Bisabolol with improved optical properties

Abstract

The present invention relates to bisabolol, a process for the production thereof, the use of charcoal to improve the optical properties and, optionally, improved oxidative stability of bisabolol and / or olfactory properties. It further concerns consumer product formulations comprising the bisabolol according to the present invention. In particular, the present invention relates to bisabolol having improved optical and, optionally improved oxidative stability and / or reduction or removal of certain impurities and / or by-products.

Description

250040Bisabolol with improved optical propertiesField of the Invention

[0001] The present invention relates to the field of bisabolol, in particular to bisabolol which has been treated to improve its purity and / or properties such as optical properties. The bisabolol may have been obtained by a biotechnological process.Background of the Invention

[0002] Natural alpha-(-)-bisabolol, often simply denoted as bisabolol, is an important constituent of the essential oil of the chamomile species Chamomilla recutita. Bisabolol is used in cosmetic and pharmaceutical applications owing to its skin-calming and anti-inflammatory properties. Furthermore, alpha-bisabolol is used as an odoriferous substance in the perfume industry.

[0003] Cultivation of plants containing high amounts of alpha-(-)-bisabolol is possible but the increasing demand has led to a search for alternative sources for alpha-(-)-bisabolol. Synthetic methods for producing bisabolol are known for several years, cf. , for example US 2013 / 289317, and for some years now, biotechnological processes gain more importance as a source for alpha-(-)-bisabolol.

[0004] Especially due to increased environmental awareness by customers and manufacturers and new environmental regulations, biotechnological processes become more and more important. Furthermore, biotechnological processes often allow for producing the desired diastereomer (alpha-bisabolol has two stereocenters) in a high excess compared to the undesired diastereomers.

[0005] In a biotechnological process a living organism, usually a microorganism, is used to produce the desired product. Examples for microorganisms are prokaryotic microorganism such as a bacterium or a eukaryotic microorganism such as a yeast. Such a biotechnological process usually included the growth of microorganisms in a growth medium (fermentation step). Enzymatic processes, such as bioconversion or enzyme catalysis may also be used.

[0006] Biotechnological processes generally may provide new challenges because different by-products and / or impurities may be obtained from such a process compared with the previous conventional processes. Thus, new methods for removing or at least reducing these different by-products and / or impurities are required which are cheap, environmentally friendly and usable on an industrial scale. It may, of course, be possible that these new methods are250040 equally applicable and successful in improving the properties of products produced by previous conventional processes.

[0007] Bisabolol may have undesirable optical properties, for example after ageing. However, since the major applications of Bisabolol are cosmetic and pharmaceutical applications owing to its anti-inflammatory, antibacterial, wound healing, skin soothing and moisturizing effects, optical properties may be decisive. Improving the optical properties of ingredients such as bisabolol reduces or eliminates the need for agents to compensate therefor, e.g., optical brighteners, bleaching agents etc., which is desirable from an ecological and economic point of view.

[0008] Thus, new methods for purifying bisabolol, for example bisabolol obtained by biotechnological processes (“Bio-Bisabolol”), are required for providing the desired quality.Summary of the Invention

[0009] Thus, in a first aspect the present invention provides a bisabolol characterized by one or two of the following properties:a) a Hazen factor, determined according to ISO 6271 , of 56 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b) a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min.

[0010] Preferably, the bisabolol according to the first aspect is characterized by both of the properties a) and b).

[0011] The bisabolol according to the first aspect is preferably further characterized by a Hazen factor, determined according to ISO 6271, of 56 or less, after oxidation for 48 hours using a ML OXIPRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 55 or less, more preferably 54 or less, even more preferably 53 or less, even more preferably 52 or less.

[0012] Preferably, the bisabolol according to the first aspect is further characterized by a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min, preferably 17 or less, even more preferably 16 or less, even more preferably 15 or less, even more preferably 14 or less and most preferably 13 or less.

[0013] The bisabolol according to the first aspect is preferably further characterized by one, two, three, four or five of the following properties:c) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less;250040 d) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;e) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C.

[0014] Preferably, the bisabolol according to the first aspect is further characterized by two of the properties c) to g), preferably, the bisabolol is characterized by three of the properties c) to g), more preferably the bisabolol is characterized by four of the properties c) to g), and most preferably the bisabolol is characterized by all five of the properties c) to g).

[0015] The bisabolol according to the first aspect is preferably further characterized in that the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0016] In a second aspect, the present invention is directed to a bisabolol characterized by one, two or three of the following properties:h) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;i) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;250040 k) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

[0017] In a third aspect, the present invention is directed to a bisabolol characterized by one, two or three of the following properties:l) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

[0018] In a fourth aspect, the present invention is directed to the bisabolol according to any one of the first, second or third aspect, being produced by a biotechnological process.

[0019] In a fifth aspect, the present invention is directed to a process for treating bisabolol, preferably bisabolol produced by a biotechnological process, comprising the steps of:contacting the bisabolol with a charcoal;separating the bisabolol from the charcoal after contacting;wherein the charcoal is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0250040 m to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, and most preferably within the range of 33.0 pm to 35.0 pm;t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, more preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably 4.10.

[0020] The process according the fifth aspect is preferably further characterized by one, two or three of the following features:v) the weight ratio bisabolokcharcoal is within the range of 100:0.10 and 100:5.0, preferably within the range of 100:0.25 and 100:2.5, and most preferably within the range of 100:0.5 and 100:2;w) the contact time between the bisabolol and the charcoal is less than 240 minutes, preferably less than 180 minutes, more preferably less than 120 minutes, and most preferably less than 90 min;x) the temperature during contacting the bisabolol with charcoal is within the range of 5.0°C to 75°C, preferably within the range of 10°C to 60°C, more preferably within the range of 10°C to 40°C, even more preferably with the range of 15°C to 30°C.

[0021] In a sixth aspect, the present invention is directed to a bisabolol obtainable by the process according to the fifth aspect.

[0022] In a seventh aspect, the present invention is directed to the process according to the fifth aspect for producing the bisabolol according to the first, second, third or fourth aspect.

[0023] In an eighth aspect, the present invention is directed to the use of charcoal which is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0 pm to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, within the range of 33.0 pm to 35.0 pm;250040 t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, more preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably 4.10,for improving the optical properties of bisabolol, preferably of bisabolol prepared by a biotechnological process.

[0024] In a nineth aspect, the present invention is directed to a consumer product formulation comprising bisabolol according to any one of the first, second, third, fourth or sixth aspect, or produced according to the process according to the fifth or seventh aspect, preferably said consumer product formulation is selected from the group consisting of cosmetics, personal care products, shampoos, rinse-off conditioners, deodorants, antiperspirants, body lotions, homecare products, textile care products, household products, liquid detergents, all-purpose cleaners, laundry and cleaning agents, fabric softeners, scent boosters, and fragrance enhancers.

[0025] Hence, the present inventors provided a bisabolol having improved optical properties, improved oxidative stability and improved purity. This generally facilities the preparation of cosmetic formulations as undesired colours do not need to be compensated for by additional compounds, such as optical brighteners, bleaching agents etc., or masked otherwise. Furthermore, due to the improved oxidative stability using a lower amount of stabilizers and / or usage of different, more environmentally friendly stabilizers can be possible. Moreover, the amount of compounds improving olfactory properties in cosmetic formulations may also be reduced.

[0026] The process provided by the present inventors, although developed starting from bisabolol obtained by a biotechnological process, can also be applied to bisabolol obtained from other sources and / or by other methods. The process can be easily run on any scale, including industrial scale, and can easily be implemented since does not require any special equipment. Furthermore, due to the improved stability of the bisabolol obtainable by the process of the present invention, it is possible to run the process in batch mode. Hence, it is not required to treat the bisabolol “on-demand”, i.e., directly use it in subsequent processes after treatment, but the bisabolol may be stored for some time.250040

[0027] The present problem is solved by the objects of the independent patent claims. Preferred embodiments are apparent from the wording of the dependent patent claims as well as the following description.

[0028] In the present invention, the terms “bisabolol”, “alpha-bisabolol” “alpha-(-)-bisabolol” and “(-)-alpha-bisabolol” are used interchangeably unless explicitly mentioned to the contrary.

[0029] All percentages are by weight unless otherwise indicated. Numeric examples given in the form "x to y" include the values given. When multiple preferred numeric ranges are specified in this format, all ranges created by combining the various endpoints are also included.

