Ketoisophorone
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Hodoodo CAT#: H558354

CAS#: 1125-21-9

Description: Ketoisophorone is a prochiral compound and a major component of saffron spice. It is a cyclic olefin.


Chemical Structure

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Ketoisophorone
CAS# 1125-21-9

Theoretical Analysis

Hodoodo Cat#: H558354
Name: Ketoisophorone
CAS#: 1125-21-9
Chemical Formula: C9H12O2
Exact Mass: 152.08
Molecular Weight: 152.190
Elemental Analysis: C, 71.03; H, 7.95; O, 21.02

Price and Availability

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5g USD 250 2 Weeks
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Synonym: Ketoisophorone; Keto isophorone; Oxopholone; Oxophorone; 6-Oxoisophorone;

IUPAC/Chemical Name: 2,6,6-Trimethylcyclohex-2-ene-1,4-dione

InChi Key: AYJXHIDNNLJQDT-UHFFFAOYSA-N

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

SMILES Code: O=C1C(C)=CC(CC1(C)C)=O

Appearance: Low MP Solid or Liquid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 152.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hegazy ME, Hirata T, Abdel-Lateff A, el-Razek MH, Mohamed Ael-H, Hassan NM, Paré PW, Mahmoud AA. Ketoisophorone transformation by Marchantia polymorpha and Nicotiana tabacum cultured cells. Z Naturforsch C. 2008 May-Jun;63(5-6):403-8. PubMed PMID: 18669027.

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4: Kataoka M, Kotaka A, Hasegawa A, Wada M, Yoshizumi A, Nakamori S, Shimizu S. Old Yellow Enzyme from Candida macedoniensis catalyzes the stereospecific reduction of the C=C bond of ketoisophorone. Biosci Biotechnol Biochem. 2002 Dec;66(12):2651-7. PubMed PMID: 12596862.

5: Tsuji N, Honda K, Wada M, Okano K, Ohtake H. Isolation and characterization of a thermotolerant ene reductase from Geobacillus sp. 30 and its heterologous expression in Rhodococcus opacus. Appl Microbiol Biotechnol. 2014 Jul;98(13):5925-35. doi: 10.1007/s00253-014-5668-9. Epub 2014 Mar 29. PubMed PMID: 24927695.

6: Daugherty AB, Govindarajan S, Lutz S. Improved biocatalysts from a synthetic circular permutation library of the flavin-dependent oxidoreductase old yellow enzyme. J Am Chem Soc. 2013 Sep 25;135(38):14425-32. doi: 10.1021/ja4074886. Epub 2013 Sep 17. PubMed PMID: 23987134.

7: Amanpour A, Sonmezdag AS, Kelebek H, Selli S. GC-MS-olfactometric characterization of the most aroma-active components in a representative aromatic extract from Iranian saffron (Crocus sativus L.). Food Chem. 2015 Sep 1;182:251-6. doi: 10.1016/j.foodchem.2015.03.005. Epub 2015 Mar 9. PubMed PMID: 25842335.

8: Goretti M, Ponzoni C, Caselli E, Marchegiani E, Cramarossa MR, Turchetti B, Forti L, Buzzini P. Bioreduction of α,β-unsaturated ketones and aldehydes by non-conventional yeast (NCY) whole-cells. Bioresour Technol. 2011 Mar;102(5):3993-8. doi: 10.1016/j.biortech.2010.12.062. Epub 2010 Dec 22. PubMed PMID: 21232941.

9: Fu Y, Castiglione K, Weuster-Botz D. Comparative characterization of novel ene-reductases from cyanobacteria. Biotechnol Bioeng. 2013 May;110(5):1293-301. doi: 10.1002/bit.24817. Epub 2013 Jan 21. PubMed PMID: 23280373.

