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Aromatic Aldols and 1,5-diketones as Optimized Fragrance Photocages

Axel G Griesbeck, Olga Hinze, Helmut Görner, Ursula Huchel, Christian Kropf, Uta Sundermeier, Thomas Gerke

Photochem Photobiol Sci. 2012 Mar;11(3):587-92.

PMID: 22322868

Abstract:

Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a-d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP57378684 δ-Damascone δ-Damascone 57378-68-4 Price
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