[0030] The expressions "at least one" or "one or more" as used herein refers to 1 or more, for example 2, 3, 4, 5, 6, 7, 8, 9 or more.

[0031] The expression “not more than” as used herein includes the number following this expression, for example “not more than 1” includes the value of 1.

[0032] The expression "and / or" expresses that a linkage exists, or an alternative is provided. For example, “A and / or B” denotes “A or B or both, i.e. , A and B”.

[0033] In the present invention properties and features are usually numbered using the alphabet, e.g., a), b), c), etc. Preferred variants of these properties and features may be specified by adding 1, 2, 3, etc. after the letter, e.g., a1), a2), a3), ..., b1), b2), b3), ..., etc. Hence, in case in the present invention it is referred to a property / feature and variants or preferred variants thereof, the property / feature numbered with a letter only and its preferred variants further containing a number are meant, e.g., property / feature a) and the preferred variants thereof a1), a2),..., etc.

[0034] The above applies mutatis mutandis to properties numbered, e.g., charl) and preferred variants thereof charl.1), charl.2),..., etc.

[0035] The letters “j” , “o”, “p” and “q” are intentionally not used for the numbering of properties or features of the present invention.Brief Description of Drawings

[0036] Figure 1: Figure 1 shows the Particle Size Distribution of the charcoal used in Preparatory Example 3 (PE3).

[0037] Figure 2: Figure 2 shows the Particle Size Distribution of the charcoal used in Preparatory Example 4 (PE4).

[0038] Figure 3: Figure 3 shows the Particle Size Distribution of the charcoal used in Preparatory Example 5 (PE5).250040

[0039] Figure 4: Figure 4 shows the Particle Size Distribution of the charcoal used in Preparatory Example 7 (PE7).Detailed Description of the Invention

[0040] Hereinafter, the present invention is described in more detail.

[0041] As already outlined above, the present invention relates to bisabolol which has been treated.

[0042] Bisabolol according to the first aspect

[0043] As also outlined above, the first aspect of the present invention provides a bisabolol characterized by one or two of the following properties:a) a Hazen factor, determined according to ISO 6271 , of 56 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b) a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min.

[0044] Preferably, the bisabolol according to the first aspect is characterized by both of the properties a) and b).

[0045] The bisabolol according to the first aspect is preferably further characterized by a Hazen factor, determined according to ISO 6271, of 56 or less, after oxidation for 48 hours using a ML OXIPRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 55 or less, more preferably 54 or less, even more preferably 53 or less, and most preferably 52 or less.

[0046] Preferably, the bisabolol according to the first aspect is further characterized by a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min, preferably 17 or less, even more preferably 16 or less, even more preferably 15 or less, even more preferably 14 or less and most preferably 13 or less.

[0047] The bisabolol according to the first aspect is preferably further characterized by one, two, three, four or five of the following properties:c) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less; d) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;250040 e) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C; and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0048] Preferably, the bisabolol according to the first aspect is further characterized by at least two of the properties c) to g) including any preferred variants thereof, preferably, the bisabolol is characterized by at least three of the properties c) to g) including any preferred variants thereof, more preferably the bisabolol is characterized by at least four of the properties c) to g) including any preferred variants thereof, and most preferably the bisabolol is characterized by all five of the properties c) to g) including any preferred variants thereof.

[0049] The bisabolol according to the first aspect is preferably further characterized in that the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0050] The bisabolol according to the first aspect may also be characterized by improved olfactory properties in addition to (an) improved optical property / properties.

[0051] In one variant, the bisabolol is characterized by one or two of the following properties:a1) a Hazen factor, determined according to ISO 6271, of 55 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 54 or less, more preferably 53 or less, and most preferably 52 or less;250040 b1) a Hazen factor, determined according to ISO 6271, of 17 or less, after irradiation with 30 W of UV light for 360 min, preferably 16 or less, more preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;and, optionally,the bisabolol is further characterized by one, two, three, four or five of the following properties:c1) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less; d1) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;e1) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f1) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g1) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C;and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0052] Preferably, the bisabolol according to this variant is characterized by both of the properties a1) and b1), and optionally,the bisabolol according to this variant is further characterized by at least two of the properties c1) to g1) including all preferred variants thereof, preferably, the bisabolol is further characterized by at least three of the properties c1) to g1) including all preferred variants thereof, more preferably the bisabolol is further250040 characterized by at least four of the properties c1) to g1) including all preferred variants thereof, and most preferably the bisabolol is further characterized by all five of the properties c1) to g1) including all preferred variants thereof; and / or the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0053] For example, the bisabolol according to this variant may further be characterized by property a1) and optionally property b1) including all preferred variants thereof; and, optionally,properties c1), d1) and f1) and, optionally, one or two of the properties e1) and g1) including all preferred variants thereof; and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0054] In a further variant, the bisabolol is characterized by one or two of the following propertiesa2) a Hazen factor, determined according to ISO 6271 , of 54 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 53 or less, and most preferably 52 or less; b2) a Hazen factor, determined according to ISO 6271, of 16 or less, after irradiation with 30 W of UV light for 360 min, preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;and, optionally,the bisabolol is further characterized by one, two, three, four or five of the following properties:c2) an overall odour intensity of 3.00 or less, more preferably 2.5 or less, determined by a panel according to Method (A);d2) an odour intensity of 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min;e2) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;250040 f2) an odour intensity of 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min;g2) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C;and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;

[0055] Preferably, the bisabolol according to this variant is characterized by both of the properties a2) and b2), and optionally,the bisabolol according to this variant is further characterized by at least two of the properties c2) to g2) including all preferred variants thereof, preferably, the bisabolol is further characterized by at least three of the properties c2) to g2) including all preferred variants thereof, more preferably the bisabolol is further characterized by at least four of the properties c2) to g2) including all preferred variants thereof, and most preferably the bisabolol is further characterized by all five of the properties c2) to g2) including all preferred variants thereof; and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

[0056] For example, the bisabolol according to this variant may be characterized by property a2) and optionally property b2) including all preferred variants thereof; and, optionally,properties c2), d2) and f2) and, optionally, one or two of the properties e2) and g2) including all preferred variants thereof;and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.250040

[0057] In yet a further variant, the bisabolol is characterized by one or two of the following propertiesa3) a Hazen factor, determined according to ISO 6271 , of 53 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 52 or less;b3) a Hazen factor, determined according to ISO 6271, of 15 or less, after irradiation with 30 W of UV light for 360 min, preferably 14 or less, and most preferably 13 or less;and, optionally,the bisabolol is further characterized by one, two, three, four or five of the following properties:c3) an overall odour intensity of 2.5 or less, determined by a panel according to Method (A);d3) an odour intensity of 2.3 or less, preferably 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min; e3) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f3) an odour intensity of 2.3 or less, preferably 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min; g3) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C;and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.3 or less, and most preferably 2.0 or less.

[0058] Preferably, the bisabolol according to the first aspect is characterized by both of the properties a3) and b3), and optionally,250040 the bisabolol according to this variant is further characterized by at least two of the properties c3) to g3) including all preferred variants thereof, preferably, the bisabolol is further characterized by at least three of the properties c3) to g3) including all preferred variants thereof, more preferably the bisabolol is further characterized by at least four of the properties c3) to g3) including all preferred variants thereof, and most preferably the bisabolol is further characterized by all five of the properties c3) to g3) including all preferred variants thereof; and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.3 or less, preferably 2.0 or less.

[0059] For example, the bisabolol according to this variant may be characterized by property a3) and optionally property b3) including all preferred variants thereof; and, optionally,properties c3), d3) and f3) and, optionally, one or two of the properties e3) and g3) including all preferred variants thereof;and / orthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.3 or less, preferably 2.0 or less.

[0060] In yet a further variant, the bisabolol is characterized by both of the following propertiesa4) a Hazen factor, determined according to ISO 6271 , of 52 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b4) a Hazen factor, determined according to ISO 6271, of 14 or less, after irradiation with 30 W of UV light for 360 min, preferably 13 or less;and, optionally,the bisabolol is further characterized by one, two, three, four or five of the following properties:c4) an overall odour intensity of 2.5 or less, determined by a panel according to Method (A);d4) an odour intensity of 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min;250040 e4) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f4) an odour intensity of 2.0 or less, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min;g4) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C;andthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.0 or less.

