Global Patent Index - EP 1458665 A1

EP 1458665 A1 20040922 - IMPROVED CITRAL DERIVATIVES

Title (en)

IMPROVED CITRAL DERIVATIVES

Title (de)

VERBESSERTE ZITRALDERIVATE

Title (fr)

DERIVES DE CITRAL AMELIORES

Publication

EP 1458665 A1 20040922 (EN)

Application

EP 02805502 A 20020820

Priority

  • US 0226446 W 20020820
  • US 34215001 P 20011219
  • US 34858002 P 20020115
  • US 37791402 P 20020503
  • US 38929802 P 20020617
  • US 35505202 P 20020207
  • US 0222120 W 20020712
  • US 0222441 W 20020712

Abstract (en)

[origin: GB2383327A] Improved citral derivatives, that have a longer useful shelf life than citral fragrances and flavorings, are disclosed. 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. In the derivatives the aldehyde group may be replaced with a nitrile, methyl ether or acetal group. The acetal groups can provide the compounds with a long lasting flavor or fragrance, where the acetals slowly hydrolyze to provide the aldehyde group in citral. Examples of suitable articles of manufacture include candles, air fresheners, perfumes, disinfectant compositions, hypochlorite (bleach) compositions, beverages such as beer and soda, denture cleanser tablets and flavored orally-delivered products such as lozenges, candies, and the like. The derivatives preferably have the structure: <EMI ID=1.1 HE=22 WI=61 LX=576 LY=1907 TI=CF> <PC>wherein Z is O, S, CR 2 or a double or a single bond provided at least one Z is O, S or CR 2 ; and X is a nitrile, methyl ether, or acetal group.

IPC 1-7

C07C 47/21; A61K 7/46; A61K 7/32; C11D 3/50; A23L 1/226

IPC 8 full level

A23G 4/00 (2006.01); A23L 2/00 (2006.01); A23L 27/00 (2016.01); A23L 27/20 (2016.01); A61K 8/00 (2006.01); A61K 8/30 (2006.01); A61K 8/33 (2006.01); A61K 8/35 (2006.01); A61Q 5/00 (2006.01); A61Q 5/02 (2006.01); A61Q 13/00 (2006.01); A61Q 15/00 (2006.01); A61Q 19/10 (2006.01); C07C 45/69 (2006.01); C07C 47/11 (2006.01); C07C 47/21 (2006.01); C07C 47/225 (2006.01); C07C 47/293 (2006.01); C07C 47/34 (2006.01); C07C 47/45 (2006.01); C11B 9/00 (2006.01); C11D 3/50 (2006.01); C12C 5/02 (2006.01); C12G 3/06 (2006.01)

CPC (source: EP)

A23L 27/20 (2016.07); A23L 27/203 (2016.07); A23L 27/2052 (2016.07); C07C 45/69 (2013.01); C07C 47/11 (2013.01); C07C 47/21 (2013.01); C07C 47/225 (2013.01); C07C 47/293 (2013.01); C07C 47/34 (2013.01); C07C 47/45 (2013.01); C11B 9/003 (2013.01); C11B 9/0076 (2013.01); C11D 3/50 (2013.01)

C-Set (source: EP)

C07C 45/69 + C07C 47/225

Citation (search report)

See references of WO 03053901A1

Citation (examination)

  • WO 03053902 A1 20030703 - FLEXITRAL INC [US], et al
  • US 3773797 A 19731120 - CHODNEKAR M, et al
  • JORRITSMA R. ET AL: "The chemistry of small ring compounds. Part 44. Solvolysis af cyclopropyl sulfides and ethers", RECUEIL, JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, vol. 100, no. 5, May 1981 (1981-05-01), pages 194 - 200, XP001199764
  • SHIRAFUJI T. ET AL: "The reduction of gem-dibromocyclopropanes by means of chromium(II) acetate or potassium pentacyanocobaltate", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 44, no. 11, November 1971 (1971-11-01), pages 3161 - 3164, XP001199763
  • GRIECO P.A. ET AL: "Construction of the gem-dimethylcyclopropane unit employing triphenylphosphonium isopropylide", TETRAHEDRON LETTERS, vol. 13, no. 36, 1972, pages 3781 - 3783, XP001199762, DOI: doi:10.1016/S0040-4039(01)94160-7
  • SEEBACH D. ET AL: "Ringöffnung von Cyclopropanon-bis-methylthio-acetalen zu Ketonen und Dimethyldisulfid in Trifluoressigsäure Br/SCH3-Austausch in Dibromcarbenaddukten", TETRAHEDRON LETTERS, vol. 14, no. 36, 1973, pages 3509 - 3512
  • JULIA M. ET AL: "Transposition homoallylique avec participation. I. - Isomérisation acide des [(butène-3'' yl)-2'], cyclopropyl-2 propanols-2 (5a cis et trans)", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, pages 1805 - 1815
  • JULIA M. ET AL: "Transposition homoallylique avec participation. III. - Isomérisation acide des [diméthyl-2,2' (butène-3''' yl)-3'] cyclopropyl-2 propanols-2 (5) cis et trans", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, pages 1822 - 1833
  • DATABASE CROSSFIRE BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN; & BULL. ACAD. SCI. USSR DIV. CHEM. SCI., vol. 26, 1977, pages 646
  • DATABASE CROSSFIRE BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN; & BULL. ACAD. SCI. USSR DIV. CHEM. SCI., vol. 26, 1977, pages 646
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  • SCHELLER M.E. ET AL: "Photochemical reactions. Photochemistry of acylsilanes: photolysis and thermolysis of cyclopropyl sylil ketones", HELVETICA CHIMICA ACTA, vol. 73, no. 4, 20 June 1990 (1990-06-20), pages 922 - 931, XP001540007, DOI: doi:10.1002/hlca.19900730420

Designated contracting state (EPC)

AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR

DOCDB simple family (publication)

GB 0219381 D0 20020925; GB 2383327 A 20030625; GB 2383327 B 20041208; AT E338017 T1 20060915; AU 2002318237 A1 20030709; AU 2002323273 A1 20030709; AU 2002332586 A1 20030709; AU 2002332586 A2 20030709; AU 2002332586 B2 20060713; AU 2002366778 A1 20030709; AU 2002366778 A2 20030709; AU 2009200217 A1 20090212; CA 2469602 A1 20030703; CA 2469604 A1 20030703; DE 60214427 D1 20061012; DE 60214427 T2 20070426; DK 1458666 T3 20061127; EP 1458665 A1 20040922; EP 1458666 A1 20040922; EP 1458666 B1 20060830; ES 2274985 T3 20070601; JP 2005513119 A 20050512; JP 2006506316 A 20060223; WO 03053887 A1 20030703; WO 03053901 A1 20030703; WO 03053902 A1 20030703; WO 03053903 A1 20030703

DOCDB simple family (application)

GB 0219381 A 20020820; AT 02752283 T 20020712; AU 2002318237 A 20020712; AU 2002323273 A 20020820; AU 2002332586 A 20020820; AU 2002366778 A 20020712; AU 2009200217 A 20090120; CA 2469602 A 20020712; CA 2469604 A 20020820; DE 60214427 T 20020712; DK 02752283 T 20020712; EP 02752283 A 20020712; EP 02805502 A 20020820; ES 02752283 T 20020712; JP 2003554618 A 20020820; JP 2003554619 A 20020712; US 0222120 W 20020712; US 0222441 W 20020712; US 0226438 W 20020820; US 0226446 W 20020820