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16817

Sigma-Aldrich

S-Ipsdienol

≥97.0% (HPLC)

Synonym(s):

(S)-(+)-2-Methyl-6-methylene-2,7-octadien-4-ol

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
Molecular Weight:
152.23
MDL number:
UNSPSC Code:
12352200

assay

≥97.0% (HPLC)

optical activity

[α]/D +16±3°, c = 1 in methanol

storage temp.

2-8°C

SMILES string

C\C(C)=C\[C@@H](O)CC(=C)C=C

Application

S-Ipsdienol has been used to study the genetic control of the enantiomeric composition of ipsdienol in the pine engraver, Ips pini. S-Ipsdienol has also been used to determine that myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Environment

signalword

Warning

hcodes

pcodes

Hazard Classifications

Aquatic Acute 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

188.6 °F

flash_point_c

87 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Michael J Domingue et al.
Journal of chemical ecology, 32(5), 1005-1026 (2006-06-02)
The genetic nature of pheromone variation within species has rarely been studied, and never for male-produced long-range pheromones. Males from western North American populations of Ips pini produce predominantly (R)-(-)-ipsdienol, whereas those from eastern North American populations produce higher proportions
Pamela Sandstrom et al.
Journal of chemical ecology, 34(12), 1584-1592 (2008-11-27)
Myrcene (7-methyl-3-methylene-1,6-octadiene) hydroxylation is likely one of the final reactions involved in the production of the Ips spp. (Coleoptera: Scolytidae) aggregation pheromone components, ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) and ipsenol (2-methyl-6-methylene-7-octen-4-ol). To gain insight into the evolution of pheromone production, we isolated a
S J Seybold et al.
Journal of chemical ecology, 21(7), 995-1016 (1995-07-01)
Thirty-five populations ofIps pini (Say) and one population each ofIps avulsus (Eichhoff) andIps bonanseai (Hopkins) were analyzed for the enantiomeric composition of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol). Populations ofI. pini occur as at least two distinct regional pheromone variants: New York type [32%-(-)
Synergistic effect of a pheromone and a kairomone on host selection and colonisation by Ips avulsus.
R Hedden et al.
Nature, 261(5562), 696-697 (1976-06-24)
Pheromonal chirality and integrity of aggregation response in southern species of the bark beetle Ips sp.
Vite, J.P., et al.
Nature, 272, 817-818 (1978)

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