[0061] Preferably, the bisabolol according to the first aspect is characterized by both of the properties a3) and b3), and,the bisabolol according to this variant is further characterized by at least two of the properties c4) to g4) including all preferred variants thereof, preferably, the bisabolol is further characterized by at least three of the properties c4) to g4) including all preferred variants thereof, more preferably the bisabolol is further characterized by at least four of the properties c4) to g4) including all preferred variants thereof, and most preferably the bisabolol is further characterized by all five of the properties c4) to g4) including all preferred variants thereof; andthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.0 or less.

[0062] For example, the bisabolol according to this variant may be characterized by property a4) and optionally property b4) including all preferred variants thereof; and, optionally,properties c4), d4) and f4) and, optionally, one or two of the properties e4) and g4) including all preferred variants thereof;andthe intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is 2.0 or less.250040

[0063] The bisabolol according to the first aspect may further be characterized by one, two, three, four, five or six of the properties h), i), k), I), m) and n) as defined in the second and third aspect of the present invention including any preferred variants thereof.

[0064] Bisabolol according to the second aspect

[0065] In a second aspect, the present invention is directed to a bisabolol characterized by one, two or three of the following properties:h) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;i) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;k) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

[0066] Preferably, the bisabolol according to the second aspect is characterized by at least two, more preferably all three of the properties h), i) and k). For example, the bisabolol according to the second aspect may be characterized by property i) and, optionally one or both of properties h) and k) or the bisabolol according to the second aspect may be characterized by properties i) and h) and, optionally by property k). In one variant, the bisabolol according to the second aspect is characterized by property i) and not by properties h) and k).

[0067] The peaks with a retention time of 9.77 min ± 0.1 min and a retention time of 17.65 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, each of which is presently considered to correspond to a specific compound, are currently believed to be the main reasons for the undesired optical properties of bisabolol. The comparison of the results prior and after treatment obtained by gas chromatography and the optical determinations support this assessment. Hence, the removal or at least reduction of the amount of at least one of them already improves the optical properties of the bisabolol according to the second aspect. However, needless to say that the removal or at least250040 reduction of both compounds is preferable. Furthermore, the olfactory properties can also be improved.

[0068] The bisabolol according to the second aspect is preferably characterized by one, two or three of the following properties:hi) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;11) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;k1) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0.

[0069] Preferably, the bisabolol according to the second aspect is characterized by at least two, more preferably all three of the properties hi), i1) and k1). For example, the bisabolol according to the second aspect may be characterized by property i1) and, optionally one or both of properties hi) and k1) or the bisabolol according to the second aspect may be characterized by properties i1) and hi) and, optionally by property k1). In one variant, the bisabolol according to the second aspect is characterized by property i1) and not by properties hi) and k1).

[0070] The bisabolol according to the second aspect is more preferably characterized by one, two or three of the following properties:h2) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.05% of the total GC-MS area;12) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.05% of the total GC-MS area;k2) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both250040 determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0.

[0071] Preferably, the bisabolol according to the second aspect is characterized by at least two, more preferably all three of the properties h2), i2) and k2). For example, the bisabolol according to the second aspect may be characterized by property i2) and, optionally one or both of properties h2) and k2) or the bisabolol according to the second aspect may be characterized by properties i2) and h2) and, optionally by property k2). In one variant, the bisabolol according to the second aspect is characterized by property i2) and not by properties h2) and k2).

[0072] The bisabolol according to the second aspect may be further characterized by the properties and features defined in the first aspect including all preferred variants thereof.

[0073] The bisabolol according to the second aspect may further be characterized by one, two or three of the properties I), m) and n) as defined in the third aspect of the present invention including all preferred variants thereof.

[0074] In one variant, the bisabolol according to the second aspect is characterized by one, two or three of the following properties:h) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;i) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;k) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0;preferably the bisabolol according to the second aspect is characterized by one, two or three of the following properties:hi) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.10%250040 of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;11) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;k1) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0.more preferably the bisabolol according to the second aspect is characterized by one, two or three of the following properties:h2) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.05% of the total GC-MS area;12) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.05% of the total GC-MS area;k2) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0. and the bisabolol according to this variant of the second aspect is further characterized by one or two of the following properties:a) a Hazen factor, determined according to ISO 6271 , of 56 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b) a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min;preferably the bisabolol according to this variant of the second aspect is further characterized one or two of the following properties:a1) a Hazen factor, determined according to ISO 6271, of 55 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of250040 80°C and 500 kPa, preferably 54 or less, more preferably 53 or less, and most preferably 52 or less;b1) a Hazen factor, determined according to ISO 6271, of 17 or less, after irradiation with 30 W of UV light for 360 min, preferably 16 or less, more preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;more preferably the bisabolol according to this variant of the second aspect is further characterized by one or two of the following properties:a2) a Hazen factor, determined according to ISO 6271 , of 54 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 53 or less, and most preferably 52 or less; b2) a Hazen factor, determined according to ISO 6271, of 16 or less, after irradiation with 30 W of UV light for 360 min, preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;even more preferably the bisabolol according to this variant of the second aspect is further characterized by one or two of the following properties:a3) a Hazen factor, determined according to ISO 6271 , of 53 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 52 or less;b3) a Hazen factor, determined according to ISO 6271, of 15 or less, after irradiation with 30 W of UV light for 360 min, preferably 14 or less, and most preferably 13 or less.

[0075] Preferably, the bisabolol according to this variant of the second aspect is characterized by at least two, more preferably all three of the properties h), i) and k). For example, the bisabolol according to the second aspect may be characterized by property i) and, optionally one or both of properties h) and k) or the bisabolol according to the second aspect may be characterized by properties i) and h) and, optionally by property k). In one variant, the bisabolol according to the second aspect is characterized by property i) and not by properties h) and k). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a) and b) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a) and b) including all preferred variants thereof.

[0076] More preferably, the bisabolol according to this variant of the second aspect is characterized by at least two, more preferably all three of the properties hi), i1) and k1). For example, the bisabolol according to the second aspect may be characterized by property i1) and, optionally one or both of properties hi) and k1) or the bisabolol according to the second250040 aspect may be characterized by properties i1) and hi) and, optionally by property k1). In one variant, the bisabolol according to the second aspect is characterized by property i1) and not by properties hi) and k1). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a1) and b1) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a1) and b1) including all preferred variants thereof.

[0077] Even more preferably, the bisabolol according to this variant of the second aspect is characterized by at least two, more preferably all three of the properties h2), i2) and k2). For example, the bisabolol according to the second aspect may be characterized by property i2) and, optionally one or both of properties h2) and k2) or the bisabolol according to the second aspect may be characterized by properties i2) and h2) and, optionally by property k2). In one variant, the bisabolol according to the second aspect is characterized by property i2) and not by properties h2) and k2). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a2) and b2) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a2) and b2) including all preferred variants thereof.

[0078] Even more preferably, the bisabolol according to this variant of the second aspect is characterized by at least two, more preferably all three of the properties h2), i2) and k2). For example, the bisabolol according to the second aspect may be characterized by property i2) and, optionally one or both of properties h2) and k2) or the bisabolol according to the second aspect may be characterized by properties i2) and h2) and, optionally by property k2). In one variant, the bisabolol according to the second aspect is characterized by property i2) and not by properties h2) and k2). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a3) and b3) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a3) and b3) including all preferred variants thereof.

[0079] Optionally, the bisabolol according to this variant of the second aspect is further characterized in that the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less; and / orthe bisabolol according to this variant of the second aspect is further characterized by one, two, three, four or five of the following properties:c) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less;250040 d) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;e) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C; more preferably, the bisabolol according to the second aspect is further characterized by at least two of the properties c) to g) including any preferred variants thereof, even more preferably, the bisabolol is characterized by at least three of the properties c) to g) including any preferred variants thereof, even more preferably the bisabolol is characterized by at least four of the properties c) to g) including any preferred variants thereof, and most preferably the bisabolol is characterized by all five of the properties c) to g) including any preferred variants thereof.

