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11067

Sigma-Aldrich

(+)-Aromadendrene

≥97.0% (sum of enantiomers, GC)

Synonym(s):
(1R,2S,8R,11R)-7-Methylene-3,3,11-trimethyltricyclo[6.3.0.02.4]undecane
Empirical Formula (Hill Notation):
C15H24
CAS Number:
Molecular Weight:
204.35
Beilstein:
2554306
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

≥97.0% (sum of enantiomers, GC)

optical activity

[α]20/D +12±1°, neat

refractive index

n20/D 1.497

bp

261-263 °C (lit.)

density

0.912 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@@H](C)[C@@]1([H])[C@@]3([H])[C@@]([H])(CCC2=C)C3(C)C

InChI

1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11+,12-,13-,14-/m1/s1

InChI key

ITYNGVSTWVVPIC-XVIXHAIJSA-N

General description

(+)-Aromadendrene, a sesquiterpenoid, is the major constituent of the essential oil of Eucalypfus globulus.

Application

(+)-Aromadendrene may be used as a chiral starting material to synthesize other sesquiterenes such as (-)-apoaromadendrone, (-)-kessane, (+)-spathulenol, (+)-ledene and (-)-isoledene.

Packaging

1 mL in glass bottle

Other Notes

Chiral building block

Certificate of Analysis

Certificate of Origin

Biotransformation of sesquiterpenoids,(+)-aromadendrene and (-)-alloaromadendrene by Glomerella cingulata
Miyazawa M, et al
Phytochemistry, 40(3), 793-796 (1995)
First preparation of (+)-spathulenol. Regio-and stereoselective oxidation of (+)-aromadendrene with ozone
Van Lier FP, et al
Tetrahedron Letters, 26(17), 2109-2110 (1985)
H.J.M. Gijsen et al.
Tetrahedron, 50, 4745-4745 (1994)
The synthesis of (-)-kessane, starting from natural (+)-aromadendrene-II.
Gijsen HJM, et al.
Tetrahedron, 47(25), 4409-4416 (1991)
C.G.J.M. Seelen et al.
Tetrahedron, 46, 7237-7237 (1990)

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