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(12) Patent Application Publication (10) Pub. No.: US 2014/0350127 A1 CANO Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0350127 A1 CANO Et Al 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. Patent Application Publication Nov. 27, 2014 Sheet 3 of 38 US 2014/035O127 A1 Patent Application Publication Nov. 27, 2014 Sheet 4 of 38 US 2014/035O127 A1 Patent Application Publication Nov. 27, 2014 Sheet 5 of 38 US 2014/035O127 A1 | ??wae *************} ****************************? 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AGA EXRAC 3000,0 33 2000 CM- 1500 : 4500 Figure 12 Patent Application Publication Nov. 27, 2014 Sheet 13 of 38 US 2014/035O127 A1 Figures 3A-E). rigts 3A Figure 38 7S SE 28 S. i*i; Figure 3D T is is is Figgie 33A. pink is 28, 38, tie ine. 53 ?tir is ow8f abstrafice, Fig.833 aings: equal abst:arces at 3$3 and S333m. figrate 30, bigge abscitatics at 83 it. Figita 338 Raw atch witi carrier. Patent Application Publication Nov. 27, 2014 Sheet 15 of 38 US 2014/035O127 A1 Figure i48 Cainfaioi (Yis 2 Qaitiatic: Cave : 88: poys & &isiniatus isthic Exteria: Stadsii 8&isit , fix:38.5" x-2533: Reis SSS33 3: SS3883 83.38.8f RFSS88 RFRS, 3. ittype iné: Zero:tough Na: Through eighted Regression ine Ystagic: 'aft: : A A&a 3. R333,88;&E8a...iii.38 AsiaS S. 4:33. 3:38.8823is ----'83 II3833. 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OH S. 00 30 00 150 alo rin 2OO 3OO 400 5OO 6OO 700 nm Patent Application Publication Nov. 27, 2014 Sheet 21 of 38 US 2014/035O127 A1 FIG. 16 YYYYYYYYYYYYY PC 8 L & a & b X Absorbancia Patent Application Publication Nov. 27, 2014 Sheet 22 of 38 US 2014/035O127 A1 **** ?% % % % ity 3%3% ; ; 2% ?%4 ^ist : ? & ae Patent Application Publication Nov. 27, 2014 Sheet 23 of 38 US 2014/035O127 A1 FIG. 18 „…”;|-·;Laer” #--->~~~~<!~~~~~#~~~~~~~#~~~~~~~~#~~~~,~\~~~~~ Kaas GLY LYS as VAL TYR TRP Patent Application Publication Nov. 27, 2014 Sheet 24 of 38 US 2014/035O127 A1 FIG. 19A Glycine mAU o:3, Sssss-s: ..., A0 (10 30 30 20 20 0 10 0-- :------------------------------- O . -------------------. .-- - ------------- ------------------------------- 8.) 80 10.) 11.0 120 fif 's- 2. 3S0 8. 8. 2. 200 ' s 15C 130 : ?o 100 O :- 13.0 li g m8U s 500-$S 3X s as 8. 0 s: *100- 400- y 300- 300 200- 200 OO- 00 v, -s. O---w--.' - - - - - - - ----------- ---------------------------------- | | | | | | 100 105 firl Patent Application Publication Nov. 27, 2014 Sheet 25 of 38 US 2014/035O127 A1 FIG. 19B Methionine mA i. :::::333 350- :8 . 400- s : s I. 300 11.0 12.0 min mAU 300K: ;-&--'73.", a x c) , 300 250- sg 250- 5 200- xx 3. 200- : 150 : 150- } : 100 100 50- w 50- O----------------------------- - - - - - - - - - CH--> --, ------------------------ - - - - - - --------------------------- 80 85 10.0 10.5 11.0 11.5 12.0 12.5 mn Patent Application Publication Nov. 27, 2014 Sheet 26 of 38 US 2014/035O127 A1 FIG. 19C r 250 20- 200 20 150 450 100 100 30 3). 3-------- -------------------------------- 3- - - - - - - - - - - - 100 11. 2. 80 14-0 C f o n- s asn. ed cis w ----------- an. | | | | | | | | | | | | | | | | 500 600 7OO mAJ xy: 300- 300 25- 230 200- 200 150- 180 O)- : 10) O- ; : 9.0 10.0 11.0 12.0 13.0 fill 10.0 13.0 20.0 ? d s C g Patent Application Publication Nov. 27, 2014 Sheet 27 of 38 US 2014/035O127 A1 8 Vida media (horas) Coeficiente de coorelación (R2) Patent Application Publication Nov. 27, 2014 Sheet 28 of 38 US 2014/035O127 A1 FIG. 21A FIG 21B Patent Application Publication Nov. 27, 2014 Sheet 29 of 38 US 2014/035O127 A1 FIG. 22 ! ~~~~~;~~~~~~ Patent Application Publication Nov. 27, 2014 Sheet 30 of 38 US 2014/035O127 A1 FIG. 23 Patent Application Publication Nov. 27, 2014 Sheet 31 of 38 US 2014/035O127 A1 FIG. 24 Pericarp et Endocarp S A sixse Mesocarp Š Patent Application Publication Nov. 27, 2014 Sheet 32 of 38 US 2014/035O127 A1 FIG. 25A Genipin S S S. 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.
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