Research Article

Comparative Chemistry of Propolis from Eight Brazilian Localities

Table 2

Constituents from the chloroform extract of samples of Brazilian propolis, characterized by GC/EIMS.

CompoundsRt (min)Molecular ion

14-Vinyl phenol4.2120 (100, C8H8O+)
2Dihydrocinnamic acid methyl ester6.4164 (40, ), 104 (100, ), 91 (60)
3p-Vinyl-O-prenyl phenol9.7188 (50, C13H16O+), 133 (100, C9H9O+)
42-T-butylnaphto-[2,3-b]-furan,4,9-dione13.5254 (30, ), 239.0 (100, M–CH3)
5p-Hydroxycinnamic acid methyl ester13.5178 (54, ), 147 (100, ), 119 (41, C8H7O+), 91 (60)
6Methyl-O-benzoylbenzoate 13.7240 (15, C15H12O3), 209 (17), 163 (100), 105 (78), 77 (73)
7Benzene ethoxy 13.8122 (13, C8H10O), 105 (16), 93 (70), 91 (24), 79 (32), 77 (21)
8n-Hexadecanoic acid methyl ester14.5270 (3) (C17H34O2), 143 (12), 87 (53), 74 (100)
9Allyl-3-prenylcinnamate14.5256 (64, ), 201 (84, ), 185 (100, ), 157 (60, ), 145 (95, )
102,2-Dimethylchromene-6-propenoic acid methyl ester15.5244 (11), 229 (100), 144 (6)
11Palmitic acid16.4256 (5, C16H32O2), 241 (8), 187 (14), 121 (51)
12Pinobanksin methyl ether16.6286 (C16H14O5) (10), 271 (100)
13Oleic acid methyl ester16.7296 (1) (C19H36O2), 264 (6)
144-Hydroxy-3-prenylcinnamic acid methyl ester16.7246 (70, ), 191 (100, ), 171 (20), 131 (23)
15n-Stearic acid methyl ester17.2298 (1) (C19H38O2), 242 (7), 143 (18), 87 (70), 74 (100)
16Ferulic acid octadiene ester17.8302 (20, C18H22O4), 287 (40), 271 (26), 257 (13), 246 (47), 231 (76), 203 (100), 187 (83)
17Methyl dehydroabietate17.8314 (8, C21H30O2), 299 (10), 239 (100), 141 (14), 128 (14)
18n-propyl-P-hydroxybenzoate18.2180 (5, C10H12O3), 161 (11), 121 (100), 105 (18), 91 (15), 77 (11)
1912,16-Epoxy-6-hydroxy-(15-16)-abeo-5,8,11,13-abietatetraene-7-one18.2312 (17, C20H24O3), 241 (5), 237 (100), 197 (25)
20Pentyl benzene18.6148 (16, C11H16), 133 (23), 121 (62), 105 (51), 91 (69), 77 (50)
21Ferulic acid octene ester19304 (29, C18H24O4), 271 (22), 247 (8), 246 (100), 231 (68), 199 (23), 191 (21), 187 (42), 185 (12), 131 (36), 177 (28), 131 (36), 115 (30), 105 (14), 91 (23), 77 (19)
22n-Phenyl hexadecane19.2302 (9, C22H38), 287 (10), 235 (8), 175 (31), 119 (51), 105 (61), 91 (77), 77 (63)
23Ethyl dehydroabietate19.5328 (25, C22H32O2), 268 (9), 254 (17), 253 (100), 187 (24), 156 (12), 141 (14)
24Hydroxy-diprenylcinnamic acid methyl ester (artepillin C)20.6314 (68, ), 259 (100, ), 243 (54, ), 211 (38), 203 (90, )
252,2-Dimethyl-8-prenylchromene-6-propenoic acid methyl ester20.7312 (14), 297 (100)
26Pinobanksin-5-methyl ether acetate20.9328 (28, ), 257 (89, M − 71), 313 (15)
