Patents Assigned to Flexitral, Inc.
  • Patent number: 7704941
    Abstract: Improved citral derivatives, and fragrances and flavorings including the derivatives, that have a longer useful shelf life than citral and/or fragrances and flavorings including citral, are disclosed. In particular, the derivatives maintain the fragrance characteristics of citral, while lowering the allergic properties, and lemony flavors and fragrances with a longer shelf-life than citral, are disclosed. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. In one embodiment, the derivatives are prepared by replacing one or more double bonds in citral with a cyclopropyl group, which can be unsubstituted, or substituted with one or two lower alkyl, preferably methyl groups. The alkyl groups can optionally be substituted, for example, with electron donating groups, electron with drawing groups, groups which increase the hydrophilicity or hydrophobocity, and the like.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: April 27, 2010
    Assignee: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20100087356
    Abstract: Improved aromachemical derivatives, and fragrances and flavorings including the derivatives, that have a longer useful shelf life than the aromachemicals from which they can be derived, are disclosed. In particular, the derivatives maintain the fragrance characteristics of the aromachemicals, while lowering the allergic properties, increasing the stability, and/or increasing the odor intensity. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. In one embodiment, the derivatives are prepared by replacing one or more double bonds in citral with a thioether, cyclopropyl, oxirane, or thiirane group. The cyclopropane ring can be unsubstituted, or substituted with one or two lower alkyl, preferably methyl groups. The alkyl groups can optionally be substituted, for example, with electron donating groups, electron with drawing groups, groups which increase the hydrophilicity or hydrophobocity, and the like.
    Type: Application
    Filed: February 16, 2009
    Publication date: April 8, 2010
    Applicant: Flexitral, Inc.
    Inventor: Luca TURIN
  • Publication number: 20090317529
    Abstract: Aromachemical compounds of Formula I, compositions comprising these compounds and processes for their preparation are disclosed, wherein R1 is H, C(O)O—CH2—CH3; C(O)O—CH3, or C(O)O—H; R2 is methyl; R3 and R4 are H; R5 and R6 are CH3; Z is C(H)2; and X is —CN. The double bond attached to X can be in the E or Z configuration.
    Type: Application
    Filed: June 15, 2009
    Publication date: December 24, 2009
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20090238785
    Abstract: A compound comprising a Schiffs base of an aldehydic musk aromachemical with a substantially nonvolatile, odorless amine, wherein the imine moiety of said Schiffs base compound is stable against oxidation to a carboxyl group or a mixture of said compounds; said Schiffs base compound being biodegradable over time to said aldehydic musk and said nonvolatile, odorless amine; as well as compositions, products, preparations or articles having improved aroma, fragrance or odor characteristics containing as active ingredient such compound or mixture of compounds; the aldehydic musks themselves, and methods for the preparation of the Schiff bases and methods of imparting fragrance characteristics to substrates.
    Type: Application
    Filed: June 24, 2005
    Publication date: September 24, 2009
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20090208627
    Abstract: An improved method for imparting a butter flavor to a product, the method comprising adding to the product an organoleptically effective amount of diacetyl, the improvement comprising substituting for the diacetyl, an organoleptically acceptable derivative of diacetyl having the formula: (formula I), or an organoleptically acceptable salt thereof, as well as compositions for carrying out the method and products and articles of manufacture comprising the additive.
    Type: Application
    Filed: July 12, 2006
    Publication date: August 20, 2009
    Applicant: Flexitral , Inc.
    Inventor: Luca Turin
  • Publication number: 20090162495
    Abstract: An improved method for imparting a flavor to a product, the method comprising adding to the product an organoleptically effective amount of a dicarbonyl or a mixture thereof, the improvement comprising substituting for the dicarbonyl, an organoleptically acceptable derivative thereof having the formula (I) or (II), wherein m=0, 1 or 2, n=1 or 2, R1 and R2 are, independently, linear or branched saturated C1-4 alkyl, with the proviso that both of R1 and R2 may not be methyl, and X is a counterion. Typically, R1 and R2 are methyl (with the above proviso), ethyl, propyl (e.g. n- or i-propyl) or butyl (e.g. n-, i- or t-butyl), or an organoleptically acceptable salt thereof, as well as compositions for carrying out the method and products and articles of manufacture comprising the additive.
    Type: Application
    Filed: July 12, 2006
    Publication date: June 25, 2009
    Applicant: FLEXITRAL INC
    Inventor: Luca Turin
  • Publication number: 20090016976
    Abstract: Improved citral and citronellal derivatives, and fragrance and flavorings including the derivatives, that have a longer useful shelf life than citral and citronellal and/or fragrances and flavoring including citral and citronellal, are disclosed. In particular, the derivatives maintain the fragrance characteristics of citral and citronellal, while lowering the allergic properties, and lemony flavors and fragrances with a longer shelf-life than citral and citronellal, are disclosed. Also discovered are methods of making the derivatives, and articles of manufacture including the derivatives. The derivatives replace the aldehyde group in citral or citronellal with a hydroxy group. In one embodiment, the derivatives also replaced one or more double bonds in citral or the double bond in citronellal with a cyclopropyl group, which can be unsubstituted, or substituted with one or two alkyl, preferably methyl, groups, or with an oxirane or thiirane ring or combinations thereof.
    Type: Application
    Filed: December 22, 2005
    Publication date: January 15, 2009
    Applicant: Flexitral Inc.
    Inventor: Luca Turin
  • Publication number: 20080305976
    Abstract: The use of at least one water-soluble sulfiting agent to reduce or prevent the discoloration of an aromachemical, odorant, flavorant or perfume component susceptible to discoloration.
