The Schulz Lab

  TU Braunschweig     |     Department of Life Sciences     |     Institute of Organic Chemistry      

MACE Data File
Compound List
Compound Structures
Schulz Lab

MACE - Mass Spectra for Chemical Ecology

Library No. Compound Reference
SC-1 Methyl syn-2,4-dimethylheptadecanoate 1
SC-2 Methyl anti-2,4-dimethylheptadecanoate 1
SC-3 Tetradecyl syn-2,4-dimethylheptadecanoate 1
SC-4 Tetradecyl anti-2,4-dimethylheptadecanoate 1
SC-5 11,15-Dimethylhentriacontane 1
SC-6 (E)-4,8-Dimethyl-1,3,7-nonatrien-5-yl acetate 2
SC-7 (E)-4,8-dimethyl-1,3,7-nonatrien-5-ol 2
SC-8 (E)-4,8-dimethyl-1,3,7-nonatrien-5-one 2
SC-9 Dehydrojasmone 2
SC-10 Isojasmol 2
SC-11 Isojasmyl acetate 2
SC-12 epi-Isojasmol 2
SC-13 1-Methylene-1H-pyrrolizine 3
SC-14 (E)-2,6-Dimethyl-2,6,8-nonatrien-4-one 4
SC-15 (E)-2,3-Epoxy-2,6-dimethyl-6,8-nonadien 4
SC-16 (E)-2,6-Dimethyl-6,8-nonadien-4-one 4
SC-17 Hydroxydanaidal 5
SC-18 Hexyl (E)-2,3-dihydrofarnesoate 6
SC-19 (Z)-3-Hexenyl (E)-2,3-dihydrofarnesoate 6
SC-20 3-Oxohexyl (E)-2,3-dihydrofarnesoate 6
SC-21 3-Oxooctyl (E)-2,3-dihydrofarnesoate 6
SC-22 Isopentyl (E)-2,3-dihydrofarnesoate 6
SC-23 Isoprenyl (E)-2,3-dihydrofarnesoate 6
SC-24 Benzyl (E)-2,3-dihydrofarnesoate 6
SC-25 2-Phenylethyl (E)-2,3-dihydrofarnesoate 6
SC-26 Hexyl geranylcitronellate 6
SC-27 (Z)-3-Hexenyl geranylcitronellate 6
SC-28 3-Oxohexyl geranylcitronellate 6
SC-29 3-Oxohexyl 3-methyl-2-butenoate 6
SC-30 3-Oxohexyl isovalerate 6
SC-31 3-Oxohexyl laurate 6
SC-32 3-Oxohexyl palmitate 6
SC-33 Danaidal 7
SC-34 Danaidone 8
SC-35 (3Z,6Z,9Z)-3,6,9-Pentacosatriene 9
SC-36 (3Z,6Z,9Z)-3,6,9-Heneicosatriene 10
SC-37 (3Z,6Z,9Z)-1,3,6,9-Heneicosatetraene 11
SC-38 (6Z,9Z)-6,9-Heneicosadiene 10
SC-39 Methyl (Z)-9-hydroxy-6-nonenoate 3
SC-40 (Z)-9-Hydroxy-6-nonenoic acid 3
SC-41 Methyl 9-hydroxy-6-nonenoate, DMDS derivative 3
SC-42 9-Hydroxynonanoic acid 3
SC-43 3-Oxooctanol 6
SC-44 1-Hydroxyhexan-3-one 6
SC-45 Methyl 9-[(9-hydroxynonanoyl)oxy]nonanoate 3
SC-46 Methyl 9-{[(Z)-9-hydroxynon-6-enoyl]oxy}nonanoate 3
SC-47 Methyl (Z)-9-[(9-hydroxynonanoyl)oxy]non-6-enoate 3
SC-48 Methyl (Z)-9-{[(Z)-9-hydroxynon-6-enoyl]oxy}non-6-enoate 3
SC-49 3-Ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one 12
SC-50 6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one 13
SC-51 Methyl hydroxydanaidoate 14
SC-52 5-Ethyl-4-undecanone 15
SC-53 6-Hydroxy-4-dodecanolide 16
SC-54 2-Eicosyl-5-pentyltetrahydrofuran 14
SC-55 Methyl (E)-7-oxotetradec-11-enoate 17
SC-56 N-Isobutylmethanesulfinamide 18
SC-57 N-Isopentylmethanesulfinamide 18
SC-58 N,N'-Diisobutyloxalamide 18
SC-59 (E)-N-(2-Methylbutyl)-1-phenylmethanimine 18
SC-60 (E)-1-(Furan-2-yl)-N-isobutylmethanimine 18
SC-61 (E)-1-(Furan-2-yl)-N-(2-methylbutyl)methanimine 18
SC-62 (E)-4-((Isobutylimino)methyl)phenol 18
SC-63 (E)-4-((Isopentylimino)methyl)phenol 18
SC-64 N,N'-Diisobutylurea 18
SC-65 Ithomiolide A 27
SC-66 1-O'-Acetylithomiolide A 28
SC-67 2,22-Dimethyloctacosane 29
SC-68 2,6-Dimethyloctacosane 29
SC-69 (4E,8E,12E)-4,8,12-Trimethyl-16-oxoheptadeca-4,8,12-trienyl stearate 30
SC-70 (4E,8E,12E)-4,8,12-Trimethyl-16-oxoheptadeca-4,8,12-trienyl oleate 30
SC-71 N-(2E,4E)-2,4-dodecadienoyl)homoserine lactone 31
SC-72 (4E,8E)-4,8-dimethyl-12-oxotrideca-4,8-dienyl stearate 30
SC-73 trans-3,7-Dimethyl-4-octanolide 32
SC-74 2,3-Dimethyl-2-hepten-4-olide 32
SC-75 cis-3,7-Dimethyl-4-octanolide 32
SC-76 beta-Cyclogeraniol 32
SC-77 2-Hydroxy-2,6,6-trimethylcyclohexan-1-one 32
SC-78 3,7-Dimethyl-2-octen-4-olide 32
SC-79 2,6,6-Trimethylcyclohex-2-en-1-one 32
SC-80 2-Methylbutyl 2-methylpropyl disulfide 33
SC-81 Bis(2-methylbutyl) disulfide 33
SC-82 2-Methylbutyl 3-methylbutyl disulfide 33
