Methods to mitigate the conversion of volatile terpene species

Abstract

The conversion of nootkatol to nootkaten in the terpene blend is mitigated or prevented by substantially or completely separating the nootkatol, such as α-nootkatol, from compounds present in the terpene blend that catalyze the chemical reaction of nootkatol to nootkaten, and / or by neutralizing at least a portion of the compounds present in the terpene blend that catalyze the chemical reaction of nootkatol to nootkaten. Also disclosed are methods of preparing the terpene blend, the terpene blend, flavor compositions containing the terpene blend, beverages and foodstuffs containing the flavor compositions, fragrance compositions containing the terpene blend, and fragranced products containing the fragrance compositions.

Description

Technical Field

[0001] The present disclosure relates to mitigating the conversion of volatile terpenes to undesirable compounds. More specifically, the present disclosure relates to methods of mitigating or preventing the conversion of nootkatone to nootkatene, methods of producing terpene blends, terpene blends, and beverages, foodstuffs, and fragrance products containing terpene blends.

Background Art

[0002] Background Nootkatone is a volatile essential oil blend derived from grapefruit and Alaska yellow cedar trees. Nootkatone oil blends are commonly used as citrus flavoring agents for food and beverages and as fragrance components. With respect to food and beverage products, the α - nootkatone molecule is widely recognized as a major component of nootkatone oil blends because α - nootkatone contributes to the acceptable sensory pungency profile of nootkatone oil blends.

[0003] Raw terpene blends containing nootkatone may also contain fatty acids and other high - boiling impurities that catalyze the reaction of nootkatone to nootkatene. In order to prepare a final commercially available nootkatone oil blend suitable for sale to customers, fractional distillation must be performed on the raw terpene blend containing nootkatone. During the fractional distillation process, the raw terpene blend containing nootkatone is heated at an elevated temperature for a long time. This elevated temperature induces the fatty acids and other high - boiling impurities present in the raw terpene blend to catalyze the undesirable reaction of nootkatone to nootkatene. This results in a decrease in the level of nootkatone and an increase in the level of nootkatene present in the terpene blend. A decrease in nootkatone level or an increase in nootkatene level will bring about changes in the taste profile of the nootkatone oil blend, and nootkatone oil blends with these changed taste profile characteristics will not meet the current market expectations.

[0004] Nootcatene, continuously generated during batch distillation processes, will contaminate the distillate fraction throughout the distillation process, hindering the production of high-quality terpene blends. Terpene blends in demand on the market contain little to nootcatene. The presence of nootcatene above a certain level in a terpene blend can affect sensory irritation properties, customer satisfaction, and may lead to rejection by customers based on analytical specifications.

[0005] Because some nootkatone oil blends contain fatty acids and other high-boiling-point impurities that catalyze the undesirable reaction of nootkitol to nootcatene, there is a need in the art to develop methods for processing raw nootkatone oil blends that maintain a desired α-nootkitol content while minimizing the formation of nootcatene. [Overview of the project]

[0006] overview According to one exemplary embodiment, a method is provided for mitigating or preventing the conversion of nootkator to nootcatene, comprising: (i) separating at least a portion of the nootkator from at least a portion of the

[0007] According to one exemplary embodiment, a method is provided for mitigating or preventing the conversion of nootakator to nootcatene, comprising providing a feed containing nootakator and at least one compound that catalyzes the conversion of nootakator to nootcatene, and separating at least a portion of the nootakator from the at least one compound that catalyzes the conversion of nootakator to nootcatene.

[0008] According to one exemplary embodiment, a method is provided for mitigating or preventing the conversion of nootakator to nootcatene, comprising providing a feed containing nootakator and at least one compound that catalyzes the conversion of nootakator to nootcatene, and neutralizing at least a portion of the at least one compound that catalyzes the conversion of nootakator to nootcatene.

[0009] In one exemplary embodiment, a method for preparing a terpene blend is also provided, comprising: providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; processing the feed to mitigate or prevent the conversion of nootkator to nootcatene; and performing fractional distillation on a second feed containing nootkator.

[0010] According to one exemplary embodiment, a method for preparing a terpene blend includes: providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; treating the feed to mitigate or prevent the conversion of nootkator to nootcatene by either (i) separating at least a portion of the nootkator from the at least one compound that catalyzes the conversion of nootkator to nootcatene to prepare a second feed containing nootkator; or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nootkator to nootcatene; and performing fractional distillation of the feed or the second feed.

[0011] According to one exemplary embodiment, a method for preparing a terpene blend includes: providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; processing the feed to mitigate or prevent the conversion of nootkator to nootcatene by separating at least a portion of the nootkator from the at least one compound that catalyzes the conversion of nootkator to nootcatene to produce a second feed containing nootkator; and performing fractional distillation on the second feed containing nootkator.

[0012] According to one exemplary embodiment, a method for preparing a terpene blend includes providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compounds present in the feed that catalyze the conversion of nootkator to nootcatene; and performing fractional distillation on the treated feed.

[0013] According to one embodiment, a terpene blend is provided which is prepared by a method comprising: (i) treating the feed to mitigate or prevent the conversion of nootakator to nootcatene by either (i) separating at least a portion of the nootakator from the at least one compound that catalyzes the conversion of nootakator to nootcatene to prepare a second feed containing nootakator, or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nootakator to nootcatene, and performing fractional distillation of the feed or the second feed.

[0014] According to one embodiment, the terpene blend is prepared according to a method comprising: providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; processing the feed to mitigate or prevent the conversion of nootkator to nootcatene by separating at least a portion of the nootkator from the at least one compound that catalyzes the conversion of nootkator to nootcatene to produce a second feed containing nootkator; and performing fractional distillation of the second feed.

[0015] According to one exemplary embodiment, the terpene blend is prepared by a method comprising: providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compounds present in the feed that catalyze the conversion of nootkator to nootcatene; and performing fractional distillation on the treated feed.

[0016] According to one exemplary embodiment, a beverage or food ingredient is provided, comprising a beverage or food base and a terpene blend prepared by processing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene, thereby mitigating or preventing the conversion of nootkator to nootcatene, and by fractional distillation of the feed.

[0017] In one exemplary embodiment, the beverage or food ingredient comprises a beverage or food ingredient base and a terpene blend prepared by processing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene, thereby mitigating or preventing the conversion of nootkator to nootcatene, by separating at least a portion of nootkator from compounds in the feed that catalyze the conversion of nootkator to nootcatene to produce a second feed containing nootkator, and by fractional distillation of the second feed.

[0018] In one exemplary embodiment, a beverage or food ingredient comprises a beverage or food ingredient base, a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene, treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compounds present in the feed that catalyze the conversion of nootkator to nootcatene, and a terpene blend prepared by fractional distillation of the treated feed.

