US 2014035O127A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0350127 A1 CANO et al. (43) Pub. Date: Nov. 27, 2014 (54) COLORANT COMPOUNDS DERVED FROM Publication Classification GENPIN OR GENPIN CONTAINING MATERLALS (51) Int. Cl. C09B 23/04 (2006.01) (71) Applicant: ECOFLORA S.A.S., Sabaneta (CO) C09B 67/54 (2006.01) C09B 67/22 (2006.01) (72) Inventors: Esteban Vargas CANO, Itagui (CO); (52) U.S. Cl. Luis Fernando Echeverri Lopez, CPC ............. C09B 23/04 (2013.01); C09B 67/0034 Medellin (CO); Juan Fernando Gil (2013.01); C09B 67/0096 (2013.01) Romero, Medellin (CO); Edwin Andrés USPC ........ 514/772.7:528/327: 528/321:524/879; Correa Garcés, Medellin (CO); Sandra 435/267; 426/540 Patricia Zapata Porras, Medellin (CO) (57) ABSTRACT (73) Assignee: ECOFLORA S.A.S., Sabaneta (CO) The present disclosure provides colorant compounds and methods of isolation of the colorant compounds derived from (21) Appl. No.: 14/285,325 a reaction of genipin and an amine. The colorant composi tions comprise purified compounds (e.g., a purified polymer (22) Filed: May 22, 2014 or a purified dimer) obtained from multiple fractioning by chromatography of the reaction resulting material. The puri Related U.S. Application Data fied polymer or dimer can be used as a colorant by itself or in (60) Provisional application No. 61/826.391, filed on May combination with another colorant for imparting color to a 22, 2013, provisional application No. 61/836,072, food, a drug, a cosmetic, a medical device, and textile prod filed on Jun. 17, 2013. uctS. Patent Application Publication Nov. 27, 2014 Sheet 1 of 38 US 2014/035O127 A1 Patent Application Publication Nov. 27, 2014 Sheet 2 of 38 US 2014/035O127 A1 s s s y wr. 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OH S. 00 30 00 150 alo rin 2OO 3OO 400 5OO 6OO 700 nm Patent Application Publication Nov. 27, 2014 Sheet 21 of 38 US 2014/035O127 A1 FIG. 16 YYYYYYYYYYYYY PC 8 L & a & b X Absorbancia Patent Application Publication Nov. 27, 2014 Sheet 22 of 38 US 2014/035O127 A1 **** ?% % % % ity 3%3% ; ; 2% ?%4 ^ist : ? & ae Patent Application Publication Nov. 27, 2014 Sheet 23 of 38 US 2014/035O127 A1 FIG. 18 „…”;|-·;Laer” #--->~~~~<!~~~~~#~~~~~~~#~~~~~~~~#~~~~,~\~~~~~ Kaas GLY LYS as VAL TYR TRP Patent Application Publication Nov. 27, 2014 Sheet 24 of 38 US 2014/035O127 A1 FIG. 19A Glycine mAU o:3, Sssss-s: ..., A0 (10 30 30 20 20 0 10 0-- :------------------------------- O . -------------------. .-- - ------------- ------------------------------- 8.) 80 10.) 11.0 120 fif 's- 2. 3S0 8. 8. 2. 200 ' s 15C 130 : ?o 100 O :- 13.0 li g m8U s 500-$S 3X s as 8. 0 s: *100- 400- y 300- 300 200- 200 OO- 00 v, -s. 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S S FIG. 25B Genipin precursor found in mesocarps Patent Application Publication Nov. 27, 2014 Sheet 33 of 38 US 2014/035O127 A1 FIG. 26A w sy 2000 Ch5-24 nmann to 1500 1000 50 O 2 ...-. ^-- -- O O.O 50 10.0 150 200 min FIG. 26B SSSYYSSW. S.S. R.S.S.S.Ssy 2000 10 OO 500 O O 1 O 20 30 n Patent Application Publication Nov. 27, 2014 Sheet 34 of 38 US 2014/035O127 A1 FIG.