[0080] Bisabolol according to the third aspect

[0081] In a third aspect, the present invention is directed to a bisabolol characterized by one, two or three of the following properties:l) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

[0082] Preferably, the bisabolol according to the third aspect is characterized by at least two, more preferably all three of the properties I), m) and n). For example, the bisabolol according to the third aspect may be characterized by property m) and, optionally one or both of properties I) and n) or the bisabolol according to the third aspect may be characterized by properties I) and m) and optionally, by property n). In one variant, the bisabolol according to the third aspect is characterized by property m) and not by properties I) and n).

[0083] Bisabolol formate and 4-Acetyl-1 -methylcyclohexene have currently been identified as the main sources of the undesired optical properties of bisabolol which seems to be supported by the olfactory determinations. Hence, the removal or at least reduction of at least one of these two compounds already significantly improves the olfactory properties of the bisabolol. However, needless to say that the removal or at least reduction of both compounds is preferable. Furthermore, the olfactory properties can also be improved.

[0084] The bisabolol according to the third aspect is preferably characterized by one, two or three of the following properties:11) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;ml) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n1) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0.

[0085] Preferably, the bisabolol according to the third aspect is characterized by at least two, more preferably all three of the properties 11), ml) and n1). For example, the bisabolol according to the third aspect may be characterized by property ml) and, optionally one or both of properties 11) and n1) or the bisabolol according to the third aspect may be characterized by properties 11) and ml) and optionally, by property n1). In one variant, the bisabolol according to the third aspect is characterized by property ml) and not by properties 11) and n1).

[0086] The bisabolol according to the third aspect is more preferably characterized by one, two or three of the following properties:12) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m2) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n2) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0.

[0087] Preferably, the bisabolol according to the third aspect is characterized by at least two, more preferably all three of the properties I2), m2) and n2). For example, the bisabolol according to the third aspect may be characterized by property m2) and, optionally one or both of properties I2) and n2) or the bisabolol according to the third aspect may be characterized by properties I2) and m2) and optionally, by property n2). In one variant, the bisabolol according to the third aspect is characterized by feature m2) and not by features I2) and n2).

[0088] The bisabolol according to the third aspect may be further characterized by the properties and features defined in the first aspect including all preferred variants thereof.

[0089] The bisabolol according to the third aspect may further be characterized by one, two, or three of the properties h), i), k) as defined in the second aspect of the present invention including all preferred variants thereof.

[0090] In one variant, the bisabolol according to the third aspect is characterized by one, two or three of the following properties:l) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, ofbetween 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0;preferably the bisabolol according to this variant of the third aspect is characterized by one, two or three of the following properties:11) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;ml) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n1) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0;more preferably the bisabolol according to this variant of the third aspect is characterized by one, two or three of the following properties:12) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m2) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n2) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0: 1.0;and the bisabolol according to this variant of the third aspect is further characterized by one or two of the following properties:a) a Hazen factor, determined according to ISO 6271 , of 56 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b) a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min;preferably the bisabolol according to this variant of the third aspect is further characterized one or two of the following properties:a1) a Hazen factor, determined according to ISO 6271, of 55 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 54 or less, more preferably 53 or less, and most preferably 52 or less;b1) a Hazen factor, determined according to ISO 6271, of 17 or less, after irradiation with 30 W of UV light for 360 min, preferably 16 or less, more preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;more preferably the bisabolol according to this variant of the third aspect is further characterized by one or two of the following properties:a2) a Hazen factor, determined according to ISO 6271 , of 54 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 53 or less, and most preferably 52 or less; b2) a Hazen factor, determined according to ISO 6271, of 16 or less, after irradiation with 30 W of UV light for 360 min, preferably 15 or less, more preferably 14 or less, and most preferably 13 or less;even more preferably the bisabolol according to this variant of the third aspect is further characterized by one or two of the following properties:a3) a Hazen factor, determined according to ISO 6271 , of 53 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 52 or less;b3) a Hazen factor, determined according to ISO 6271, of 15 or less, after irradiation with 30 W of UV light for 360 min, preferably 14 or less, and most preferably 13 or less.

[0091] Preferably, the bisabolol according to this variant of the third aspect is characterized by at least two, more preferably all three of the properties I), m) and n). For example, the bisabolol according to the third aspect may be characterized by property m) and, optionally one or both of properties I) and n) or the bisabolol according to the third aspect may be characterized by properties m) and I) and, optionally by property n). In one variant, the bisabolol according to this variant of the third aspect is characterized by property m) and not by properties I) and n). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a) and b) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a) and b) including all preferred variants thereof.250040

[0092] More preferably, the bisabolol according to this variant of the third aspect is characterized by at least two, more preferably all three of the properties 11), ml) and n1). For example, the bisabolol according to this variant of the third aspect may be characterized by property ml) and, optionally one or both of properties 11) and n1) or the bisabolol according to this variant of the third aspect may be characterized by properties ml) and 11) and, optionally by property n1). In one variant, the bisabolol according to this variant of the third aspect is characterized by property ml) and not by properties 11) and n1). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a1) and b1) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a1) and b1) including all preferred variants thereof.

[0093] Even more preferably, the bisabolol according to this variant of the third aspect is characterized by at least two, more preferably all three of the properties I2), m2) and n2). For example, the bisabolol according to this variant of the third aspect may be characterized by property m2) and, optionally one or both of properties I2) and n2) or the bisabolol according to this variant of the third aspect may be characterized by properties m2) and I2) and, optionally by property n2). In one variant, the bisabolol according to this variant of the third aspect is characterized by property m2) and not by properties I2) and n2). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a2) and b2) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a2) and b2) including all preferred variants thereof.

[0094] Even more preferably, the bisabolol according to this variant of the third aspect is characterized by at least two, more preferably all three of the properties I2), m2) and n2). For example, the bisabolol according to this variant of the third aspect may be characterized by property m2) and, optionally one or both of properties I2) and n2) or the bisabolol according to this variant of the third aspect may be characterized by properties m2) and I2) and, optionally by property n2). In one variant, the bisabolol according to this variant of the third aspect is characterized by property m2) and not by properties I2) and n2). In addition, in this variant, the bisabolol is preferably further characterized by one or both of the properties a3) and b3) including all preferred variants thereof, preferably, the bisabolol is characterized by both of the properties a3) and b3) including all preferred variants thereof.

[0095] Optionally, the bisabolol according to this variant of the third aspect is further characterized in that the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;and / or250040 the bisabolol according to this variant of the third aspect is further characterized by one, two, three, four or five of the following properties:c) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less; d) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;e) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C; more preferably, the bisabolol according to this variant of the third aspect is further characterized by at least two of the properties c) to g) including any preferred variants thereof, preferably, the bisabolol is characterized by at least three of the properties c) to g) including any preferred variants thereof, more preferably the bisabolol is characterized by at least four of the properties c) to g) including any preferred variants thereof, and most preferably the bisabolol is characterized by all five of the properties c) to g) including any preferred variants thereof.

[0096] Bisabolol according to the fourth aspect

[0097] In a fourth aspect, the present invention is directed to the bisabolol according to any one of the first, second or third aspect, being produced by a biotechnological process.

[0098] Hence, all features and properties of the bisabolol according to the first, second and third aspect including all preferred variants thereof are also preferred features according to the fourth aspect.

[0099] The bisabolol according to the first, second, third and fourth aspect of the present invention is usually a-(-)-bisabolol which is also referred to as levomenol. Hence, in the250040 bisabolol according to the first, second, third and fourth aspect of the present invention a-(-)-bisabolol is usually present in an amount of at least 99.0 wt.% based on the total weight of the bisabolol, preferably present in an amount of at least 99.5 wt.% based on the total weight of the bisabolol and more preferably present in an amount of at least 99.7 wt.% based on the total weight of the bisabolol.

[0100] Suitable biotechnological process processes for producing bisabolol usable in the present invention are, for example, described in:Han, G.H., Kim, S.K., Yoon, P.KS. et al. Fermentative production and direct extraction of (-)-a-bisabolol in metabolically engineered Escherichia coli. Microb Cell Fact 15, 185 (2016);South Korean Patent KR 101 958 113 B1;Young-Jin Son, Moonhyuk Kwon, Dae-Kyun Ro, Soo-Un Kim; Enantioselective microbial synthesis of the indigenous natural product (-)-a-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita). Biochem J 15 October 2014; 463 (2): 239-248.

[0101] Usually, the biotechnological process used for preparing the bisabolol according to the first, second, third and fourth aspect of the present invention is using yeast, e.g., saccharomyces cerevisiae.