SC-83 3-Methylbutyl 2-methylpropyl disulfide 33
SC-84 Butyl 2-methylbutyl disulfide 33
SC-85 2-Methylpropyl propyl disulfide 33
SC-86 2-Methylbutyl propyl disulfide 33
SC-87 Butyl 3-methylbutyl disulfide 33
SC-88 Ethyl 2-methylbutyl disulfide 33
SC-89 2-Methylbutyl pentyl disulfide 33
SC-90 2-Methylpropyl pentyl disulfide 33
SC-91 Cinnamomeoventrolide 34
SC-92 (2R*,5Z,10S*)-2,6,10-trimethyl-5-undecen-11-olide 34
SC-93 (2R*,5E,10R*)-2,6,10-trimethyl-5-undecen-11-olide 34
SC-94 (2R*,5Z,10R*)-2,6,10-trimethyl-5-undecen-11-olide 34
SC-95 2,24-Dimethylheptacosyl methyl ether 61
SC-96 24-Methylheptacosyl methyl ether 61
SC-97 2,10,24-Trimethylheptacosyl methyl ether 61
SC-98 5-Methylheptacosane 1
SC-99 (3E,5E)-Undeca-3,5-dien-2-one 62
SC-100 3,5,5-Trimethylcyclohex-3-en-1-yl acetate 62
SC-101 5-Ethyl-4-nonanone 15
SC-102 3-Ethyl-2-nonanone 15
SC-103 2-Ethyldodecanal 15
SC-104 3-Ethyl-4,6-nonandione 15
SC-105 Amorph-4-en-10b-ol 63
SC-106 δ-Cadinol 63
SC-107 Θ-Cadinol 63
SC-108 Θ-Muurolol 63
SC-109 α-Cadinol 63
SC-110 Epoxyniaviolide 64
SC-111 1,3-Hexanediyl diisobutyrate 65
SC-112 3-Ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene 12
SC-113 Octadecyl 2,4,6-trimethyloctanoate 71
SC-114 Eicosyl 2,4,6-trimethyloctanoate 71
SC-115 Methyl 3,7-dimethyldodecanoate 71
SC-116 Pyridin-3-ylmethyl 3,7-dimethyldodecanoate 71
SC-117 Pyridin-3-ylmethyl 9-hexadecenoate 71
SC-118 14-Methyloctadecyl nicotinate 71
SC-119 (Z)-3-Hexenyl citronellate 72
SC-120 3-Oxohexyl citronellate 72
SC-121 3-Oxooctyl citronellate 72
SC-122 Butyl (Z)-dodec-3-enoate 72
SC-123 Isobutyl (Z)-dodec-3-enoate 72
SC-124 Pentyl (Z)-dodec-3-enoate 72
SC-125 3-Methylbutyl (Z)-dodec-3-enoate 72
SC-126 Hexyl (Z)-dodec-3-enoate 72
SC-127 (Z)-3-Hexenyl (Z)-dodec-3-enoate 1
SC-128 Butyl (Z)-dec-3-enoate 72
SC-129 Butyl (E)-dec-2-enoate 72
SC-130 Butyl (E)-undec-3-enoate 72
SC-131 Butyl (E)-tetradec-3-enoate 72
SC-132 Isobutyl (E)-tetradec-3-enoate 72
SC-133 3-Oxodecyl oleate 72
SC-134 (E)-5-Methylhexa-3,5-dien-1-yl oleate 72
SC-135 5-Methylhex-4-enyl (E)-2,3-dihydrofarnesoate 72
SC-136 (E)-5-Methylhexa-3,5-dienyl (E)-2,3-dihydrofarnesoate 72
SC-137 trans,trans-3,4,13,14-Bismethylene-24-methyldotriacontane 73
SC-138 Sarekensane 73
SC-139 cis-10,11-Methylenenonacosane 73
SC-140 cis,cis-8,9,20,21-bismethylenehentriacontane 73
SC-141 (3Z,13Z)-24-Methyldotriaconta-3,13-diene 73
SC-142 (3E,13E)-24-Methyldotriaconta-3,13-diene 73
AN-1 (6Z,9Z)-Henicosa-6,9-diene 19
AN-1 (6Z,9Z)-Henicosa-6,9-diene 19
AN-1 (6Z,9Z)-Henicosa-6,9-diene 19
AN-1 (6Z,9Z)-Henicosa-6,9-diene 19
AN-2 (3Z,6Z,9Z)-Henicosa-3,6,9-triene 19
AN-3 (3Z,6Z,9Z)-Henicosa-1,3,6,9-tetraene 19
AN-4 (3Z,6Z,9Z,11E)-Nonadeca-3,6,9,11-tetraene 19
AN-5 (6Z,9Z,11E)-Henicosa-6,9,11-triene 19
AN-6 (4E,6Z,9Z)-Nonadeca-4,6,9-triene 19
AN-7 (Z)-cis-6,7-Epoxynonadec-9-ene 19
AN-8 (Z)-cis-9,10-Epoxynonadec-6-ene 19
AN-9 (6Z,9Z)-cis-3,4-Epoxynonadeca-6,9-diene 19
AN-10 (3Z,6Z)-cis-6,7-Epoxynonadeca-3,9-diene 19
AN-11 (3Z,6Z)-cis-9,10-Epoxynonadeca-3,6-diene 19
AN-12 (3Z,6Z,9Z,12Z)-Octadeca-3,6,9,12-tetraene 23
AN-13 (3Z,6Z,9Z,12Z)-Eicosa-3,6,9,12-tetraene 24
AN-14 5-Methyloctadecan-2-one 25
AN-15 5-Methylhexadecan-7-ol 26
AN-16 4-Methylhexadecan-6-ol 26
AN-17 6-Methylheptadecan-8-ol 25
AN-18 5-Methylheptadecan-7-ol 26
AN-19 4-Methylheptadecan-6-ol 26
AN-20 6-Methyloctadecan-8-ol 25
AN-21 5-Methyloctadecan-7-ol 25
AN-22 Octadecan-7-ol 26
AN-23 Octadecan-9-ol 26
AN-24 (4E,6Z,9Z)-henicosa-4,6,9-triene 35
AN-25 (2Z,4E,6Z,9Z)-henicosa-2,4,6,9-tetraene 35
AN-26 6,10,13-trimethyltetradecan-2-one 36
AN-27 6-methyloctadecan-2-one 37
AN-28 14-Methyloctadecan-2-one 37
AN-29 6,14-dimethyloctadecan-2-one 37
AN-30 (E)-Dec-8-en-1-ol 38
AN-31 (E)-Deca-7,9-dien-1-ol 38