10: Raimondi S, Romano D, Amaretti A, Molinari F, Rossi M. Enoate reductases from non conventional yeasts: bioconversion, cloning, and functional expression in Saccharomyces cerevisiae. J Biotechnol. 2011 Dec 20;156(4):279-85. doi: 10.1016/j.jbiotec.2011.08.033. Epub 2011 Sep 16. PubMed PMID: 21933690.

11: Reich S, Kress N, Nestl BM, Hauer B. Variations in the stability of NCR ene reductase by rational enzyme loop modulation. J Struct Biol. 2014 Feb;185(2):228-33. doi: 10.1016/j.jsb.2013.04.004. Epub 2013 Apr 17. PubMed PMID: 23602815.

12: Fawaz EY, Allan SA, Bernier UR, Obenauer PJ, Diclaro JW 2nd. Swarming mechanisms in the yellow fever mosquito: aggregation pheromones are involved in the mating behavior of Aedes aegypti. J Vector Ecol. 2014 Dec;39(2):347-54. doi: 10.1111/jvec.12110. PubMed PMID: 25424264.

13: Lechtenberg M, Schepmann D, Niehues M, Hellenbrand N, Wünsch B, Hensel A. Quality and functionality of saffron: quality control, species assortment and affinity of extract and isolated saffron compounds to NMDA and sigma1 (sigma-1) receptors. Planta Med. 2008 Jun;74(7):764-72. doi: 10.1055/s-2008-1074535. Epub 2008 May 21. PubMed PMID: 18496783.

14: Zhang B, Zheng L, Lin J, Wei D. Characterization of an ene-reductase from Meyerozyma guilliermondii for asymmetric bioreduction of α,β-unsaturated compounds. Biotechnol Lett. 2016 Sep;38(9):1527-34. doi: 10.1007/s10529-016-2124-1. Epub 2016 May 19. PubMed PMID: 27193896.

15: Jerković I, Tuberoso CI, Gugić M, Bubalo D. Composition of sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds. Molecules. 2010 Sep 9;15(9):6375-85. doi: 10.3390/molecules15096375. Erratum in: Molecules. 2013 ;18(11):13434. Tuberso, Carlo I G [corrected to Tuberoso, Carlo I G]. PubMed PMID: 20877229.

16: Romano D, Contente ML, Molinari F, Eberini I, Ruvutuso E, Sensi C, Amaretti A, Rossi M, Raimondi S. Recombinant S. cerevisiae expressing Old Yellow Enzymes from non-conventional yeasts: an easy system for selective reduction of activated alkenes. Microb Cell Fact. 2014 Apr 25;13:60. doi: 10.1186/1475-2859-13-60. PubMed PMID: 24767246; PubMed Central PMCID: PMC4013436.

17: Chen K, Sun Y, Wang C, Yao J, Chen Z, Li H. Aerobic oxidation of β-isophorone catalyzed by N-hydroxyphthalimide: the key features and mechanism elucidated. Phys Chem Chem Phys. 2012 Sep 21;14(35):12141-6. doi: 10.1039/c2cp41617d. Epub 2012 Jul 31. PubMed PMID: 22850899.

18: Jerković I, Mastelić J, Marijanović Z. A variety of volatile compounds as markers in unifloral honey from dalmatian sage (Salvia officinalis L.). Chem Biodivers. 2006 Dec;3(12):1307-16. PubMed PMID: 17193245.

19: Aliakbarzadeh G, Sereshti H, Parastar H. Pattern recognition analysis of chromatographic fingerprints of Crocus sativus L. secondary metabolites towards source identification and quality control. Anal Bioanal Chem. 2016 May;408(12):3295-307. doi: 10.1007/s00216-016-9400-8. Epub 2016 Feb 27. PubMed PMID: 26922339.

20: Richter N, Gröger H, Hummel W. Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans. Appl Microbiol Biotechnol. 2011 Jan;89(1):79-89. doi: 10.1007/s00253-010-2793-y. Epub 2010 Aug 18. PubMed PMID: 20717668.