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Volumn 76, Issue 2, 2008, Pages 1001-1005

Synthesis of γ-valerolactones as the tea catechin metabolites

Author keywords

( ) Epigallocatechin Gallate; Green Tea; Metabolism; Microbial Degradation; Optically Active Form

Indexed keywords

EID: 61549136998 PISSN: 03855414 EISSN: None Source Type: Journal
DOI: 10.3987/COM-08-S(N)62 Document Type: Article

Times cited : (11)

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22
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- Data for (R)-5-phenyl-y-valerolactone (1, α]D26 -22.1 (c 0.28, CHCl3, lit, 17 [α]D25 +24.7 (c 1, CHCl3, 1H-NMR (400 MHz, CDCl3) δ 7.36-7.22 (5H, m, 4.74 (1H, dddd, J= 6.1, 6.3, 6.8, 7.6 Hz, 3.10 (1 H, dd, J, 6.1, 13.9 Hz, 2.93 (1H, dd, J, 6.3, 13.9 Hz, 2.47 (1 H, dt, J, 17.6, 9.2 Hz, 2.38 (1H, ddd, J, 4.6, 9.3, 17.5 Hz, 2.26 (1H, dddd, J, 4.9, 6.8, 9.7, 12.9 Hz, 1.96 (1H, ddt, J, 7.6, 12.9, 9.3 Hz, 13C-NMR (100 MHz, CDCl3) δ 177.0, 135.9, 129.4, 128.6, 127.0, 80.8, 41.3, 28.6, 27.1; ESI-MS (m/z) 177 (M+H, 199 (M+Na, ESI-HRMS m/z M+Na, calcd for C11H12O2Na, 199.0756; found. 199.0730
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24
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- Acetate (19) was synthesized from 14 in 5 steps, 26% yield with the same synthetic manner of 13 describing at Scheme 2.
- Acetate (19) was synthesized from 14 in 5 steps, 26% yield with the same synthetic manner of 13 describing at Scheme 2.

25
- 61549135786
- Data for (S)-5-(3,4-dihydroxyphenyl)-γ-valerolactone (2, α]D26 +39.6 (c 0.1, McOH, 1H-NMR (400 MHz, CD3OD) δ 6.68 (1H, d, J, 8.0 Hz, 6.67·(1H, d, J, 2.0 Hz, 6.60 (1H, dd, J, 2.0, 8.0 Hz, 4.75-4.69 (1H, m, 2.86 (1H, dd, J, 6.1, 14.1 Hz, 2.77 (1H, dd, J, 6.1, 14.1 Hz, 2.47 (1H, ddd, J, 8.8, 9.8, 17.8 Hz, 2.32 (1H, ddd, J, 4.9, 9.5, 17.8. Hz, 2.22 (1H, dddd, J, 4.9, 6.8, 9.7, 12.9 Hz, 1.94 (1H, ddt, J, 7.3, 12.7, 9.7 Hz, 13C-NMR (100 MHz, CD3OD) δ 180.5, 146.5, 145.4, 129.3, 122.1, 117.9, 116.6, 83.5, 41.7, 29.7, 28.1; IR (neat, cm-1) 3331 (w, 1742 (s, 1604 (w, 1517 (m, 1444 (m, 1356 (m, 1281 (m, 1179 (s, 1113 (m, 1015 (m, 987 (m, 925 (m, 871 (m, 805 (m, ESI-MS (m/z) 209 (M+H, ESI-HRMS m/z M+H, calcd for C11H13O4, 209.0809; found. 209.0808
- 4, 209.0809; found. 209.0808.

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