3-Methyl-2-cyclohexen-1-one Property

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

Odor Type

nutty

Water Solubility 

insoluble

JECFA Number

1107

BRN 

1560601

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

Hazard Codes 

Xn

Risk Statements 

22-36-20/21/22

Safety Statements 

36/37/39-26-24/25

WGK Germany 

3

RTECS 

GW7340000

F 

10

TSCA 

Yes

HS Code 

29142990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

3-Methyl-2-cyclohexen-1-one Chemical Properties,Usage,Production

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-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.

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.

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