메뉴 건너뛰기




Volumn 55, Issue 13, 2007, Pages 5050-5052

Efficient synthesis of (±)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus oryctes (Coleoptera: Dynastidae, Scarabaeidae)

Author keywords

4 methyloctanoic acid; Claisen rearrangement; Ethyl 4 methyloctanoate; Oryctes elegans; Oryctes monoceros; Oryctes rhinoceros; Pheromone synthesis; Rhinoceros beetles

Indexed keywords

COLEOPTERA; DYNASTIDAE; ORYCTES ELEGANS; ORYCTES MONOCEROS; ORYCTES RHINOCEROS; SCARABAEIDAE;

EID: 34447294246     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0704662     Document Type: Article
Times cited : (15)

References (24)
  • 1
    • 0029201657 scopus 로고    scopus 로고
    • Hallett, R. H.; Perez, A. R.; Gries, G.; Gries, R.; Pierce, H. D., Jr.; Yue, J.; Oehlschlager, A. C.; Gonzalez, L. M.; Borden, J. H. Aggregation pheromone of coconut rhinoceros beetle, Oryctes rhinoceros (L.) (Coleoptera: Scarabaeidae). J. Chem. Ecol. 1995, 21, 1549-1570 and references cited therein.
    • Hallett, R. H.; Perez, A. R.; Gries, G.; Gries, R.; Pierce, H. D., Jr.; Yue, J.; Oehlschlager, A. C.; Gonzalez, L. M.; Borden, J. H. Aggregation pheromone of coconut rhinoceros beetle, Oryctes rhinoceros (L.) (Coleoptera: Scarabaeidae). J. Chem. Ecol. 1995, 21, 1549-1570 and references cited therein.
  • 3
    • 12144291034 scopus 로고    scopus 로고
    • Rochat, D.; Mohammadpoor, K.; Malosse, C.; Avand-Faghih, A.; Lettere, M.; Beauhaire, J.; Morin, J. P.; Pezier, A.; Renou, M.; Abdollahi, G. A. Male aggregation pheromone of date palm fruit stalk borer Oryctes elegans. J. Chem. Ecol. 2004, 30, 387-407 and references cited therein.
    • Rochat, D.; Mohammadpoor, K.; Malosse, C.; Avand-Faghih, A.; Lettere, M.; Beauhaire, J.; Morin, J. P.; Pezier, A.; Renou, M.; Abdollahi, G. A. Male aggregation pheromone of date palm fruit stalk borer Oryctes elegans. J. Chem. Ecol. 2004, 30, 387-407 and references cited therein.
  • 4
    • 34447315220 scopus 로고    scopus 로고
    • Chung, G. F.; Sim, S. S.; Tan, M. W. Chemical control of rhinoceros beetles in the nursery and immature oil palms. In Proceedings of the PORIM International Palm Oil Conference - Progress, Prospects and Challenges towards the 21st Century, Module I, Agriculture; Basiron, Y., Sukaimi, J., Chang, K. C., Cheah, S. C., Henson, I. E., Norman, K., Paranjothy, K., Rajanaidu, N., Dolmat, H. T., Darus, A., Eds.; Kaula Lumpur, Malaysia, 1991; pp 380-395.
    • Chung, G. F.; Sim, S. S.; Tan, M. W. Chemical control of rhinoceros beetles in the nursery and immature oil palms. In Proceedings of the PORIM International Palm Oil Conference - Progress, Prospects and Challenges towards the 21st Century, Module I, Agriculture; Basiron, Y., Sukaimi, J., Chang, K. C., Cheah, S. C., Henson, I. E., Norman, K., Paranjothy, K., Rajanaidu, N., Dolmat, H. T., Darus, A., Eds.; Kaula Lumpur, Malaysia, 1991; pp 380-395.
  • 5
    • 33747112426 scopus 로고
    • Piegeage olfactif a l'aide du chrysanthemate d'ethyle. Recherches sur Oryctes monoceros (Olivier) en Cote d'Ivoire
    • Julia, J. F.; Mariau, D. Piegeage olfactif a l'aide du chrysanthemate d'ethyle. Recherches sur Oryctes monoceros (Olivier) en Cote d'Ivoire. Oleagineux 1976, 31, 263-276.
    • (1976) Oleagineux , vol.31 , pp. 263-276
    • Julia, J.F.1    Mariau, D.2
  • 8
    • 33747084806 scopus 로고
    • Oryctes monoceros trapping with synthetic pheromone and palm material in Ivory Coast
    • and references cited therein. 2006
    • Allou, K.; Morin, J. P.; Kouassi, P.; Hala N'Klo, F.; Rochat, D. Oryctes monoceros trapping with synthetic pheromone and palm material in Ivory Coast. J. Chem. Ecol. 2006, 32, 1743-1754 and references cited therein.
