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 2-methyl-4-pheny1-1,3-dioxolaneUSPTO Application #: 20070027060Title: 2-methyl-4-pheny1-1,3-dioxolane Abstract: The sensory properties of the diastereomeric enantiomer pairs and of the pure enantiomers of the compound 2-methyl-4-phenyl-1,3-dioxolane are described. The cis compounds (2 S,4 R)-2-methyl-4-phenyl-1,3-dioxolane and (2 S,4 R)-2-methyl-4-phenyl-1,3-dioxolane are the most sensorially valuable. These enantiomers and mixtures thereof are particularly suitable for use as a sensorially active substance, for example as a fragrance. (end of abstract) Agent: Akerman Senterfitt - West Palm Beach, FL, US Inventors: Wilhelm Pickenhagen, Dietmar Schatkowski USPTO Applicaton #: 20070027060 - Class: 512002000 (USPTO) Related Patent Categories: Perfume Compositions, Perfume Compositions, With Preservative, Stabilizer, Or Fixative (e.g., Retarding Evaporation) The Patent Description & Claims data below is from USPTO Patent Application 20070027060. Brief Patent Description - Full Patent Description - Patent Application Claims
CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of co-pending U.S. patent application Ser. No. 09/738,388, filed on Dec. 15, 2000, the entire contents of which are hereby incorporated by reference, which claims priority to German patent application DE 199 61 431.8, filed on Dec. 17, 1999. BACKGROUND OF THE INVENTION [0002] The present invention relates to the compound 2-methyl-4-phenyl-1,3-dioxolane, and to certain diastereomeric enantiomer pairs and to enantiomers of this compound. FIELD OF THE INVENTION [0003] 2-Methyl-4-phenyl-1,3-dioxolane is known. As early as 1900, the German Patent Specification 109176 (Albert Verley) was published, in which the synthesis of 2-methyl-4-phenyl-1,3-dioxolane in strongly protic media, but not the isomer distribution of the resulting mixture, is described; the odor of 2-methyl-4-phenyl-1,3-dioxolane, which is not defined in more detail with regard to its composition, is referred to as a jasmine odor in DE 109176. [0004] In 1975, K. Kulka and J. W. Dittrick reported extensively on the sensory properties of a large number of synthesized acetals [K. Kulka, J. W. Dittrick, Cosmetics & Perfumery, Vol. 90, 90-95, (1975)]. However, the sensory evaluation of the synthesized acetals was again only undertaken by reference to the diastereomer mixtures. Isolation of the epimers or enantiomers from the mixtures or the synthesis thereof was not carried out, nor were the epimers or enantiomers sensorially evaluated. [0005] Despite being known for a long time, 2-methyl-4-phenyl-1,3-dioxolan-e (as diastereomer mixture as described in DE 109176) is currently not a fragrance which is available commercially. This is due in particular to the presence of undesired chocolate notes which do not harmonize with the basic jasmine odor and lead to an unclean sensory overall character. SUMMARY OF THE INVENTION [0006] The object of the present invention was therefore to provide a sensorially active substance (fragrance and/or flavor) which has a powerful floral and/or jasmine odor, but, compared with the odor of 2-methyl-4-phenyl-1,3-dioxolane (as described in DE 109176 or by Kulka and Dittrick in Cosmetics & Perfumery), has only attenuated chocolate notes, or none at all. [0007] This object is achieved by providing the enantiomers (2R,4S)-2-methyl-4-phenyl-1-1,3-dioxolane and (2S,4R)-2-methyl-4-phenyl-1,3-di-oxolane, which have hitherto neither been isolated nor investigated with regard to their sensory properties. Both compounds have strong sensory activity and, surprisingly, an odor which does not include an undesired chocolate note. The enantiomers according to the invention can therefore be advantageously used in perfume compositions of any odor type both as one of the main components and also in the trace range. Use in flavor compositions is likewise possible. [0008] The invention is based on the surprising finding that diastereomer mixtures of 2-methyl-4-phenyl-1,3-dioxolane have very characteristic odiferous properties depending on the choice of reaction conditions, and differ significantly from one another. [0009] In particular, it has been found that diastereomer mixtures of 2-methyl-4-phenyl-1,3-dioxolane (cf. the general formula (4) in FIG. 1) which have a comparatively high proportion of cis isomers (cf. formula (4a) in FIG. 1) are sensorially more valuable than diastereomer mixtures which have a particularly high proportion of trans isomers (cf. formula (4b) in FIG. 1). BRIEF DESCRIPTION OF THE DRAWINGS [0010] FIG. 1 shows diasteriomer mixtures, cis isomers and trans isomers; [0011] FIG. 2 and 3 illustrates the process by which enatiomercially pure diols 5 (FIG. 2) and 9 (FIG. 3) are converted to epimeric actetals 7, 8, 11, and 12, respectfully. DETAILED DESCRIPTION OF THE INVENTION [0012] Preferred sensorially active substances (preferred fragrances or flavors) are mixtures which comprise one part by weight of cis enantiomers (4a), i.e. [0013] (2R,4S)-2-methyl-4-phenyl-1,3-dioxolane and/or (2S,4R)-2-methyl-4-phenyl-1,3-dioxolane and less than two, preferably less than one, parts by weight of trans enantiomers (4b), i.e. [0014] (2R,4R)-2-methyl-4-phenyl-1,3-dioxolane and/or (2S,4S)-2-methyl-4-phenyl-1,3-dioxolane. [0015] The weight ratio of cis enantiomers (4a) to trans enantiomers (4b) should therefore be at least greater than 1:2, but preferably even greater than 1:1. [0016] The preferred mixture of the cis isomers (4a) has a strong, animal, narcotically-green odor reminiscent of hyacinths. The after-odor here has clearly woody, ozone-like odor properties. [0017] By contrast, the less preferred mixture of the trans isomers (4b) has weak, slightly animal odor effects with clearly defined odor impressions, clearly reminiscent of chocolate. [0018] It is likewise possible to clearly differentiate between the sensory properties of the pure enantiomers accessible from the epimer series (2R,4S)-2-methyl-4-phenyl-1,3-dioxolane (cis; cf. formula (7) in FIG. 2), (2S,4R)-2-methyl-4-phenyl-1,3-dioxolane (cis; cf. formula (11) in FIG. 3) or (2S,4R)-2-methyl-4-phenyl-1,3-dioxolane (trans; cf. formula (8) in FIG. 2), (2S,4S)-2-methyl-4-phenyl-1,3-dioxolane (trans; cf. formula (12) in FIG. 3). Continue reading... Full patent description for 2-methyl-4-pheny1-1,3-dioxolane Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this 2-methyl-4-pheny1-1,3-dioxolane patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. 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