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Chemical Compound Review:

SureCN112671 4-(2,6,6-trimethyl-1- cyclohex-2-enyl)but-3...

Synonyms: AG-F-01237, AG-F-78314, ANW-73126, AC1L2NLN, CTK4G5578, ...

Lutz-Wahl, S. et al., Hartman, D.A. et al., Mahattanatawee, K. et al., Jung, D.M. et al., Tang, Y.X. et al., et al.

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Disease relevance of ALPHA-IONONE

A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate beta- and/or alpha-ionone to the respective 3-hydroxy derivatives [1].

High impact information on ALPHA-IONONE

Stereo- and regioselective hydroxylation of alpha-ionone by Streptomyces strains [1].
Four norisoprenoids, alpha-ionone, beta-ionone, beta-cyclocitral, and beta-damascenone, along with their putative carotenoid precursors, were identified in Valencia orange juice using time-intensity GC-O, GC-MS, and photodiode array HPLC. alpha-Ionone and beta-cyclocitral are reported in orange juice for the first time [2].
The greatest binding affinity occurred at pH 9 and the lowest at pH 11. alpha-Ionone showed binding evidence only at pH 9, and the binding was significantly weaker than that obtained for beta-ionone at the same pH [3].
Immobilized cells of Nicotiana tabacum reduced the carbon-carbon double bond adjacent to the carbonyl group and then the carbonyl group itself of the dienone compounds, alpha-ionone and beta-ionone [4].
Models of retinoid metabolism: microbial biotransformation of alpha-ionone and beta-ionone [5].

Biological context of ALPHA-IONONE

Hydroxylation of racemic alpha-ionone [(6R)-(-)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S, 6S)-hydroxy-alpha-ionone [1].

Associations of ALPHA-IONONE with other chemical compounds

In this study two fungi, Aspergillus niger ATCC 16888 and Cunninghamella blakesleeana ATCC 8688a, were found to biotransform beta-ionone [2] and alpha-ionone [8] and may serve as models for the mammalian metabolism of retinoic acids [5].

Analytical, diagnostic and therapeutic context of ALPHA-IONONE

Enantiomer separation of alpha-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases [6].

References

Stereo- and regioselective hydroxylation of alpha-ionone by Streptomyces strains. Lutz-Wahl, S., Fischer, P., Schmidt-Dannert, C., Wohlleben, W., Hauer, B., Schmid, R.D. Appl. Environ. Microbiol. (1998) [Pubmed]
Identification and aroma impact of norisoprenoids in orange juice. Mahattanatawee, K., Rouseff, R., Valim, M.F., Naim, M. J. Agric. Food Chem. (2005) [Pubmed]
Investigation of binding behavior of alpha- and beta-ionones to beta-lactoglobulin at different pH values using a diffusion-based NOE pumping technique. Jung, D.M., Ebeler, S.E. J. Agric. Food Chem. (2003) [Pubmed]
Biotransformation of alpha- and beta-ionones by immobilized cells of Nicotiana tabacum. Tang, Y.X., Suga, T. Phytochemistry (1994) [Pubmed]
Models of retinoid metabolism: microbial biotransformation of alpha-ionone and beta-ionone. Hartman, D.A., Pontones, M.E., Kloss, V.F., Curley, R.W., Robertson, L.W. J. Nat. Prod. (1988) [Pubmed]
Enantiomer separation of alpha-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases. Quattrini, F., Biressi, G., Juza, M., Mazzotti, M., Fuganti, C., Morbidelli, M. Journal of chromatography. A. (1999) [Pubmed]

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