Ketoisophorone (HCID 62374)

Overview

2,6,6-Trimethyl-2-cyclohexene-1,4-dione is a member of cyclohexenones.

Names & identifiers

Preferred name: Ketoisophorone
IUPAC: 2,6,6-trimethylcyclohex-2-ene-1,4-dione
English name: 2,6,6-Trimethyl-2-cyclohexene-1,4-dione
Molecular formula: C9H12O2
Molecular weight: 152.19

Names & synonyms

Ketoisophorone1125-21-92,6,6-Trimethyl-2-cyclohexene-1,4-dione2,6,6-Trimethylcyclohex-2-ene-1,4-dioneketo-Isophorone2-CYCLOHEXENE-1,4-DIONE, 2,6,6-TRIMETHYL-FEMA No. 3421DTXSID902168572WY3KLB5RDTXCID701685RefChem:83049TMEC-E-D

Show more names

FEMA 3421OXOISOPHORONE4-OXOISOPHORON2,2,6-trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)

214-406-24-Oxoisophorone4-KetoisophoroneOxopholoneOxophorone6-Oxoisophorone4-Oxo-alpha-isophorone3,5,5-Trimethyl-2-cyclohexene-1,4-dione

Database identifiers

CAS: 1125-21-9
PubChem CID: 62374
DTXSID: DTXSID9021685
ChEBI: CHEBI:179251
UNII: 72WY3KLB5R
EC Number: 214-406-2
Nikkaji: J94.748B

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 246

Experimental & physicochemical properties

FragrancesFragrance Ingredient (2,6,6-Trimethylcyclohex-2-ene-1,4-dione) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Flavoring AgentsEU Flavoring substances

Solubility · 3 items

slightly

Slightly soluble in water

Soluble (in ethanol)

Boiling Point92.00 to 94.00 °C. @ 11.00 mm Hg

Melting Point21 °C

Physicochemical properties

Melting point: 26 · 26-28 °C (lit.)
Boiling point: 222 °C · 222 °C (lit.) 92-94 °C/11 mmHg (lit.)
Density: 1.03 · 1.03
refractive index: 20 · n20/D 1.491(lit.)
FEMA: 3421 · 3421 | 2,6,6-TRIMETHYLCYCLOHEX-2-ENE-1,4-DIONE
FLAVIS Number: 7.109 · 07.109 | 2,6,6-Trimethylcyclohex-2-en-1,4-dione
Flash point: 201 °F · 201 °F
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Liquid
color: Pale Yellow to Yellow
Odor: 1 % · at 1.00 % in dipropylene glycol. musty woody sweet tea tobacco leaf
Odor Type: musty
biological source: synthetic
JECFA Number: 1857 · 1857
BRN: 2207030 · 2207030
Major Application: flavors and fragrances
Cosmetics Ingredients Functions: PERFUMING
InChI: 1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
InChIKey: AYJXHIDNNLJQDT-UHFFFAOYSA-N
SMILES: CC1=CC(=O)CC(C)(C)C1=O
LogP: 0.76 · 0.76
CAS DataBase Reference: 1125 · 1125-21-9(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): 2 · 2,6,6-TRIMETHYLCYCLOHEX-2-ENE-1,4-DIONE
FDA UNII: 72 WY3KLB5R · 72WY3KLB5R
NIST Chemistry Reference: 2 · 2,6,6-Trimethyl-2-cyclohexene-1,4-dione(1125-21-9)
EPA Substance Registry System: 2 · 2-Cyclohexene-1,4-dione, 2,6,6-trimethyl- (1125-21-9)
UNSPSC Code: 85151701 · 85151701
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 317 · H317
Precautionary statements: 280 · P280-P302+P352
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn,Xi
Risk Statements: 22 · 22-43-36/37/38
Safety Statements: 26 · 26-36/37-37/39-24/25
RIDADR: 2811 · UN 2811 6.1/PG 3
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29142900 · 29142900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 1 · Skin Sens. 1
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 3.4% (54 of 1568) of reports.

Warning

H302 (85.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1568 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 2-Cyclohexene-1,4-dione, 2,6,6-trimethyl-

Regulation (EC) No 1831/2003 (amended)

Status: Active Update: 29-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/16629

2-Cyclohexene-1,4-dione, 2,6,6-trimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Cyclohexene-1,4-dione, 2,6,6-trimethyl-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (85.3%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk: 3
tsca: TSCA listed
ridadr: UN 2811 6.1/PG 3
hs_code: 29142900
risk_code: 22-43-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,Xi
safety_code: 26-36/37-37/39-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H317
REACH Registrations: Active
Hazard Classifications: Skin Sens. 1
Precautionary statements: P280-P302+P352

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2-Cyclohexene-1,4-dione, 2,6,6-trimethyl-: ACTIVE

Applications · 3 items

OccurrenceReported found among the volatile components in saffron and in cigarette smoke. Also reported found in saffron, cognac, black tea, green tea, microbial fermented tea, lemon balm, cooked shrimp, roasted shrimp, corn oil and lamb’s lettuce.

Uses4-Oxoisophorone is one of the major components of saffron (Crocus sativus L.) and also found to be a product of degradation of carotenoids in paprika, tomato and marigold oleoresins.

General Description2,6,6-Trimethyl-2-cyclohexene-1,4-dione is also known as 4-ketoisophorone and is the major component of saffron spice. It is a cyclic olefin and was reported as a product of the thermal degradation of β-carotene in aqueous suspension.