Chrysanthemyl 2-acetoxy-3-methylbutanoate: the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae

Ashraf M. El-Sayed; C. Rikard Unelius; Andrew Twidle; Vanessa Mitchell; Lee Anne Manning; Lyn Cole; David M. Suckling; M. Fernanda Flores; Tania Zaviezo; Jan Bergmann

doi:10.1016/j.tetlet.2009.12.106

Chrysanthemyl 2-acetoxy-3-methylbutanoate: the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae

Ashraf M. El-Sayed, C. Rikard Unelius, Andrew Twidle, Vanessa Mitchell, Lee Anne Manning, Lyn Cole, David M. Suckling, M. Fernanda Flores, Tania Zaviezo, Jan Bergmann

INSTITUTE OF CHEMISTRY

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

Headspace volatiles collected from virgin females of the citrophilous mealybug, Pseudococcus calceolariae, contain three compounds not present in the headspace of control samples. The main female-specific compound is identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-acetoxy-3-methylbutanoate (chrysanthemyl 2-acetoxy-3-methylbutanoate). The other two compounds are identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol (chrysanthemol) and [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-hydroxy-3-methylbutanoate (chrysanthemyl 2-hydroxy-3-methylbutanoate). Traps baited with 100 μg and 1000 μg of chrysanthemyl 2-acetoxy-3-methylbutanoate captured 4- and 20-fold more males than traps baited with virgin females.

Original language	English
Pages (from-to)	1075-1078
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2009.12.106
State	Published - 17 Feb 2010

Keywords

Chrysanthemol
Chrysanthemyl 2-acetoxy-3-methylbutanoate
Chrysanthemyl 2-hydroxy-3-methylbutanoate

Access to Document

10.1016/j.tetlet.2009.12.106

Cite this

@article{ab9b21791937405f8dda860a0a361a1a,

title = "Chrysanthemyl 2-acetoxy-3-methylbutanoate: the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae",

abstract = "Headspace volatiles collected from virgin females of the citrophilous mealybug, Pseudococcus calceolariae, contain three compounds not present in the headspace of control samples. The main female-specific compound is identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-acetoxy-3-methylbutanoate (chrysanthemyl 2-acetoxy-3-methylbutanoate). The other two compounds are identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol (chrysanthemol) and [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-hydroxy-3-methylbutanoate (chrysanthemyl 2-hydroxy-3-methylbutanoate). Traps baited with 100 μg and 1000 μg of chrysanthemyl 2-acetoxy-3-methylbutanoate captured 4- and 20-fold more males than traps baited with virgin females.",

keywords = "Chrysanthemol, Chrysanthemyl 2-acetoxy-3-methylbutanoate, Chrysanthemyl 2-hydroxy-3-methylbutanoate",

author = "El-Sayed, {Ashraf M.} and Unelius, {C. Rikard} and Andrew Twidle and Vanessa Mitchell and Manning, {Lee Anne} and Lyn Cole and Suckling, {David M.} and Flores, {M. Fernanda} and Tania Zaviezo and Jan Bergmann",

year = "2010",

month = feb,

day = "17",

doi = "10.1016/j.tetlet.2009.12.106",

language = "English",

volume = "51",

pages = "1075--1078",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "7",

}

TY - JOUR

T1 - Chrysanthemyl 2-acetoxy-3-methylbutanoate

T2 - the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae

AU - El-Sayed, Ashraf M.

AU - Unelius, C. Rikard

AU - Twidle, Andrew

AU - Mitchell, Vanessa

AU - Manning, Lee Anne

AU - Cole, Lyn

AU - Suckling, David M.

AU - Flores, M. Fernanda

AU - Zaviezo, Tania

AU - Bergmann, Jan

PY - 2010/2/17

Y1 - 2010/2/17

N2 - Headspace volatiles collected from virgin females of the citrophilous mealybug, Pseudococcus calceolariae, contain three compounds not present in the headspace of control samples. The main female-specific compound is identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-acetoxy-3-methylbutanoate (chrysanthemyl 2-acetoxy-3-methylbutanoate). The other two compounds are identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol (chrysanthemol) and [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-hydroxy-3-methylbutanoate (chrysanthemyl 2-hydroxy-3-methylbutanoate). Traps baited with 100 μg and 1000 μg of chrysanthemyl 2-acetoxy-3-methylbutanoate captured 4- and 20-fold more males than traps baited with virgin females.

AB - Headspace volatiles collected from virgin females of the citrophilous mealybug, Pseudococcus calceolariae, contain three compounds not present in the headspace of control samples. The main female-specific compound is identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-acetoxy-3-methylbutanoate (chrysanthemyl 2-acetoxy-3-methylbutanoate). The other two compounds are identified as [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol (chrysanthemol) and [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl 2-hydroxy-3-methylbutanoate (chrysanthemyl 2-hydroxy-3-methylbutanoate). Traps baited with 100 μg and 1000 μg of chrysanthemyl 2-acetoxy-3-methylbutanoate captured 4- and 20-fold more males than traps baited with virgin females.

KW - Chrysanthemol

KW - Chrysanthemyl 2-acetoxy-3-methylbutanoate

KW - Chrysanthemyl 2-hydroxy-3-methylbutanoate

UR - http://www.scopus.com/inward/record.url?scp=73649111022&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.12.106

DO - 10.1016/j.tetlet.2009.12.106

M3 - Article

AN - SCOPUS:73649111022

SN - 0040-4039

VL - 51

SP - 1075

EP - 1078

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Chrysanthemyl 2-acetoxy-3-methylbutanoate: the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this