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.10.10. 3,4-Dihydroxy-benzenepropanoic acid (12a)
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1
55
Oil. H NMR (200 MHz, CDCl
.70 (2H, m, CH ), 6.50–6.65 (3H, m, Ph-H). C NMR (50 MHz,
) d (ppm) 31.5 (CH ), 37.2 (CH ), 116.3 (CH), 116.4 (CH),
20.5 (CH), 133.8 (C), 144.1 (C), 146.2 (C), 177.1 (C). MS, m/z: 384
3 H 2
) d (ppm) 2.47 (2H, m, CH ),
5
13
2
CDCl
1
2
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Arslan, A.; Kiralp, S.; Toppare, L.; Yagci, Y. Int. J. Biol. Macromol. 2005, 35,
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C
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1
1
1
1
0. Jaafar, A.; Musa, A.; Nadarajah, K.; Lee, Y. H.; Hamidah, S. Sens. Actuators, B
2006, 114, 604.
+
(M ), 369 (MꢀCH
[MꢀSi(CH ], 295 [MꢀOSi(CH
[MꢀOSi(CH ], 222 [MꢀOSi (CH
3
), 354 [Mꢀ(CH
3
)
2
], 339 [Mꢀ(CH
3
)
3
], 311
1. Sanz, V. C.; Mena, M. L.; Gonzalez-Cortes, A.; Yanez-Sedeno, P.; Pingarron, J. M.
Anal. Chim. Acta 2005, 528, 1.
3
)
3
3
)
3
], 280 [MꢀOSi(CH
) ], 265
3 4
2. Zejli, H.; Hidalgo-Hidalgo de Cisneros, J. L.; Naranjo-Rodriguez, I.; Liu, B.;
Temsamani, K. R.; Marty, J. L. Anal. Chim. Acta 2008, 612, 198.
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5
2
3
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6
].
4
.10.11. 3,4-dihydroxy-benzeneacetic acid (13a)
1
Oil. H NMR (200 MHz, CDCl
.49–7.10 (3H, m Ph-H), 9.4 (3H, br s, OH). C NMR (50 MHz,
) d (ppm) 41.2 (CH ), 114.5 (CH), 116.8 (CH), 120.6 (CH),
26.1 (C), 145.2 (C), 145.4 (C), 175.0 (C). MS, m/z: 384 (M ), 369
), 354 (Mꢀ(CH ), 339 [Mꢀ(CH ], 311 [MꢀSi(CH ],
95 [MꢀOSi (CH ], 280 [MꢀOSi(CH ], 265 [MꢀOSi(CH ], 222
(CH ].
3 H 2
) d (ppm) 3.56 (2H, s, CH ),
13
14. Tuncagil, S.; Kayahan, S. K.; Bayramoglu, G.; Arica, M. Y.; Toppare, L. J. Mol.
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CDCl
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(
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MꢀCH
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3
3 3
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4
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1
7. Yahsi, A.; Sahin, F.; Demirel, G.; Tumturk, H. Int. J. Biol. Macromol. 2005, 36, 253.
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.10.12. 4-(para-Hydroxybenzyl)-pyrocatechol (4-[(4-
hydroxyphenyl)methyl]-1,2-Benzenediol) (14a)
1
Oil. H NMR (200 MHz, CDCl
) d
3 H
(ppm) 4.10 (2H, m, CH
2
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1
2
9. Decher, G.; Schmitt, J. Prog. Colloid Polym. Sci. 1992, 89, 160.
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13
6
.51–7.22 (7H, m. Ph-H). C NMR (50 MHz, CDCl
3
) d (ppm) 42.2
C
(
(
4
CH), 115.5 (CH), 116.1 (2 ꢁ CH), 116.5 (CH), 121.3 (CH), 130.2
2
1. (a) de Faria, R. O.; Rotuno-Moure, V.; Lopes de Almeida, M. A.; Krieger, N.;
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2 ꢁ C), 133.5 (C), 134.5 (C), 144.2 (C), 145.3 (C), 156.1 (C). MS, m/z:
+
32 (M ), 417 (M-CH
3
), 402 [M-(CH
3
)
2
], 359 [M-Si(CH
3
)
3
], 343 [M-
OSi (CH
3
)
3
], 329 [M-OSi(CH
3
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4
], 314 [M-OSi(CH
3
)
5
], 298 [M-
22. (a) Ho, P. Y.; Chiou, M. S.; Chao, A. C. Appl. Biochem. Biotechnol. 2003, 111, 139;
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995, 1204, 33.