[0019] Also disclosed are flavor compositions comprising a terpene blend prepared according to the method of this disclosure and a flavor base. Also disclosed are food or beverage products comprising a terpene blend prepared according to the method of this disclosure, or a flavor composition comprising a terpene blend and a flavor product base. Also disclosed is a method for preparing a food or beverage product, which includes mixing a terpene blend, or a flavor composition containing a terpene blend, prepared according to the method of this disclosure, with a food or beverage product base.

[0020] According to one exemplary embodiment, a fragrance product comprising a fragrance product base and a terpene blend prepared by treating a feed containing at least one compound that catalyzes the conversion of nootkator to nootcatene to mitigate or prevent the conversion of nootkator to nootcatene, and performing fractional distillation on the treated feed.

[0021] In one exemplary embodiment, the fragrance product comprises a fragrance product base and a terpene blend prepared by processing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene, by separating at least a portion of nootkator from at least one compound that catalyzes the conversion of nootkator to nootcatene to produce a second feed containing nootkator, thereby mitigating or preventing the conversion of nootkator to nootcatene, and by performing fractional distillation on the second feed.

[0022] In one exemplary embodiment, the fragrance product comprises a fragrance product base, a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene, treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compounds present in the feed that catalyze the conversion of nootkator to nootcatene, and a terpene blend prepared by fractional distillation of the treated feed.

[0023] Also disclosed are fragrance compositions comprising a terpene blend and a fragrance base prepared according to the method of this disclosure. Also disclosed are fragrance products comprising a terpene blend, or a fragrance composition containing a terpene blend, prepared according to the method of this disclosure, and a fragrance product base. Also disclosed is a method for preparing a fragrance product, which includes mixing a terpene blend, or a fragrance composition containing a terpene blend, prepared according to the method of this disclosure, with a fragrance product base.

[0024] The use of a terpene blend as a fragrance in a flavor product is also provided, the terpene blend being prepared by treating a feed containing at least one compound that catalyzes the conversion of nootkatone to its nor-ketone and fractionating the treated feed to mitigate or prevent the conversion of nootkatone to its nor-ketone.

[0025] According to an exemplary embodiment, the use of a terpene blend as a fragrance in a flavor product is provided, the terpene blend being prepared by separating at least a portion of nookatone from at least one compound that catalyzes the conversion of nookatone to its nor-ketone to produce a second feed containing nookatone, treating a feed containing at least one compound that catalyzes the conversion of nookatone and its nor-ketone to mitigate or prevent the conversion of nookatone to its nor-ketone, and fractionating the second feed.

[0026] According to an exemplary embodiment, the use of a terpene blend as a flavor in a beverage or food product is provided, the terpene blend being prepared by separating at least a portion of nookatone from at least one compound that catalyzes the conversion of nookatone to its nor-ketone to produce a second feed containing nookatone, treating a feed containing at least one compound that catalyzes the conversion of nookatone and its nor-ketone to mitigate or prevent the conversion of nookatone to its nor-ketone, and fractionating the second feed.

[0027] According to one exemplary embodiment, there is provided the use of a terpene blend as a fragrance in a fragrance product, the terpene blend comprising providing a feed containing at least one compound that catalyzes the conversion of nootkatone and nootkatone to nootkatene, treating the feed by neutralizing at least a portion of the compounds present in the feed that catalyze the conversion of nootkatone to nootkatene to mitigate or prevent the conversion, and fractionating the treated feed.

[0028] According to one exemplary embodiment, there is provided the use of a terpene blend as a flavor in a beverage or food product, the terpene blend comprising providing a feed containing at least one compound that catalyzes the conversion of nootkatone and nootkatone to nootkatene, treating the feed by neutralizing at least a portion of the compounds of the feed that catalyze the conversion of nootkatone to nootkatene to mitigate or prevent the conversion, and fractionating the treated feed.

[0029] Detailed Description The starting terpene blend may contain nootkatone. As used herein, the term "nootkatone" includes α - nootkatone and β - nootkatone. According to one embodiment, the starting terpene blend contains at least one nootkatone. According to an exemplary embodiment, the starting terpene blend contains α - nootkatone. According to another exemplary embodiment, the starting terpene blend contains β - nootkatone. According to a further exemplary embodiment, the starting terpene blend contains both α - nootkatone and β - nootkatone.

[0030] A raw material terpene blend containing nootkator may contain acidic compounds and other high-boiling impurities that catalyze the reaction of nootkator to nootcatene at the elevated temperature used in a typical fractional distillation process performed on the raw material terpene blend to prepare a nootkatone blend for use as a flavor or fragrance component. Disclosed are methods to mitigate or prevent the conversion of nootkator to nootcatene that typically occurs during the high-temperature fractional distillation process performed on the nootkator-containing terpene blend before performing the fractional distillation process, so that the amount of nootcatene produced during fractional distillation is reduced to a commercially acceptable level.

[0031] In one embodiment, a raw material terpene blend used in accordance with the method of the present disclosure contains at least α-nootkator and at least one compound or molecule that catalyzes the chemical reaction from α-nootkator to nootkatone. In one exemplary embodiment, the raw material terpene blend may contain one or more nootkators, such as a mixture of α-nootkator and β-nootkator, and at least one compound or molecule that catalyzes the chemical reaction from α-nootkator to nootkatone. In a further exemplary embodiment, the raw material blend may contain α-nootkator, β-nootkator, β,γ-nootkatone, nootketene, nootkatone, and valencene, as well as at least one compound or molecule that catalyzes the chemical reaction from α-nootkator to nootkatone.

[0032] In one embodiment, the raw material terpene blend may be prepared by microbial fermentation using a suitable microorganism capable of performing a fermentation process to produce a terpene blend containing at least one nootkatone. The disclosure is not limited to the use of terpene blends prepared by microbial fermentation, and the raw material blend may contain a composition containing a sesquiterpene substrate such as nootkatone extracted from grapefruit, Alaska yellow cedar tree, vetiver grass, or valencene, which can be oxidized to nootkatone by any means of oxidation, such as chemical oxidation, enzymatic oxidation, or whole cell biotransformation, without limitation. Methods for enzymatic oxidation of sesquiterpene substrates to oxygenated sesquiterpenes (e.g., nootkatone and / or nootkatone) are disclosed in WO 2016 / 029187 and WO 2016 / 029153, both of which are incorporated herein by reference.

[0033] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene includes separating a portion of the nootkator present in a feed, such as a feed containing a raw material terpene blend, from one or more compounds that catalyze the chemical conversion of nootkator to nootcatene, which is also present in the material feed.

[0034] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene includes neutralizing an acid compound present in a terpene blend or feed containing nootkator that catalyzes the chemical conversion of nootkator to nootcatene.

[0035] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene comprises neutralizing an acid compound present in a terpene blend containing nootkator that catalyzes the chemical conversion of nootkator to nootcatene, and subsequently separating a portion of the nootkator from the remaining compound that catalyzes the chemical conversion of nootkator to nootcatene.

