Catechuic acid and ethyl 2,4,5-trihydroxybenzoate from d-glucose

Carbohydrate Research

Volumn 344, Issue 6, 2009, Pages 734-738

  Bhujbal, Namdeo N ^a   Bande, Omprakash P ^a   Dhavale, Dilip D ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

Ketoester; Aldol reaction; Carbocycles; Carbohydrates; Phenolic acids

Indexed keywords

ALDOL REACTION; ALDOL-TYPE CONDENSATIONS; BASIC MEDIAS; CARBASUGAR; CARBOCYCLES; D GLUCOSE; ENOLIZATION; ESTER HYDROLYSIS; MILD ACIDS; PHENOLIC ACIDS;

CARBOHYDRATES; GLUCOSE; HYDROGENATION; HYDROLYSIS; HYDROXYLATION; ORGANIC ACIDS; PHENOLS; SUGAR (SUCROSE);

ESTERS;

BENZOIC ACID DERIVATIVE; CATECHIN; ESTER DERIVATIVE; ETHYL 2,4,5 TRIHYDROXYBENZOATE; GLUCOSE; PHENOL; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; HYDROGENATION; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

CATECHIN; GLUCOSE; HYDROXYBENZOIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 63549106056     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.02.002     Document Type: Article

References (51)

1. Bunzel M., Ralph J., and Steinhart H. Czech J. Food Sci. 22 (2004) 64-69
2. Ralph J., Bunzel M., Marita J.M., Hatfield R.D., Lu F., Kim H., Schatz P.F., Grabber J.H., and Steinhart H. Phytochem. Rev. 3 (2004) 79-96
3. Waldron K.W., Smith A.C., Parr A.J., Na A., and Parker M.L. Trends Food Sci. Technol. 8 (1997) 213-221
4. Birosova L., Mikulasova M., and Vaverkova S. J. Agric. Food Chem. 55 (2007) 10183-10186
5. Gomes C.A., Girao da Cruz T., Andrade J.L., Milhazes N., Borges F., and Marques M.P.M. J. Med .Chem. 46 (2003) 5395-5401
6. Saulnier L., Crépeau M., Lahaye M., Thibault J., Garcia-Conesa M.T., Kroon P.A., and Williamson G. Carbohydr. Res. 320 (1999) 82-92
7. Corey E.J., and Battacharyya S. Tetrahedron Lett. (1979) 3919-3922
8. Bluhm M.E., Kim S.S., Dertz E.A., and Raymond K.N. J. Am. Chem. Soc. 124 (2002) 2436-2437
9. Jacobs A. Br. J. Haematol. 43 (1979) 1
10. Neilands J.B. In: Martell A.E., Anderson W.F., and Badman D.G. (Eds). Development of Iron Chelators for Clinical Use (1981), Elsevier, Amsterdam
11. Jacobs A., White G.P., and Tait G.H. Biochem. Biophys. Res. Commun. 74 (1977) 1626-1630
12. Nakamura Y., Torikai K., and Ohigashi H. J. Agric. Food Chem. 49 (2001) 5674-5678
13. Ueda J., Saito N., Shimazu Y., and Ozawa T. Arch. Biochem. Biophys. 333 (1996) 377-384
14. Birosova L., Mikulasova M., and Vaverkova S. Biomed. Pap. Med. Fac. Univ. Palacky Olomoc Czech Repub. 149 (2005) 489-491
15. Belicova A., Kriskova L., Nayg M., Krajcovic J., and Ebringer L. Folia Microbiol. 47 (2001) 511-514
16. Carajal G., Penna S., and Carbojal E.J. J. Revista Latiinoamericana. de. Microbiol. 5 (1962) 45-53
17. Draths K.M., and Frost J.W. J. Am. Chem. Soc. 117 (1995) 2395-2400
18. Li K., and Frost J.W. J. Am. Chem. Soc. 120 (1998) 10545-10546
19. Hansen C.A., Dean A.B., Draths K.M., and Frost J.W. J. Am. Chem. Soc. 121 (1999) 3799-3800
20. Kambourakis S., and Frost J.W. J. Org. Chem. 65 (2000) 6904-6909