[0102] Process

[0103] In the fifth aspect, the present invention is directed to a process for treating bisabolol, preferably bisabolol produced by a biotechnological process. As outlined above, the process is also applicable to bisabolol obtained from other sources and methods, however, it has been found that the process is particular effective in case of bisabolol produced by a biotechnological process.

[0104] Using charcoal for purifying chemical compounds is generally known in the art. However, regarding bisabolol, it has been found that the optical (and olfactory) properties of the treated bisabolol vary to a significant extent between different charcoals. It has particularly been found that different charcoals lead to different optical (and olfactory) results and it may occur that no improvement of the optical (and olfactory) properties could be detected or even a slight deterioration may occur. It is currently believed that the optical (and olfactory) properties of the treated bisabolol depend on the particle size and / or particle distribution of the used charcoal.

[0105] The process according to the fifth aspect for treating bisabolol, preferably bisabolol produced by a biotechnological process, comprises the steps of:contacting the bisabolol with a charcoal;250040 separating the bisabolol from the charcoal after contacting;wherein the charcoal is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0 pm to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, and most preferably within the range of 33.0 pm to 35.0 pm;t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, even more preferably at least 3.9, even more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably at least 4.10.

[0106] It has been found that a charcoal meeting at least one of the above properties lead to improved optical properties compared with charcoals not meeting at least one of these properties.

[0107] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties r), s), t) and u) including all preferred variants thereof. For example, the charcoal may be characterized by property r) and, optionally, by one, two or three of the properties s), t) and u) including all preferred variants thereof or, preferably, the charcoal may be characterized by properties r) and t) and, optionally, by one, or two of the properties s) and u) including all preferred variants thereof.

[0108] Usually, the D(v, 0.9) particle size of the charcoal is not more than 500 pm, preferably, the D(v, 0.9) particle size of the charcoal is not more than 400 pm, more preferably the D(v, 0.9) particle size of the charcoal is not more than 300 pm and most preferably, the D(v, 0.9) particle size of the charcoal is not more than 200 pm.

[0109] Usually, the ratio D(v, 0.9) / D(v, 0.5) is not more than 8.00, preferably the ratio D(v, 0.9) / D(v, 0.5) is not more than 7.00, more preferably the ratio D(v, 0.9) / D(v, 0.5) is not more than 6.00 and most preferably, the ratio D(v, 0.9) / D(v, 0.5) is not more than 5.00.250040

[0110] Usually, the span is not more than 7.00, preferably not more than 6.00, more preferably not more than 5.00.

[0111] The charcoal is preferably further characterized by one, two, three or four of the following properties:charl) a volume weighted mean D[4,3] of at least 45.0 pm, preferably of at least 50.0 pm, more preferably of at least 55.0 pm, and most preferably of at least 60.0 pm; usually, the volume weighted mean D[4,3] is not more than 100.0 pm, preferably not more than 90.0 pm, more preferably not more than 80.0 pm, and most preferably not more than 70.0 pm;char2) a surface area mean diameter D[3,2] within the range of 11.5 pm to 19.5 pm, preferably within the range of 13.0 pm to 19.0 pm, more preferably within the range of 14.5 pm to 18.5 pm, and most preferably within the range of 16.0 to 18.0 pm;char3) a Specific Surface Area (SSA) within the range of 0.310 m2 / g to 0.530 m2 / g, preferably within the range of 0.320 m2 / g to 0.470 m2 / g, more preferably within the range of 0.330 m2 / g to 0.410 m2 / g, and most preferably within the range of 0.340 m2 / g to 0.360 m2 / g;char4) a uniformity of at least 0.850, more preferably of at least 0.950, preferably of at least 1.025, more preferably of at least 1.100, even more preferably of at least 1.175, even more preferably at least 1.250, and most preferably at least 1.300; usually, the uniformity is not more than 2.000, preferably not more than 1.800, even more preferably not more than 1.600, and most preferably not more than 1.400.

[0112] It has been found that by using charcoals fulfilling at least one of the properties charl), char2), char3) and / or char4), the properties of the treated bisabolol can be further improved, in particular the optical properties, the olfactory properties or both.

[0113] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties charl), char2), char3) and char4) including all preferred variants thereof.

[0114] In one variant, the charcoal used in the process according to the fifth aspect of the present invention is characterized by one, two, three or four of the following properties:r1) the D(v, 0.9) particle size is at least 110 pm, preferably at least 120 pm, more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm and, optionally, the D(v, 0.9) particle size is not more250040 than 400 m, preferably the D(v, 0.9) particle size is not more than 300 pm and most preferably, the D(v, 0.9) particle size is not more than 200 pms1) the D(v, 0.5) particle size is within the range of 28.0 pm to 36.5 pm, preferably within the range of 30.0 pm to 36.0 pm, more preferably within the range of 32.0 pm to 35.5 pm, and most preferably within the range of 33.0 pm to 35.0 pm; t1) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.6, preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4 and, optionally, the ratio D(v, 0.9) / D(v, 0.5) is not more than 7.00, preferably the ratio D(v, 0.9) / D(v, 0.5) is not more than 6.00 and most preferably, the ratio D(v, 0.9) / D(v, 0.5) is not more than 5.00 u1) the span, which is the measurement of the width of the distribution, is at least 3.25, preferably at least 3.50, even more preferably at least 3.75, more preferably at least 4.00, and most preferably at least 4.10 and, optionally, the span is not more than 6.00, preferably not more than 5.00.

[0115] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties r1), s1), t1) and u1) including all preferred variants thereof. For example, the charcoal may be characterized by property r1) and, optionally, by one, two or three of the properties s1), t1) and u1) including all preferred variants thereof or, preferably, the charcoal may be characterized by properties r1) and t1) and, optionally, by one, or two of the properties s1) and u1) including all preferred variants thereof.

[0116] The charcoal according to this variant is preferably further characterized by one, two, three or four of the following properties:charl.1) a volume weighted mean D[4,3] of at least 50.0 pm, preferably of at least 55.0 pm, and most preferably of at least 60.0 pm; usually, the volume weighted mean D[4,3] is not more than 90.0 pm, preferably not more than 80.0 pm, and most preferably not more than 70.0 pm;char2.1) a surface area mean diameter D[3,2] within the range of 11.5 pm to 19.5 pm, preferably within the range of 13.0 pm to 19.0 pm, more preferably within the range of 14.5 pm to 18.5 pm, and most preferably within the range of 16.0 to 18.0 pm;char3.1) a Specific Surface Area (SSA) within the range of 0.320 m2 / g to 0.470 m2 / g, preferably within the range of 0.330 m2 / g to 0.410 m2 / g, and most preferably within the range of 0.340 m2 / g to 0.360 m2 / g;char4.1) a uniformity of at least 1.025, preferably of at least 1.100, more preferably of at least 1.175, even more preferably at least 1.250, and most preferably250040 at least 1.300; usually, the uniformity is not more than 1.800, more preferably not more than 1.600, and most preferably not more than 1.400.

[0117] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties charl.1), char2.1), char3.1) and char4.1) including all preferred variants thereof.

[0118] In a further variant, the charcoal used in the process according to the fifth aspect of the present invention is characterized by one, two, three or four of the following properties: r2) the D(v, 0.9) particle size is at least 130 pm, preferably at least 140 pm, and most preferably at least 150 pm and, optionally, the D(v, 0.9) particle size is not more than 200 pms2) the D(v, 0.5) particle size is within the range of 32.0 pm to 35.5 pm, and most preferably within the range of 33.0 pm to 35.0 pm;t2) the ratio D(v, 0.9) / D(v, 0.5) is at least 4.2, and most preferably at least 4.4 and, optionally, the ratio D(v, 0.9) / D(v, 0.5) is not more than 6.00 and most preferably, the ratio D(v, 0.9) / D(v, 0.5) is not more than 5.00u2) the span, which is the measurement of the width of the distribution, is at least 3.75, more preferably at least 4.00, and most preferably at least 4.10 and, optionally, the span is not more than 5.00.

[0119] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties r2), s2), t2) and u2) including all preferred variants thereof. For example, the charcoal may be characterized by property r2) and, optionally, by one, two or three of the properties s2), t2) and u2) including all preferred variants thereof or, preferably, the charcoal may be characterized by properties r2) and t2) and, optionally, by one, or two of the properties s2) and u2) including all preferred variants thereof.