[0036] According to the method for mitigating or preventing the conversion of nootkator to nootcatene of the present invention, nootkator is separated from one or more compounds that catalyze the reaction from nootkator to nootcatene in a shorter time and at a lower temperature than that obtained by fractional distillation of a starting terpene blend containing nootkator, or one or more compounds that catalyze the reaction from nootkator to nootcatene are neutralized.

[0037] Separating a desired terpene, including α-nootkator, from a compound that catalyzes the conversion of nootkator to nootcatene, or neutralizing the catalyst compound present in the starting terpene blend, allows the terpene blend to be fractionated at a higher temperature over a longer period with virtually no loss to the total amount of nootkator recovered from the fractional distillation process. In one exemplary embodiment, performing a treatment step to separate a desired terpene from a catalyst compound present in the starting terpene blend, or to neutralize the catalyst compound present in the starting terpene blend, reduces the loss to the total amount of nootkator recovered after fractional distillation to 10 weight percent or less, compared to the expected recovery rate of nootkator after the fractional process without performing the disclosed treatment step(s) first.

[0038] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene comprises separating nootkator and at least a portion of other desired terpenes present in a terpene feed containing a blend of terpenes from one or more compounds that catalyze the conversion of nootkator to nootcatene present in the terpene feed containing a blend of terpenes.

[0039] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene includes providing a feed containing nootkator, another desired terpene species, and at least one compound that catalyzes the conversion of nootkator to nootcatene. At least a portion of the nootkator present in the terpene feed is separated from the at least one compound that catalyzes the conversion of nootkator to nootcatene and further processed.

[0040] According to one exemplary embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene includes providing a feed containing a blend of terpenes comprising nootkator, another desired terpene, and at least one compound that catalyzes the conversion of nootkator to nootcatene. At least a portion of the nootkator and at least a portion of the other desired terpenes present in the terpene feed are separated from the at least one compound that catalyzes the conversion of nootkator to nootcatene.

[0041] In one exemplary embodiment, one or more compounds present in the feed material catalyzing the conversion of nootkator to nootcatene include at least one acid. The acid may include any acid-containing molecule that catalyzes the conversion of nootkator to nootcatene. The acid includes inorganic (mineral) acids and organic acids. In one embodiment, the acid catalyzing the conversion of nootkator to nootcatene includes a fatty acid. For example, without limitation, the fatty acid may include a carboxylic acid and a hydrocarbon tail having 2 to 28 carbon atoms. The hydrocarbon tail may be linear or branched and may include a cyclic structure. This includes short-chain fatty acids, medium-chain fatty acids, and long-chain fatty acids.

[0042] The fatty acids may be selected from saturated or unsaturated fatty acids. The hydrocarbon tail of an unsaturated fatty acid may contain one or more double bonds. The hydrogen atoms adjacent to the double bonds in the hydrocarbon tail of an unsaturated fatty acid may be in either a cis or trans configuration. In one embodiment, without limitation, exemplary examples of at least one fatty acid are selected from pelargonic acid (C9:0), capric acid (C10:0), undecanoic acid (C11:0), lauric acid (C12:0), tridecanoic acid (C13:0), myristic acid (C14:0), pentadecanoic acid (C15:0), palmitic acid (C16:0), linoleic acid (C18:2), oleic acid (C18:1), elaidic acid (C18:1), stearic acid (C18:0), and combinations thereof.

[0043] According to one embodiment, the step of separating an acid from a terpene feed containing nootcatol and an acid that catalyzes the conversion of nootcatol to nootcatene includes a distillation process. According to the disclosed method, the distillation includes single-stage distillation. According to one embodiment, the single-stage distillation process is carried out for 60 to 180 minutes at a pot temperature of 25 to 260°C, a vapor temperature of 25 to 140°C, and a pressure of 0 to 50 mmHg. According to another embodiment, the single-stage distillation step is carried out for 80 to 130 minutes at a pot temperature of 140 to 240°C, a vapor temperature of 40 to 130°C, and a pressure of 0 to 20 mmHg. According to yet another embodiment, the single-stage distillation process is carried out for 90 to 110 minutes at a pot temperature of 160 to 200°C, a vapor temperature of 75 to 120°C, and a pressure of 0 to 1 mmHg.

[0044] In one exemplary embodiment, the conversion of nootkator to nootcatene is mitigated by treating a feed containing nootkator and compounds that catalyze the conversion of nootkator to nootcatene by adding a base to the feed. The base has chemical properties that neutralize acids or increase the pH of a liquid. Adding a base to the feed neutralizes at least some of the compounds that catalyze the conversion of nootkator to nootcatene present in the feed, thereby mitigating or preventing the conversion to nootcatene.

[0045] A base added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene can be selected from any base capable of at least partially or completely neutralizing one or more acid compounds. According to one exemplary embodiment, a base added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene, to at least partially neutralize the acid, comprises at least one nitrogen-containing compound. According to one exemplary embodiment, a nitrogen-containing compound added to a feed containing nootkator and at least one acid compound that catalyzes the conversion of nootkator to nootcatene, to at least partially neutralize the acid, comprises at least one amine. According to one exemplary embodiment, an amine compound added to a feed containing nootkator and an acid compound that catalyzes the conversion of nootkator to nootcatene, to at least partially neutralize the acid, comprises at least one alkylamine.

[0046] In one exemplary embodiment, an amine compound added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene, to at least partially neutralize the acid, comprises at least one secondary or tertiary amine. In one exemplary embodiment, an amine compound added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene, to at least partially neutralize the acid, comprises at least one trialkylamine. Without limitation, for illustrative purposes only, the tertiary amine may be selected from one or more trioctylamines, toridodecylamines and combinations thereof. In another embodiment, a base added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene may be selected from hydroxide bases. Without limitation, for illustrative purposes only, the hydroxide bases include ammonium hydroxide, calcium hydroxide, lithium, magnesium hydroxide, potassium, sodium hydroxide and mixtures thereof.

[0047] According to other exemplary embodiments, the nitrogen-containing compound added to a feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene, to at least partially neutralize the acid, includes ammonia. According to one embodiment, ammonia is introduced into the feed as a gas by passing gaseous ammonia through the feed containing nootkator and one or more acid compounds that catalyze the conversion of nootkator to nootcatene, to at least partially neutralize the acid. According to one embodiment, the step of passing ammonia gas through the feed containing nootkator and one or more acid compounds includes sparging the ammonia gas into the feed.

[0048] According to one embodiment, a method for mitigating or preventing the conversion of nootkator to nootcatene comprises providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene. At least a portion of the nootkator and one or more desired terpenes present in the feed are separated from at least one compound by distillation, and the nootkator is collected as a distillate. According to one embodiment, at least a portion of the nootkator and one or more desired terpenes present in the feed are separated from at least one compound by single-stage distillation, and the nootkator is collected as a distillate.

[0049] According to one embodiment, a method for preparing a nootkatone composition includes providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene. The feed is treated to mitigate or prevent the conversion of nootkator to nootcatene by separating nootkator from the feed by distillation to produce a second feed containing nootkator and other desired terpenes, and by collecting the nootkator as a distillate. Subsequently, fractional distillation is performed on the treated feed containing the collected nootkator distillate.

