Fragrance material review on cinnamyl alcohol

Letizia, C.S.; Cocchiara, J.; Lalko, J.; Lapczynski, A.; Api, A.M.

doi:10.1016/j.fct.2004.09.012

Cited by 35 publications

(29 citation statements)

References 96 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, Ca possessed antioxidant, anti-inflammatory and anticancer properties [4–6]. Cal is a fragrance ingredient, which is used in cosmetics, shampoos, soaps and other toiletries [7]. Cin exhibited antifungal, antipyretic, antioxidant, antimicrobial and larvicidal activities [8–10], as well as modulating T-cell differentiation [11].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of Cinnamomum cassia Constituents and Effects of Pifithrin‐Alpha on Their Apoptotic Signaling Pathways in Hep G2 Cells

2011

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

Cinnamaldehyde (Cin), cinnamic acid (Ca) and cinnamyl alcohol (Cal), major constituents of Cinnamomum cassia, have been shown to possess antioxidant, anti-inflammatory, anticancer and other activities. In this study, our aim was to evaluate the antiproliferative activity of these compounds in human hepatoma Hep G2 cells and examine the effects of pifithrin-alpha (PFTα; a specific p53 inhibitor) on their apoptotic signaling transduction mechanism. The antiproliferative activity was measured by XTT assay. Expression of apoptosis-related proteins was detected by western blotting. Results showed that at a concentration of 30 μM, the order of antiproliferative activity in Hep G2 cells was Cin > Ca > Cal. Cin (IC50 9.76 ± 0.67 μM) demonstrated an antiproliferative potency as good as 5-fluorouracil (an anti-cancer drug; IC50 9.57 ± 0.61 μM). Further studies on apoptotic mechanisms of Cin showed that it downregulated the expression of Bcl-XL, upregulated CD95 (APO-1), p53 and Bax proteins, as well as cleaving the poly (ADP-ribose) polymerase (PARP) in a time-dependent pattern. PFTα pre-incubation significantly diminished the effect of Cin-induced apoptosis. It markedly upregulated the anti-apoptotic (Bcl-XL) expression and downregulated the pro-apoptotic (Bax) expression, as well as effectively blocking the CD95 (APO-1) and p53 expression, and PARP cleavage in Cin-treated cells. This study indicates that Cin was the most potent antiproliferative constituent of C. cassia, and its apoptotic mechanism in Hep G2 cells could be mediated through the p53 induction and CD95 (APO-1) signaling pathways.

show abstract

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of Cinnamomum cassia Constituents and Effects of Pifithrin‐Alpha on Their Apoptotic Signaling Pathways in Hep G2 Cells

2011

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

show abstract

“…Some fragrances are not electrophilic and protein‐reactive themselves; they need to be activated first, either via autoxidation (prehapten) or bioactivation (prohapten) (5). The toxicological and dermatological properties of cinnamyl alcohol have been extensively reviewed (6). As cinnamyl alcohol lacks structural alerts for protein reactivity, it has been shown to act as a prohapten by forming the hapten cinnamal via metabolic oxidation in the skin (7, 8).…”

mentioning

confidence: 99%

Cinnamyl alcohol oxidizes rapidly upon air exposure

et al. 2013

View full text Add to dashboard Cite

show abstract

“…9 The liquid phase, selective hydrogenation of cinnamaldehyde (CinnALD) to cinnamyl alcohol (CinnOH) illustrated in Scheme 1 is of significant interest due to the widespread use of this allylic alcohol in perfumes and flavourants. [16][17][18][19] Platinum is a promising catalyst for this challenging reaction, in which hydrogenation of the C=C bond is both kinetically and thermodynamically more favourable than the C=O function, 20 and hence the influence of the physicochemical properties of platinum nanoparticles is a topic of much intensive recent investigation in batch reactors. Particle size effects upon CinnOH selectivity have proved controversial, with oleic acid/oleylamine stabilised mono-and bimetallic colloidal Pt nanoparticles reported to exhibit a strong size dependence of CinnOH selectivity, with low coordination sites favoring C=C hydrogenation, 21, 22 whereas Zhu and Zaera reported that CinnOH selectivity was insensitive to the size of silica supported Pt nanoparticles albeit over a narrow size range.…”