AN-32 (3R*,13R*,1'S*)-1'-Ethyl-2'-methylpropyl 3,13-dimethylpentadecanoate 39
AN-33 (10S*,14S*)-10,14-Dimethyloctadec-1-ene 40
AN-34 (10E,14E)-Hexadeca-10,14-dienal 41
AN-35 (6E,11Z)-Hexadeca-6,11-dienal 42
AN-36 (4E,9Z)-Tetradeca-4,9-dienyl acetate 42
AN-37 (Z)-Hexadec-13-enyl acetate 43
AN-38 (Z)-Hexadec-12-enyl acetate 43
AN-39 (Z)-Hexadec-11-enyl acetate 43
AN-40 (3Z,13Z)-Octadeca-3,13-dien-1-ol 44
AN-41 (3E,13Z)-Octadeca-3,13-dien-1-ol 45
AN-42 (3Z,13Z)-Octadeca-3,13-dienyl acetate 46
AN-43 (3E,13Z)-Octadeca-3,13-dienyl acetate 46
AN-44 (2E,13Z)-Octadeca-2,13-dien-1-ol 47
AN-45 (2E,13Z)-Octadeca-2,13-dienyl acetate 47
AN-46 (2E,13Z)-Octadeca-2,13-dienal 47
AN-47 (6Z,9Z,11E)-cis-3,4-Epoxynonadeca-6,9,11-triene 48
AN-48 (3Z,9Z,11E)-cis-6,7-Epoxynonadeca-3,9,11-triene 48
AN-49 (3Z,6Z,11E)-cis-9,10-Epoxynonadeca-3,6,11-triene 48
AN-50 (3Z,6Z,9Z)-trans-11,12-Epoxynonadeca-3,6,9-triene 48
AN-51 (3Z,6Z,11E)-Nonadeca-3,6,11-trien-9-one 48
AN-52 (6Z,9Z,11E)-cis-3,4-epoxyhenicosa-6,9,11-triene 48
AN-53 (3Z,9Z,11E)-cis-6,7-Epoxyhenicosa-3,9,11-triene 48
AN-54 (3Z,6Z,11E)-cis-9,10-Epoxyhenicosa-3,6,11-triene 48
AN-55 (3Z,6Z,9Z)-trans-11,12-epoxyhenicosa-3,6,9-triene 48
AN-56 (3Z,6Z,11E)-Henicosa-3,6,11-trien-9-one 48
AN-57 (9Z,11E)-cis-6,7-Epoxynonadeca-9,11-diene 48
AN-58 (6Z,11E)-cis-9,10-Epoxynonadeca-6,11-diene 48
AN-59 (6Z,9Z)-trans-11,12-Epoxynonadeca-6,9-diene 48
AN-60 (6Z,11E)-Nonadeca-6,11-dien-9-one 48
AN-61 (9Z,11E)-cis-6,7-Epoxyhenicosa-9,11-diene 48
AN-62 (6Z,11E)-ciss-9,10-Epoxyhenicosa-6,11-diene 48
AN-63 Posticlure 48
AN-64 (6Z,11E)-Henicosa-6,11-dien-9-one 48
MI-1 p-Mentha-1,3-dien-9-ol 49
MI-2 Macropophorone 50
MI-3 (E)-(6R*,7S*)-6,7-Epoxy-2-nonenal 51
MI-4 (E)-2,6,10-Trimethylundeca-5,9-dienal 51
MI-5 (E)-6,10-Dimethyl-5,9-undecadien-2-yl acetate 52
ZA-1 Phyllisolide 53
FR-1 (Z)-Nonacos-10-ene 54
FR-2 (8Z,20Z)-8,20-Hentriacontadiene 54
TA-1 ((1R*,3R*)-2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl)methyl acetate 55
TA-2 (E)-2-isopropyl-5-methylhexa-2,4-dien-1-yl acetate 55
TA-3 Ethyl (E)-7-methyl-4-octenoate 56
TA-4 Ethyl (Z)-7-methyl-4-octenoate 56
TA-5 Isopropyl (E)-7-methyl-4-octenoate 56
TA-6 Isopropyl (Z)-7-methyl-4-octenoate 56
TA-7 Ethyl (E)-7-methyl-4-nonenoate 56
TA-8 Ethyl (Z)-7-methyl-4-nonenoate 56
TA-9 Isopropyl (E)-7-methyl-4-nonenoate 56
TA-10 Isopropyl (Z)-7-methyl-4-nonenoate 56
GR-1 N-4-methylvaleroyl-O-isobutyroyl-serine methyl ester 57
GR-2 N-4-methylvaleroyl-O-hexanoyl-serine methyl ester 57
GR-3 N-4-methylvaleroyl-O-butyroyl-serine methyl ester 57
JO-1 Gosodesmine 58
JO-2 (E)-N-(2-(4-Hydroxyphenyl)ethyl)-2-methylpent-2-enamide 59
JO-3 N-(2-(4-Hydroxyphenyl)ethyl)-2-methylpentanamide 59
JO-4 N-(4-hydroxyphenethyl)-2-oxobutanamide 59
JO-5 2-Hydroxy-N-(4-hydroxyphenethyl)butanamide 59
JO-6 cis-3-Heptyl-5-methylhexahydro-1H-pyrrolizine 66
JO-7 cis-3-Butyl-5-hexylhexahydro-1H-pyrrolizine 66
JO-8 N-(4-Hydroxyphenethyl)-5-methyl-2-oxohexanamide 59
JO-9 trans-9-(5-Hexylpyrrolidin-2-yl)nonan-2-one 67
JO-10 Deoxybuzonamine 68
JO-11 (3S*,5R*,7R*)-3,5,7-Trimethyldecane-2,8-dione 68
JO-12 cis-3-Hexyl-5-methyloctahydroindolizine 69
JO-13 4-Methyl-6-propyloctahydro-2H-quinolizine 74
PO-1 (2E,4Z,7Z)-2,4,7-Decatrienal 75
GO-1 p-Mentha-1_8-dien-4-ol
RU-1 Albireticulene 76
RU-2 Gersemiene A 76
RU-3 Gersemiene B 76
RU-4 Prenylgermacrene A 76
RU-5 Benditerpe-2,6,15-triene 76
RU-6 iso-Albireticulene 76
RU-7 Albiretol 76
RU-8 Albireticulone A 76
RU-9 Albiretriene 76
MO-1 4,6-Dimethyltetrahydro-2H-pyran-2-one
MO-2 4,6-Dimethyltetrahydro-2H-pyran-2-one
DI-1 (1R,3E,7E,11S*,12S*)-18-hydroxydolabella-3,7-diene 60