    Type: Application
    Filed: June 13, 2006
    Publication date: December 11, 2008
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20080279800
    Abstract: A compound of formula (I): wherein each R independently represents H, methanol or ethanol, and Z represents O or S.
    Type: Application
    Filed: February 28, 2008
    Publication date: November 13, 2008
    Applicant: Flexitral, Inc.
    Inventor: Luca TURIN
  • Publication number: 20080260669
    Abstract: A compound of formula (I): wherein R1 and R2 represent, independently, linear or branched C1-4 alkyl, n=0 to 4 and m=0 to 3. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavouring and in articles of manufacture is also provided.
    Type: Application
    Filed: April 23, 2007
    Publication date: October 23, 2008
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Patent number: 7342042
    Abstract: Improved cyclamenaldehyde derivatives, and fragrances and flavorings including the derivatives, are disclosed. In particular, the derivatives maintain the fragrance characteristics of cyclamenaldehyde, while enhancing the odorant intensity. In addition, when present in a fragrance they heighten the effect of the remainder of the formulation. Further, they heighten the perceived intensity of other olfactory stimuli, e.g. food and ambient smells. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. The derivatives are prepared by replacing the phenyl moiety in cyclamenaldehyde with a thiophene moiety, which can be unsubstituted, or substituted with one or two lower alkyl, preferably isopropyl groups. The aldehyde group in cyclamenaldehyde can also be replaced with an acetal, methyl ether, nitrile or ester functionality.
    Type: Grant
    Filed: June 16, 2004
    Date of Patent: March 11, 2008
    Assignee: Flexitral, Inc.
    Inventor: Luca Turin
  • Patent number: 7323606
    Abstract: The present invention provides a compound having one of the following formulae: R and R1 are each independently H or C1-5 alkyl provided that in formula (I) when R is methyl, R1 is H or C2-5 alkyl. R2 has from 1 to about 12 carbon atoms and is a straight or branched aliphatic group, or a cyclic, heterocyclic or aromatic group. R3 and R4 are each independently H or CH3. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavoring and in articles of manufacture is also provided.
    Type: Grant
    Filed: February 17, 2006
    Date of Patent: January 29, 2008
    Assignee: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20080015136
    Abstract: Improved citral derivatives, and fragrances and flavorings including the derivatives, that have a longer useful shelf life than citral and/or fragrances and flavorings including citral, are disclosed. In particular, the derivatives maintain the fragrance characteristics of citral, while lowering the allergic properties, and lemony flavors and fragrances with a longer shelf-life than citral, are disclosed. Also disclosed are methods of making the derivatives, and articles of manufacture including the derivatives. In one embodiment, the derivatives are prepared by replacing one or more double bonds in citral with a cyclopropyl group, which can be unsubstituted, or substituted with one or two lower alkyl, preferably methyl groups. The alkyl groups can optionally be substituted, for example, with electron donating groups, electron with drawing groups, groups which increase the hydrophilicity or hydrophobicity, and the like.
    Type: Application
    Filed: September 26, 2007
    Publication date: January 17, 2008
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20070276152
    Abstract: A compound or mixture of compounds of formulae: wherein R1 and R2 are each independently H or CH3.
    Type: Application
    Filed: April 2, 2007
    Publication date: November 29, 2007
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20070264340
    Abstract: A compound of formula (I): wherein R is —CH2OH, —C(O)H, —C(OR3)2H, —C(OR4)(OH)H, —CH?NC6H4C(O)OR5 or —CH?NR6; R1 and R2 are each independently H or CH3; R3 and R4 are each independently H or a straight or branched aliphatic group having from 1 to 12 carbon atoms, or each R3 is covalently linked to the other R3 to form a cyclic acetal having from 1 to 4 carbon atoms; R5 is H or a straight or branched aliphatic group, or a cyclic, heterocyclic or aromatic group having from 1 to 12 carbon atoms; and R6 has at least 10 carbon atoms and is an aliphatic group or an aromatic group. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavouring and in articles of manufacture is also provided.
    Type: Application
    Filed: April 2, 2007
    Publication date: November 15, 2007
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20070259042
    Abstract: A compound of formula (I): wherein R is —CH2OH, —C(O)H, —C(OR3)2H, —C(OR4)(OH)H, —CH?NC6H4C(O)OR5 or —CH?NR6; R1 and R2 are each independently H or CH3; R3 and R4 are each independently H or a straight or branched aliphatic group having from 1 to 12 carbon atoms, or each R3 is covalently linked to the other R3 to form a cyclic acetal having from 1 to 4 carbon atoms; R5 is H or a straight or branched aliphatic group, or a cyclic, heterocyclic or aromatic group having from 1 to 12 carbon atoms; and R6 has at least 10 carbon atoms and is an aliphatic group or an aromatic group. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavouring and in articles of manufacture is also provided.
    Type: Application
    Filed: April 2, 2007
    Publication date: November 8, 2007
    Applicant: Flexitral, Inc.
    Inventor: Luca Turin
  • Publication number: 20070032401
    Abstract: A compound comprising a macrocyclic ketone having at least one double bond and 15-20 carbon atoms, wherein at least one double bond has been converted to oxirane or thiirane or a macrocyclic lactone or dilactone having at least one double bond and 14-19 carbon atoms, wherein at least one double bond has been converted to oxirane or thiirane; or one of said oxiranes or thiiranes containing a methyl substituent on the ring and/or an ether oxygen or thioether sulfur substituting for a CH2 somewhere in the ring and compositions, products, preparations or articles having improved aroma, fragrance, odor, flavor and/or taste characteristics containing as active ingredient a compound or mixture of the compounds.
    Type: Application
    Filed: March 12, 2004
    Publication date: February 8, 2007
    Applicant: FLEXITRAL, INC.
    Inventor: Luca Turin