The Salvia divinorum Research and Information Center - Shroomery

loliolide
CH 3 ), 1.472 (3H, s, 1 α -CH 3 ), 1.535 (1H, dd, J = 3.52 14.62Hz, H2α), 1.619 (1H, d, J = 2.81Hz, 3 -OH),
1.785 (1H, dd, J = 3.79, 14.03Hz, H4α), 1.787 (3H, s, 5-CH 3 ), 1.981 (1H, ddd, J = 2.64, 2.64, 14.62Hz,
H2β), 2.466 (1H, ddd, J = 2.64, 2.64, 14.03Hz, H4β), 4.338 (1H, m, H3), 5.697 (1H, s, H7). 13C NMR δ
26.58 (q), 27.07 (q), 30.66 (q), 35.89 (s), 45.75 (t), 47.43 (t), 66.84 (d), 86.60 (s), 112.97 (d), 171.75 (s),
182.33 (s). Ir (KBr) ν (max) cm-1 3436 (s), 3020 (w), 2975, 2949, 2923, 2884, 1725 (s), 1682, 1620 (s),
1474, 1455, 1423, 1418, 1391, 1375, 1328, 1314, 1286, 1274, 1264, 1233, 1192, 1177, 1161, 1125, 1099,
1028, 980, 963, 950, 943, 881, 867, 801, 783, 684, 617, 609, 575, 569 cm-1 ; cims (NH3 ) 40eV m/z (rel.
int.) 215.1 (M + +19, 12%), 214.1 (M + +18, 100), 198.1 (M + +2, 4), 197.1 (M + +1, 35), 94.0 (5); eims
40eV m/z (rel. int.) 197.1 (M + +1, 4%), 196.1 (M + , 7), 178.1 (26), 163.1 (12), 140.1 (32), 135.1 (18),
112.1 (23), 111.1 (100), 110.1 (15), 109.1 (17), 107.2 (20), 97.1 (18), 95.1 (26), 93.1 (11), 85.1 (35), 81.1
(16), 79.1 (12), 69.1 (18), 67.1 (23), 57.1 (42), 55.1 (12), 43.0 (91), 41.0 (24); [α]D -101.2º (c, 1.0,
CHCl3 ), literature: -92º to -100.5º. Uv λ (max) 218 nm, ε = 8,600 (EtOH), literature: 212 to 215 nm, ε =
14,200 to 14,800.
Previous LOLIOLIDE isolations: CA = Chemical Abstracts (Through volume 100)
2(4H)Benzofuranone-5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl 6S-cis [5989-02-6]
Tripetalia paniculata: CA 76:56610k
Lythrum salicaria: CA 78:94863a
Cocculus carolinus: CA 78:20143n
Arnica montana: CA 83:20377v
Nicandra physaloides: CA 84:122127b
Plantago lanceolata: CA 84:147657n
"Tobacco": CA 85:59847g
Canscora decussata: CA 86:29952y
Pimelea spp.: CA 92:141462b
"Tea" : CA 94:80231e
"Mollusk": CA 94:27680z
Maytenus confertiflorus: CA 95:138482b
Padina tetrastromatica: CA 97:178798g
Verbascum phlomoides: CA 99:85139n
Gentiana pedicellata: CA 100:171540p
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