1 M. Gerbaulet, A. Möllerke, K. Weiss, S. Chinta, J. M. Schneider, S. Schulz, Identification of cuticular and web lipids of the spider Argiope bruennichi, J. Chem. Ecol., online (2022). doi: 10.1007/s10886-021-01338-y
2 P. Stamm, F. Etl, A. C. D. Maia, S. Dötterl, S. Schulz, Synthesis, Absolute Configuration and Biological Activity of Floral Scent Compounds from Night-Blooming Araceae, J. Org. Chem. 86, 5245 (2021). doi: 10.1021/acs.joc.1c00145
3 P. Stamm, F. Mann, M. McClure, M. Elias, S. Schulz, Chemistry of the Androconial Secretion of the Ithomiine Butterfly Oleria onega, J. Chem. Ecol. 45, 768-778 (2019). doi: 10.1016/S0040-4020(01)01149-8
4 R. Wegener, S. Schulz, Identification and Synthesis of Homomonoterpenoids Emitted from Elm Leaves after Elicitation by Beetle Eggs, Tetrahedron 58, 315-319 (2002). doi: 10.1007/s10886-019-01100-5
5 S. Schulz, W. Francke, M. Boppre, T. Eisner, J. Meinwald, Insect pheromone biosynthesis: Stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae), Proc. Natl. Acad. Sci. USA 90, 6834-6838 (1993) doi: 10.1073/pnas.90.14.6834
6 S. Ehlers, D. Szczerbowski, T. Harig, M. Stell, S. Hötling, K. Darragh, C. D. Jiggins, S. Schulz, Identification and composition of clasper scent gland components of the butterfly Heliconius erato and its relation to mimicry, ChemBioChem 22, 3300-3313 (2021). doi: 10.1002/cbic.202100372
7 S. B. Krasnoff, L. B. Bjostad, W. L. Roelofs, Quantitative and qualitative variation in male pheromones ofPhragmatobia fuliginosa and Pyrrharctia isabella (Lepidoptera: Arctiidae), J. Am. Chem. Soc. 88, 1305-1310 (1966). doi: 10.1007/BF01020162
8 J. Meinwald, Y. C. Meinwald, Structure and Synthesis of the Major Components in the Hairpencil Secretion of a Male Butterfly, Lycorea ceres ceres (Cramer), J. Am. Chem. Soc. 88, 1305-1310 (1966). doi: 10.1021/ja00958a039
9 V. Witte, S. Foitzik, R. Hashim, U. Maschwitz, S. Schulz, Fine Tuning of Social Integration in two Myrmecophiles of the Ponerine Army Ant Leptogenys distinguenda, J. Chem. Ecol.. 35, 355-367 (2009). doi: 10.1007/s10886-009-9606-8
10 T. W. Bell, J. Meinwald, Pheromones of two arctiid moths (Creatonotos transiens and C. gangis), J. Chem. Ecol. 12, 385-709 (1986). doi: 10.1007/BF01020563
11 S. C. Jain, D. E. Dussourd, W. E. Conner, T. Eisner, A. Guerrero, J. Meinwald, Polyene pheromone components from an arctiid moth (Utetheisa ornatrix): characterization and synthesis, J. Org. Chem. 48, 2266-2270 (1983). doi: 10.1021/jo00161a024
12 V.Sinnwell, S.Schulza, W.Francke, R.Kittmann, D.Schneider, Identification of pheromones from the male swift moth Hepialus Hecta L., Tetrahedron Letters 26, 1707-1710 (1985). doi: 10.1016/S0040-4039(00)98317-5
13 W. Francke, W. Mackenroth, W. Schroder, S. Schulz, J. Tengoe,E. Engels, W. Engels, R. Kittmann, D. Schneider, Identification of Cyclic Enolethers from Insects: Alkyldihydropyranes from Bees and AIkyldihydro-4H-pyran-4-ones from a Male Moth*, Polyene pheromone components from an arctiid moth (Utetheisa ornatrix): characterization and synthesis, Zeitschrift für Naturforschung C 40, 145-147 (1985). doi: 10.1021/jo00161a024
14 S. Schulz, W. Francke, J. Edgar und D. Schneider, Volatile compounds from androconial organs of danaine and ithomiine butterflies, Zeitschrift für Naturforschung C 43, 99-104 (1988). doi: 10.1515/znc-1988-1-219
15 K. Krückert, B. Flachsbarth, S. Schulz, U. Hentschel, P. J. Weldon, Ethyl-Branched Aldehydes, Ketones, and Diketones from Caimans (Caiman and Paleosuchus; Crocodylia, Reptilia), J. Nat. Prod. 69, 863-870 (2006). doi: 10.1021/np0600797
16 S.Schulz, R.Nishida, The pheromone system of the male danaine butterfly, Idea leuconoe, Bioorganic & Medicinal Chemistry 4, 341-349 (1996). doi: 10.1016/0968-0896(96)00011-9