21. Gibson J.M., Thomas P.S., Thomas J.D., Barker J.L., Chandran S.S., Harrup M.K., Draths K.M., and Frost J.W. Angew .Chem., Int. Ed. 40 (2001) 1945-1946
22. Ran N., Knop D.R., Draths K.M., and Frost J.W. J. Am. Chem. Soc. 123 (2001) 10927-10934
23. Li W., Xie D., and Frost J.W. J. Am. Chem. Soc. 127 (2005) 2874-2882 and references cited therein
24. Achkar J., Xian M., Zhao H., and Frost J.W. J. Am. Chem. Soc. 127 (2005) 5332-5333
25. Koppisch A.T., Hotta K., Fox D.T., Ruggiero C.E., Kim C., Sanchez T., Iyer S., Browder C.C., Unkefer P.J., and Unkefer C.J. J. Org. Chem. 73 (2008) 5759-5765
26. Sainsbury M., Dyke S.F., and Moon B.J. J. Chem. Soc. C (1970) 1797-1800
27. Groseclose E.E., and Ribbons D.W. Biochem. Biophys. Res. Commun. 55 (1973) 897-903
28. Fetzner S., Muller R., and Lingens F. Biol. Chem. Hoppe-Seyler 370 (1989) 1173-1182
29. Daumy G.O., Mccoll A.S., and Andrews G.C. J. Chem. Soc., Chem. Commun. (1979) 1073a
30. Shindo K., Nakamura R., Osawa A., Kagami O., Kanob K., Furukawa K., and Misawa N. J. Mol. Catal. B: Enzym. 35 (2005) 134-141
31. Gramer C.J., and Raymond K.N. Org. Lett. 3 (2001) 2827-2830
32. De Voss J.J., Rutter K., Schroeder B.G., Su H., Zhu Y., and Barry III C.E. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 1252-1257
33. Nakanishi I., Nishizawa C., Ohkubo K., Takeshita K., Suzuki K.T., Ozawa T., Hecht S.M., Tanno M., Sueyoshi S., Miyata N., Okuda H., Fukuzumi S., Ikota N., and Fukuhara K. Org. Biomol. Chem. 3 (2005) 3263-3265
34. Saito S., and Kawabata J. Helv. Chim. Acta 89 (2006) 1395-1406
35. Forrest J., and Petrow V. J. Chem. Soc. (1950) 2340-2342
36. Rajgopalan S., and Varadrajan S. Proc. Indian Acad. Sci. Sect. A 30 (1949) 265-269
37. Aghoramurthy K., and Seshadri T.R. Proc. Indian Acad. Sci. Sect. A 35 (1952) 327-331
38. Huang D.-S., and Ting S.-H. J. Chem. Res. (S) (1994) 500-501
39. Sher M., Tam Dang T.H., Ahmed Z., Rashid M.A., Fischer C., and Langer P. J. Org. Chem. 72 (2007) 6284-6286
40. Ferrier R.J. J. Chem. Soc., Perkin Trans. 1 (1979) 1455-1458
41. Ferrier R.J. Chem. Rev. 93 (1993) 2779 and references cited therein
42. Chida N., Othuuka M., Ogura K., and Ogawa S. Bull. Chem. Soc. Jpn. 64 (1991) 2118-2121
43. Dhavale D.D., Bhujbal N.N., Joshi P., and Desai S.G. Carbohydr. Res. 263 (1994) 303-307
44. Vyavahare V.P., Chakraborty C., Maity B., Chattopadhyay S., Puranik V.G., and Dhavale D.D. J. Med. Chem. 50 (2007) 5519-5523
45. Vyavahare V.P., Chattopadhyay S., Puranic V.G., and Dhavale D.D. Synlett (2007) 559-562
46. Dhavale D.D., Saha N.N., and Desai V.N. J. Org. Chem. 62 (1997) 7482-7484
47. Saha N.N., Desai V.N., and Dhavale D.D. J. Org. Chem. 64 (1994) 1715-1719
48. Karche N.P., Jachak S.M., and Dhavale D.D. J. Org. Chem. 68 (2003) 4531-4534
49. Karche N.P., Jachak S.M., and Dhavale D.D. J. Org. Chem. 66 (2001) 6323-6332
50. Paul M.D. Medicinal Natural Products, A Biosynthetic Approach. 2nd ed. (2001), John Wiley and Sons, New York pp 61, 124
51. Mirza S., Molleyres L., and Vasella A. Helv. Chim. Acta 68 (1985) 988-996