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Safety Information

93192

Sigma-Aldrich

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:
127-51-5
Molecular Weight:
206.32
EC Number:
204-846-3
MDL number:
MFCD00034582
UNSPSC Code:
12352200
PubChem Substance ID:
57653524
NACRES:
NA.52

grade

for molecular biology

Quality Level

100

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

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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

Pictograms

Environment
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

230.5 °F - closed cup

Flash Point(C)

110.3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

93192-VAR-F:
93192-10ML-F:
93192-BULK-F:
93192-50ML-F:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2514
BCCM5874
BCCC6233
BCCB3118
BCBX6031

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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.
Valerie T Politano et al.
International journal of toxicology, 31(6), 595-601 (2013-01-04)
Alpha-iso-methylionone (AIM), a fragrance ingredient, was evaluated for systemic toxicity in rats. Male and female Sprague Dawley rats were administered 0, 5, 30, or 500 mg/kg/d AIM via gavage for 90 days. Statistically significant changes in blood chemistry parameters (reduced
A Lapczynski et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 45 Suppl 1, S280-S289 (2007-11-27)
A toxicologic and dermatologic review of alpha-iso-methylionone when used as a fragrance ingredient is presented.
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
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