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329517

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

Name: 2,6,6-Trimethyl-2-cyclohexene-1,4-dione
Brand: ALDRICH

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

Beilstein:

2207030

EC Number:

214-406-2

MDL number:

MFCD00043119

UNSPSC Code:

12352100

PubChem Substance ID:

24859797

NACRES:

NA.22

Quality Level

100

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.)

SMILES string

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

InChI

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

InChI key

AYJXHIDNNLJQDT-UHFFFAOYSA-N

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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. It is a cyclic olefin and was reported as a product of the thermal degradation of β-carotene in aqueous suspension.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280 - P302 + P352

Hazard Classifications

Skin Sens. 1

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Worldwide market screening of saffron volatile composition.

Maggi L, et al.

Journal of the Science of Food and Agriculture, 89(11), 1950-1954 (2011)

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)

Ketoisophorone transformation by Marchantia polymorpha and Nicotiana tabacum cultured cells.

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

Enoate reductases from non conventional yeasts: bioconversion, cloning, and functional expression in Saccharomyces cerevisiae.

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.

Bioreduction of α,β-unsaturated ketones and aldehydes by non-conventional yeast (NCY) whole-cells.

Marta Goretti et al.

Bioresource technology, 102(5), 3993-3998 (2011-01-15)

The bioreduction of α,β-unsaturated ketones (ketoisophorone, 2-methyl- and 3-methyl-cyclopentenone) and aldehydes [(S)-(-)-perillaldehyde and α-methyl-cinnamaldehyde] by 23 "non-conventional" yeasts (NCYs) belonging to 21 species of the genera Candida, Cryptococcus, Debaryomyces, Hanseniaspora, Kazachstania, Kluyveromyces, Lindnera, Nakaseomyces, Vanderwaltozyma, and Wickerhamomyces was reported. The

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