[0050] According to one embodiment, a method for preparing a nootkatone composition includes providing a feed containing nootkator and at least one compound that catalyzes the conversion of nootkator to nootcatene. The feed is treated to mitigate or prevent the conversion by adding a base to the feed, thereby neutralizing the compound that catalyzes the conversion of nootkator to nootcatene present in the feed. The treated feed is then fractionally distilled to produce a nootkatone composition.

[0051] In one embodiment, by pre-treating a feed containing nootkator and compounds that catalyze the chemical conversion of nootkator to nootcatene, at least a portion of the nootkator is separated from compounds present in the feed that catalyze the reaction of nootkator to nootcatene, or by neutralizing compounds present in the feed that catalyze the reaction of nootkator to nootcatene with a neutralizing compound or molecule (such as a base), or by first separating at least a portion of the nootkator from compounds present in the feed that catalyze the reaction of nootkator to nootcatene, and then neutralizing compounds present in the feed that catalyze the reaction of nootkator to nootcatene with a neutralizing compound or molecule, the amount of nootkator retained in the terpene blend after fractional distillation is at least 50 weight percent, or at least 45 weight percent, or at least 40 weight percent, or at least 35 weight percent, or at least 30 weight percent, or at least 25 weight percent, or at least 20 weight percent, or at least 15 weight percent, or at least 10 weight percent.

[0052] In one embodiment, by pre-treating a feed containing nootkator and a compound that catalyzes the chemical conversion of nootkator to nootcatene, at least a portion of the nootkator is separated from the compound present in the feed that catalyzes the reaction of nootkator to nootcatene, or by neutralizing the compound present in the feed that catalyzes the reaction of nootkator to nootcatene with a neutralizing compound or molecule (such as a base), or by first separating at least a portion of the nootkator from the compound that catalyzes the reaction of nootkator to nootcatene present in the feed, and then neutralizing the compound that catalyzes the reaction of nootkator to nootcatene present in the feed with a neutralizing compound or molecule, the terpene blend after the fractional distillation step contains 1 weight percent or less of nootcatene. In other exemplary embodiments, the terpene blend prepared according to the disclosed method contains nootcatene in amounts of 0.9% by weight or less, 0.8% by weight or less, 0.7% by weight or less, 0.6% by weight or less, 0.5% by weight or less, 0.4% by weight or less, 0.3% by weight or less, 0.2% by weight or less, or 0.1% by weight or less.

[0053] Furthermore, distillate fractions useful for preparing terpene blends are disclosed, the distillate fractions comprising at least 50 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 45 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 40 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 35 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 30 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 25 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 20 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 15 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 10 weight percent α-nootcatol and 1 weight percent or less nootcatene.

[0054] According to one embodiment, a distillate fraction useful for preparing a terpene blend comprises at least 50 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 45 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 40 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 35 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 30 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 25 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 20 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 15 weight percent α-nootcatol and 0.5 weight percent or less nootcatene, or at least 10 weight percent α-nootcatol and 0.5 weight percent or less nootcatene.

[0055] According to other exemplary embodiments, distillate fractions useful for preparing terpene blends include at least 50 wt percent α-nootkator and 1 wt percent or less nootcatene, or at least 45 wt percent α-nootkator and 0.25 wt percent or less nootcatene, or at least 40 wt percent α-nootkator and 0.25 wt percent or less nootcatene, or at least 35 wt percent α-nootkator and 0.25 wt percent or less nootcatene, or at least 30 It contains, by weight percent, α-nootocator and 0.25% by weight or less of nootcatene, or at least 25% by weight, α-nootocator and 0.25% by weight or less of nootcatene, or at least 20% by weight, α-nootocator and 0.25% by weight or less of nootcatene, or at least 15% by weight, α-nootocator and 0.25% by weight or less of nootcatene, or at least 10% by weight, α-nootocator and 0.25% by weight or less of nootcatene.

[0056] According to other exemplary embodiments, distillate fractions useful for preparing a terpene blend include at least 50 weight percent α-nootcatol and 1 weight percent or less nootcatene, or at least 45 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 40 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 35 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 30 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 25 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 20 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 15 weight percent α-nootcatol and 0.1 weight percent or less nootcatene, or at least 10 weight percent α-nootcatol and 0.1 weight percent or less nootcatene.

[0057] Furthermore, a terpene blend prepared according to the disclosed method is disclosed. The terpene blend may include fractional distillates prepared according to the method of this disclosure, or a blend of fractions prepared according to the method of this disclosure, in order to achieve a desired concentration of one or more terpenes.

[0058] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 40 to about 60 weight percent nootkatone, or about 40 to about 55 weight percent nootkatone, or about 40 to about 50 weight percent nootkatone, or about 45 to about 55 weight percent nootkatone, or about 48 to about 52 weight percent nootkatone, or about 49 to about 51 weight percent nootkatone.

[0059] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 5 to about 25 weight percent of α-nootkitol, or about 5 to about 20 weight percent of α-nootkitol, or about 5 to about 15 weight percent of α-nootkitol, or about 5 to about 10 weight percent of α-nootkitol, or about 10 to about 25 weight percent of α-nootkitol, or about 10 to about 20 weight percent of α-nootkitol, or about 10 to about 20 weight percent of α-nootkitol, or about 10 to about 15 weight percent of α-nootkitol, or about 12 to about 20 weight percent of α-nootkitol, or about 13.5 to about 17.5 weight percent of α-nootkitol, or about 15 to about 25 weight percent of α-nootkitol, or about 15 to about 20 weight percent of α-nootkitol.

[0060] According to one exemplary embodiment, the terpene blend contains, based on the total weight of the terpene blend, approximately 0.001 to approximately 5 weight percent of β-nootkitol, or 0.01 to approximately 5 weight percent of β-nootkitol, or 0.05 to approximately 5 weight percent of β-nootkitol, or 0.1 to approximately 5 weight percent of β-nootkitol, or 0.25 to approximately 5 weight percent of β-nootkitol, or 0.5 to approximately 5 weight percent of β-nootkitol, or 0.75 to approximately 5 weight percent of β-nootkitol, or 0.3 to approximately 0.6 weight percent of β- - May contain nootkitol, or 0.35 to about 0.45 weight percent of β-nootkitol, or 1 to about 5 weight percent of β-nootkitol, or 1.5 to about 5 weight percent of β-nootkitol, or 2 to about 5 weight percent of β-nootkitol, or 2.5 to about 5 weight percent of β-nootkitol, or 3 to about 5 weight percent of β-nootkitol, or 3.5 to about 5 weight percent of β-nootkitol, or 4 to about 5 weight percent of β-nootkitol, or 4.5 to about 5 weight percent of β-nootkitol.

