CHARACTERIZATION OF THE PRODUCTS OF NONENZYMIC AUTOXIDATIVE PHENOLIC REACTIONS IN A CAFFEIC ACID MODEL SYSTEM

被引：157

作者：

CILLIERS, JJL ^{[1
]}

SINGLETON, VL ^{[1
]}

机构：

[1] UNIV CALIF DAVIS, DEPT VITICULTURE & ENOL, DAVIS, CA 95616 USA

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 1991年 / 39卷 / 07期

关键词：

LICARIA-CHRYSOPHYLLA; BRAZILIAN LAURACEAE; OXIDATION; SUBSTITUENT; NEOLIGNANS; CHEMISTRY; PROPACIN;

D O I：

10.1021/jf00007a021

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Products of nonenzymic autoxidation of caffeic acid were analyzed and isolated by analytical and preparative HPLC with diode array detection. By H-1 and C-13 nuclear magnetic resonance spectrometry, UV-visible spectrophotometry, and fast atom bombardment mass spectrometry, these oxidation products are shown to be specific (structures given) dimers and trimers of caffeic acid formed by reactions involving the side chain of at least one of the caffeic acid units. Compounds analogous to natural lignans and neolignans result, with dioxane, furan, or cyclohexene bridges between the caffeic units. The large effect of pH on the production rate indicates the involvement of phenolate anions in the formation of these products.

引用

页码：1298 / 1303

页数：6

共 30 条

[1]

ANTUS S, 1986, LIEBIGS ANN CHEM, P647

[2]

ARNOLDI A, 1984, HETEROCYCLES, V22, P1537

[3] SYNTHESIS AND SWEET TASTE OF SOME 2-PHENYLBENZODIOXANES [J].

ARNOLDI, A ;

CAMARDA, L ;

MERLINI, L .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1986, 34 (02) :339-344

[4] AQUILLOCHIN, A COUMARINOLIGNAN FROM AQUILARIA-AGALLOCHA [J].

BHANDARI, P ;

PANT, P ;

RASTOGI, RP .

PHYTOCHEMISTRY, 1982, 21 (08) :2147-2149

[5] NEOLIGNANS FROM VIROLA-CARINATA FRUIT [J].

CAVALCANTE, SH ;

YOSHIDA, M ;

GOTTLIEB, OR .

PHYTOCHEMISTRY, 1985, 24 (05) :1051-1055

[6]

CHA JA, 1986, AICHE J, V32, P477, DOI 10.1002/aic.690320314

[7] CHARACTERIZATION OF 2-S-GLUTATHIONYLCAFTARIC ACID AND ITS HYDROLYSIS IN RELATION TO GRAPE WINES [J].

CHEYNIER, VF ;

TROUSDALE, EK ;

SINGLETON, VL ;

SALGUES, MJ ;

WYLDE, R .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1986, 34 (02) :217-221

[8] OXIDATION OF TRANS-CAFTARIC ACID AND 2-S-GLUTATHIONYLCAFTARIC ACID IN MODEL SOLUTIONS [J].

CHEYNIER, VF ;

VANHULST, MWJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (01) :10-15

[9] NONENZYMIC AUTOXIDATIVE PHENOLIC BROWNING REACTIONS IN A CAFFEIC ACID MODEL SYSTEM [J].

CILLIERS, JJL ;

SINGLETON, VL .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (04) :890-896

[10]

CILLIERS JJL, 1989, THESIS U CALIFORNIA

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