Takasago International Corporation

Hideo Ujihara

Kenya Ishida

Kenji Yagi

Takeshi Yamamoto

Shigeru Tanaka

Toshimitsu Hagiwara

Shinya Watanabe

Michael E Lankin

Carter B Green

Louis J Lombardo

Amrit S Mankoo

Hiroyuki Matsuda

Tomohiko Hakamata

Jennifer B Tartaglia

Yasuhiro Komatsuki

Mitsuhiko Fujiwhara

Kenichiro Adachi

Hiroki Ito

Jennifer B Mei

Takehiro Maeda

Ayano Habu

The present application provides a synthetic spilanthol flavor composition that includes (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide. The synthetic spilanthol composition can also contain, and at least one of (2E,6E,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide and (2E,6Z,8Z)&#x2014;N-(2-methylpropyl)-2,6,8-decatrienamide, the (N-(2-methylpropyl)-2,6,8-decatrienamide being present in amounts effective to impart a salivating or tingle effect while reducing the perception of off notes, as compared to the off-notes perceived upon consumption of natural spilanthol (e.g. spilanthol obtained from jambu oleoresin). Methods of increasing salivation and/or providing a tingling sensation upon consuming an orally consumable product that include adding to the product a synthetic spilanthol flavor composition are also provided. Synthetic spilanthol flavor compositions can be added to orally consumed products, such as, but not limited to, foods, beverages, pharmaceuticals, nutraceuticals, or therapeutic compositions, oral personal care products, gums (e.g. chewing gum or bubble gum), candy or lozenges.

Synthetic spilanthol and use thereof

A fragrance composition contains (3S)-(6E)-2,3-dihydrofarnesal. A chemical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 90 mass % or more and an optical purity of the (3S)-(6E)-2,3-dihydrofarnesal is 50% e.e. or more. A fragrance or cosmetic contains the fragrance composition. An odor is improved by using the fragrance composition containing (3S)-(6E)-2,3-dihydrofarnesal having a chemical purity of 90 mass % or more and an optical purity of 50% e.e. or more.

Fragrance composition

A method for producing an optically active 2,3-dihydrofarnesal of formula (1) is disclosed. The method includes subjecting &#x3b2;-farnesene f formula (2) to amination in the presence of a lithium salt of an amine to obtain (2E)-farnesyl allylamine of general formula (3); subjecting the (2E)-farnesyl allylamine to asymmetric isomerization to obtain an optically active farnesyl enamine of general formula (4); and subjecting the optically active farnesyl enamine to solvolysis: 

Method for producing optically active 2,3-dihydrofarnesal

Provided is an amide ester that is useful as an intermediate manufacturing product for an aroma compound such as spilanthol or the like. Also provided is a spilanthol manufacturing method using said amide ester. High-purity spilanthol can be manufactured by reacting an amide ester represented by general formula (1) with a basic compound. (In the formula, Rrepresents a C1-6 alkyl group or a phenyl group that may be substituted with a Calkyl group, a Calkoxy group, or a halogen atom; Rrepresents a Chydrocarbon group; and the wavy lines represent cis configurations, trans configurations, or a mixture of the two configurations.)

Method for manufacturing spilanthol and intermediate manufacturing product therefor

The present application provides a synthetic spilanthol flavor composition that includes (2E,6Z,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide. The synthetic spilanthol composition can also contain, and at least one of (2E,6E,8E)-N-(2-methylpropyl)-2,6,8-decatrienamide and (2E,6Z,8Z)-N-(2-methylpropyl)-2,6,8-decatrienamide, the (N-(2-methylpropyl)-2,6,8-decatrienamide being present in amounts effective to impart a salivating or tingle effect while reducing the perception of off notes, as compared to the off-notes perceived upon consumption of natural spilanthol (e.g. spilanthol obtained from jambu oleoresin). Methods of increasing salivation and/or providing a tingling sensation upon consuming an orally consumable product that include adding to the product a synthetic spilanthol flavor composition are also provided. Synthetic spilanthol flavor compositions can be added to orally consumed products, such as, but not limited to, foods, beverages, pharmaceuticals, nutraceuticals, or therapeutic compositions, oral personal care products, gums (e.g. chewing gum or bubble gum), candy or lozenges.

The present invention relates to a method comprising (A) reacting a &#x3b2;-keto ester with a 2-halo ester under basic conditions to obtain a 2-aceto-3-methyl-succinic acid ester; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, optionally followed by a decarboxylation reaction and hydrolysis, etc., to obtain an &#x3b1;-methyl-&#x3b3;-keto acid; and (C) reducing the resulting &#x3b1;-methyl-&#x3b3;-keto acid to obtain wine lactone or a stereoisomer thereof or a mixture thereof. Alternatively, the present invention relates to a method comprising step (A) as recited above; (B) reacting the resulting 2-aceto-3-methyl-succinic acid ester with methyl vinyl ketone under basic conditions, followed by decarboxylation reaction to obtain an &#x3b1;-methyl-&#x3b3;-keto acid ester; and (E) reducing the resulting &#x3b1;-methyl-&#x3b3;-keto acid ester in the presence of a ruthenium complex having a specific structure and in the presence of a hydrogen donor to obtain wine lactone or a stereoisomer thereof or a mixture thereof.

Process for producing wine lactone

A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.

Production method of (2E,6Z,8E)-N-isobutyl-2,6,8-decatrienamide (spilanthol), and food or drink, fragrance or cosmetic, or pharmaceutical comprising the same

A geometrical isomer composition excellent in odor and in chemical resistance, which is applicable to a base material containing a strongly alkaline chemical or a strongly acidic chemical, which can suppress the deterioration with time and the color change of the base material in the case that the material is exposed to light, and which also have highly tasteful and unique fruity floral fragrance. A geometrical isomer composition containing 93 to 99% by weight of optically active trans-1-(2,2,6-trimethylcyclohexyl)-2-buten-1-one represented by Formula-1 or a mixture thereof and 7 to 1% by weight of optically active cis-1-(2,2,6-trimethylcyclohexyl)-2-buten-1-one represented by Formula-2 or a mixture thereof is, respectively, used

Isomer composition excellent in chemical resistance containing optically active trans-1-(2,2,6-trimethylcyclohexyl)-2-buten-1-one and fragrance compositions containing the isomer composition

Process for producing 2-alkyl-2cyclopentenones

Production process of cyclohexenyl ketones

(1S,6R)-2,2,6-Trimethylcyclohexyl methyl ketone and/or (1R,6S)-2,2,6-trimethylcyclohexyl methyl ketone, process for producing the same, and perfume composition containing the same

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Kanagawa, Japan

Hideo Ujihara