[0061] According to one exemplary embodiment, the terpene blend is based on the total weight of the terpene blend and contains approximately 0.1 to approximately 5 weight percent of β,γ-nootkatone, or approximately 0.25 to approximately 5 weight percent of β,γ-nootkatone, or approximately 0.5 to approximately 5 weight percent of β,γ-nootkatone, or approximately 0.75 to approximately 5 weight percent of β,γ-nootkatone, or approximately 1 to approximately 5 weight percent of β,γ-nootkatone, or approximately 1.5 to approximately 5 weight percent of β,γ-nootkatone, or approximately 2 to approximately The blend contains 5 weight percent of β,γ-nootkatone, or about 2.5 to about 5 weight percent of β,γ-nootkatone, or about 3 to about 5 weight percent of β,γ-nootkatone, or about 3.5 to about 5 weight percent of β,γ-nootkatone, or about 4 to about 5 weight percent of β,γ-nootkatone, or about 4.5 to about 5 weight percent of β,γ-nootkatone, or about 2 to about 3 weight percent of β,γ-nootkatone, or about 2.5 to about 3 weight percent of β,γ-nootkatone. According to one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, β,γ-nootkatone or less than or equal to 5 weight percent of β,γ-nootkatone, or about 4 weight percent or less of β,γ-nootkatone, or about 3 weight percent or less of β,γ-nootkatone, or about 2 weight percent or less of β,γ-nootkatone, or about 1 weight percent or less of β,γ-nootkatone.

[0062] According to one exemplary embodiment, the terpene blend contains, based on the total weight of the terpene blend, approximately 0.01 to approximately 1 weight percent nootcatene, or 0.02 to approximately 1 weight percent nootcatene, or 0.03 to approximately 1 weight percent nootcatene, or 0.04 to approximately 1 weight percent nootcatene, or 0.05 to approximately 1 weight percent nootcatene, or 0.06 to approximately 1 weight percent nootcatene, or 0.07 to approximately 1 weight percent nootcatene, or 0.08 to approximately 1 weight percent nootcatene, or 0.09 to approximately 1 weight percent nootcatene, or 0. 1 to approximately 1 weight percent nootcatene, or 0.15 to approximately 1 weight percent nootcatene, or 0.2 to approximately 1 weight percent nootcatene, or 0.25 to approximately 1 weight percent nootcatene, or 0.3 to approximately 1.25 weight percent nootcatene, or 0.3 to approximately 1 weight percent nootcatene, or 0.35 to approximately 1 weight percent nootcatene, or 0.4 to approximately 1 weight percent nootcatene, or 0.45 to approximately 1 weight percent nootcatene, or 0.55 to approximately 1 weight percent nootcatene, or It may also contain 0.6 to approximately 1 weight percent nootcatene, or 0.65 to approximately 1 weight percent nootcatene, or 0.7 to approximately 1 weight percent nootcatene, or 0.75 to approximately 1 weight percent nootcatene, or 0.8 to approximately 1 weight percent nootcatene, or 0.85 to approximately 1 weight percent nootcatene, or 0.9 to approximately 1 weight percent nootcatene, or 0.95 to approximately 1 weight percent nootcatene.

[0063] According to one exemplary embodiment, the terpene blend is based on the total weight of the terpene blend and contains approximately 0.001 to approximately 15 weight percent of valensene, or approximately 0.01 to approximately 15 weight percent of valensene, or approximately 0.025 to approximately 15 weight percent of valensene, or approximately 0.05 to approximately 15 weight percent of valensene, or approximately 0.075 to approximately 15 weight percent of valensene, or approximately 0.1 to approximately 15 weight percent of valensene, or approximately 0.25 to approximately 15 weight percent of valensene, or It may also contain approximately 0.5 to 15 weight percent of valensen, or approximately 0.75 to 15 weight percent of valensen, or approximately 0.03 to 1.5 weight percent of valensen, or approximately 0.03 to 0.55 weight percent of valensen, or approximately 0.4 to 1.5 weight percent of valensen, or approximately 1 to 15 weight percent of valensen, or approximately 5 to 15 weight percent of valensen, or approximately 10 to 15 weight percent of valensen, or approximately 5 to 10 weight percent of valensen.

[0064] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 5 to about 25 weight percent of α-nootkatol, about 0.001 to about 5 weight percent of β-nootkatol, about 0.1 to about 5 weight percent of β,γ-nootkatone, about 40 to about 60 weight percent of nootkatone, about 0.01 to about 1 weight percent of -nootkatene, and about 0.001 to about 15 weight percent of valencene.

[0065] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 12 to about 20 weight percent of α-nootkatol, about 0.3 to about 0.6 weight percent of β-nootkatol, about 2.5 to about 3 weight percent of β,γ-nootkatone, about 48 to about 52 weight percent of nootkatone, about 0.3 to about 1.2 weight percent of nootkatene, and about 0.4 to about 1.5 weight percent of valencene.

[0066] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 12 to about 20 weight percent of α-nootkator, about 0.3 to about 0.6 weight percent of β-nootkator, about 2.5 to about 3 weight percent of β,γ-nootkatone, about 48 to about 52 weight percent of nootkatone, about 0.3 to about 1.2 weight percent of nootcatene and about 0.4 to about 1.5 weight percent of valencene, about 0.2 to about 0.5 weight percent of 1,10-dihydronootkatone, and about 25 to about 30 weight percent of other sesquiterpenes.

[0067] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 13.5 to about 17 weight percent of α-nootkatol, about 0.35 to about 0.45 weight percent of β-nootkatol, about 0.55 to about 1.4 weight percent of β,γ-nootkatone, about 49 to about 51 weight percent of nootkatone, about 0.3 to about 1 weight percent of nootkatene, and about 0.03 to about 0.55 weight percent of valencene.

[0068] In one exemplary embodiment, the terpene blend may contain, based on the total weight of the terpene blend, about 13.5 to about 17 weight percent of α-nootkator, about 0.35 to about 0.45 weight percent of β-nootkator, about 0.55 to about 1.4 weight percent of β,γ-nootkatone, about 49 to about 51 weight percent of nootkatone, about 0.3 to about 1 weight percent of nootkatene, and about 0.03 to about 0.55 weight percent of valencene, about 0.2 to about 0.35 weight percent of 1,10-dihydronootkatone, and about 25 to about 30 weight percent of other sesquiterpenes.

[0069] A fragrance composition containing a terpene blend prepared in accordance with this disclosure may further contain one or more additional fragrance compounds. In one exemplary embodiment, without limitation, additional fragrance compounds may include one or more aldehyde compounds, one or more balsamic compounds, one or more different citrus compounds, one or more floral compounds, one or more fruity compounds, one or more gourmand compounds, one or more green compounds, one or more marine compounds, one or more mossy compounds, one or more musk compounds, one or more piney compounds, one or more spicy compounds, and / or one or more woody compounds, or a combination thereof.