17 S. Schulz, W. Francke, M. Boppré, Carboxylic Acids from Hairpencils of Male Amauris Butterflies (Lep.: Danainae), Biol. Chem. 369, 633-638 (1988). doi: 10.1515/bchm3.1988.369.2.633
18 T. Harig, C. Schlawis, L. Ziesche, M. Pohlner, B. Engelen, S. Schulz, Nitrogen-Containing Volatiles from Marine Salinispora pacifica and Roseobacter-Group Bacteria, J. Nat. Prod. 80, 3289-3295 (2017). doi: 10.1021/acs.jnatprod.7b00789
19 M. Yamamoto, R. Yamakawa, T. Oga, Y. Takei, M. Kinjo, T. Ando, Synthesis and Chemical Characterization of Hydrocarbons with a 6,9,11-, 3,6,9,11-, or 1,3,6,9-Polyene System, Pheromone Candidates in Lepidoptera, J Chem Ecol 34, 1057-1064 (2008). doi: 10.1007/s10886-008-9461-z
20 Y. Muraki, R. Yamakawa, M. Yamamoto, H. Naka, A. Honma, J. Mappes, K. Suisto, T. Ando, GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of Arctia plantaginis (Erebidae: Arctiinae), Am. J. Anal. Chem. 8, 645-656 (2017). doi: 10.4236/ajac.2017.810047
21 T. Ando, H. Kishi, N. Akashio, X.-R. Qin, N. Saito, H. Abe, S. Hashimoto, Sex attractants of geometrid and noctuid moths: Chemical characterization and field test of monoepoxides of 6,9-dienes and related compounds, J Chem Ecol 21, 299--311 (1995). doi: 10.1007/BF02036719
22 T. Ando, H. Ohsawa, T. Ueno, H. Kishi, Y. Okamura, S. Hashimoto, Hydrocarbons with a homoconjugated polyene system and their monoepoxy derivatives: Sex attractants of geometrid and noctuid moths distributed in Japan, J Chem Ecol 19, 787-798 (1993). doi: 10.1007/BF00985009
23 R. Yamakawa, N. D. Do, M. Kinjo, Y. Terashima, T. Ando, Components of the Sex Pheromones Produced by Emerald Moths: Identification, Synthesis, and Field Evaluation, J Chem Ecol 37, 105-113 (2011). doi: 10.1007/s10886-010-9895-y
24 R. Yamakawa, N. D. Do, M. Kinjo, Y. Terashima, M. Kinjo T. Ando, (6Z,9Z,12Z)-6,9,12-Octadecatriene and (3Z,6Z,9Z,12Z)-3,6,9,12-icosatetraene, the novel sex pheromones produced by emerald moths, Tetrahedron Letters 50, 4738-4740 (2009). doi: 10.1016/j.tetlet.2009.06.027
25 Y. Adachi, N. D. Do, M. Kinjo, S. Makisako, R. Yamakawa, K. Mori, T. Ando, Positions and Stereochemistry of Methyl Branches in the Novel Sex Pheromone Components Produced by a Lichen Moth, Lyclene dharma dharma, J Chem Ecol 36, 814-823 (2010). doi: 10.1007/s10886-010-9813-3
26 Y. Muraki, T. Taguri, R. Yamakawa, T. Ando, Synthesis and Field Evaluation of Stereoisomers and Analogues of 5-Methylheptadecan-7-ol, an Unusual Sex Pheromone Component of the Lichen Moth, Miltochrista calamina, J Chem Ecol 40, 250-258 (2014). doi: 10.1007/s10886-014-0405-5
27 S. Schulz, Absolute Configuration and Synthesis of 2-Hydroxy-2-(1-hydroxyethyl)-3-methyl-γ-butyrolactone, a Presumed Pheromone of Ithomiine Butterflies, Liebigs Ann. Chem., 829-834 (1992). doi: 10.1002/jlac.1992199201137
28 S. Schulz, G. Beccaloni, K. S. Brown, M. Boppré, A. V. L. Freitas, P. Ockenfels, J. R. Trigo, Semiochemicals derived from pyrrolizidine alkaloids in male ithomiine butterflies (Lepidoptera: Nymphalidae: Ithomiinae), Biochem. Syst. Ecol. 32, 699-713 (2004). doi: 10.1016/j.bse.2003.12.004
29 S. Schulz, Composition of the Silk Lipids of the Spider Nephila clavipes, Lipids 36, 637-647 (2001). doi: 10.1007/s11745-001-0768-7
30 D. Szczerbowski, S. Ehlers, K. Darragh, C. Jiggins, S. Schulz, Head and Tail Oxidized Terpenoid Esters from Androconia of Heliconius erato Butterflies, J. Nat. Prod. 85, 699-713 (2004). doi: 10.1021/acs.jnatprod.2c00300
31 L. Ziesche, L. Wolter, H. Wang, T. Brinkhoff, M. Pohlner, B. Engelen, I. Wagner-Döbler, S. Schulz, An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria, Mar. Drugs 17, 20 (2019). doi: 10.3390/md17010020
