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| Hai Lala Mo at an Uit Dituri a to Od |HAI LALA MO ATUS009890286B2 AN UIT DITURI A TOOD HUT (12 ) United States Patent ( 10 ) Patent No. : US 9 ,890 ,286 B2 Vargas Cano et al . (45 ) Date of Patent: Feb . 13, 2018 ( 54 ) COLORANT COMPOUNDS DERIVED FROM ( 58 ) Field of Classification Search GENIPIN OR GENIPIN CONTAINING None MATERIALS See application file for complete search history . ( 71 ) Applicant: ECOFLORA S . A . S . , Sabaneta , Antioquia ( CO ) ( 56 ) References Cited ( 72 ) Inventors : Esteban Vargas Cano , Itagui ( CO ) ; U . S . PATENT DOCUMENTS Luis Fernando Echeverri Lopez , 4 ,247 ,698 A 1 / 1981 Toyama et al. Medellin (CO ) ; Juan Fernando Gil 4 ,347 ,356 A 8 / 1982 Touyama et al . Romero , Medellin (CO ) ; Edwin (Continued ) Andrés Correa Garcés , Medellin (CO ) ; Sandra Patricia Zapata Porras, FOREIGN PATENT DOCUMENTS Medellin (CO ) CN 101104745 1 /2008 ( 73 ) Assignee : ECOFLORA S . A . S ., Sabaneta ( CO ) CN 101735642 A 6 / 2010 (Continued ) ( * ) Notice : Subject to any disclaimer , the term of this patent is extended or adjusted under 35 OTHER PUBLICATIONS U . S . C . 154 ( b ) by 0 days. “ Genipa Americana” in Food and Fruit Bearing Forest Species , 3 : ( 21 ) Appl. No .: 15 / 166 , 391 Examples from Latin America , 1986 , FAO United Nations, Rome, pp . 141 - 143 . * (22 ) Filed : May 27, 2016 (Continued ) (65 ) Prior Publication Data Primary Examiner - Daniel R Carcanague US 2016 / 0376442 A1 Dec. 29 , 2016 (74 ) Attorney , Agent, or Firm — Sterne, Kessler , Related U . S . Application Data Goldstein & Fox P . L . L . C . (62 ) Division of application No . 14 / 285 , 325 , filed on May 22 , 2014 , now Pat. No . 9 ,376 , 569. (57 ) ABSTRACT ( Continued ) The present disclosure provides colorant compounds and (51 ) Int. CI. methods of isolation of the colorant compounds derived from a reaction of genipin and an amine . The colorant C09B 23 /04 ( 2006 .01 ) compositions comprise purified compounds ( e . g ., a purified C09B 67 / 22 (2006 . 01) polymer or a purified dimer ) obtained from multiple frac (Continued ) tioning by chromatography of the reaction resulting mate ( 52 ) U .S . CI. rial. The purified polymer or dimer can be used as a colorant ??? .. .. .. .. CO9B 61 /00 ( 2013 .01 ) ; A23L 5 / 43 by itself or in combination with another colorant for impart (2016 . 08 ) ; A61K 8 /84 (2013 .01 ) ; A61K 4734 ing color to a food , a drug , a cosmetic , a medical device , and ( 2013 .01 ) ; C09B 23 / 04 ( 2013 .01 ) ; C09B textile products . 67 /0034 (2013 .01 ) ; C09B 67/ 0096 (2013 .01 ) ; A23V 2002 /00 ( 2013 .01 ) ; A61K 2800 / 30 ( 2013 .01 ) 14 Claims, 38 Drawing Sheets CO . Me CoMe O . HOT - OH US 9 ,890 ,286 B2 Page 2 Related U . S . Application Data Fujikawa , S . , et al . , " Structure ofGenipocyanin G , A Spontaneous ( 60 ) Provisional application No . 61/ 836 ,072 , filed on Jun . Reaction Product Between Genipin and Glycine, " Tetrahedron 17 , 2013 , provisional application No . 61 /826 ,391 , Letters 28 (40 ) :4699 -4700 , Pergamon Journals Ltd ., United King filed on May 22 , 2013 . dom ( 1987 ) . Fujikawa , S . , et al. , “ Brilliant Skyblue Pigment Formation from (51 ) Int. Cl. Gardenia Fruits ,” J. Ferment. Technol. 65 ( 4 ) :419 -424 , Elsevier C09B 67 /54 ( 2006 . 01 ) Science B . V ., Netherlands ( 1987 ) . C09B 61 / 00 ( 2006 . 01 ) Inouye , H . et al. , “ Structure of Blue Pseudoazulene - Skeleton Pig A23L 5 /43 ( 2016 .01 ) ment derived from Genipin and Amino acids, " 26th Symposium on A61K 8 /84 ( 2006 .01 ) the Chemistry of Natural Product, Kyoto , pp . 