[0070] For illustrative purposes only and without limitation, suitable aldehyde compounds include, but are not limited to, ALDEHYDE C 12 MNA (2-methylundecanal); ALDEHYDE C 8 OCTYLIC (octanal); ALDEHYDE C 8 OCTYLIC (octanal); ALDEHYDE C 9 (nonanal); ALDEHYDE C 6 HEXYLIC (hexanal); CALYPSONE (6-methoxy-2,6-dimethyloctanal); ALDEHYDE C 7 HEPTYLIC (heptanal); ALDEHYDE C 10 decanal; ALDEHYDE C 12 dodecanal; acetaldehyde; n-butyraldehyde; and saturated alkylaldehydes, including isobutyraldehyde. In one embodiment, the saturated alkylaldehyde is selected from the group consisting of ALDEHYDE C 12 MNA and CALYPSONE.

[0071] In another embodiment, preferred odor-reducing materials include, but are not limited to, DECEN-1-AL, CIS-4((Z)-deca-4-enal); DECENAL-4-TRANS((E)-deca-4-enal); DECENAL-9(9-decenal), MELONAL(2,6-dimethylhepta-5-enal); CYCLAL The formula includes unsaturated alkylaldehydes, including C(2,4-dimethylcyclohexa-3-encarbaldehyde); NONADIENAL((2E,6Z)-nona-2,6-dienal); PINOACETALDE(3-(6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)propanal); SHISOLIA(4-vinylcyclohexa-1-encarbaldehyde); MACEAL(bicyclo[2.2.2]octa-5-en-2-carboxaldehyde); cinnamaldehyde; citronellal; trans-2-hexenal; trans-2-decenal, cis-3-hexanal and cis-4-heptenal. In one embodiment, the unsaturated alkylaldehyde is selected from the group consisting of MELONAL, CYCLAL C, SHISOLIA and MACEAL.

[0072] In another embodiment, preferred odor-reducing materials include, but are not limited to, aromatic aldehydes, including anisyl aldehyde; AUBEPINE PARA CRESOL (4-methoxybenzaldehyde), FLORHYDRAL (3-(3-isopropylphenyl)butanal); benzaldehyde; PHENYL PROPIONIC ALDEHYDE (3-phenylpropanal); and TOLYL ALDEHYDE PARA (4-methylbenzaldehyde).

[0073] For illustrative purposes only and not limiting, suitable citrus compounds may include citral, citronellal, L-citronellol, decanal, limonene, myrcenolate, sinensal, bergamot oil, grapefruit oil, lemon oil, lime oil, and / or orange oil.

[0074] For illustrative purposes only and not limiting, suitable floral compounds include: anisyl acetate, anisaldehyde, benzyl acetate, bourgeon, butyl acetate, cyclamenaldehyde, cyclohexyllactone, delta-damascone, farnesal, L-farnesal, farnesol, flohydral), floral ozone, geraniol, geranyl acetate, piperonal, hexione, heliobuquet, hexyl cinnamaldehyde, hexyl salicylate, indole, α-ionone, β-ionone, isopropoxyethyl salicylate It may be rhat, jasmodione, cis-jasmone, kovanol, laurinol, linalool, linalyl acetate, mayol, methyl dihydrojasmonate, γ-methyl ionone, methoxymelonal, nerol, nerolione, neryl acetate, 2-pentylcyclopentanone, phenoxanol, phenoxyethyl isobutyrate, phenylacetaldehyde, phenylethyl alcohol, rose oxide, suzaral, undecaverthol, geranium oil, lavender oil, rose oil, and / or ylang-ylang oil. Fruity compounds include aldehyde C-C16, allyl caproate, allylcyclohexanepropionate, allylheptanoate, amyl acetate, benzaldehyde, L-citronellyl acetate, L-citronellyl nitrile, cyclacet, damascenone, β-decalactone, γ-decalactone, diethylmalonate, dimethylphenylethylcarbinol, dimethyl sulfide, γ-dodecalactone, ethyl acetate, ethyl butyrate, ethyl caproate, and ethyl decalactone. Dienotate, ethyl-2-methylbutyrate ethyl acetate, ethyl propionate, florol, hexyl acetate, hexyl isobutyrate, isoamyl acetate, jasmolactone, manzanate, melonal, methylheptyl ketone, γ-nonalactone, γ-octaractone, phenylethyl isobutyrate, raspberry ketone, ringonol, tesalon, tollaldehyde, γ-undecalactone, vanoris, and / or verdox.

[0075] For illustrative purposes only, and not limiting, suitable gluman compounds may include caprylic acid, coumarin, ethyl freson, ethyl vanillin, ethyl maltol, filbertone, furaneol, guaiacol, maple furonone, 2-acetylpyrazine, 2,5-dimethylpyrazine, and / or vanillin.

[0076] For illustrative purposes only, and not limited to, preferred green compounds may include dynascone, galbanolene, trans-2-hexenal, cis-3-hexenol, hexen-1-ol, cis-3-hexenyl acetate, cis-3-hexenyl butyrate, cis-3-hexenyl salicylate, liffarome, methyl octin carbonate, 2,6-nonadienal, oxane, stemone, styraryl acetate, triplal, undecavertol, violet methyl carbonate, vionil, and / or violet leaf extract.

[0077] For illustrative purposes only and not limiting, suitable musk compounds may include ambretlides, ambretones, ambroxan, exaltlides, galaxolides, habanolides, helvetolides, (1'R)-3-methyl-5-(2,2,3-trimethylcyclopentan-1-yl)-2-pentanone, muscenone, musk T, L-muscone, and / or tonalides.

[0078] For illustrative purposes only, and not limiting, suitable piney compounds may include α-pinene, β-pinene, and mixtures thereof. For illustrative purposes only and not limiting, suitable spicy compounds may include β-caryophyllene, cinnamaldehyde, cuminaldehyde, eugenol, isoeugenol, perilla aldehyde, cardamom oil, clove oil, ginger extract, and / or black pepper extract.

[0079] For illustrative purposes only and not limiting, suitable woody compounds may include amber core, amber extreme, ambroxan, bacdanol, cedramber, cedanol, ebanol, hinginol, hinokitiol, javanol, norlimbanol dextro, osyrol, patchone, polyambrol, α-pinene, β-pinene, sandalwood core, santalex T, orbitone, cedarwood oil, patchouli oil, sandalwood oil, and / or vetiver oil.

[0080] The terpene blends disclosed herein may be included in a wide range of food and beverage products. The terpene blends of this disclosure may be included in a wide variety of food products that would benefit from citrus aromas and / or flavors.

[0081] Muffins (e.g., English muffins), crackers (e.g., salt crackers, toasted crackers, graham crackers, etc.), rolls (e.g., soft rolls, dinner rolls, crescent rolls), biscuits (e.g., buttermilk biscuits, cobbler biscuits), pie crusts, bread (e.g., focaccia, bruschetta, sourdough bread, soda bread, breadsticks, cornbread, etc.), bagels, brownies, cookies, turnovers, donuts, cakes, pastries, pies, scones, etc.

