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(10) Patent No.: US 9376569 B2 US0093.76569B2 (12) United States Patent (10) Patent No.: US 9,376,569 B2 Cano et al. (45) Date of Patent: Jun. 28, 2016 (54) COLORANT COMPOUNDS DERIVED FROM USPC ........ 514/772.7: 426/540: 524/879; 528/321, GENPIN OR GENPIN CONTAINING 528/327; 435/267 MATERLALS See application file for complete search history. (71) Applicant: ECOFLORA S.A.S., Sabaneta, Antioquia (CO) (56) References Cited U.S. PATENT DOCUMENTS (72) Inventors: Esteban Vargas Cano, Itagui (CO); 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 Andrés (Continued) Correa Garcés, Medellin (CO); Sandra Patricia Zapata Porras, Medellin (CO) FOREIGN PATENT DOCUMENTS CN 101104745 1, 2008 (73) Assignee: ECOFLORA S.A.S., Sabaneta (CO) JP 52-053932 4, 1977 (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS (21) Appl. No.: 14/285,325 Paik; J. Agric. Food Chem. 2001, 49, 430-432.* (Continued) (22) Filed: May 22, 2014 Prior Publication Data Primary Examiner — Janet L. Andres (65) Assistant Examiner — Daniel Carcanague US 2014/O35O127 A1 Nov. 27, 2014 (74) Attorney, Agent, or Firm — Sterne, Kessler, Goldstein & FOX PLLC Related U.S. Application Data (60) Provisional application No. 61/826.391, filed on May (57) ABSTRACT 22, 2013, provisional application No. 61/836,072, filed on Jun. 17, 2013. The present disclosure provides colorant compounds and methods of isolation of the colorant compounds derived from (51) Int. C. a reaction of genipin and an amine. The colorant composi C09B 67/54 (2006.01) tions comprise purified compounds (e.g., a purified polymer C09B 23/04 (2006.01) or a purified dimer) obtained from multiple fractioning by C09B 67/22 (2006.01) chromatography of the reaction resulting material. The puri (52) U.S. C. fied polymer or dimer can be used as a colorant by itself or in CPC ............. C09B 23/04 (2013.01); C09B 67/0034 combination with another colorant for imparting color to a (2013.01); C09B 67/0096 (2013.01) food, a drug, a cosmetic, a medical device, and textile prod (58) Field of Classification Search uctS. CPC ........ C09B 67/54; C09B 23/04; C09B 67/22: C09B 67/0034; C09B 67/0096 24 Claims, 38 Drawing Sheets US 9,376,569 B2 Page 2 (56) References Cited ters 28(40):4699-4700, Pergamon Journals Ltd., United Kingdom (1987). U.S. PATENT DOCUMENTS Fujikawa, S., et al., "Brilliant Skyblue Pigment Formation from Gardenia Fruits.” J. Ferment. Technol. 65(4):419-424. Elsevier Sci 4,878,921 A 11/1989 Koga et al. ence B.V., Netherlands (1987). 7,279,189 B2 10/2007 Lauro Jnouye, H. et al., “Structure of Blue PseudoaZulene-Skeleton Pig 7,649,014 B2 1/2010 Zhang et al. ment derived from Genipin and Amino acids,” 26th Symposium on 7,927,637 B2 4/2011 Echeverry et al. the Chemistry of Natural Product, Kyoto, pp. 577-584. (Abstract) 2005, OOO874.6 A1 1/2005 Becket al. 1983. 2008/0260668 A1 10/2008 Vidalenc 2009, 0223000 A1 9, 2009 Ferreira Moritome N., et al., “Properties of red pigments prepared from 2009,0246343 A1 10, 2009 Wu et al. geniposidic acid and amino acids.” J Sci Food Agric 7.9:810-814, 2012/0114772 A1 5, 2012 Roesler et al. Society of Chemical Industry, London (1999). 2013/01 15252 A1 5, 2013 Wu et al. Muller, J., “Analytical Characterization of a Lyophilized Juice 2013/0202703 A1* 8/2013 Sadano ......................... 424/479 Sample of Genipa americana and a Blue Colorant Based on the 2013,0345427 A1 12/2013 Echeverry et al. Juice.” AnalytiCon Discovery, Nov. 14, 2010, 28 pages. Pino, Chala. “Handmade extraction of coloring natural, an alternative FOREIGN PATENT DOCUMENTS ofuse of the biological diversity of Choco, Columbia.” Acta Biologica Colombiana 8(2):95-98, (2003) Abstract. JP 52-053934 4, 1977 Touyama, R., et al., “Studies on the Blue Pigments Produced from JP 55-164625 12, 1980 Genipin and Methylamine. I. Structures of the Brownish-Red Pig JP 57-81466 5, 1982 ments, Intermediates Leading to the Blue Pigments.” Chem. Pharm. JP 57-209958 12/1982 Bull. 42(3):668-673, Pharmaceutical Society of