % A Dehymuls PGPH Polyglyceryl-2 3.00 dipolyhydroxystearate Beeswax 8100 Beeswax 1.00 Monomuls 90-0-18 Glyceryl Oleate 1.00 Zinc stearate Zinc stearate 1.00 Cetiol SN Cetearyl Isononanoate 5.00 Cetiol OE Dicaprylyl Ether 5.00 Tegosoft TN C12-15 alkyl benzoate 4.00 Vitamin E Tocopherol 0.50 Solbrol P Propyl Paraben 0.10 Neo Heliopan OS Ethylhexyl Salicylate 5.00 Neo Heliopan AV Ethylhexyl 7.50 Methoxycinnamate Uvinul T150 Ethylhexyl Triazone 1.50 B Water, distilled Water (Aqua) Ad 100 Trilon BD Disodium EDTA 0.10 Glycerin Glycerin 5.00 Solbrol M Methylparaben 0.20 Phenoxyethanol Phenoxyethanol 0.70 Neo Heliopan AP Disodium Phenyl 15.00 10% solution, neutral- Dibenzimidazole ized with NaOH Tetrasulfonate C Perfume oil C2 Perfume (Fragrance) 0.25 from example 3 Alpha Bisabolol Bisabolol 0.10

Manufacturing Techniques

[0379] Part A: Heat to approx. 85 C.

[0380] Part B: Heat to approx. 85 C. Add B to A. Allow to cool while stirring.

[0381] Part C: Add and then homogenise.

Example 9: Hair Coloring Cream for a Blonde Shade

[0382]

TABLE-US-00018 PArt Material Manufacturer INCI name wt. % A Oxowax LCW, France Cethyl alcohol, 21.00 Oleyl alcohol, Cetearyl alcohol, Stearic acid Volpo CS 25 Croda GmbH, Ceteareth25 4.00 Germany Berol 175 Brenntag Eurochem Laureth-8 10.00 GmbH, Germany Lanette E BAST Personal Sodium Cetearyl 1.00 Care & Nutrition Sulfate GmbH Covaquat 16 LCW, France Polyquaternium-6 4.00 Water Water (Aqua) 49.30 B Ammonia Merk Eurolab Ammonia 10.20 (20% in water) C Perfume oil D2 Symrise AG Perfume 0.50 from example 4
Mix parts A, B and C other than Covaquat 16 together and heat at 80 C. for 20 minutes. After the product is homogeneous let it cool down. Add Covaquat 16 at 50 C. When the product starts to thicken stop stirring. Add NH.sub.4OH at room temperature and stir until homogenized.

Example 10: Candle

[0383]

TABLE-US-00019 Material wt. % Candle wax 95.00 Perfume oil D2 5.00 from example 4
Melt the candle wax and stir. Add the perfume oil and stir well. Pour into the desired mould.

Example 11: Perfume Oils for Eau De Toilette (10% in Ethanol)

[0384]

TABLE-US-00020 J1 J2 (comparative (example according example) to invention) ACETOACETIC ACID ETHYL 50 50 ESTER FLORALOZONE 10% DPG 50 50 HEXENOL CIS-3 30 30 HEXENYLACETATE CIS-3 10% DPG 10 10 LEAFOVERT 20 20 CYCLOGALBANAT 10% DPG 30 30 MAGNOLAN 305 305 STYROLYLACETATE 20 20 METHYLANTHRANILATE 10% DPG 20 20 RED BERRIES EXTRACT 30 30 ALDEHYDE C14 SO-CALLED 20 20 EXTRA ETHYLMETHYLBUTYRATE-2 30 30 1% DPG MANZANATE 1% DPG 50 50 APRIFLOREN 10 10 DAVANAOEL F. PARF. 10% DPG 30 30 CASSIS 345F TYPE BASE 20 20 LILIAL 100 100 CALONE 1% DPG 100 100 HELIONAL 200 200 FLOROSA 300 300 ETHYLLINALOOL 470 470 ROSE OXIDE D 10% DPG 50 50 PHENYLETHYL ALCOHOL PURE 20 20 CITRONELLOL 950 50 50 DAMASCENONE 10% DPG 30 30 ROSACETATE 10 10 HEDIONE HC/70 1,500.00 1,400.00 UNDECAVERTOL 30 30 IONON BETA 230 230 ISO E SUPER NON DISCOLORING 300 300 EVERNYL 10% DPG 10 10 AMBROXIDE 50 50 ETHYLENE BRASSYLATE 1,000.00 1,000.00 GLOBALIDE 600 500 GLOBANONE 400 400 GALAXOLID PURE 1,800.00 1,800.00 TONALID 500 500 MESACONIC ACID DIETHYL ESTER 200 INDOLE FF 10% DPG 25 25

[0385] The chord with mesaconic acid diethyl ester gives a natural intense pear-like impression.