[0082] Without limitation, and for illustrative purposes only, exemplary dairy products include ice cream, impulse ice cream, ice cream desserts, frozen yogurt, milk, fresh / pasteurized milk, whole-fat fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / UHT milk, whole-fat long-life / UHT milk, semi-skimmed long-life / UHT milk, fat-free long-life / UHT milk, goat's milk, condensed milk / evaporated milk, plain condensed milk / evaporated milk, flavored, functional and other condensed milk, flavored milk beverages, dairy-only flavored milk beverages, soy milk, fermented milk beverages, coffee creamer / whitener, milk powder, flavored milk powder beverages, cream, yogurt, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, yogurt drinks, and other dairy-based desserts.

[0083] Without limitation, and for illustrative purposes only, exemplary flavored food products include salted snacks (potato chips, crisps, nuts, tortilla tostadas, pretzels, cheese snacks, corn snacks, potato snacks, ready-to-eat popcorn, microwave popcorn, pork rice, nuts, crackers, cracker snacks, breakfast cereals, meat, preserved meat, luncheon / breakfast meat, tomato products, peanut butter, soups, canned vegetables, pasta sauces, and flavored biscuits, crackers, and bread substitutes).

[0084] Without limitation and for illustrative purposes only, sweet products include breakfast cereals, ready-to-eat ("RTE") cereals, home breakfast cereals, flakes, muesli, other RTE cereals, children's breakfast cereals, and hot cereals.

[0085] The terpene blends and / or flavor compositions comprising terpene blends of this disclosure may be included in citrus beverages. Suitable citrus beverages include, but are not limited to, alcoholic citrus cocktails, citrus flavored beverages, citrus liqueurs, citrus flavored sodas, citrus flavored soft drinks, citrus flavored waters, citrus flavored stills, citrus flavored carbonated waters, etc. The terpene blends and / or flavor compositions comprising terpene blends of this disclosure may be included in flavor compositions or foods and beverages that contain citrus components, including tropical flavors (e.g., coconut, guava, kiwi, mango, papaya, passion fruit, and pineapple flavors).

[0086] Terpene blends and flavor compositions containing terpene blends may be used in pharmaceuticals, cosmetics, and personal care products such as toiletries.

[0087] When used in cosmetics and toiletries, it may be used in any of the "Reported Product Categories" listed in the Cosmetic, Toiletries and Fragrance Association's "International Cosmetic Ingredient Dictionary and Handbook," and may be used in combination with one or more of the ingredients cited as being used in the Reported Product Category.The reported Product Categories include: aftershave lotions, baby lotions, oils, powders and creams, general baby products, baby shampoos, base coats and undercoats, bath capsules, bath oils, tablets and salts, general bath products, bath soaps and detergents, beard softeners, brushes, body and hand products, bubble baths, cleansers, colognes and toilet water, exfoliants, toothpaste, deodorants, hair removal products, dots, eye lotions, general eye makeup products, eye makeup removers, eyeshadows, eyebrow pencils, eyeliners, face and neck products, face powders, women's hygiene deodorants, foot powders and sprays, foundations, general fragrance products, fragrance removers, hair bleach, hair color sprays, general hair coloring products, hair conditioners, hair dyes and colors, colored hair lighteners, hair products, and hair Arinse, hair shampoo, hair spray, hair straightener, hair tint, hair wave set, indoor tanning products, leg and body paint, lipstick, makeup base, makeup fixative, makeup products, all kinds of manicure products, mascara, men's talcum, moisturizers, mouthwash and breath freshener, nail cream and lotion, nail extender, nail polish and enamel remover, nail polish and enamel, night skincare products, all kinds of oral hygiene products, paste masks, perfumes, permanent waves, all kinds of personal clean products, powders, pre-shave lotion, lipstick, sachets, shampoo, shaving cream, all kinds of shaving products, shaving soap, all kinds of skincare products, skin freshener, suntan gel, cream and liquid, all kinds of suntan products, sonics, dressings and other hair grooming aids.

[0088] "Oral care" or "oral hygiene" products may encompass any products applied to the oral cavity for the purpose of cleaning, refreshing, healing, or deodorizing the oral cavity or any part thereof. Without limitation, for illustrative purposes only, such oral care and oral hygiene compositions include toothpaste, tooth gel, tooth powder, teeth whitening products, mouth rinse, mouthwash, gargle compositions, lozenges, dental floss, toothpicks, anti-plaque and anti-gingivitis compositions, throat lozenges, throat candies, compositions for treating nasal symptoms, cold symptoms, and cold relief.

[0089] The nootkatone oil compositions of this disclosure may be incorporated into a wide variety of other consumer products. Without limiting them, for illustrative purposes only, consumer products may be selected from fine fragrances, home care products, and air care products.

[0090] In one exemplary embodiment, without limitation, fine fragrance products may be selected from parfums, extravagant parfums, eau de parfums, millésimes, parfums de toilettes, eau de toilettes, eau de colognes, body splashes, aftershaves, body mists, and baby colognes.

[0091] In one exemplary embodiment, without limitation, home care products may be selected from fabric conditioners, fabric softeners, laundry detergents, laundry additives, rinse additives, bleaches, dryer sheets, perfume beads, car care products, dishwashing detergents, and hard surface cleaners.

[0092] In one exemplary embodiment, without limitation, the air care product may be selected from candles, aerosols, air fresheners, liquid electric air fresheners, fragrance diffusers, gel air fresheners, plug-in air fresheners, plug-in oils, and wax melts.

[0093] example The following examples further describe exemplary embodiments of the disclosed methods and illustrate methods for mitigating or preventing the conversion of α-nootkitol to nootcatene in terpene blends. The examples should not be construed as limiting the mitigation of the chemical conversion of α-nootkitol to nootcatene in terpene blend feeds, methods for producing terpene blends, terpene blends, flavor compositions, fragrance compositions, beverage products, food products, fragrance products, methods for producing beverage products, methods for producing food products, and methods for producing fragrance products.

[0094] Comparative Example 1 A raw material blend of citrus terpenes containing approximately 1.61% total fatty acids was fractionally distilled under complete vacuum. Table 1A below shows the initial amounts of each component in the raw material terpene blend, as well as the amounts of each component recovered from the high-temperature fractional distillation process typically used to prepare nootkatone blends for use as flavor and fragrance components. Table 1B below shows the temperature and composition of the fractions as the fractional distillation progresses.

[0095] [Table 1-A]

[0096] [Table 1-B]

[0097] The fractional distillation results indicate a significant decrease in the mass of nootcatol and a corresponding increase in the mass of nootcatene during the batch distillation process. Furthermore, each fraction except the first fraction contained more than 1% nootcatene, which is evidence of its continuous generation throughout the fractional distillation process.

[0098] Comparative Example 2 / Example 3-4 Samples of the same raw material blend of citrus terpenes containing approximately 1.61% total fatty acids used in Comparative Example 1 were evaluated to determine the effect of single-stage distillation (Example 3) or treatment of the raw material terpene blend with a base (Example 4) on the catalytic reaction of α-nootkator to nootkatone. 5% by weight of trioctylamine was added as a base material to the terpene blend of Example 4. The samples were heated under a nitrogen pad at 1 ATM for 5 hours and at a temperature reaching 130°C under reflux. Tables 2A-2C below show the amounts (grams) of nootkator, nootkatone, nootkatone, and other components present in the terpene blends charged into the reaction vessel (i.e., flask) and recovered after heat treatment.