Japan, Japan (1994). JP 61-47167 3, 1986 International Search Report for International Application PCT/ JP 64-22820 1, 1989 IB2013/001854, Eurpean Patent Office, Netherlands, mailed on Oct. JP 5-339134 12/1993 JP T-310O23 11, 1995 24, 2013. JP 8-301739 11, 1996 STN Database Registry Record: CAS Registry No. 1313734-13-2, WO WO 2009/120579 A1 10/2009 entered STN Jul 26, 2011. WO WO 2014/OO1910 A1 1, 2014 STN Database Registry Record: CAS Registry No. 1313734-14-3, WO WO 2014, 188275 A2 11/2014 entered STN Jul 26, 2011. International Search Report for International Patent Application No. OTHER PUBLICATIONS PCT/IB2014/001735, European Patent Office, Rijswijk, Nether lands, mailed Jan. 7, 2015. Park; Agric. Chem. Biotechnol. 2001, 44, 190-193.* Office Action mailed Oct. 1, 2014, from co-pending U.S. Appl. No. Yang; Modern Food Science and Technology, 2008, 24, 352-356.* 13/532,757, inventors, Echeverry, L.F., et al., filed Jun. 25, 2012. Djerassi, C., et al., “Naturally Occurring Oxygen Heterocyclics. IX. STN Database Registry Record: CAS Registry No. 1314879-21-4. Isolation and Characterization of Genipin.” Journal of Organic entered STNAug. 4, 2011. Chemistry 25:2174-2177. American Chemical Society, United States Office Action mailed Apr. 30, 2015, front co-pending U.S. Appl. No. (1960). 13/532,757, inventors, Echeverry, L.F., et al., filed Jun. 25, 2012. Fujikawa, S., et al., "Structure of Genipocyanin G, A Spontaneous Reaction Product Between Genipin and Glycine.” Tetrahedron Let * cited by examiner U.S. Patent Jun. 28, 2016 Sheet 1 of 38 US 9,376,569 B2 U.S. Patent Jun. 28, 2016 Sheet 2 of 38 US 9,376,569 B2 U.S. Patent Jun. 28, 2016 Sheet 3 of 38 US 9,376,569 B2 89"SOI U.S. Patent Jun. 28, 2016 Sheet 4 of 38 US 9,376,569 B2 U.S. Patent US 9,376,569 B2 szogsuookszuosisauudd tw) U.S. Patent Jun. 28, 2016 Sheet 6 of 38 US 9,376,569 B2 00: 09: U.S. Patent Jun. 28, 2016 Sheet 7 Of 38 US 9,376,569 B2 s |-|--|--|--|-- U.S. Patent Jun. 28, 2016 Sheet 8 of 38 US 9,376,569 B2 F.G. 8 U.S. Patent Jun. 28, 2016 Sheet 10 of 38 US 9,376,569 B2 sagie: A342 , w -xxis'' 8 S is: 3 8 6. i: 3C part ses irg gaixa 8: i. 'S 8 : 6) i 2 8 S3 i 3C opin gigstycs R::::: RC:C: Fis - (sig-Eig- side C iša-Šs scia C is 88 -: AES38 -88. eiercaroratic lysoxy:E-3- -SSR Castoxylic acid RC Sri Ri: C-8 sets CR sexide Suitone C-SC-R C-C-R ise RCORs Aikyne R&CS E. Figure 10 U.S. Patent Jun. 28, 2016 Sheet 11 of 38 US 9,376,569 B2 tata: RPAC (0.08322H2e 16 Ma 28; 4:6 Cai, ECA, apha v AB 16 kiar 203 : Sinaiz Biotects Axina Costice:E8 38.3.2:08.85: .ade it&ai SARA.S, Py8, 18, 8iak8d, Pixt,3833 (bin 136 %int, 4 frvisume 1127 mV. Profiles -73 Smooth Av 50 rwrwrawira-saw-wrotrowra-rowra-rowaworwarra 3. 3: i S: 609, f{} 8 9 (E) tic -298. At 01542.028°AC 00008322}{2} inear rode rig 2,000-{{O}} Figure 11 U.S. Patent Jun. 28, 2016 Sheet 12 of 38 US 9,376,569 B2 ANEX NSC: 3 EANO GA EXRAC 76.8 i{{0,0 38 Cit. SO Figure 12 U.S. Patent Jun. 28, 2016 Sheet 13 of 38 US 9,376,569 B2 Figures 3A). rigt's 3A Figure 38 308 issionsESESs TTT S. OOOOOOOO15. 25 100 2 S 50. 2. : S S is 32s 3 FS fit 585; 338 8. 38 45: ;58 4. S 3335 29 2. s O r is-e------- si -----& SR 35 -, A.S. is 2: 8 FS 28 5 S is C 8 SE. S. 8 , S: ; ; S. it Figgie 33A. pink is 24, 3r, ice ine. 53 ?tir is owe? abstrace, Figi's 33, aids; equal abst:arices at 2s.{ ai: 88 h. figrate 30, bigge assitatics at S3 , Figiite 338. Raw atch witi carrier. U.S. Patent Jun. 28, 2016 Sheet 17 Of 38 US 9,376,569 B2 Figure i4) Cairation otive : Fix}=294,35X - 3807.3 R2s).982 tastate: C.E.8 333 poys & &saiiaty sticci , Exteria: Stassists *::::::::s , fixe3883.SS'x-383.3 Rise 98.58348 R3:3288 :3:288.3 RFSR388. RSSS it:ype ié&F Žesoireigh : Not trough eighted Regression the etext{f Nafe : A A&a 3's 3. A83%i-S --T-I-28 a 3:38. IIII 23:33 U.S. Patent Jun. 28, 2016 Sheet 20 of 38 US 9,376,569 B2 FIG. 15 3. ; : i ; g 83 g3 83 23.8 i 5'8 3. 18. g 2. 2OO 30 O 4OO 5O O 60O 70O 8 \ s -- A i.irrorso.us.a.s.... Yor-sous sovo.............................. 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