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R 1 C O R 1 C O R 2 C O R 2 C O 1.Amino acids 2. 2H 2 O R R 1 N 2 R R 1 N 2 R 1 H N R 2 [ O ] R 1 N R 2 R 2 N R 1 R 2 N R1 R 2 N R 1 H N R 2 R 1 43
44
HO OH CH CH COOH CH CH 2 HO OH Chlorogenic acid HO H H H OH OH CH H COOH H H HO H Quinic acid CH C O O pyrolysis O O C O H H H H H HO H OH OH H Quinide OH Hydrolysis COOH HO OH Caffeic acid COOH Benzoic acid OH OH OH 1, 2, 4 trihydroxybenzene 4 COOH OH OCH 3 3 methoxy 4 hydroxystyrene COOH OH OH 3 hydroxybenzoic acid hydroxybenzoic acid HO Pyrogallol OH OH Phenol OH OH OH OH Pyrocatecchol Resorcinol OH OH Hydroquinone 45
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CHO C C CHO C C C OH O CH 3 C OH O C 2 H 5 VANILLIN ETHYLVANILLIN H O H O B GLUCOSIDASE C 6 H 12 O 6 GLUCOSE O CH 3 O CH 3 O C 6 H 11 O 5 GLUCOVANILLIN OH VANILLIN (WIILD-ALTAMIRANO, C.1969) 64
CH 3 C O C OH C OH CH 2 OH CH 3 C O H C OH C OH C H 2 OH HO O CH 3 OH O (R 2 H) HO H 2 O O CH 3 O 65
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OH OCH 3 OH OCH 3 CH 2 CH 3 4 e t h y l g u a i a c o l 68
OH OCH 3 CH CH 2 2 m e t h o x y 4 v i n y l p h e n o l 69
OH H 3 C O COOH CH 3 OH 2 OH OH CH CH CH 2 1/ 2 O OH2 2 CH 3 CO 2 3/ 2 O 2 H 3 C O H 3 C O Et h y l g u a i a c o l Fe r u l i c a c i d P r o p e n y l gu a i a c o l CO2 HO OH 2 H 3 CCHO HO CH 2 H CH 2 o CH 2 O HO CH 3 H 3 CO Gu ai a c o l H 3 CO 4 v i n y l g u a i a c o l H 3 C O M e t h y l g u a i a c o l 2H 2 O O2 CH 2 O 1/ 2 O 2 CH 3 OH HO H 3 C O CH 2 OH HO H 3 C O C O H HO H 3 C O C O CH 3 Va n i l l i c a l c o h o l Va n i l l i n A c e t y l g u a i a c o l,a 70
CH 3 N CH 3 CH 3 C O H CNH 2 H C O H 3 C N H C O H 2 CH 3 C O CN H 2 N H N 3 C CH 3 CH 3 OH O CH 3 HCOH HC O CH 3 R H 2 N C COOH H N N R R= H CH 3 71
RCH 2 CHO H (R)HC C NH 3 CH(R) (RCH 2 )HC CH O C (RCH 2 )HC H C N C C [O] PH 2 C R N R H H H 2 RCH 2 CHO (R)HC HC C C CH(R) (R)HC CH(R) RCH(COOH)NH 2 HC C(R')COOH O O N H H _ H 2 O _ CO 2 [O] R N R R H C H 2 C CX H C CH O O HC HC H C O H CX CH O NH 3 H 2 O H C H C HC N H H CX CH O H 2 O N X 72
O HO 2 C C NH 2 O HO 2 C N HO R H R O N C R CO 2 H O N C CO 2 R OH CO 2 N C H R O 73
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pyrazine pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazine 5H-5-methyl-6,7-dihydrocyclopentapy razine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopentapy razine furfuryl pentanoate 4-ethyl-2-methoxy phenol 86
23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol pyrazine -- -- -- -- -- pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazi ne 5H-5-methyl-6,7-dihydrocyclope ntapyrazine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclope ntapyrazine furfuryl pentanoate 87
4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol pyrazine pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyraz ine 5H-5-methyl-6,7-dihydrocyclopentapyr azine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 88
2-methyl-5H-6,7-dihydrocyclopentapyr azine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy-4-vinyl phenol pyrazine pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazine 5H-5-methyl-6,7-dihydrocyclopenta pyrazine 3,5-diethyl-2-methyl pyrazine 89
2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopenta pyrazine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol pyrazine 0.00 0.61 0.49 1.01 3.52 pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyraz 90
ine 5H-5-methyl-6,7-dihydrocyclopentapyr azine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopentapyr azine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy-4-vinyl phenol pyrazine 13.00 13.83 13.58 0.00 7.28 pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine -- 5-methyl-2-furancarboxaldehyde 91
furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazi ne 5H-5-methyl-6,7-dihydrocyclopentapyr azine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopentapyr azine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy-4-vinyl phenol 1.02 0.38 1.24 0.56 6.82 92
-- -- 23 pyrazine pyridine methyl pyrazine 93
2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazi ne 5H-5-methyl-6,7-dihydrocyclope ntapyrazine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclope ntapyrazine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol pyrazine -- pyridine 94
methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine -- -- 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazine 5H-5-methyl-6,7-dihydrocyclopent apyrazine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopent apyrazine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol pyrazine 95
pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine -- -- -- 5-methyl-2-furancarboxaldehyd e furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyraz ine 5H-5-methyl-6,7-dihydrocyclop entapyrazine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclop entapyrazine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol 96
pyrazine 0.00 0.57 1.02 1.63 2.71 pyridine methyl pyrazine 2-furanmethanol 2,5-dimethyl pyrazine 2,5-dimethyl-3(2H)-furanone 3-methyl pyridine -- 5-methyl-2-furancarboxaldehyde furfuryl acetate 2-ethyl-6-methyl pyrazine 2-ethyl-3-methyl pyrazine 2-ethyl-3,5-dimethyl pyrazine 2-furanmethanol propanoate 2-methoxy phenol 6,7-dihydro-5H-cyclopentapyrazine 5H-5-methyl-6,7-dihydrocyclopent apyrazine 3,5-diethyl-2-methyl pyrazine 2-(2-furanylmethyl)-5-methyl furan 1-(2-furanylmethyl)-1H-pyrrole 2-methyl-5H-6,7-dihydrocyclopent apyrazine furfuryl pentanoate 4-ethyl-2-methoxy phenol 23 2,2'-(oxybis(methylene)) furan 2-methoxy -4-vinyl phenol 97
98 23
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