[0099] [Table 2-A] [Table 2-B]

[0100] [Table 2-C]

[0101] Both the simple distillate (Example 3) and the amine spike (Example 4) resulted in less nootcatene formation and retention of nootcatel. In Examples 3 and 4, the conversion reaction from nootcatel to nuctene occurred, but to a much smaller extent compared to comparative / control Example 2. The simple distillation performed (Example 3) carried over a certain limit of undesirable high-boiling-point substances, including some acidity. From these results, without being bound by any particular theory, terminating this process at a lower pot temperature could further reduce or eliminate the carryover of acidity and other high-boiling-point substances, which would improve the stability of nootcatel compared to the results for Example 3 shown above. Alternatively, the addition of a larger amount of tertiary amine to the starting terpene blend may result in better nootcatel stability and less nootcatene formation compared to Example 4.

[0102] Example 5-6 A citrus terpene raw material blend containing approximately 1.61% total fatty acids was processed according to embodiments of the present disclosure. Following either simple single-stage distillation (Example 5) or the addition of 5 wt% base, trioctylamine, to the terpene blend (Example 6), two samples of the same citrus terpene raw material blend were subjected to fractional distillation. Tables 3A and 3C below show the temperature and composition of the fractions as the fractional distillation progresses. Tables 3B-3D below show the amounts (grams) of nootkator, nootcatene, nootkatone, and other components present in the terpene blend charged into a reaction vessel (i.e., a flask) and recovered after heat treatment.

[0103] [Table 3-A]

[0104] [Table 3-B]

[0105] [Table 3-C]

[0106] [Table 3-D]

[0107] The yields of α-nootcatol for both amine spike (Example 6) and simple distillation fractionation (Example 5) improved from 43% (Table 1A comparison / control) to 86% and 93%, respectively. Both simple distillation and amine pretreatment were effective in retaining α-nootcatol and suppressing the formation of nootcatene during fractionation. It is thought that the tertiary amine buffered the pH of the sample and catalyzed the reaction, thus preventing acidity, and that simple distillation separated the desired terpenes from high-boiling fatty acids. The nootcatene concentrations in the fractions in Tables 3A and 3C were considerably lower overall compared to fractions from distillation of untreated terpene blend samples.

[0108] Where a range of values ​​is described in this disclosure, it is intended that all values ​​within the range encompassing the endpoints be considered disclosed. For example, the “range of 50 to 100” for a component will be read as referring to all possible numbers along the continuum between 50 and 100. It will be understood that the inventors acknowledge and understand that all values ​​within the range are considered identified, and that the inventors possess the entire range and all values ​​within it.

[0109] In this disclosure, the term “about” as used in relation to a value encompasses the given value and has meanings indicated by the context. For example, it includes at least the degree of error associated with measuring a particular value. Those skilled in the art will understand that the term “about” as used herein means that in the compositions and / or methods of this disclosure, an amount “about” of the stated value provides the desired degree of effect. Those skilled in the art will further understand that the measurement and boundaries of “about” with respect to the percentage, amount or quantity value of any component in an embodiment can be determined by varying the value, determining the effectiveness of the composition for each value, and determining the range of values ​​that produce a composition having the desired degree of effectiveness according to this disclosure. The term “about” is further used to reflect the possibility that a composition may contain trace components of other materials that do not alter the effectiveness or safety of the composition.

[0110] Any weight percentage of any composition disclosed herein is based on the total weight of the terpene blend, flavor composition, fragrance composition, food product, beverage product, or fragrance product, as the circumstances indicate. It will be understood by those skilled in the art that the total weight percentage of any particular blend, composition, or product cannot exceed 100%. For example, it will be readily apparent to those skilled in the art that a beverage product containing 50–95 weight percent of a beverage base and 5–50 weight percent of a terpene-based flavor composition will not exceed 100%. Those skilled in the art will understand that the amount of an ingredient can be adjusted to contain a desired amount of the ingredient without exceeding 100% by weight of the blend, composition, or product.

[0111] The above text provides a broad description of numerous different aspects of this disclosure. This description should be interpreted as illustrative only, and not all possible aspects are described because it would be impractical, if not impossible, to describe all possible aspects. Any feature, characteristic, component, composition, ingredient, product, step, or methodology described herein may be deleted in whole or in part, and may be combined with or substituted for any other feature, characteristic, component, composition, ingredient, product, step, or methodology described herein.

[0112] Methods for causing the chemical conversion of nootcatol to nootcatene in terpene blend feeds, methods for producing terpene blends, terpene blends, flavor compositions, fragrance compositions, beverage products, food products, fragrance products, methods for producing beverage products, methods for producing food products, and methods for producing fragrance products have been described in relation to various exemplary embodiments. It should be understood that other similar exemplary embodiments may be used to perform the same function, or that modifications and additions may be made. Furthermore, various exemplary embodiments may be combined to produce the desired result.

[0113] Accordingly, the methods for chemically converting nootcatol to nootcatene in terpene blend materials, methods for producing terpene blends, terpene blends, flavor compositions, fragrance compositions, beverage products, food products, and fragrance products should not be limited to any single embodiment, but rather their breadth and scope should be interpreted in accordance with the descriptions of the appended claims. The embodiments described herein are merely illustrative, and those skilled in the art will understand that variations and modifications can be made without departing from the spirit and scope of the invention. All such variations and modifications are intended to fall within the scope of the invention as described herein. Furthermore, since various embodiments of the invention can be combined to provide the desired results, not all disclosed embodiments necessarily have to be alternative means.

Claims

1. A method for mitigating or preventing the conversion of nootcatel to nootcatene, the following: To provide a feed containing nootkator and at least one fatty acid; and (i) Separating nootkator from fatty acids by distillation other than fractional distillation, (ii) Neutralizing at least a portion of the fatty acids, or The method, including the method described above.

2. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 1, wherein the feed comprises a blend of volatile terpenes including α-nootkator.

3. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 1 or 2, wherein at least one fatty acid is selected from saturated and unsaturated fatty acids having 2 to 28 carbon atoms.

4. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 1, wherein the distillation includes single-stage distillation.

5. A method for mitigating or preventing the conversion of nootcatol to nootcatene according to claim 1, comprising adding a base to the feed before distillation.

6. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 1, wherein the method comprises performing fractional distillation after either (i) or (ii).

7. A method for mitigating or preventing the conversion of nootcatol to nootcatene according to claim 6, wherein the base is a nitrogen-containing compound.

8. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 7, wherein the nitrogen-containing compound comprises an amine.

9. A method for mitigating or preventing the conversion of nootkator to nootcatene according to claim 8, wherein the amine comprises a tertiary amine.

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