[0120] The charcoal according to this variant is preferably further characterized by one, two, three or four of the following properties:charl .2) a volume weighted mean D[4,3] of at least 55.0 pm, and most preferably of at least 60.0 pm; usually, the volume weighted mean D[4,3] is not more than 80.0 pm, preferably not more than 70.0 pm;char2.2) a surface area mean diameter D[3,2] within the range of 14.5 pm to 18.5 pm, and most preferably within the range of 16.0 to 18.0 pm; char3.2) a Specific Surface Area (SSA) within the range of 0.330 m2 / g to 0.410 m2 / g, and most preferably within the range of 0.340 m2 / g to 0.360 m2 / g;250040 char4.2) a uniformity of at least 1.250, preferably at least 1.300; usually, the uniformity is not more than 1.400.

[0121] More preferably, the charcoal is characterized by at least two, even more preferably by at least three, and most preferably by all four of the properties char1.2), char2.2), char3.2) and char4.2) including all preferred variants thereof.

[0122] In the following further properties of the process according to the fifth aspect including all variants thereof are described unless explicitly mentioned to the contrary.

[0123] The step of “contacting the bisabolol with a charcoal” may be effected using procedures and apparatuses well-known in the art. For example, the charcoal may be in the form of a filter, e.g. in the form of a plate, as loose material on a porous support. Alternatively, the charcoal maybe combined with the bisabolol in a vessel and stirred, the latter being preferred.

[0124] The bisabolol may be diluted prior to contacting the bisabolol with a charcoal using solvents known in the art. In case solvents are used, the weight ratio bisaboloksolvent is preferably not more than 70:30, more preferably not more than 80:20, even more preferably not more than 90:10, even more preferably not more than 95:5. However, it is preferred that no solvent is used prior or during contacting the bisabolol with charcoal.

[0125] Likewise, the step of separating the bisabolol from the charcoal after contacting may be effected using procedures and apparatuses well-known in the art. For example centrifugation, filtration or both may be used. Preferably at least filtration is used, more preferably only filtration is used. It is particularly preferred that no solvent is used prior or during the step of separating the bisabolol from the charcoal.

[0126] Most preferably, in the process according to the fifth aspect no solvents are used.

[0127] The process according the fifth aspect including all variants thereof is preferably further characterized by one, two or three of the following features:v) the weight ratio bisabolokcharcoal is within the range of 100:0.10 and 100:5.0, preferably within the range of 100:0.25 and 100:2.5, more preferably within the range of 100:0.5 and 100:2;w) the contact time between the bisabolol and the charcoal is less than 240 minutes, preferably less than 180 minutes, more preferably less than 120 minutes, and most preferably less than 90 min;x) the temperature during contacting the bisabolol with charcoal is within the range of 5.0°C to 75°C, preferably within the range of 10°C to 60°C, more preferably within the range of 10°C to 40°C, even more preferably with the range of 15°C to 30°C.250040

[0128] More preferably, the process according the fifth aspect is characterized by two or three of the features v), w) and x), for example, the process according the fifth aspect may be characterized by feature v) and, optionally, one or two of the features w) and x), or the process according the fifth aspect may be characterized by features v) and x) and, optionally, feature w). Most preferably, the process according the fifth aspect is characterized by all three of the features v), w) and x).

[0129] It has been found that the weight ratio according to feature v) is adequate to treat the bisabolol to obtain the properties as described herein. It has also been found that lower amounts may, in principle, be used in case the purity obtainable thereby is considered sufficient for the respective application. Furthermore, using higher amounts is of course possible but further improvements of the bisabolol properties seem to be minimal and, although the amount of bisabolol absorbed by the charcoals as defined in the fifth aspect is very low, using higher amounts of charcoal may lead to a loss of product not worth the minimal further improvement of the bisabolol properties. The preferred weight ratio according to feature v) balances this conflict of aims.

[0130] It is expected that that a longer contact time as defined in feature w) does not further improve the properties of the bisabolol in a relevant manner.

[0131] It is needless to say and immediately apparent to the skilled person that a certain minimum contact time is required to treat the bisabolol. In particular, in case a very small amount of bisabolol is treated, e.g., in a 100 ml beaker, the contact time can be lower compared with a 100 litre or even 1000 litre vessel. The contact time according to feature w) is usually at least 15 min, preferably at least 30 min and most preferably at least 45 min. With such contact times the results according to the present invention are usually obtained independent from the size of the vessel.

[0132] Since bisabolol is a slightly viscous liquid, the temperature needs to be selected such that the treatment can be effected but not so high as to potentially deteriorate the properties of the bisabolol during treatment. It has been found that the temperature range according to feature x) is suitable to obtain the desired results.

[0133] In a preferred variant, process according the fifth aspect including all variants thereof is further characterized by one, two or three of the following features:v1) the weight ratio bisabolokcharcoal is within the range of 100:0.25 and 100:2.5, preferably within the range of 100:0.5 and 100:2;w1) the contact time between the bisabolol and the charcoal is less than 120 minutes, and preferably less than 90 min;250040 x1) the temperature during contacting the bisabolol with charcoal is within the range of 10°C to 40°C, preferably with the range of 15°C to 30°C.

[0134] More preferably, the process according the fifth aspect is characterized by two or three of the features v1), w1) and x1), for example, the process according the sixth aspect may be characterized by feature v1) and, optionally, one or two of the features w1) and x1), or the process according the fifth aspect may be characterized by features v1) and x1) and, optionally, feature w1). Most preferably, the process according the fifth aspect is characterized by all three of the features v1), w1) and x1).

[0135] Bisabolol obtainable by the process according to the present invention

[0136] In a sixth aspect, the present invention is directed to a bisabolol obtainable by the process according to the fifth aspect.

[0137] Hence, all features and properties of the process according to the fifth aspect including all preferred variants thereof are also features and properties of the sixth aspect of the present invention.

[0138] As will be immediately apparent to the skilled person, in the process according to the fifth aspect of the present invention several impurities and / or by-products are removed or their amount at least significantly reduced. Usually, it is not feasible and / or reasonable to determine the chemical structure of all these compounds, e.g., of small peaks or shoulders in a gas chromatogram. Hence, although the bisabolol according to the present invention is defined herein by its properties, the amount(s) of certain impurities which were identified, etc., the bisabolol obtainable by the process according to the sixth aspect is further characterized by the reduction / removal of additional compounds not (easily) identifiable. Hence, a definition by the process is the only viable option.

[0139] The bisabolol according to the sixth aspect may further be characterized by one, two, three, four, five, six or seven of the properties a), b), c), d), e), f) and g) as defined in the first aspect of the present invention including any preferred variants thereof and / or by one, two, three, four, five or six of the properties h), i), k), I), m) and n) as defined in the second and third aspect of the present invention including any preferred variants thereof.

[0140] Further process

[0141] In a seventh aspect, the present invention is directed to the process according to the fifth aspect for producing the bisabolol according to the first, second, third or fourth aspect.

[0142] Hence, all features and properties of the process according to the fifth aspect including all preferred variants thereof and all features and properties of the bisabolol according to the first, second, third or fourth aspect including all preferred variants thereof are also features and properties of the seventh aspect of the present invention.250040

[0143] Use

[0144] In an eighth aspect, the present invention is directed to the use of charcoal which is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0 pm to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, within the range of 33.0 pm to 35.0 pm;t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, more preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably 4.10,for improving the optical properties of bisabolol preferably for improving the optical properties of bisabolol prepared by a biotechnological process.

[0145] Preferred features and properties of the charcoal as defined in the fifth aspect including all preferred variants thereof are also preferred features and properties of the charcoal according to the eighth aspect.

[0146] Preferably, in the eighth aspect, the charcoal is further used to improve the oxidative stability of the bisabolol.

[0147] Preferably, the use according to the eighth aspect involvescontacting the bisabolol with a charcoal;separating the bisabolol from the charcoal after contacting.

[0148] These steps and preferred features and properties thereof have been described in the fifth aspect. Said description of the steps and preferred features and properties thereof are also preferred features and properties of the use according to the eighth aspect.

