6-acetyl-8-hydroxy-2,2-dimethylchromene, an antioxidant in sunflower seeds; Its isolation and synthesis and antioxidant activity of its derivatives

Heterocycles

Volumn 44, Issue 1, 1997, Pages 139-142

  Tsuda, Hideyuki ^a   Ishitani, Youichi ^a   Takemura, Yoshiyuki ^a   Suzuki, Yoshiaki ^a   Kato, Tadahiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

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Indexed keywords

EID: 0346242616     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-s47     Document Type: Article

References (17)

1. In addition to the chromene (1), new antioxidants having arylindanc skeleton were elucidated. The results will be reported elsewhere.
2. The arrows show the positive NOE between protons indicated.
3. a). M. I. Aguilar, G. Delgado, R. Bye, and E. Linares, Phytochemistry, 1993, 33, 1161. The related references cited therein.
4. b). F. Bohlmann, P. K. Mahanta, A. A. Natu, R. M. King, and H. Robinson, Phytochemistry,1978, 17, 471.
5. K. W. Rosenmund and H. Lohfert, Ber., 1928, 61B, 2601.
6. For an example, T. Kato, I. Ichinose, T. Hosogai, and Y. Kitahara, Chem. Lett., 1976, 1187.
7. W. G. Dauben, J. M. Cogen, and V. Behar, Tetrahedron Lett., 1990, 31, 3241.
8. 3 (2.5 equiv) in the presence of catalytic amounts of TBAI in DMF at room temperature.
9. M. Harfenist and E. Thorn, J. Org. Chem., 1972, 37, 841.
10. J. T. North, D. R. Kronenthal, A. J. Pullockaran, S. D. Real, and H. Y. Chen, J. Org. Chem., 1995, 60, 3397.
11. 3) δ 199.6 (s), 148.5 (s), 139.9 (s), 132.3 (d), 126.2 (s), 124.5 (d), 121.1 (s), 120.9 (d), 113.3 (d), 76.6 (s), 28.8 (q), and 27.6 (q) x 2.
12. Prepared from 8 by catalytic hydrogenation to give 14 (R = MOM) followed by oxidation with PCC and then deprotection of MOM group by HCl treatment.
13. 3 (5.4 equiv) in DMF, and then with HCl-MeOH to give 13 in 70% yield.
14. The values (%) show the concentration ratio of β-carotene in solution before and after photooxidation. The concentrations were estimated by measurement of absorbance at 500 nm due to β-carotene. The photooxidation was carried out in the absence (control) or presence of the examined compounds at the described concentration.
15. 8-Hydroxychromene compounds are known as stabilizer of photographic silver halide materials. 16
16. a). Japanese Patents (JP) 61-158331:18, July,1986. H. Takagaki, M. Watanabe, S. nakanishi, K. Yamazaki, H. Ishihama, T. Ota, and K. Kawamura, Chem. Abstr., 1987, 107, 769.
17. b).Patent Cooperation Treaty (PCT). International Publication Number: WO 91-11749. 8, August 1991.