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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

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About This Item

Empirical Formula (Hill Notation):
C15H24
CAS Number:
1135-66-6
Molecular Weight:
204.35
Beilstein:
2207559
EC Number:
214-494-2
MDL number:
MFCD00042616
UNSPSC Code:
12352200
PubChem Substance ID:
57651645
NACRES:
NA.22

Quality Level

100

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.

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
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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