58924
(−)-Isolongifolene
≥98.0% (sum of enantiomers, GC)
Synonym(s):
(1R)-2,2,7,7-Tetramethyltricyclo[6.2.1.01.6]undec-5-ene
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About This Item
Empirical Formula (Hill Notation):
C15H24
CAS Number:
Molecular Weight:
204.35
UNSPSC Code:
12352200
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-494-2
Beilstein/REAXYS Number:
2207559
MDL number:
Assay:
≥98.0% (sum of enantiomers, GC)
InChI key
CQUAYTJDLQBXCQ-NHYWBVRUSA-N
InChI
1S/C15H24/c1-13(2)8-5-6-12-14(3,4)11-7-9-15(12,13)10-11/h6,11H,5,7-10H2,1-4H3/t11-,15-/m0/s1
SMILES string
CC1(C)CCC=C2C(C)(C)[C@H]3CC[C@@]12C3
assay
≥98.0% (sum of enantiomers, GC)
optical activity
[α]20/D −138±2°, c = 1% in ethanol
refractive index
n20/D 1.499
bp
255-256 °C
density
0.930 g/mL at 20 °C (lit.)
Quality Level
Related Categories
General description
(-)-Isolongifolene is a sesquiterpene that can be found in pine cone and Japanese cedar essential oils.
Application
(-)-Isolongifolene may be used in the preparation of (-)-isolongifolenone, a potent insect repellent.
Other Notes
This (-)-isolongifolene has an enantiomeric purity of 93%; it is thus the highest purity material ever offered commercially; the double bond can be epoxidized
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Isolongifolenone: a novel sesquiterpene repellent of ticks and mosquitoes.
Zhang A, et al.
Journal of Medical Entomology, 46(1), 100-106 (2009)
R. Ranganathan et al.
Tetrahedron, 26, 621-621 (1970)
Suppression of SOS-inducing activity of chemical mutagens by metabolites from microbial transformation of (-)-isolongifolene.
Sakata K, et al.
Journal of Agricultural and Food Chemistry, 58(4), 2164-2167 (2010)
Rienaecker, R. and Graefe, J
Angewandte Chemie (International Edition in English), 97, 348-348 (1985)
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