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89230

Sigma-Aldrich

α,β-Thujone

technical, ~70% α-thujone basis, ~10% β-thujone basis

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Synonym(s):
(−)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
Empirical Formula (Hill Notation):
C10H16O
CAS Number:
76231-76-0
Molecular Weight:
152.23
MDL number:
MFCD00135597
UNSPSC Code:
12352100
PubChem Substance ID:
57653335
NACRES:
NA.22

Quality Level

100

grade

technical

form

liquid

composition

α-thujone, ~70%
β-thujone, ~10%

refractive index

n20/D 1.455 (lit.)
n20/D 1.46

bp

84-86 °C/17 mmHg (lit.)

density

0.925 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2.CC(C)[C@@]34C[C@@H]3[C@H](C)C(=O)C4

InChI

1S/2C10H16O/c2*1-6(2)10-4-8(10)7(3)9(11)5-10/h2*6-8H,4-5H2,1-3H3/t7-,8+,10-;7-,8-,10+/m01/s1

InChI key

AKPBIVZAUPVDMO-APEKEWONSA-N

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Application

α,β-Thujone can be used as a chiral synthon in the total synthesis of (+)-β-cyperone and several bicyclo[3.n.1] alkanone systems.

Preparation Note

isolated from natural oil of cedar-leaves

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synergistic Catalysis: Metal/Proton?Catalyzed Cyclization of Alkynones Toward Bicyclo [3. n. 1] alkanones.
Zhu S, et al.
Angewandte Chemie (International Edition in English), 54(32), 9414-9418 (2015)
The chemistry of thujone. III. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of (+)-β-cyperone.
Kutney J P, et al.
Canadian Journal of Chemistry, 58(23), 2641-2644 (1980)
Jin-Young Lee et al.
Reproduction (Cambridge, England), 159(6), 745-756 (2020-04-03)
α,β-Thujone is a natural terpenoid found in many medicinal herbs, such as Artemisia absinthium (wormwood), that exhibits antioxidant, anti-diabetic, and anti-tumorigenic effects. α,β-Thujone has numerous functions; it serves as a food ingredient, cosmetic additive, and medicinal remedy. Although the therapeutic

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