93192
α-Cetone
odorant used in allergy studies
Synonym(s):
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, α-Cetone, Isomethyl-α-ionone
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About This Item
Empirical Formula (Hill Notation):
C14H22O
CAS Number:
Molecular Weight:
206.32
NACRES:
NA.52
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
204-846-3
MDL number:
grade
Molecular Biology
Quality Level
form
liquid
composition
iso-ɑ-methylionone, ≥85% , iso-β-methylionone, ≤10%
density
0.93 g/mL at 20 °C (lit.)
storage temp.
room temp
SMILES string
CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C
InChI
1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+
InChI key
JRJBVWJSTHECJK-PKNBQFBNSA-N
General description
3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one is fragrant sensitizer added frequently to deodorants and perfumes. It is one of the allergens responsible for axillary dermatitis.
Application
Suitable for
- contact sensitization studies to identify allergens present in cosmetic preparations
- elucidation of molecular pathways related to allergic reactions
- analytical standard
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 2
Storage Class
10 - Combustible liquids
wgk
WGK 2
flash_point_f
230.5 °F - closed cup
flash_point_c
110.3 °C - closed cup
ppe
Eyeshields, Gloves
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Susumu Ishizaki et al.
Bioscience, biotechnology, and biochemistry, 68(5), 1164-1166 (2004-06-01)
The main biodegradation product of (+/-)-alpha-isomethylionone (2) with standard activated sludge was characterized as (+/-)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)propan-2-one (1) by its analysis and synthesis. Both enantiomers (1a and 1b) of 1 were synthesized by starting from (R)- and (S)-2,4,4-trimethyl-2-cyclohexen-1-ol (3a and 3b), respectively.
Valerie T Politano et al.
International journal of toxicology, 26(3), 271-276 (2007-06-15)
Alpha-iso-methylionone, a widely used fragrance ingredient, was evaluated for developmental toxicity in presumed pregnant Sprague-Dawley rats (25/group). Oral dosages of 0, 3, 10, or 30 mg/kg/day alpha-iso-methylionone in corn oil were administered by gavage on gestational days 7 to 17.
Susun An et al.
Contact dermatitis, 53(6), 320-323 (2005-12-21)
The purpose of this study is to determine the frequency of responses to selected fragrances in patients with suspected fragrance allergy and to evaluate the risk factors. 9 dermatology departments of university hospitals have participated in this study for the