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Merck

329517

2,6,6-Trimethyl-2-cyclohexene-1,4-dione

98%

Synonym(s):

4-Oxoisophorone, Ketoisophorone

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About This Item

Empirical Formula (Hill Notation):
C9H12O2
CAS Number:
1125-21-9
Molecular Weight:
152.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24859797
EC Number:
214-406-2
Beilstein/REAXYS Number:
2207030
MDL number:
MFCD00043119

Key Documents

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Product Name

2,6,6-Trimethyl-2-cyclohexene-1,4-dione, 98%

InChI key

AYJXHIDNNLJQDT-UHFFFAOYSA-N

InChI

1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3

SMILES string

CC1=CC(=O)CC(C)(C)C1=O

assay

98%

form

solid

refractive index

n20/D 1.491 (lit.)

bp

222 °C (lit.)
92-94 °C/11 mmHg (lit.)

mp

26-28 °C (lit.)

functional group

ketone

Quality Level

100

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1 of 4

This Item
264679W34210616797
2,6,6-Trimethyl-2-cyclohexene-1,4-dione 98%

Sigma-Aldrich

329517

2,6,6-Trimethyl-2-cyclohexene-1,4-dione

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde technical grade, 80%

Sigma-Aldrich

264679

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

4-Oxoisophorone ≥98%, FG

Sigma-Aldrich

W342106

4-Oxoisophorone

3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one analytical standard

Supelco

16797

3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one

assay

98%

assay

80%

assay

≥98%

assay

≥90.0% (GC)

Quality Level

100

Quality Level

100

Quality Level

400

Quality Level

100

mp

26-28 °C (lit.)

mp

-

mp

26-28 °C (lit.)

mp

-

form

solid

form

liquid

form

-

form

-

bp

222 °C (lit.)

bp

58-59 °C/0.4 mmHg (lit.)

bp

222 °C (lit.), 92-94 °C/11 mmHg (lit.)

bp

-

refractive index

n20/D 1.491 (lit.)

refractive index

n20/D 1.485 (lit.)

refractive index

n20/D 1.491 (lit.)

refractive index

n20/D 1.495-1.505

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4510
STBL2642
STBJ2519
STBH8492
S56137V

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Description of volatile compounds generated by the degradation of carotenoids in paprika, tomato and marigold oleoresins.
Rios JJ, et al.
Food Chemistry, 106(3), 1145-1153 (2008)
Worldwide market screening of saffron volatile composition.
Maggi L, et al.
Journal of the Science of Food and Agriculture, 89(11), 1950-1954 (2011)
Mohamed-Elamir F Hegazy et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 63(5-6), 403-408 (2008-08-02)
Stereospecific olefin (C=C) and carbonyl (C=O) reduction of the readily available prochiral compound ketoisophorone (2,2,6-trimethyl-2-cyclohexene-1,4-dione) (1) by Marchantia polymorpha and Nicotiana tabacum cell suspension cultures produce the chiral products (6R)-levodione (2), (4R,5S)-4-hydroxy-3,3,5-trimethylcyclohexanone (3), and (4R,6R)-actinol (4) as well as the
Stefano Raimondi et al.
Journal of biotechnology, 156(4), 279-285 (2011-09-22)
Old yellow enzymes (OYEs, EC 1.6.99.1) are flavin-dependent oxidoreductases that catalyze the stereoselective trans-hydrogenation of the double bond, representing a promising alternative to metal-based catalysis. Bioconversion of ketoisophorone (KIP) by 28 non-conventional yeasts belonging to 16 different species was investigated.
Matthias Lechtenberg et al.
Planta medica, 74(7), 764-772 (2008-05-23)
Extracts from saffron, the dried stigmata from Crocus sativus L., are being used more and more in preclinical and clinical trials for the treatment of cancer and depression. Because of the known quality problems of saffron, HPLC methods on RP(18)
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