32 D. Koteska,S. S. Garcia, I. Wagner-Döbler, S. Schulz, Identification of Volatiles of the Dinoflagellate Prorocentrum cordatum, Mar. Drugs 20, 371 (2022). doi: 10.3390/md20060371
33 P. Biwer, M. Neumann-Schaal, P. Henke, D. Jahn, S. Schulz , Thiol Metabolism and Volatile Metabolome of Clostridioides difficile, Front. Microbiol. 13, 864587 (2022). doi: 10.3389/fmicb.2022.864587
34 J. Kuhn, S. Schulz, Cinnamomeoventrolide - Double Bond Regioisomerism in Frog Semiochemicals, J Chem Eco (2022). doi: 10.1007/s10886-022-01370-6
35 Y. Muraki, R. Yamakawa, M. Yamamoto, H. Naka, A. Honma, J. Mappes, K. Suisto, T. Ando, GC/FT-IR Analysis of Novel 4,6,9-Triene and 2,4,6,9-Tetraene Occurring in a Female Pheromone Gland of Arctia plantaginis (Erebidae: Arctiinae), Am. J. Anal. Chem. 8, 645-656 (2017). doi: 10.4236/ajac.2017.810047
36 Y. Muraki,T. Taguri,M. Yamamoto,P. H. G. Zarbin,T. Ando, Synthesis of All Four Stereoisomers of 6,10,13-Trimethyltetradecan-2-one, a Sex Pheromone Component Produced by Males of the Stink Bug Pallantia macunaima, Eur. J. Org. Chem. 11, 2209-2215 (2013). doi: 10.1002/ejoc.201201688
37 M. Yamamoto, T. Kamata, N. D. Do, Y. Adachi, M. Kinjo, T. Ando, A Novel Lepidopteran Sex Pheromone Produced by Females of a Lithosiinae Species, Lyclene dharma dharma, in the Family of Arctiidae, Biosci. Biotechnol. Biochem 71, 2860-2863 (2007). doi: 10.1271/bbb.70551
38 H. Shibasaki, M. Yamamoto, Q. Yan, H. Naka, T. Suzuki, T. Ando, Identification of the Sex Pheromone Secreted by a Nettle Moth, Monema flavescens, Using Gas Chromatography/Fourier Transform Infrared Spectroscopy, J Chem Eco 39, 350-357 (2013). doi: 10.1007/s10886-013-0253-8
39 T. Taguri, M. Yamamoto, T. Fujii, Y. Muraki, T. Ando, Synthesis of Four Stereoisomers of (S)-2-Methylpent-3-yl 3,13-Dimethylpentadecanoate, a Sex Pheromone of the Bagworm Moth Clania variegate, Using Stereospecific Inversion of Secondary Sulfonates as a Key Step, Eur. J. Org. Chem. 30, 6924-6933 (2013). doi: 10.1002/ejoc.201300874
40 T. Taguri, K. Yaginuma, M. Yamamoto, T. Fujii,T. Ando, Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer, Biosci. Biotechnol. Biochem. 78, 761-765 (2014). doi: 10.1080/09168451.2014.905187
41 Q. Yan, L. V. Vang, C. Nguyen Q. Khanh, H. Naka, T. Ando, Reexamination of the Female Sex Pheromone of the Sweet Potato Vine Borer Moth: Identification and Field Evaluation of a Tricosatriene, J Chem Eco 40, 590-598 (2014). doi: 10.1007/s10886-014-0446-9
42 Q. Yan, A. Kanegae, T. Miyachi, H. Naka, H. Tatsut, T. Ando , Female Sex Pheromones of Two Japanese Saturniid Species, Rhodinia fugax and Loepa sakaeiy: Identification, Synthesis, and Field Evaluation, J Chem Eco 41, 1-8 (2015). doi: 10.1007/s10886-014-0538-6
43 Q. Yan, K. Kuriyama, K. Nishikawa, S. Tominaga, H. Tatsuta, T. Ando, H. Naka, (Z)-13-Hexadecenyl Acetate: a Novel Moth Sex Pheromone Component from Herpetogramma submarginale (Lepidoptera: Crambidae), J Chem Eco 41, 441-445 (2015). doi: 10.1007/s10886-015-0576-8
44 H. Naka, T. Nakazawa, M. Sugie, M. Yamamoto, Y. Horie, R. Wakasugi, Y. Arita, H. Sugie, K. Tsuchida, T. Ando, Synthesis and Characterization of 3,13- and 2,13-Octadecadienyl Compounds for Identification of the Sex Pheromone Secreted by a Clearwing Moth, Nokona pernix, Biosci. Biotechnol. Biochem. 70, 508-516 (2006). doi: 10.1271/bbb.70.508
45 H. Naka, S. Kubota, F. Kuchiki, H. Shibasaki, M. Yamamoto, Y. Soejima, Y. Arita, T. Ando, Identification and field attraction of the female sex pheromone of a kiwifruit pest, Nokona feralis (Lepidoptera: Sesiidae), Biosci. Biotechnol. Biochem. 82, 1468-1472 (2018). doi: 10.1080/09168451.2018.1484274