(
1
OSi(CH ) ].
3 6
2
3. (a) Baratto, L.; Candido, A.; Marzorati, M.; Sagui, F.; Riva, S.; Danieli, B. J. Mol.
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0
0
4
.10.13. 4,4 -Methylenedi-pyrocatechol (4,4 -methylenebis-1,2-
benzenediol) (14b)
1
24. Masamoto, Y.; Iida, S.; Kubo, M. Planta Med. 1980, 40, 361.
Oil. H NMR (200 MHz, CDCl
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3 H
(ppm) 4.12 (2H, m, CH
2
),
3
)
25. Martın, M. T.; Plou, F. J.; Alcalde, M.; Ballesteros, A. J. Mol. Catal. B: Enzym. 2003,
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6
.62–7.10 (6H, m. Ph-H), 8.13 (4H, s, OH). C NMR (50 MHz, CDCl
(ppm) 40.2 (CH
), 115.5 (2 ꢁ CH), 116.2 (2 ꢁ CH), 121.1
2 ꢁ CH), 135.4 (2 ꢁ C), 144.3 (2 ꢁ C), 145.2 (2 ꢁ C). MS, m/z: 520
21, 299.
d
C
2
26. Knezevic, Z.; Milosavic, N.; Bezbradica, D.; Jakovljevic, Z.; Prodanovic, R.
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(
(
[
2
+
M ), 505 (MꢀCH
3
), 447 [MꢀSi(CH
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)
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3
)
3
], 417
].
V.; Sen, R.; Kundu, S. C. Biotechnol. J. 2008, 3, 226233.
MꢀOSi (CH ], 343 [MꢀO
3
)
4
2
Si (CH
2
3
)
6
], 329 [MꢀO Si (CH
2
2
3
)
7
28. Onda, M.; Ariga, K.; Kunitake, T. J. Biosci. Bioeng. 1999, 87, 69.
2
3
9. Lineweaver, H.; Burk, D. JACS 1934, 56, 658.
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4
.10.14. 3,4-Dihydroxyphenylethanol (hydroxytyrosol) (15a)
1
56
Oil. H NMR (200 MHz, acetone-d
), 3.67 (2H, mt, CH ), 6.54–6.72 (3H, m, Ph-H), 7.67 (2H, br s,
NMR (50 MHz, acetone-d (ppm) 39.7 (CH ),
), 115.9 (CH), 116.8 (CH), 121.0 (CH), 131.9 (C), 144.0
6 H
) d (ppm) 2.65 (2H, m,
3
3
1. Sukhorukov, G.; Fery, A.; Möhwald, H. Prog. Polym. Sci. 2005, 30, 885.
2. Espin, G. J. C.; Tomas, B. F.; Garcia, V.M.C.; Ferreres, A. F.; Soler, R. C.; Wichers,
H. J. US 20030180833, EP1310562A1, 2003.
CH
2
2
1
3
2
6
H);
4.2(CH
C
6
)
d
C
2
2
33. Kazandjiand, R.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 5448.
34. Moreno-Álvarez, S. A.; Martínez-Castañón, G. A.; Niño-Martínez, N.; Reyes-
Macías, J. F.; Patiño-Marín, N.; Loyola-Rodríguez, J. P.; Ruiz, F. J. Nanopart. Res.
+
(
3
[
C), 145.6 (C); MS, m/z: 386 (M ), 371 (MꢀCH
41 [MꢀSi(CH ], 269 [MꢀSi(CH ], 253 [MꢀOSi(CH
MꢀOSi(CH ], 223 [MꢀOSi(CH ], 208 [MꢀOSi(CH ].
3
), 356 [MꢀSi(CH
3 2
) ],
], 238
)
3 3
3
)
3
3 3
)
2010, 12, 2741.
3
)
4
3
)
5
3
)
6
35. Chanwitheesuka, A.; Teerawutgulraga, A.; Kilburnb, J. D.; Rakariyathama, N.
Food Chem. 2007, 100, 1044.
Acknowledgment
3
3
3
6. Satoa, Y.; Itagaki, S.; Kurokawaa, T.; Ogura, J.; Kobayashia, M.; Hirano, T.;
Sugawaraa, M. Int. J. Pharm. 2011, 403, 136.
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8. Tuerker, B. H.; Ilhami, G.; Abdullah, M.; Sueleyman, G.; Ertan, S. J. Enzyme Inhib.
Med. Chem. 2010, 25, 685.
Italian MIUR PRIN 2008 is acknowledged.
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