| Identification | More | [Name]
3-Methyl-2-cyclohexen-1-one | [CAS]
1193-18-6 | [Synonyms]
3-METHYL-2-CYCLOHEXEN-1-ONE
3-METHYL-2-CYCLOHEXENE-1-ONE
3-METHYL-2-CYCLOHEXENONE
FEMA 3360
TIMTEC-BB SBB007736
3-methyl-2-cyclohexen-1-on
3-methyl-2-cyclohexenone-1
3-methyl-cyclohex-2-enone
MCH
Methylcyclohexenone
Seudenone
3-methylcyclohex-2-en-1-one
3-METHYL-2-CYCLOHEXEN-1-ONE 98+%
2-Cyclohexen-1-one, 3-methyl-
2-Cyclohexen-1-one,3-methy
1-Methyl-1-cyclohexen-3-one
1-Methyl-1-cyclohexene-3-one
1-Methylcyclohexene-3-one
5-Methyl-5-cyclohexene-1-one | [EINECS(EC#)]
214-769-7 | [Molecular Formula]
C7H10O | [MDL Number]
MFCD00001581 | [Molecular Weight]
110.15 | [MOL File]
1193-18-6.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID | [Melting point ]
-21°C | [Boiling point ]
199-200 °C(lit.) | [density ]
0.971 g/mL at 25 °C(lit.)
| [FEMA ]
3360 | [refractive index ]
n20/D 1.494(lit.)
| [Fp ]
155 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [color ]
Clear very slightly yellow to brown | [Specific Gravity]
0.971 | [Odor]
at 1.00 % in dipropylene glycol. nut caramel phenolic cherry | [biological source]
synthetic | [Odor Type]
nutty | [Water Solubility ]
insoluble | [JECFA Number]
1107 | [BRN ]
1560601 | [Major Application]
flavors and fragrances | [InChI]
1S/C7H10O/c1-6-3-2-4-7(8)5-6/h5H,2-4H2,1H3 | [InChIKey]
IITQJMYAYSNIMI-UHFFFAOYSA-N | [SMILES]
CC1=CC(=O)CCC1 | [LogP]
1.04 | [CAS DataBase Reference]
1193-18-6(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Cyclohexen-1-one, 3-methyl-(1193-18-6) | [EPA Substance Registry System]
3-Methyl-2-cyclohexen-1-one (1193-18-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
GW7340000
| [F ]
10 | [TSCA ]
Yes | [HS Code ]
29142990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
May be prepared by acid hydrolysis and decarboxylation of the
corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-l-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid. | [Chemical Properties]
3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma | [Chemical Properties]
CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID | [Occurrence]
Reported found in oil of Mentha pulegium, cocoa, coffee, filbert, sweet corn, dried bonito, katsuobushi, wild
rice and clam. Also produced by some animals in vivo | [Uses]
3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:
- In the total synthesis of (?)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.
- To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.
- In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.
| [Uses]
3-Methyl-2-cyclohexen-1-one was used in the synthesis of 19-nor-1α, 25-dihydroxyvitamin D(3) derivatives. It was also used in sex pheromone of the Douglas-fir beetle. Used in nut flavor. | [Definition]
ChEBI: 3-Methyl-2-cyclohexen-1-one is a cyclic olefin. | [Preparation]
By acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-1-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric
acid. | [Aroma threshold values]
Aroma characteristics at 2.0%: sweet, nutty, phenolic, walnut, fruity, almond and benzoin | [Taste threshold values]
Taste characteristics at 50 ppm: nutty, musty, phenolic and woody with grain-like nuances. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 101, p. 494, 1979 DOI: 10.1021/ja00496a044
The Journal of Organic Chemistry, 42, p. 1349, 1977 DOI: 10.1021/jo00428a017
Tetrahedron Letters, 17, p. 3, 1976 |
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