Example 12: Perfume Oils for Eau De Toilette (10% in Ethanol)

[0386]

TABLE-US-00021 K2 K1 (example (comparative according to example) invention) ACETOACETIC ACID ETHYL 10 10 ESTER HEXENOL CIS-3 2.5 2.5 HEXENYLACETATE CIS-3 1% DPG 4 4 LEAFOVERT 10% DPG 5 5 VERTOCITRAL 10% DPG 4 4 PHENYLACETALDEHYDE 3 3 DIMETHYLACETAL 10% DPG CYCLOGALBANAT 10% DPG 6 6 MAGNOLAN 9 9 STYROLYLACETATE 1 1 DIHYDROMYRCENOL 6 6 LINALYLACETATE 36 36 ITAL. CITRIC OIL 10 10 ORANGE OIL ITAL.SWEET UNF. 2 2 AMAROCIT 1 1 OXANE 1% DPG 3 3 METHYLANTHRANILATE 1 1 10% DPG ISOAMYLACETATE 1 1 ALDEHYDE C14 SOG 1.5 1.5 DECALACTONE GAMMA 10% DPG 2 2 CASSIS BASE 345 BB 10 10 FRAMBINON 1.5 1.5 ETHYLMALTOL 50 50 BOURGEONAL 2.5 2.5 HELIONAL 5 5 FLOROSA BM/PYRANOL 55 50 HYDROXYCITRONELLAL 20 20 ETHYLLINALOOL 38 33 LINALOOL 14 14 DIMETHYLBENZYLCARB- 5 5 INYLBUTYRATE ROSE OXIDE 1.5 1.5 PHENIRAT 3 3 PHENYLETHYL ALCOHOL 1 1 PHENYLETHYLISOBUTYRATE 3 3 10% DPG CITRONELLOL 950 2 2 GERANIOL SUPRA 3 3 NEROL 900 2 2 CITRONELLYL FORMATE 5 5 10% DPG GERANYL FORMATE SUPRA 1 1 DAMASCENONE 1 1 DAMASCON ALPHA 10% DPG 3 3 BENZYLACETATE 6.5 6.5 HEDIONE HC/30 69 69 HEXYLCINNAMIC ALDEHYDE 2 2 ALPHA JASMINLACTONE 1.5 1.5 BENZYLSALICYLATE 32 32 HEXENYLSALICYLATE CIS-3 13 13 DIHYDROIONONE BETA 15 15 ISORALDEIN 95 8 8 ETHYLVANILLIN 36 36 VANILLIN 19 19 CINNAMYL ALCOHOL 1 1 COUMARIN 4 4 AGRUMEX LC 1 1 CASHMERAN 12 12 CEDRAMBER 12 12 ISO E SUPER 150 150 TRIMOFIX O 15 15 PATCHOULI OIL ENTF. DM 22 22 ISOBORNYLCYCLOHEXANOL 35 35 AMBROXIDE 3 3 AMBRETTOLIDE 8 8 MACROLIDE SUPRA 22 22 GALAXOID 50% IN IPM 52.5 52.5 HELVETOLIDE 20 20 INDOLE FF 10% DPG 3 3 MESACONIC ACID DIETHYL 10 ESTER BENZYL ALCOHOL DD 3 3

[0387] The base note is clearly more pear-like with mesaconic acid diethyl ester.

Example 13: Perfume Oil for Eau De Toilette (10% in Ethanol)

[0388]

