3-Methyl-2-cyclohexen-1-one

HCID 14511
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
1193-18-6
Standard SMILES
CC1=CC(=O)CCC1
InChIKey
IITQJMYAYSNIMI-UHFFFAOYSA-N
Molecular formula
C7H10O
Average molar mass
110.15 g/mol
Monoisotopic mass
110.07316494

Overview

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

Names & identifiers

Preferred name
3-Methyl-2-cyclohexen-1-one
IUPAC
3-methylcyclohex-2-en-1-one
English name
3-Methyl-2-cyclohexen-1-one
Molecular formula
C7H10O
Molecular weight
110.15

Names & synonyms

3-METHYL-2-CYCLOHEXEN-1-ONE1193-18-63-Methylcyclohex-2-en-1-one3-Methyl-2-cyclohexenoneSeudenone2-Cyclohexen-1-one, 3-methyl-FEMA No. 3360DTXSID8035186NSC-43632786Y352V9XDTXCID6015186MCH CPD
Show more names
MCHL6V BUTJ C13-methyl-2-cyclohexenone-11-Methylcyclohexene-3-one3-methyl-cyclohex-2-enone
RefChem:94730214-769-7MethylcyclohexenoneMFCD000015813-Methyl-2-cyclohexene-1-oneghl.PD_Mitscher_leg0.6993-methyl-cyclohex-2-en-1-oneCaswell No. 561AB

Database identifiers

CAS
1193-18-6
PubChem CID
14511
DTXSID
DTXSID8035186
ChEMBL
CHEMBL3139347
ChEBI
CHEBI:88428
UNII
786Y352V9X
EC Number
214-769-7
Nikkaji
J109.957D

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.967-0.972
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

miscible in water

Miscible at room temperature (in ethanol)

Boiling Point199-200 °C

Physicochemical properties

Melting point
-21 °C · -21°C
Boiling point
199 · 199-200 °C(lit.)
Density
0.971 g/mL · 0.971 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.494(lit.)
FEMA
3360 · 3360 | 3-METHYL-2-CYCLOHEXEN-1-ONE
FLAVIS Number
7.098 · 07.098 | 3-Methylcyclohex-2-en-1-one

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 83.7% (236 of 282) of all reports.

Warning

H302 (16.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 282 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: 2-Cyclohexen-1-one, 3-methyl-

Regulation (EC) No 1334/2008 (amended)

2-Cyclohexen-1-one, 3-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (16.3%)

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
GW7340000
hs_code
29142990

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 2 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2-Cyclohexen-1-one, 3-methyl-: ACTIVE
Applications · 4 items

DescriptionMay 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.

OccurrenceReported 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

Uses3-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.

Uses3-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 methods

PreparationBy 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.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes

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

Related reactions

21 records
New reaction record

Compound notes

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