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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

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About This Item

Empirical Formula (Hill Notation):
C15H24
CAS Number:
489-39-4
Molecular Weight:
204.35
Beilstein/REAXYS Number:
2554306
EC Number:
207-694-6
MDL number:
MFCD00062951
UNSPSC Code:
12352002
PubChem Substance ID:
57646882

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,[1] is the major constituent of the essential oil of Eucalypfus globulus.[2]

Application

(+)-Aromadendrene may be used as a chiral starting material to synthesize other sesquiterenes such as (-)-apoaromadendrone,[2] (-)-kessane,[3] (+)-spathulenol,[4] (+)-ledene and (-)-isoledene.[5]

Other Notes

Chiral building block[6][7]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

194.0 °F - closed cup

flash_point_c

90 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
435553/1
1357453
370629/1
268092/1

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The conversion of natural (+)-aromadendrene into chiral synthons-I.
Gijsen HJM, et al.
Tetrahedron, 46(20), 7237-7246 (1990)
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)
Chemistry of (+)-aromadendrene. Part 6: Rearrangement reactions of ledene, isoledene and their epoxides.
Moreno-Dorado FJ, et al.
Tetrahedron, 59(39), 7743-7750 (2003)
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