2014
DOI: 10.1021/jo500605c
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Synthesis and Characterization of Quantum Dot Nanoparticles Bound to the Plant Volatile Precursor of Hydroxy-apo-10′-carotenal

Abstract: This study is focused on the synthesis and characterization of hydroxy-apo-10'-carotenal/quantum dot (QD) conjugates aiming at the in vivo visualization of β-ionone, a carotenoid-derived volatile compound known for its important contribution to the flavor and aroma of many fruits, vegetables, and plants. The synthesis of nanoparticles bound to plant volatile precursors was achieved via coupling reaction of the QD to C27-aldehyde which was prepared from α-ionone via 12 steps in 2.4% overall yield. The formation… Show more

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Cited by 8 publications
(4 citation statements)
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“…Samples of 3-acetoxy-α-ionone ( 9 ) (2:1 cis / trans mixture), of 4-acetoxy-γ-ionone ( 24 ) (4:1 cis / trans mixture) and of 3-acetoxy-β-ionone ( 19 ) were prepared starting from α-ionone according to the procedure described by Tu [47], by Serra [42] and Khachik [48], respectively. A sample of 3-acetoxy-α-damascone ( 38 ) (1:1 cis / trans mixture) was prepared starting from ethyl 3-hydroxy-α-cyclogeraniate according to the procedure described by Takei [49].…”
Section: Methodsmentioning
confidence: 99%
“…Samples of 3-acetoxy-α-ionone ( 9 ) (2:1 cis / trans mixture), of 4-acetoxy-γ-ionone ( 24 ) (4:1 cis / trans mixture) and of 3-acetoxy-β-ionone ( 19 ) were prepared starting from α-ionone according to the procedure described by Tu [47], by Serra [42] and Khachik [48], respectively. A sample of 3-acetoxy-α-damascone ( 38 ) (1:1 cis / trans mixture) was prepared starting from ethyl 3-hydroxy-α-cyclogeraniate according to the procedure described by Takei [49].…”
Section: Methodsmentioning
confidence: 99%
“…QD systems for drug delivery have allowed real‐time monitoring and localized treatment at specific disease sites, improve stability of drugs, lengthen drug circulation time in vivo (Zhao & Zhu, ) and enhance drug uptake and retention (Al‐Jamal et al., ). QD have been used in plant biology research for in situ hybridization in plant chromosome analysis (Muller et al., ), study of nanoparticle uptake in plants (Al‐Salim et al., ), imaging of plant volatile precursors (Tu et al., ), and investigating the proteomic response of Arabidopsis thaliana (Marmiroli et al., ).…”
Section: Introductionmentioning
confidence: 99%
“…They operate as accessory light-harvesting components (antenna complex) 2, 3 of photosynthetic systems, light induced antioxidants (brought about by the low-lying triplet state poised to quench triplet chlorophyll and singlet oxygen 4 ), membrane fluidity regulators, pigments (yellow to red-orange; important in attracting pollinators) 2 for leaves, vegetables, and fruits. 5 Along with carotenoids being essential in plants, carotenoid-derived products serve as important sources of bioactive compounds called apocarotenoids. 6 Apocarotenoids serve as pigments, hormones (abscisic acid and strigolactones), 7 aroma and scent compounds, regulatory compounds and molecules with yet to be determined functions.…”
Section: Introductionmentioning
confidence: 99%