46 H. Naka, T. Nakazawa, M. Sugie, M. Yamamoto, Y, Horie, R. Wakasugi, Y. Arita, H. Sugie, K. Tsuhida, T. Ando, Synthesis and Characterization of 3,13- and 2,13-Octadecadienyl Compounds for Identification of the Sex Pheromone Secreted by a Clearwing Moth, Nokona pernix , Biosci. Biotechnol. Biochem. 70, 508-516 (2006). doi: 10.1271/bbb.70.508
47 H. Naka, S. Inomata, K. Matsuoka, M. Yamamoto, H. Sugie, K. Tsuchida, Y. Arita, T. Ando, Sex Pheromones of Two Melittini Species, Macroscelesia Japona and M. Longipes: Identification and Field Attraction, J Chem Eco 33, 591-601 (2007). doi: 10.1007/s10886-006-9242-5
48 M. Yamamoto, R. Maruyama, Y. Murakami, Y. Sakamoto, R. Yamakawa, T. Ando, Characterization of posticlure and the structure-related sex pheromone candidates prepared by epoxidation of (6Z,9Z,11E)-6,9,11-trienes and (3Z,6Z,9Z,11E)-3,6,9,11-tetraenes, Anal. Bioanal. Chem. 405, 7405-7414 (2013). doi: 10.1007/s00216-013-7144-2
49 M. A. Molander, B. Eriksson, K. Arriola, A. B. Richards, L. M. Hanks, M. C. Larsson, J. G. Millar, p-Mentha-1,3-dien-9-ol: A novel aggregation-sex pheromone for monitoring longhorn beetles (Cerambycidae) in Eurasia and North America, J Appl Entomol. 146, 1098-1108 (2022). doi: 10.1111/jen.13059
50 W. D. Silva, Y. Zou, L. M. Hanks, J. MaurĂ­cio S. Bento, J. G. Millar, Pheromone Component for the South American Cerambycid Beetle Macropophora accentifer, J Chem Eco (2022). doi: 10.1007/s10886-022-01362-6
51 T. Xu, H. Yasui, S. A. Teale, N. Fujiwara-Tsujii, J. D. Wickham, M. Fukaya, L. Hansen, S. Kiriyama, D. Hao, A. Nakano, L. Zhang, T. Watanabe, M. Tokoro, J. G. Millar, Identification of a male-produced sex-aggregation pheromone for a highly invasive cerambycid beetle, Aromia bungii, Sci. Rep. 7, 7330 (2017). doi: 10.1038/s41598-017-07520-1
52 L. R. Meier, Y. Zou, J. G. Millar, J. A. Mongold-Diers, L. M. Hanks , Synergism between Enantiomers Creates Species-Specific Pheromone Blends and Minimizes Cross-Attraction for Two Species of Cerambycid Beetles, J Chem Eco 42, 1181-1192 (2016). doi: 10.1007/s10886-016-0782-z
53 D. J. Melo, E. O. Borges, D. Szczerbowski, D. M. Vidal, S. Schulz, P. H. G. Zarbin, Identification and Synthesis of a Macrolide as an Anti-aphrodisiac Pheromone from Males of Heliconius erato phyllis, Org. Lett. 24, 3772-3775 (2022). doi: 10.1021/acs.orglett.2c01160
54 J. Mant, C. Brändli, N. J. Vereecken, C. M. Schulz, W. Francke, F. P. Schiestl, Cuticular Hydrocarbons as Sex Pheromone of the Bee Colletes cunicularius and the Key to its Mimicry by the Sexually Deceptive Orchid, Ophrys exaltata, J Chem Eco 31, 1765-1787 (2005). doi: 10.1007/s10886-005-5926-5
55 J. Tabata, Genetic Basis Underlying Structural Shift of Monoterpenoid Pheromones in Mealybugs, J Chem Eco 48, 546-553 (2022). doi: 10.1007/s10886-021-01339-x
56 J. Tabata, H. Yasui, Sex Pheromone of the Azalea Mealybug With a Non-Terpene Structure, J Chem Eco 48, 609-617 (2022). doi: 10.1007/s10886-022-01376-0
57 A. Fischer, R. Gries, S. K. Alamsetti, E. Hung, A. C. Roman Torres, Y. Fernando, S. Meraj, W. Ren, R. Britton, G. Gries, Origin, structure and functional transition of sex pheromone components in a false widow spider, Commun Biol 5, 1156 (2022). doi: 10.1038/s42003-022-04072-7
58 M. F. Hassler, D. P. Harrison, T. H. Jones, C. H. Richart, R. A. Saporito, Gosodesmine, a 7-Substituted Hexahydroindolizine from the Millipede Gosodesmus claremontus, J. Nat. Prod. 9, 2764-2768 (2020). doi: 10.1021/acs.jnatprod.0c00722
59 A. R. Luo, M. F. Hassler, T. H. Jones, R. K. Vander Meer, R. M. M. Adams, The Evolution of Tyramides in Male Fungus-Growing Ants (Formicidae: Myrmicinae: Attini: Attina), J Chem Eco 48, 782-790 (2022). doi: 10.1007/s10886-022-01382-2