mentioning

confidence: 99%

Platinum-catalysed cinnamaldehyde hydrogenation in continuous flow

2015

View full text Add to dashboard Cite

Platinum is one of the most widely used hydrogenation catalysts. Here we describe the translation of batch reactions to continuous flow, affording tunable C=O versus C=C hydrogenation over a Pt/SiO2 catalyst, resulting in high steady state activity and singlepass yields in the selective hydrogenation of cinnamaldehyde to cinnamyl alcohol under mild conditions. Negligible catalyst deactivation occurs under extended flow operation due to removal of reactively-formed poisons from the reaction zone. Process intensification imparts a four-fold enhancement in cinnamyl alcohol productivity.Chemoselectivity underpins 21 st century catalysis, 1, 2 permitting the targeted modification of specific functional groups within complex starting materials, 3-7 notably from biomass-derived feedstocks. 8 Catalytic hydrogenation of organic compounds possessing multiple unsaturated bonds such as α,β-unsaturated aldehydes is particularly challenging, 9-11 necessitating active sites able to discriminate and preferentially activate closely related moieties. Platinum is widely employed in heterogeneously catalysed hydrogenation of diverse functional groups including C=C, 12 C≡C, 13 C=O, 13 C≡N, 14 NO2 15 and aromatics. 15 The selective hydrogenation of allylic and benzylic aldehydes to unsaturated alcohols is a commercially important industrial process within the flavour, fragrance, agrochemical and pharmaceutical sectors, 9, 16 in which active and selective heterogeneous catalysts for such transformations are essential to circumvent the greater thermodynamic stability of C=O relative to C=C bonds. 9 The liquid phase, selective hydrogenation of cinnamaldehyde (CinnALD) to cinnamyl alcohol (CinnOH) illustrated in Scheme 1 is of significant interest due to the widespread use of this allylic alcohol in perfumes and flavourants. [16][17][18][19] Platinum is a promising catalyst for this challenging reaction, in which hydrogenation of the C=C bond is both kinetically and thermodynamically more favourable than the C=O function, 20 and hence the influence of the physicochemical properties of platinum nanoparticles is a topic of much intensive recent investigation in batch reactors. Particle size effects upon CinnOH selectivity have proved controversial, with oleic acid/oleylamine stabilised mono-and bimetallic colloidal Pt nanoparticles reported to exhibit a strong size dependence of CinnOH selectivity, with low coordination sites favoring C=C hydrogenation, 21, 22 whereas Zhu and Zaera reported that CinnOH selectivity was insensitive to the size of silica supported Pt nanoparticles albeit over a narrow size range. 23 Guo et al have shown that confinement of Pt nanoclusters within the cavity of metal-organic frameworks also promotes CinnOH selectivity; with steric constraints on CinnALD believed to hinder C=C planar adsorption with consequent preferential C=O activation. 24 Kinetics of CinnALD hydrogenation are also a function of support properties 25 and hydrogenation pressure. We recently reported a detailed mechanistic study of the structura...

show abstract

Fragrance material review on cinnamyl alcohol

Cited by 35 publications

References 96 publications

Antiproliferative Activity of Cinnamomum cassia Constituents and Effects of Pifithrin‐Alpha on Their Apoptotic Signaling Pathways in Hep G2 Cells

Antiproliferative Activity of Cinnamomum cassia Constituents and Effects of Pifithrin‐Alpha on Their Apoptotic Signaling Pathways in Hep G2 Cells

Cinnamyl alcohol oxidizes rapidly upon air exposure

Platinum-catalysed cinnamaldehyde hydrogenation in continuous flow

Contact Info

Product

Resources

About