    • (1743) J. Chem. Ecol , vol.32
    • Allou, K.1    Morin, J.P.2    Kouassi, P.3    Hala N'Klo, F.4    Rochat, D.5
  • 9
    • 0001321812 scopus 로고
    • Volatile medium chain fatty acids and mutton flavor
    • Wong, E.; Nixon, L. N.; Johnson, C. B. Volatile medium chain fatty acids and mutton flavor. J. Agric. Food Chem. 1975, 23, 495-498.
    • (1975) J. Agric. Food Chem , vol.23 , pp. 495-498
    • Wong, E.1    Nixon, L.N.2    Johnson, C.B.3
  • 10
    • 0027981509 scopus 로고
    • Stereoisomeric flavour compounds LXVIII. 2-, 3-, and 4-alkylbranched acids, part 2: Chirospecific analysis and sensory evaluation
    • Karl, V.; Gutser, J.; Dietrich, A.; Maas, B.; Mosandl, A. Stereoisomeric flavour compounds LXVIII. 2-, 3-, and 4-alkylbranched acids, part 2: chirospecific analysis and sensory evaluation. Chirality 1994, 6, 427-434.
    • (1994) Chirality , vol.6 , pp. 427-434
    • Karl, V.1    Gutser, J.2    Dietrich, A.3    Maas, B.4    Mosandl, A.5
  • 11
    • 0037467139 scopus 로고    scopus 로고
    • Study of light-induced volatile compounds in goat's milk cheese
    • Kim, G. Y.; Lee, J. H.; Min, D. B. Study of light-induced volatile compounds in goat's milk cheese. J. Agric. Food Chem. 2003, 51, 1405-1409.
    • (2003) J. Agric. Food Chem , vol.51 , pp. 1405-1409
    • Kim, G.Y.1    Lee, J.H.2    Min, D.B.3
  • 12
    • 33644773254 scopus 로고
    • Branched-chain fatty acids. III. New method of introducing the branching methyl group. Synthesis of 15-methyloctadecanoic acid and 14-methyltetracosanoic acid
    • Cason, J.; Adams, C. E.; Bennett, L. L., Jr.; Register, U. D. Branched-chain fatty acids. III. New method of introducing the branching methyl group. Synthesis of 15-methyloctadecanoic acid and 14-methyltetracosanoic acid. J. Am. Chem. Soc. 1944, 66, 1764-1767.
    • (1944) J. Am. Chem. Soc , vol.66 , pp. 1764-1767
    • Cason, J.1    Adams, C.E.2    Bennett Jr., L.L.3    Register, U.D.4
  • 13
    • 0000923065 scopus 로고
    • The chemistry of polythienyls. II
    • Wynberg, H.; Bantjes, A. The chemistry of polythienyls. II J. Am. Chem. Soc. 1960, 82, 1447-1450.
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 1447-1450
    • Wynberg, H.1    Bantjes, A.2
  • 14
    • 51249176342 scopus 로고
    • Synthesis and lipase catalysed hydrolysis of thiolesters of 2-, 3-, and 4-methyloctanoic acids
    • Sonnet, P. E.; Baillargeon, M. W. Synthesis and lipase catalysed hydrolysis of thiolesters of 2-, 3-, and 4-methyloctanoic acids. Lipids 1989, 24, 434-437.
    • (1989) Lipids , vol.24 , pp. 434-437
    • Sonnet, P.E.1    Baillargeon, M.W.2
  • 15
    • 0037095037 scopus 로고    scopus 로고
    • Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
    • Hedenstrom, E.; Nguyen, B. V.; Silks, L. A.; III. Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids. Tetrahedron: Asymmetry 2002, 13, 835-844.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 835-844
    • Hedenstrom, E.1    Nguyen, B.V.2    Silks III, L.A.3
  • 16
    • 0242353675 scopus 로고
    • Asymmetric synthesis of 2-, 3-, and 4-methyloctanoic acids
    • Sonnet, P. E.; Cazzillo, J. Asymmetric synthesis of 2-, 3-, and 4-methyloctanoic acids. Org. Prep. Proced. Int. 1990, 22, 203-208.
    • (1990) Org. Prep. Proced. Int , vol.22 , pp. 203-208
    • Sonnet, P.E.1    Cazzillo, J.2
  • 17
    • 0028048654 scopus 로고
    • Stereoisomeric flavour compounds LXVII. 2-, 3-, and 4-alkylbranched acids, part 1: General approach to the synthesis of the enantiopure acids