60 J. S. Dickschat, J. Rinkel, P. Rabe, A. B. Kashkooli, H. J. Bouwmeester, 18-Hydroxydolabella-3,7-diene synthase - a diterpene synthase from Chitinophaga pinensis, Beilstein J. Org. Chem. 13, 1770-1780 (2017). doi: 10.3762/bjoc.13.171
61 S. Schulz, S. Toft, Branched long chain alkyl methyl ethers: a new class of lipids from spider silk, Tetrahedron 49, 6805-6820 (2001). doi: 10.1016/S0040-4020(01)80424-5
62 D. Koteska, P. Marter, S. Huang, S. Pradella, J. Petersen, S. Schulz, Volatiles of the Apicomplexan Alga Chromera velia and Associated Bacteria, ChemBioChem 24, e202200530 (2022). doi: 10.1002/cbic.202200530
63 A. Ladwig, M. Kroll, S. Schulz, Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris, Beilstein J. Org. Chem. 19, 167-175 (2023). doi: 10.3762/bjoc.19.16
64 K. Stritzke, S. Schulz, M. Boppré, Niaviolides, New Macrocyclic Sesquiterpenes Secreted by Males of the African Butterfly Amauris niavius, EurJOC 7, 1337-1342 (2003). doi: 10.1002/ejoc.200390189
65 S. Schulz, J. Gross, M. Hilker, Origin of the defensive secretion of the leaf beetle Chrysomela lapponica, Tetrahedron 53, 9203-9212 (1997). doi: 10.1016/S0040-4020(97)00618-2
66 T. H. Jones, M. S. Blum, H. M. Fales, C. R. Thompson, (5Z,8E)-3-Heptyl-5-methylpyrrolizidine from a thief ant, J. Org. Chem. 45, 4778-4780 (1980). doi: 10.1021/jo01311a048
67 R. M. M. Adams, T. H. Jones, J. T. Longino, R. G. Weatherford, U. G. Mueller, Alkaloid Venom Weaponry of Three Megalomyrmex Thief Ants and the Behavioral Response of Cyphomyrmex costatus Host Ants, J Chem Eco 41, 373-385 (2015). doi: 10.1007/s10886-015-0565-y
68 T. H. Jones, D. P. Harrison, C. Menegatti, E. Mevers, K. Knott, P. Marek, D. A. Hennen, M. T. Kasson, A. M. Macias, B. Lovett, R. A. Saporito, Deoxybuzonamine Isomers from the Millipede Brachycybe lecontii (Platydesmida: Andrognathidae), J. Nat. Prod. 85, 1134-1140 (2022). doi: 10.1021/acs.jnatprod.2c00077
69 T. H. Jones, D. M. Guthrie, C. T. Hogan, D. J. Robinson, R. Mesibov, W. A. Shear, T. F. Spande, R. A. Saporito, The Chemistry of Some Dalodesmidean Millipedes from Tasmania (Diplopoda, Polydesmida), J. Nat. Prod. 81, 171-177 (2018). doi: 10.1021/acs.jnatprod.7b00806
70 J. S. T. Gorman, T. H. Jones, T. F. Spande, R. R. Snelling, J. A. Torres, H. M. Garraffo, 3-Hexyl-5-Methylindolizidine Isomers from Thief Ants, Solenopsis (Diplorhoptrum) Species, J Chem Eco 24, 933-943 (1998). doi: 10.1023/A:1022381719471
71 J. Holste, C. Mügge, C. Distler, S. Schulz, The uropygial gland of the Great Cormorant (Phalacrocorax carbo): II. Biochemical analysis of the uropygial secretion, J. Ornitho., 164:605-619 (2023). doi: 10.1007/s10336-023-02073-9
72 S. Ehlers, R. Blow, D. Szczerbowski, C. Jiggins, St. Schulz, Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot, ChemBioChem. 24, e2023005 (2023). doi: 10.1002/cbic.202300537
73 A. Möllerke, J. Bello, H. P. Leinaas, S. Schulz, Cyclopropane Hydrocarbons from the Springtail Vertagopus sarekensis-A New Class of Cuticular Lipids from Arthropods, Online (2023). doi: 10.1021/acs.jnatprod.3c00789
74 T. H. Jones, J. S. T. Gorman, R. R. Snelling, J. H. C. Delabie, M. S. Blum, H. M. Garraffo, P. Jain, J. W. Daly, T. F. Spande, Further Alkaloids Common to Ants and Frogs: Decahydroquinolines and a Quinolizidine, J. Chem. Ecol. 25, 1179-1193 (1999). doi: 10.1023/A:1020898229304
75 A. Barofsky, G. Pohnert, Biosynthesis of Polyunsaturated Short Chain Aldehydes in the Diatom Thalassiosira rotula, Org. Lett. 9, 1017-1020 (2007). doi: 10.1021/ol063051v
76 Z. Li, B. Xu, T. A. Alsup, X. Wei, W. Ning, D. G. Icenhour, M. A. Ehrenberger, I. Ghiviriga, B. Giang, J. D. Rudolf, Cryptic Isomerization in Diterpene Biosynthesis and the Restoration of an Evolutionarily Defunct P450, J. Am. Chem. Soc. 41, 22361-22365 (2023). doi: 10.1021/jacs.3c09446