27Benzoic acid, 4(4-hydroxybenzoyl)-methylester21.2256 (6, ), 241 (9), 161 (12), 121 (100), 147 (11)
283-Hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid methyl ester21.4330 (100, ), 297 (30, ), 272 (50, ), 225 (60, ), 197 (50, ), 171 (50)
29Benzoic acid, 2-propoxy-(4-hydroxybenzoyl)-methyl ester 21.8314 (3, C18H18 O5), 121 (100), 109 (21), 105 (25), 91 (30), 81 (47)
30Benzylic alcohol, 2-propoxy-(4-hydroxybenzoyl)-methyl ester22316 (4, C18H20 O5), 301 (4), 257 (10), 189 (22), 147 (10), 121 (100), 105 (26)
31Benzoic acid, 2(4-hydroxybenzoyl)-methyl ester22.7256 (10), 255 (50), 121 (100), 105 (33), 91 (44), 77 (35)
32n-Docosanoic acid methyl ester23354 (4) (C23H46 O2), 87 (70), 74 (100)
33n-Heptacosane23.11C27H56: m/z 380, C27
34n-Tetracosanoic acid methyl ester23.4382 (4, C25H50 O2), 143 (14), 87 (60), 74 (100)
354-Dihydrocinnamoiloxy-3-prenylcinnamic acid methyl ester24.7378 (2, ), 246 (84, ), 105 (82, ), 91 (100)
36n-Nonacosane24.9C29H60: m/z 408, C29
37n-Hentriacontane26.7(C31H64): m/z 436, C31
38Carbomethoxy benzyl caffeate ester26.9328 (60) (C18H16O6), 327 (50), 285 (40), 268 (33), 207 (40), 181 (40), 150 (40), 135 (100), 115 (40), 107 (30), 105 (30), 94 (30), 91 (45), 77 (60)
39Dihydrocaffeoyl-dihydrocinnamoyl-glyceride27.21430 (9, C23H26O8), 399 (9), 380 (25), 281 (25), 232 (30), 180 (25), 175 (29), 161 (100), 105 (12), 95 (11), 93 (9), 81 (16), 77 (16)
40β-Amyrin28426 (16, C30H50O+), 408 ( ), 218 (100, ), 203 (40, ), 189 (25, )
41Propyl carbomethoxy benzyl dihydrocaffeate ester28.1372 (24, C21H24 O6), 371 (26), 357 (70), 314 (30), 299 (30), 207 (42), 167 (30), 135 (100), 107 (50), 91 (50), 93 (50), 95 (57), 77 (69)
42Ergosterol28.96396 (16, C28H44O), 381 (26), 281 (35), 232 (35), 217 (34), 207 (19), 165 (10), 164 (27), 161 (30), 151 (39)
43Lupenone29.5424 (7, C30H48O), 218 (50), 205 (100), 189 (50), 177 (50), 109 (56), 105 (24)
44β-Amyrinone30.5424 (6, C30H48O), 218 (100), 205 (60), 203 (40), 189 (23)
45 -Amyrinone30.9424 (6), 218 (100), 205 (60), 203 (20), 189 (23)
46 -Amyrin31426 (6, C30H50O), 411 (15), 218 (100), 207 (90), 203 (18), 189 (24)
47β-Amyrin acetate31.6468 (1, C32H52 O2), 218 (100), 203 (40), 189 (45)
48α-Amyrin acetate32.5468 (1, C32H52 O2), 218 (100), 203 (20), 189 (35)
49Taraxerone33.4424 (4), 205 (80), 189 (76), 109 (74), 69 (100)
50Oleanene33.9410 (95), 395 (100, M–CH3), 174 (40), 165 (58)
51Pteron-14-en-7-one35.6424 (66), 409 (100), 383 (64), 371 (56), 165 (50)
52Olean-14-en-3,28-dione36.2440 (30, C30H46 O2), 425 (100), 409 (78), 397 (76), 385 (60), 183 (75), 165 (70)