TABLE-US-00022 L2 L1 (example (comparative according to example) invention) ACETOACETIC ACID ETHYL 1 1 ESTER HEXENOL CIS-3 10% DPG 5 5 HEXENYLACETATE CIS-3 4 4 10% DPG HEXENYLISOBUTYRATE CIS-3 5 5 10% DPG LEAFOVERT 10% DPG 5 5 STYROLYLACETATE 2 2 BERGAMOT OIL REAL 5 5 LINALYLACETATE 20 20 ORANGE OIL GUINEA 2 2 AMAROCIT 6 6 BUTYL ACETATE 10% DPG 1 1 HEXYLACETATE 4 4 ISOAMYL ACETATE 10% DPG 1 1 PRENYL ACETATE 10% DPG 2 2 ALDEHYDE C14 SO-CALLED 2 2 EXTRA DECALACTONE GAMMA 1.5 1.5 MANZANATE 1% DPG 5 5 WINE YEAST OIL GREEN 5 5 MAXIMAROME 1% DPG ETHYLMALTOL 10 10 MALTOL 2.5 2.5 BOURGEONAL 1 1 CYCLAMENALDEHYDE 1.5 1.5 HELIONAL 5 5 FLOROSA 40 40 HYDROXYCITRONELLAL 5 5 ETHYLLINALOOL 20 20 LINALOOL 15 15 DIMETHYLBENZYLCARBINYL 2 2 ACETATE PHENYLETHYL ALCOHOL PURE 5 5 CITRONELLOL 950 8 8 GERANIOL SUPRA 5 5 CITRONELLA ACETATE EXTRA 5 5 GERANYLACETATE PURE 10 10 NERYLACETATE 5 5 DAMASCENONE TOTAL 10% DPG 5 5 DAMASCON ALPHA 10% DPG 6 6 BENZYLACETATE FG 2 2 HEDIONE 120 100 HEXYLCINNAMIC ALDEHYDE 6 6 ALPHA JASMON CIS 10% DPG 3 3 BENZYLSALICYLATE 30 30 HEXENYLSALICYLATE CIS-3 10 10 HEXYLSALICYLATE 30 30 UNDECAVERTOL 2 2 ISORALDEIN 95 10 10 ISOEUGENOL ACETATE 10% DPG 3 3 ETHYLVANILLIN 10% DPG 1 1 VANILLIN 3 3 CINNAMON TALKOHOL 2 2 CUMARIN 3 3 AGRUMEX HC 5 5 CEDAR WOOD OIL VIRGINIA 10 10 AMBERWOOD F 10 10 CASHMERAN 10 10 ISO E SUPER NON DISCOLORING 85 85 POLYSANTOL (MYSANTOL) 5 5 AMBROXIDE 8 8 AMBRETTOLIDE 10 10 GLOBALIDE 10 10 MACROLIDE SUPRA 50 50 GALAXOID 50% IN IPM 115 105 HELVETOLIDE 10 10 MESACONIC ACID DIETHYL 30 ESTER DIPROPYLENE GLYCOL 19.5 19.5

[0389] Stronger fruity pear smell with mesaconic acid diethyl ester.

Example 14: Sensory and Physicochemical Evaluation of Mesaconic Acid Diethyl Ester

[0390]

TABLE-US-00023 Mesaconic acid Test Scale diethyl ester Threshold value in DEP .sup.1) 1-13 6.3 Effect on blotting paper .sup.1) 1-9 5 Dwell time on blotting paper .sup.1) 1-9 2.7 Threshold value in air .sup.1) 5-13 6.4 Threshold value in air .sup.1) ppm 0.047 Intensity in air .sup.1) 1-9 4 Diffuseness 1-9 7.2 Flowering from water .sup.1) 1-9 6 Anosmia .sup.2) % 0 Water solubility .sup.3) 1-9 6.2 Polarity .sup.4) 1-9 3.4 Volatility .sup.5) 1-9 6.4 Estimated stability alkalis .sup.6) Estimated stability acids .sup.6) Estimated stability against oxidation .sup.6) Reduction of bathroom odour .sup.8) 0-7 4.1 Scent intensity in the bathroom .sup.9) 1-9 5.4 Reduction of kitchen odour .sup.8) 0-7 4.5 Scent intensity in the kitchen .sup.9) 1-9 4.9 Reduction of sweat odour .sup.8) 0-7 4.2 Scent intensity sweat .sup.9) 1-9 5.1 Reduction of smoke odour .sup.8) 1-7 3.5 Fragrance intensity smoke .sup.9) 1-9 4.5 In this context: .sup.1) The higher the value, the higher the olfactory performance. .sup.2) Percentage of subjects unable to perceive the odour .sup.3) The higher the value, the higher the water solubility. .sup.4) The higher the value, the lower the polarity. .sup.5) The higher the value, the higher the volatility, the lower the value, the higher the adhesion. .sup.6) Classification: high-moderate-low .sup.7) Standard: Linalool (value = 5) .sup.8) Scale 1 (strong unpleasant odor) to 7 (no unpleasant odor) .sup.9) Scale 1 (no odor) to 9 (strong odor)

Example 15: Stability Studies

[0391] Mesaconic acid diethyl ester (MSDEE) was stored alone and as a component of various formulations for 24 and 72 hours respectively under drastic conditions at 60 C. and 5 bar pressure. The remaining amount of active substance was then determined. The results are summarised in Table 3 below:

TABLE-US-00024 TABLE 3 Storage stability Proportion After After MSDEEE 24 h 72 h Product [wt. %] [%] [%] MSDEE 100 98 98 eau de toilette 4.5 99 99 deodorant 0.5 94 48 shampoo 0.5 100 100 fabric softener 0.5 92 89