577 -584 , ( Abstract ) A61K 4734 ( 2017 .01 ) 1983 . Moritome, N ., et al. , “ Properties of red pigments prepared from ( 56 ) References Cited geniposidic acid and amino acids, " J Sci Food Agric 79 :810 -814 , Society of Chemical Industry , London ( 1999 ) . U . S . PATENT DOCUMENTS Muller , J ., “ Analytical Characterization of a Lyophilized Juice 4 , 878 , 921 A 11/ 1989 Koga et al . Sample of Genipa americana and a Blue Colorant Based on the 7 ,279 ,189 B2 10 / 2007 Lauro Juice ,” AnalytiCon Discovery, Nov . 14 , 2010 , 28 pages . 7 , 649 , 014 B2 1 / 2010 Zhang et al . Pino , Chala . “ Handmade extraction of coloring natural , an alterna 7 ,927 , 637 B2 4 / 2011 Echeverry et al . tive of use of the biological diversity of Choco , Columbia ” Acta 2005 /0008746 AL 1 / 2005 Beck et al . Biologica Colombiana 8 ( 2 ) : 95 - 98 , ( 2003 ) Abstract . 2008 / 0260668 A1 10 / 2008 Vidalenc 2009 / 0223000 A 9 / 2009 Ferreira Touyama, R . , et al. , “ Studies on the Blue Pigments Produced from 2009 / 0246343 Al 10 / 2009 Wu et al. Genipin and Methylamine. I . Structures of the Brownish -Red Pig 2010 / 0083448 AL 4 / 2010 Lopez et al. ments , Intermediates Leading to the Blue Pigments , ” Chem . Pharm . 2012 /0114772 AL 5 / 2012 Roesler et al . Bull. 42 ( 3 ) : 668 -673 , Pharmaceutical Society of Japan , Japan 2013 /0115252 A1 5 / 2013 Wu et al. 2013 /0202703 AL 8 / 2013 Sadano ( 1994 ) . 2013 /0345427 Al 12/ 2013 Echeverry et al . International Search Report for International Application PCT/ IB2013 /001854 , Eurpean Patent Office , Netherlands, dated Oct . 24 , FOREIGN PATENT DOCUMENTS 2013 . STN Database Registry Record : CAS Registry No . 1313734 - 13 - 2 , CN 101831469 A 9 / 2010 entered STN Jul. 26 , 2011 . CN 101899484 A 12 / 2010 CN 102014670 A 4 /2011 STN Database Registry Record : CAS Registry No . 1313734 - 14 - 3 , CN 102171292 A 8 / 2011 entered STN Jul . 26 , 2011 . CN 102174608 A 9 / 2011 International Search Report for International Patent Application No. CN 102448327 A 5 /2012 PCT / IB2014 / 001735 , European Patent Office, Rijswijk , Nether CN 104685004 A 6 / 2015 lands , dated Jan . 7 , 2015 . 52 -053932 4 / 1977 52 -053934 4 / 1977 Office Action dated Oct . 1 , 2014 , from co - pending U . S . Appl. No. 55 - 164625 12 / 1980 13 /532 ,757 , inventors , Echeverry, L . F ., et al. , filed Jun . 25 , 2012 . 57 - 81466 5 / 1982 STN Database Registry Record : CAS Registry No . 1314879 - 21 - 4 , 57 -209958 12 / 1982 entered STN Aug . 4 , 2011 . 61 - 47167 3 / 1986 Office Action dated Apr. 30 , 2015 , from co - pending U . S . Appl. No . 64 - 22820 1 / 1989 5 - 339134 12 / 1993 13 / 532 , 757 , inventors , Echeverry , L . F . , et al. , filed Jun . 25 , 2012 . Eeeeeeee 7 - 310023 11/ 1995 Paik , Y .- S . , et al ., “ Physical Stability of the Blue Pigments Formed JP 8 - 301739 11 / 1996 from Geniposide of Gardenia Fruits : Effects of pH , Temperature , WO WO 2009 / 120579 Al 10 / 2009 and Light ," J . Agric . Food Chem 49 :430 -432 , American Chemical WO WO 2012 /043173 AL 4 / 2012 Society , United States ( 2001) . WO WO 2014 /001910 AL 1 / 2014 Park , J . - E . , et al. , “ Separation and Characterization ofWater Soluble WO WO 2014 / 188275 A2 11 /2014 Blue Pigments Formed from Geniposide ofGardenia Fruits , ” Agric . Chem . Biotechnol. 44 ( 4 ) :190 - 193 , Korean Society of Agricultural OTHER PUBLICATIONS Chemistry and Biotechnology , Korea ( 2001) . Cho ; Biotech and Bioprocess Eng 2006 , 11, 230 - 234. * Yang , Z . , et al. , “ Isolation and Purification of Gardenia Blue Djerassi, C ., et al ., “ Naturally Occuring Oxygen Heterocyclics. IX . Pigment with Ultra Filtration ,” Modern Food Science Technology Isolation and Characterization of Genipin ,” Journal of Organic 24 : 352 - 356 , Gai Kan Bianjibn , China (2008 ) . Chemistry 25 :2174 - 2177 , American Chemical Society , United States ( 1960 ) . * cited by examiner U . S . 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