    • Karl, V.; Kaunzinger, A.; Gutser, J.; Steuer, P.; Angles-Angel, J.; Mosandl, A. Stereoisomeric flavour compounds LXVII. 2-, 3-, and 4-alkylbranched acids, part 1: general approach to the synthesis of the enantiopure acids. Chirality 1994, 6, 420-426.
    • (1994) Chirality , vol.6 , pp. 420-426
    • Karl, V.1    Kaunzinger, A.2    Gutser, J.3    Steuer, P.4    Angles-Angel, J.5    Mosandl, A.6
  • 18
    • 0035149580 scopus 로고    scopus 로고
    • The effect of ethanol on the kinetics of lipase mediated enantioselective esterification of 4-methyloctanoic acid and the hydrolysis of its ethyl ester
    • Heinsman, N. W. J. T.; Valente, A. M.; Smienk, H. G. F.; van der Padt, A.; Franssen, M. C. R.; de Groot, A.; van't Riet, K. The effect of ethanol on the kinetics of lipase mediated enantioselective esterification of 4-methyloctanoic acid and the hydrolysis of its ethyl ester. Biotechnol. Bioeng. 2001, 76, 193-199.
    • (2001) Biotechnol. Bioeng , vol.76 , pp. 193-199
    • Heinsman, N.W.J.T.1    Valente, A.M.2    Smienk, H.G.F.3    van der Padt, A.4    Franssen, M.C.R.5    de Groot, A.6    van't Riet, K.7
  • 20
    • 0033570244 scopus 로고    scopus 로고
    • Exploration of lipase-catalysed direct amidation of free carboxylic acids with ammonia in organic solvents
    • Litjens, M. J. J.; Straathof, A. J. J.; Jongejan, J. A.; Heijnen, J. J. Exploration of lipase-catalysed direct amidation of free carboxylic acids with ammonia in organic solvents. Tetrahedron 1999, 55, 12411-12418.
    • (1999) Tetrahedron , vol.55 , pp. 12411-12418
    • Litjens, M.J.J.1    Straathof, A.J.J.2    Jongejan, J.A.3    Heijnen, J.J.4
  • 21
    • 1642397559 scopus 로고
    • Alkenyl copper reagents-18. Carbocupration of acetylenic acetals and ketals. Synthesis of manicone, geranial and 2,4-(E-Z)-dienals
    • Alexakis, A.; Commerçon, A.; Coulentianos, C.; Normant, J. F. Alkenyl copper reagents-18. Carbocupration of acetylenic acetals and ketals. Synthesis of manicone, geranial and 2,4-(E-Z)-dienals. Tetrahedron 1984, 40, 715-731.
    • (1984) Tetrahedron , vol.40 , pp. 715-731
    • Alexakis, A.1    Commerçon, A.2    Coulentianos, C.3    Normant, J.F.4
  • 22
    • 0345686471 scopus 로고    scopus 로고
    • Fluoride-promoted rearrangement of organosilicon compounds; a new synthesis of 2-(arylmethyl)aldehydes from 1-alkynes
    • Aronica, L. A.; Raffa, P.; Caporusso, A. M.; Salvadori, P. Fluoride-promoted rearrangement of organosilicon compounds; a new synthesis of 2-(arylmethyl)aldehydes from 1-alkynes. J. Org. Chem. 2003, 68, 9292-9298.
    • (2003) J. Org. Chem , vol.68 , pp. 9292-9298
    • Aronica, L.A.1    Raffa, P.2    Caporusso, A.M.3    Salvadori, P.4
  • 23
    • 0004744212 scopus 로고
    • Efficient conversion of aldehyde acetals into α-alkylacrylaldehydes
    • Menicagli, R.; Wis, M. L. Efficient conversion of aldehyde acetals into α-alkylacrylaldehydes. J. Chem. Res. (S) 1978, 262-263.
    • (1978) J. Chem. Res. (S) , pp. 262-263
    • Menicagli, R.1    Wis, M.L.2
  • 24
    • 0001685085 scopus 로고
    • A simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene
    • Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T. T.; Faulkner, D. J.; Petersen, M. R. A simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene. J. Am. Chem. Soc. 1970, 92, 741-743.
    • (1970) J. Am. Chem. Soc , vol.92 , pp. 741-743
    • Johnson, W.S.1    Werthemann, L.2    Bartlett, W.R.3    Brocksom, T.J.4    Li, T.T.5    Faulkner, D.J.6    Petersen, M.R.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.