[0149] Consumer product formulation

[0150] In a nineth aspect, the present invention is directed to a consumer product formulation comprising bisabolol according to any one of the first, second, third, fourth or sixth aspect, or produced according to the process according to the fifth or seventh aspect, preferably saidconsumer product formulation is selected from the group consisting of cosmetics, personal care products, shampoos, rinse-off conditioners, deodorants, antiperspirants, body lotions, homecare products, textile care products, household products, liquid detergents, all-purpose cleaners, laundry and cleaning agents, fabric softeners, scent boosters, and fragrance enhancers.

[0151] Such consumer product formulations and the ingredients thereof are generally known in the art.

[0152] The bisabolol according to first, second, third, fourth or sixth aspect, or produced according to the process according to the fifth or seventh aspect can be used to replace the bisabolol currently used in such consumer product formulations.

[0153] However, as outlined above, due to the improved properties of the bisabolol according to the present invention reducing the amounts of stabilizers, optical brighteners, odiferous substances, masking agents, etc may be reduced which is desirable from an ecological and economical viewpoint.Examples

[0154] Optical properties

[0155] Colour values are measured with Lico690 in 11 mm round glass cuvettes. The colorimetric mode is used to determine absolute colour numbers in the colour scales according to Hazen, Gardner or CIE-L*a*b*. All optical properties were determined on undiluted samples unless explicitly stated to the contrary.

[0156] The Color: L*, a* and b* values were determined according to CIE color system (Commission Internationale d'Eclairage).

[0157] The Gardner value was determined according to DIN-ISO 4630.

[0158] The Hazen factor was determined according to DIN-ISO 6271.

[0159] Olfactory determinations

[0160] Method (A): The samples (described below) were placed in glass bottles. Trained panelists (N = 16) were asked to rate the odour intensity (scale 0-9) and give an odour description of each sample in a predetermined, randomized order. Mean intensities were calculated by the arithmetic mean.

[0161] Method (B): 100 pl of the respective sample (described below) were transferred into an SPME headspace vial (20 mL). Volatiles were sampled during 20 min at either 35°C or 60°C using an SPME arrow (fibre PDMS / DVB (pink) 23 ga). The volatiles were injected into an Agilent 7890 A gas chromatograph with a DB-1 MS column (20 m, 0.18 mm, 0.18 pm) coupled to an Agilent mass spectrometer 5975 C. The volatiles were eluted with a flow ofHelium atmosphere 1.0 ml / min using a temperature gradient moving from 60°C to 230°C at 10°C / min with a split ratio 1 / 5. GC-0 evaluation was conducted using a Gerstel Olfactory Detection Port ODP3. Sensory impressions of 3 trained GC-0 panelists are given on a scale from 1-4.

[0162] Gas chromatography-mass spectrometry (GC-MS)

[0163] 100 pl of the respective sample were transferred into an SPME headspace vial (20 mL). Volatiles were sampled during 20 min at 60°C using an SPME arrow (fibre PDMS / DVB (pink) 23 ga). The volatiles were injected into an Agilent 7890 A gas chromatograph with a Zebron ZB-1 MS column (20 m, 0.18 mm, 0.18 pm) coupled to an Agilent mass spectrometer 5975 C. The volatiles were eluted with a flow of Helium atmosphere 1.0 ml / min using a temperature gradient moving from 60°C (hold time 5 min) to 230°C at 10°C / min with a split ratio 1 / 5.

[0164] Charcoal properties

[0165] The charcoal properties were determined using a Malvern Mastersizer 2000.

[0166] An adequate amount of the sample is conveyed automatically over the oscillating trough into the system and dispersed with air using a Scirocco 2000 dispersing modules. After the measurement the size distribution is displayed graphically, as a table and other reporting parameters can be calculated. All relevant measurement parameters are stored in the standard operating procedures in the instrument software (like the sample and background measuring time of 5 seconds equate 5000 single measurements, attenuation of light range 2-10).

[0167] The following properties were determined.

[0168] The concentration is the volume concentration. It is calculated from the Beer-Lambert law and is expressed as a percentage.

[0169] D[4,3] which is the Volume Weighted Mean expressed in pm.

[0170] D[3,2] is the surface area mean diameter expressed in pm. This is also known as the Sauter mean.

[0171] SSA, which is the Specific Surface Area, i.e., the total area of the particles divided by the total weight. It is expressed in m2 / g.

[0172] D(v, 0.5) is the size in pm at which 50% of the sample is smaller and 50% is larger. This value is also known as the Mass Median Diameter (MMD) or the median of the volume distribution. The v in the expression D(v, 0.5) shows that this refers to the volume distribution.

[0173] Correspondingly, D(v, 0.1) is the size of particles in pm below which 10% of the sample lies and D(v, 0.9) is the size of particles in pm below which 90% of the sample lies.

[0174] Span which is the measurement of the width of the distribution. The narrower the distribution, the smaller the span becomes. The span is calculated as[D(v, 0.9)-D(v, O.1)] / D(v, 0.5).

[0175] Uniformity is a measure of the absolute deviation from the median.

[0176] Bisabolol used in the experiments

[0177] Dragosantol® 100 obtainable by Symrise, which is bisabolol obtained by a non-biotechnological process. Dragosantol® 100 in untreated from is used as Reference Example 1 (RE1).

[0178] A bisabolol produced by a biotechnological process using saccharomyces cerevisiae, in untreated form (i.e., prior to contacting with charcoal) is used as Reference Example 2 (RE2).

[0179] Preparatory Example 3 (PE3)

[0180] A charcoal filter plate ACF 07.10 obtainable from EATON BECO-CARBON, having a diameter of 6 cm has been clamped into a stainless steel pressure filtration unit. The resulting, effective filter has a diameter of 5.1 cm. Then 50 g of the bisabolol according to Reference Example 2 have been added to the stainless steel pressure filtration unit and the unit has been sealed pressure-tight. Nitrogen has been applied with a pressure of 150 kPa. The bisabolol is obtained as a clear liquid.

[0181] The above procedure has been repeated with a second portion of 50 g of the bisabolol according to Reference Example 2 and a new charcoal filter plate and the two obtained bisabolol portions have been combined to have sufficient material for testing.

[0182] Preparatory Example 4 (PE4)

[0183] 69.3 g of the bisabolol according to Reference Example 2 are placed in a 100 ml glass bottle and combined with 0.7 g of ACTICARBONE® SM charcoal, obtainable from the Chemviron Carbon GmbH, resulting in a bisabolokcharcoal weight ratio of about 100:1. The obtained mixture is then stirred at 20°C for 60 min. Subsequently, the charcoal is removed by filtration using 0.2 pm syringe filters.

[0184] Preparatory Example 5 (PE5)

[0185] The procedure of Example 2 has been repeated except that as charcoal CN-1, obtainable from NORIT, has been used instead of ACTICARBONE® SM charcoal.

[0186] Preparatory Example 6 (PE6)

[0187] The procedure of Example 2 has been repeated except that as charcoal C40 / 4, obtainable from Calgon Carbon Corporation, has been used instead of ACTICARBONE® SM charcoal. According to the manufacturer’s data sheet, it has a particle size (“Korndurchmesser”) of 4 mm.

[0188] Preparatory Example 7 (PE7)

[0189] The procedure of Example 2 has been repeated except that as Fischer Scientific C / 4040 / 60. CAS No. 7440-44-0, Art.no. 1000005 has been used instead of ACTICARBONE® SM charcoal.

[0190] Overview of the charcoal properties used in the Preparatory Examples:> >The charcoal was removed from the filter plate by gentle stirring in a beaker with water. The charcoal was allowed to settle, the water was decanted and the charcoal has been dried. “ average value of two measurements, also shown in the graphs

[0191] Example s

[0192] The olfactory properties of RE1, RE2 and PE3 to PE7 have been determined according to Method (A) described above. The results are shown in the following table 1

[0193] Table 1

[0194] Example 10

[0195] Furthermore, the olfactory properties of RE1, RE2 and PE4 were determined using Method (B) described above. The results are shown in the following tables250040

[0196] Table 2, properties of RE1 , when sampled at 60°C

[0197] Table 4, properties of RE2, when sampled at 60°C

[0198] Table 6, properties of PE4, when sampled at 60°C250040

[0199] Table 3, properties of RE1 , when sampled at 35°C

[0200] Table 5, properties of RE2, when sampled at 35°C

[0201] Table 7, properties of PE4, when sampled at 35°C

[0202] As can be seen from the above tables, the creamy, coconut-like off-note at around 9.77 min retention time (which has been identified as 4-Acetyl-1-methylcyclohexene) and the250040 technical, plastic, ozonic off-note at around 17.6 min retention time (which has been identified as bisabolol formate) have been significantly reduced.

