Synthesis and GC–MS analysis of angelates and tiglates as an aid to identification of these components in essential oils

Abstract

One-hundred-and-forty-one angelates and tiglates were synthesized and their Kováts retention indices and mass spectra are presented. It is anticipated that the publication of these data will aid in the identifi cation of angelates and tiglates from natural sources.

Artemisia magellanica. Chemical Composition of the Essential Oil from an Unexplored Endemic Species of Patagonia

“…728 [19] -975 [19] tr 0.1 ethyl isobutyrate [a] 754 755 [19] 1014 1018 [19] tr 0.1 methyl isovalerate 754 754 [19] 1039 1038 [20] 0.1 0.1 methyl 2-methylbutyrate 769 796 [19] -1056 [19] tr tr propyl propionate [a] 826 827 [18] 1240 1216 [18] tr tr (E)-2-hexenal 827 [b] 1057 [b] 0.1 0.6 ethyl 2-methylbutyrate 829 836 [18] 1073 1067 [18] 0.2 0.8 ethyl isovalerate 829 844 [19] -1044 [19] 0.1 0.2 propyl isobutyrate [a] 831 [b] 1392 [b] 0.1 tr (Z)-3-hexenol 844 852 [19] 1076 1087 [19] -0.1 isobutyl propionate 849 868 [19] -1132 [19] tr 2-methylbutyl acetate [a] 863 886 [19] -1120 [19] tr 0.4 propyl butyrate [a] 879 890 [19] -1132 [19] tr 0.1 butyl propanoate [a] 895 900 [19] 1100 1092 [19] 0.1 0.6 isobutyl isobutyrate 916 923 [19] -1244 [21] 0.1 tr ethyl tiglate [a] 925 936 [19] 1142 1150 [19] 0.2 0.6 propyl 2-methylbutyrate 926 933 [19] -1144 [19] 0…”

“…1038 [18] 1260 1250 [18] 0.1 0.3 (E)-β-ocimene 1032 [b] 1272 [b] 0.1 0.3 isoamyl butyrate 1043 1057 [18] 1538 1552 [18] tr tr octanol 1067 1064 [23] -1364 [19] tr -isobutyl tiglate 1076 1075 [19] 1398 1410 [19] tr tr (Z)-3-hexenyl propionate 1077 1079 [19] 1409 1415 [19] tr tr rosefuran 1081 [b] 1549 [b] 0.5 tr linalool 1081 1094 [19] 1270 1274 [19] 0.9 1.8 isoamyl 2-methylbutyrate 1086 1085 [19] 1280 1286 [19] 8.2 17.8 2-methylbutyl 2-methylbutyrate 1087 1126 [19] 1290 1325 [19] 2.1 5.1 amyl 2-methylbutyrate 1115 1116 [18] 1385 1367 [18] tr tr (Z)-alloocimene 1121 [b] 1396 [b] tr 0.2 (Z)-3-hexenyl isobutyrate 1125 1131 [19] 1346 1353 [24] 0.1 tr hexyl isobutyrate 1141 [b] 1771 [b] tr tr methyl phenylacetate 1164 [b] 1614 [b] tr tr terpinen-4-ol 1169 [b] 1789 [b] tr tr methyl salicylate 1170 1192 [19] 1399 1472 [21] 0.1 -2-methylbutyl tiglate 1174 1178 [18] 1684 1671 [18] tr 0.1 methyl chavicol 1215 [19] 1481 1482 [25] 0.1 0.2 (Z)-3-hexenyl 2-methylbutyrate 1215 [b] 1745 [b] 0.1 -carvone 1216…”

Chromatographic and spectral characteristic of some esters of a common monoterpene alcohols

“…In 2010 Adams described the series of tiglates and angelates for the same reasons. [5] The aim of this work was to create such a database. The searchable NIST format mass spectra library is available in the supporting information.…”

Essential‐oil inspired synthetic libraries: synthesis, spectral and gas‐chromatographic properties of new fenchyl esters

“…Although previous applications of SLA were mainly targeted ones (libraries of compounds were designed to resolve problems related to a single EO sample), the possible benefits of a more general employment of SLA in EO chemistry was already recognized . In this more universal approach, chemical profiles of previously studied essential oils are used as ‘sources of the likely SL‐parent‐structures’ (SL‐synthetic library), Figure , route c, step 1.…”

“…In this more universal approach, chemical profiles of previously studied essential oils are used as ‘sources of the likely SL‐parent‐structures’ (SL‐synthetic library), Figure , route c, step 1. Such libraries were comprised of compounds (possibly new, previously unreported natural products) that were structurally and biosynthetically related to the already known secondary metabolites . Such EO‐tailored SLs are adequate sources of MS, RI and NMR data (the upgrades of existing MS/RI libraries) .…”