58924

Sigma-Aldrich

(−)-Isolongifolene

≥98.0% (sum of enantiomers, GC)

Synonym(s):
(1R)-2,2,7,7-Tetramethyltricyclo[6.2.1.01.6]undec-5-ene
Empirical Formula (Hill Notation):
C15H24
CAS Number:
Molecular Weight:
204.35
Beilstein/REAXYS Number:
2207559
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

SMILES string

CC1(C)CCC=C2C(C)(C)[C@H]3CC[C@@]12C3

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

InChI key

CQUAYTJDLQBXCQ-NHYWBVRUSA-N

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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.

Packaging

1 mL in glass bottle

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

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2319 3 / PGIII

WGK Germany

WGK 3

Flash Point(F)

120.2 °F - closed cup

Flash Point(C)

49 °C - closed cup

Certificate of Analysis

Certificate of Origin

R. Ranganathan et al.
Tetrahedron, 26, 621-621 (1970)
Isolongifolenone: a novel sesquiterpene repellent of ticks and mosquitoes.
Zhang A, et al.
Journal of Medical Entomology, 46(1), 100-106 (2009)
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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