[0203] Hence, by filtration with charcoal, the overall number of sensory impressions was reduced, especially those with a negative association such as pungent, burnt, or acidic. Additionally, the plastic, technical off-note at -17.6 min was completely removed and only a pleasant floral note was perceived, correlating to the scent perception when smelling the sample neat.

[0204] Example 11 (oxidative stability testing)

[0205] A ML Oxipres® (Mikrolab Aarhus A / S) with Paralog Software Version 3 has been used to determine the oxidative stability. The conditions used in all experiments was 80°C / 500 kPa / 48h.

[0206] Furthermore, UV irradiation was conducted with a Xenotest 440 (with XenoLogic™) (manufacturer ATLAS I AMETEK), Version V 3.27 with an intensity 30 W for 6 hours. The wavelength range used was 300-400 nm. The vessels used for irradiation were tubular glass bottles (“Rbhrenglasflasche”) GL20, 15 ml, clear, 24x60 mm, 3. hydrolytical class (Demareis GmbH, article no.113-0015-20-N, material no. 216505).

[0207] A fresh sample was used for each of the experiments.

[0208] The results are as follows.

[0209] Table 8250040n.d. not determinedAs can be seen from the table above, after purification, the oxidative stability is improved.

Claims

250040Claims1. A bisabolol characterized by one or two of the following properties:a) a Hazen factor, determined according to ISO 6271 , of 56 or less, after oxidation for 48 hours using an ML OXI PRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa;b) a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min.

2. The bisabolol according to claim 1 , wherein the bisabolol is characterized by both of the properties a) and b).

3. The bisabolol according to any one of the preceding claims 1 or 2, characterized by a Hazen factor, determined according to ISO 6271, of 56 or less, after oxidation for 48 hours using a ML OXIPRES® (Mikrolab Aarhus A / S ) under the conditions of 80°C and 500 kPa, preferably 55 or less, more preferably 54 or less, even more preferably 53 or less, even more preferably 52 or less.

4. The bisabolol according to any one of the preceding claims 1 to 3, characterized by a Hazen factor, determined according to ISO 6271, of 18 or less, after irradiation with 30 W of UV light for 360 min, preferably 17 or less, even more preferably 16 or less, even more preferably 15 or less, even more preferably 14 or less and most preferably 13 or less.

5. The bisabolol according to any one of the preceding claims 1 to 4, by one, two, three, four or five of the following properties:c) an overall odour intensity of 3.25 or less, determined by a panel according to Method (A), preferably 3.00 or less, and most preferably 2.5 or less; d) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 17.65 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;e) a floral olfactory impression, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a250040 retention time of 17.65 min ± 0.1 min, preferably the floral olfactory impression is free of technical or plastic scents;f) an odour intensity of below 3.0, determined by a panel according to Method (B) at a temperature of 35°C, of the substance in the bisabolol identified by the peak at a retention time of 9.77 min ± 0.1 min, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less;g) the odour intensity of the substance in the bisabolol identified by peak at a retention time of 17.65 min ± 0.1 min is less than the odour intensity of the substance in the bisabolol identified by peak at a retention time of 9.77 min ± 0.1 min, both determined by a panel according to method (B) at a temperature of 35°C.

6. The bisabolol according to claim 5, wherein the bisabolol is characterized by two of the properties c) to g), preferably, the bisabolol is characterized by three of the properties c) to g), more preferably the bisabolol is characterized by four of the properties c) to g), and most preferably the bisabolol is characterized by all five of the properties c) to g).

7. The bisabolol according to any one of the preceding claims 5 or 6, wherein the intensity of all substances having a retention time of 30 min or less, determined by a panel according to Method (B) at a temperature of 35°C, is below 3.0, preferably 2.7 or less, more preferably 2.3 or less, and most preferably 2.0 or less.

8. A bisabolol characterized by one, two or three of the following properties:h) a peak area of the peak with a retention time of 17.65 min ± 0.1 min, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;i) a peak area of the peak with a retention time of 9.77 min ± 0.1 min determined by gas chromatography-mass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;k) a ratio of the peak area of the peak with a retention time of 17.65 min ± 0.1 min to the peak area of the peak with a retention time of 9.77 min ± 0.1 min, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, morepreferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

9. A bisabolol characterized by one, two or three of the following properties:l) the amount of bisabolol formate, determined by gas chromatography-mass spectrometry (GC-MS) at 60°C is less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;m) the amount of 4-Acetyl-1-methylcyclohexene, determined by gas chromatographymass spectrometry (GC-MS) at 60°C of less than 0.50% of the total GC-MS area, preferably less than 0.10% of the total GC-MS area, and most preferably less than 0.05% of the total GC-MS area;n) a ratio of the amounts of bisabolol formate to 4-Acetyl-1 -methylcyclohexene, both determined by gas chromatography-mass spectrometry (GC-MS) at 60°C, of between 10:1.0 and 1.0:5.0, preferably between 5.0:1.0 and 1.0:2.5, more preferably between 2.5: 1.0 and 1.0: 1.5 and most preferably between 2.0:1.0 and 1.0:1.0.

10. The bisabolol according to any one of the preceding claims 1 to 9, being produced by a biotechnological process.

11. A process for treating bisabolol, preferably bisabolol produced by a biotechnological process, comprising the steps of:contacting the bisabolol with a charcoal;separating the bisabolol from the charcoal after contacting;wherein the charcoal is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0 pm to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, within the range of 33.0 pm to 35.0 pm;t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, more preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably 4.10.

12. The process according to claim 11, further characterized by one, two or three of the following features:v) the weight ratio bisabolokcharcoal is within the range of 100:0.10 and 100:5.0, preferably within the range of 100:0.25 and 100:2.5, more preferably within the range of 100:0.5 and 100:2;w) the contact time between the bisabolol and the charcoal is less than 240 minutes, preferably less than 180 minutes, more preferably less than 120 minutes, and most preferably less than 90 min;x) the temperature during contacting the bisabolol with charcoal is within the range of 5.0°C to 75°C, preferably within the range of 10°C to 60°C, more preferably within the range of 10°C to 40°C, even more preferably with the range of 15°C to 30°C.

13. A bisabolol obtainable by the process according to any one of the claims 11 or 12.

14. The process according to any one of the claims 11 or 12 for producing the bisabolol according to any one of the preceding claims 1 to 10.

15. Use of charcoal which is characterized by one, two, three or four of the following properties:r) the D(v, 0.9) particle size is at least 90 pm, preferably at least 100 pm, more preferably at least 110 pm, even more preferably at least 120 pm, even more preferably at least 130 pm, even more preferably at least 140 pm, and most preferably at least 150 pm;s) the D(v, 0.5) particle size is within the range of 26.0 pm to 37.0 pm, preferably within the range of 28.0 pm to 36.5 pm, more preferably within the range of 30.0 pm to 36.0 pm, even more preferably within the range of 32.0 pm to 35.5 pm, within the range of 33.0 pm to 35.0 pm;t) the ratio D(v, 0.9) / D(v, 0.5) is at least 3.0, preferably at least 3.3, more preferably at least 3.6, more preferably at least 3.9, more preferably at least 4.2, and most preferably at least 4.4;u) the span, which is the measurement of the width of the distribution, is at least 2.75, more preferably at least 3.00, even more preferably at least 3.25, even more preferably at least 3.50, even more preferably at least 3.75, even more preferably at least 4.00, and most preferably at least 4.10,for improving the optical properties of bisabolol, preferably of bisabolol prepared by a biotechnological process.

16. Consumer product formulation comprising bisabolol according to any one of the preceding claims 1 to 10 or 13, or produced according to the process according to any one of the claims 11, 12 or 14, preferably said consumer product formulation is selected from the group consisting of cosmetics, personal care products, shampoos, rinse-off conditioners, deodorants, antiperspirants, body lotions, homecare products, textile care products, household products, liquid detergents, all-purpose cleaners, laundry and cleaning agents, fabric softeners, scent boosters, and fragrance enhancers.

Images