Higher Straight-Chain Aliphatic Aldehydes: Importance as Odor-Active Volatiles in Human Foods and Issues for Future Research

Tsuzuki, Satoshi

doi:10.1021/acs.jafc.9b01131

Cited by 27 publications

(19 citation statements)

References 36 publications

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“…Yet, many challenges obstruct the different biocatalytic paths that can be envisioned, especially for the water insoluble and poorly reactive unactivated long chain aliphatic alcohols 9,10 . Amongst the broad class of aldehydes, long chain aliphatic aldehydes from C6 to C13 [11][12][13] are of main importance for the flavor and fragrance industry. Indeed, such aldehydes have been identified as one of the most prominent classes of "key food odorants" 11 , and are also major fragrance ingredients, used in quasi-all types of perfumes 6 .…”

Section: Introductionmentioning

confidence: 99%

“…Amongst the broad class of aldehydes, long chain aliphatic aldehydes from C6 to C13 [11][12][13] are of main importance for the flavor and fragrance industry. Indeed, such aldehydes have been identified as one of the most prominent classes of "key food odorants" 11 , and are also major fragrance ingredients, used in quasi-all types of perfumes 6 . Typically, long chain aliphatic aldehydes provide green, fruity, fresh, citrus-like, fatty, or the so-called aldehydic notes 14,15 .…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive Insights into the Production of Long Chain Aliphatic Aldehydes Using a Copper-Radical Alcohol Oxidase as Biocatalyst

Ribeaucourt

Bissaro

Guallar

et al. 2021

ACS Sustainable Chem. Eng.

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The oxidation of alcohols is a cornerstone reaction in chemistry, notably in the flavors and fragrances industry where long chain aliphatic aldehydes are major odorant compounds. In a context where greener alternatives are sought after, biocatalysis holds many promises. Here, we investigated the ability of the alcohol oxidase from Colletotrichum graminicola (CgrAlcOx) -an organic cofactor-free enzyme belonging to the copper-radical oxidases (CROs) class -to convert industrially-relevant long chain aliphatic alcohols. CgrAlcOx is a competent catalyst for the conversion of octan-1-ol, when supported by the accessory enzymes peroxidase and catalase. Detailed examination of the products revealed the occurrence of an overoxidation step leading to the production of carboxylic acid for some aliphatic aldehydes and benzaldehyde derivatives. The partition between aldehyde and acid products varied upon substrate properties (chain length and propensity to form geminal-diols), enzyme specificity, and could be tuned by controlling the reaction conditions. In silico analyses suggested an inhibitory binding mode of long chain aliphatic geminal-diols and a substrate-induced fit mechanism for a benzyl alcohol-derivative. By demonstrating their natural ability to perform long chain aliphatic alcohol oxidation, the present study establishes the potential of fungal CRO-AlcOx as promising candidates for the green production of flavors and fragrances compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comprehensive Insights into the Production of Long Chain Aliphatic Aldehydes Using a Copper-Radical Alcohol Oxidase as Biocatalyst

Ribeaucourt

Bissaro

Guallar

et al. 2021

ACS Sustainable Chem. Eng.

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“…Straight-chain aliphatic aldehydes were the most abundant ones, being present at 33.3% and 19.9% in Malaysian and Indonesian fruits, respectively. They likely serve as important food odorants in tropical grown A. carambola fruit [53]. Nonanal, the major straight-chain aliphatic aldehyde [54], was detected in all fruits at 13.8-33.5%.…”

Section: Aldehydesmentioning

confidence: 94%

Nutrient and Sensory Metabolites Profiling of Averrhoa Carambola L. (Starfruit) in the Context of Its Origin and Ripening Stage by GC/MS and Chemometric Analysis

et al. 2020

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Averrhoa carambola L. is a tropical tree with edible fruit that grows at different climatic conditions. Despite its nutritive value and reported health benefits, it is a controversial fruit owing to its rich oxalate content. The present study aimed at investigating aroma and nutrient primary metabolites distribution in A. carambola fruits grown in Indonesia, Malaysia (its endemic origin) versus Egypt, and at different ripening stages. Two techniques were employed to assess volatile and non-volatile metabolites including headspace solid-phase micro-extraction (HS-SPME) joined with gas chromatography coupled with mass-spectrometry (GC-MS) and GC-MS post silylation, respectively. Twenty-four volatiles were detected, with esters amounting for the major class of volatiles in Egyptian fruit at ca. 66%, with methyl caproate as the major component, distinguishing it from other origins. In contrast, aldehydes predominated tropically grown fruits with the ether myristicin found exclusively in these. Primary metabolites profiling led to the identification of 117 metabolites viz. sugars, polyols and organic acids. Fructose (38–48%) and glucose (21–25%) predominated sugar compositions in ripe fruits, whereas sorbitol was the major sugar alcohol (2.4–10.5%) in ripe fruits as well. Oxalic acid, an anti-nutrient with potential health risks, was the major organic acid detected in all the studied fruits (1.7–2.7%), except the Malaysian one (0.07%). It increases upon fruit ripening, including considerable amounts of volatile oxalate esters detected via SPME, and which must not be omitted in total oxalate determinations for safety assessments.

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“…Aldehydes are responsible for the attractive smell of many fruits and flowers like lavender [24,25,26], and are present in many highly appreciated foods [27]. One aldehyde in particular, hexanal, was previously found to increase interpersonal trust between humans [6].…”

Section: Introductionmentioning

confidence: 99%

No effect of the smell of hexanal on trust in human-robot interaction

Croijmans¹,

Erp²,

Bakker³

et al. 2022

Preprint

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The level of interpersonal trust among people is partially determined through the sense of smell. Hexanal, a molecule which smell resembles freshly cut grass, can increase trust in people. Here, we ask the question if smell can be leveraged to facilitate human-robot interaction and test whether hexanal also increases the level of trust during collaboration with a social robot. In a preregistered double-blind, placebo-controlled study, we tested if trial-by-trial and general trust during perceptual decision making in collaboration with a social robot is affected by hexanal across two samples (n = 46 and n = 44). It was hypothesized that unmasked hexanal and hexanal masked by eugenol, a molecule with a smell resembling clove, would increase the level of trust in human-robot interaction, compared to eugenol alone or a control condition consisting of only the neutral smelling solvent propylene glycol. Contrasting previous findings in human interaction, no significant effect of unmasked or eugenol-masked hexanal on trust in robots was observed. These findings indicate that the conscious or nonconscious impact of smell on trust might not generalise to interactions with social robots. One explanation could be category- and context-dependency of smell leading to a mismatch between the natural smell of hexanal, a smell also occurring in human sweat, and the mechanical physical or mental representation of the robot.

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Higher Straight-Chain Aliphatic Aldehydes: Importance as Odor-Active Volatiles in Human Foods and Issues for Future Research

Cited by 27 publications

References 36 publications

Comprehensive Insights into the Production of Long Chain Aliphatic Aldehydes Using a Copper-Radical Alcohol Oxidase as Biocatalyst

Comprehensive Insights into the Production of Long Chain Aliphatic Aldehydes Using a Copper-Radical Alcohol Oxidase as Biocatalyst

Nutrient and Sensory Metabolites Profiling of Averrhoa Carambola L. (Starfruit) in the Context of Its Origin and Ripening Stage by GC/MS and Chemometric Analysis

No effect of the smell of hexanal on trust in human-robot interaction

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