3-Methyl-2-cyclohexen-1-one

Synonym(s):nutty cyclohexenone

CAS NO.：1193-18-6
Empirical Formula: C7H10O
Molecular Weight: 110.15
MDL number: MFCD00001581
EINECS: 214-769-7
SAFETY DATA SHEET (SDS)
Update Date: 2025-01-27 09:38:02

What is 3-Methyl-2-cyclohexen-1-one?

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

CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID

Chemical properties

3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma

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

The Uses of 3-Methyl-2-cyclohexen-1-one

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.

The Uses of 3-Methyl-2-cyclohexen-1-one

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.

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.

Definition

ChEBI: 3-Methyl-2-cyclohexen-1-one is a cyclic olefin.

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

Properties of 3-Methyl-2-cyclohexen-1-one

Melting point:	-21°C
Boiling point:	199-200 °C(lit.)
Density	0.971 g/mL at 25 °C(lit.)
refractive index	n20/D 1.494(lit.)
FEMA	3360 \| 3-METHYL-2-CYCLOHEXEN-1-ONE
Flash point:	155 °F
storage temp.	Inert atmosphere,Room Temperature
form	Liquid
color	Clear very slightly yellow to brown
Specific Gravity	0.971
Odor	at 1.00 % in dipropylene glycol. nut caramel phenolic cherry
Water Solubility	insoluble
JECFA Number	1107
BRN	1560601
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 information for 3-Methyl-2-cyclohexen-1-one

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H227:Flammable liquids H302:Acute toxicity,oral
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. P501:Dispose of contents/container to..…