Benzyl Alcohol and β‐Phenethyl Alcohol

Mookherjee, Braja D.; Wilson, Richard A.

doi:10.1002/0471238961.0205142613151511.a01

Cited by 4 publications

(3 citation statements)

References 27 publications

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“…Relatively less is known about the roles that phenethyl alcohol, hexanal, and 4-ethyl phenol have on burying beetle behavior. Phenethyl alcohol could potentially have an important role driving gravid female avoidance of aged carcasses, as it has been shown to be an effective repellent in other invertebrate systems as well [ 47 , 48 ]. Interestingly, 4-ethyl phenol is an attractant and oviposition stimulant in other insect systems [ 49 ].…”

Section: Discussionmentioning

confidence: 99%

Olfactory Choice for Decomposition Stage in the Burying Beetle Nicrophorus vespilloides: Preference or Aversion?

Delclós

Bouldin

Tomberlin

2020

Insects

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Sensory cues predicting resource quality are drivers of key animal behaviors such as preference or aversion. Despite the abundance of behavioral choice studies across the animal kingdom, relatively few studies have tested whether these decisions are driven by preference for one choice or aversion to another. In the burying beetle Nicrophorus vespilloides, adult pairs exhibit parental care to raise their offspring on a small carrion resource. We tested whether carrion decomposition stage affected brood quantity and quality and found that mating pairs had significantly more offspring on fresher carcasses. To determine whether this observed reproductive benefit correlates with maternal preference behavior, we conducted a series of olfactory trials testing mated female preferences for mouse carcasses of differing decomposition stages. When given the option between fresh and older carcasses, females associated significantly more with fresher, 1-day old carcasses. However, this behavior may be driven by aversion, as females that were given a choice between the 7-day old carcass and a blank control spent significantly more time in the control chamber. We characterized volatile organic compound profiles of both carcass types, highlighting unique compounds that may serve as public information (sensu lato) conveying resource quality information to gravid beetles.

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Section: Discussionmentioning

confidence: 99%

Olfactory Choice for Decomposition Stage in the Burying Beetle Nicrophorus vespilloides: Preference or Aversion?

Delclós

Bouldin

Tomberlin

2020

Insects

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“…2-PE is a valuable ingredient in the cosmetic and perfume industries [10] and it is also used as the substrate for the synthesis of additives and preservatives in the food industry and the pharmaceutical sector [11,12]. Although 2-PE can be extracted from certain flowers, the majority of 2-PE is chemically synthesized [13,14] in processes that use toxic solvents and catalysts, aggressive reaction conditions, which yield high amounts of undesirable sideproducts which decrease the quality of the resulting 2-PE.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of fragrance 2-phenylethanol from sugars by Pseudomonas putida

Godoy,

Udaondo,

Duque

et al. 2024

Biotechnol Biofuels

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Background Petrochemicals contribute to environmental issues, with concerns ranging from energy consumption and carbon emission to pollution. In contrast, microbial biorefineries offer eco-friendly alternatives. The solvent-tolerant Pseudomonasputida DOT-T1E serves as a suitable host for producing aromatic compounds, specifically l-phenylalanine and its derivative, 2-phenylethanol (2-PE), which find widespread applications in various industries. Results This study focuses on enhancing 2-PE production in two l-phenylalanine overproducing strains of DOT-T1E, namely CM12-5 and CM12-5Δgcd (xylABE), which grow with glucose and glucose-xylose, respectively. To synthesize 2-PE from l-phenylalanine, these strains were transformed with plasmid pPE-1, bearing the Ehrlich pathway genes, and it was found higher 2-PE production with glucose (about 50–60 ppm) than with xylose (< 3 ppm). To understand the limiting factors, we tested the addition of phenylalanine and intermediates from the Ehrlich and shikimate pathways. The results identified intracellular l-phenylalanine as a key limiting factor for 2-PE production. To overcame this limitation, a chorismate mutase/prephenate dehydratase variant—insentive to feedback inhibition by aromatic amino acids—was introduced in the producing strains. This led to increased l-phenylalanine production and subsequently produced more 2-PE (100 ppm). Random mutagenesis of the strains also produced strains with higher l-phenylalanine titers and increased 2-PE production (up to 120 ppm). The improvements resulted from preventing dead-end product accumulation from shikimate and limiting the catabolism of potential pathway intermediates in the Ehrlich pathway. The study explored agricultural waste substrates, such as corn stover, sugarcane straw and corn-syrup as potential C sources. The best results were obtained using 2G substrates at 3% (between 82 and 100 ppm 2-PE), with glucose being the preferred sugar for 2-PE production among the monomeric sugars in these substrates. Conclusions The findings of this study offer strategies to enhance phenylalanine production, a key substrate for the synthesis of aromatic compounds. The ability of P.putida DOT-T1E to thrive with various C-sources and its tolerance to substrates, products, and potential toxicants in industrial wastes, are highlighted. The study identified and overcome possible bottlenecks for 2-PE production. Ultimately, the strains have potential to become efficient microbial platforms for synthesizing 2-PE from agro-industrial waste materials.

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“…2-Phenylethanol (2-PE), whose chemical structure is presented in figure 1, is a colorless liquid possessing a faint but lasting rose petal odor, and occurs naturally in the essential oils of many flowers and plants, such as hyacinths, jasmines, narcissi and lilies (1). The rose fragrance is highly desired, making 2-PE one of the most commercially used fragrance chemicals in perfumes, soaps, and detergents (2).…”

Section: Introductionmentioning

confidence: 99%

PRODUCTION OF 2-PHENYLETHANOL IN THE BIOTRANSFORMATION OF CINNAMYL ALCOHOL BY THE PLANT PATHOGENIC FUNGUS <I>Colletotrichum acutatum</I>

et al. 2010

Vitae

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Biocatalytic processes may offer a cheaper alternative to natural production of flavours. The biotransformation of cinnamyl alcohol is investigated using the plant pathogenic fungus Colletotrichum acutatum as a biocatalyst. Results show that substrate is converted to 3-phenyl-1-propanol, 1-phenyl-1,3- propanediol, 2-phenylethanol, 1-phenyl-1,2-ethanediol, 3-phenyl propyl acetate, and hydrocinnamic acid. The structures of the metabolic products are elucidated on the basis of their spectral data. 2-phenylethanol has a sweet, floral odor and a wide variety of applications, especially, for the perfume and food industries. A time-course experiment demonstrates that 2-phenylethanol appeared after 120 hours, reaching almost 8% of relative abundance. Additionally, the influence that the culture broth has on the conversion capacity is investigated. It has been discovered that cinnamyl alcohol is converted faster when the substrate is incorporated in a Sabouraud medium; under this condition, 2-phenylethanol is the most common product after 288 hours reaching about 90% of the relative abundance. Biotransformation of cinnamyl alcohol using C. acutatum in a Sabouraud medium can offer a simple and efficient way to obtain 2-phenylethanol with high yield.

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Benzyl Alcohol and β‐Phenethyl Alcohol

Cited by 4 publications

References 27 publications

Olfactory Choice for Decomposition Stage in the Burying Beetle Nicrophorus vespilloides: Preference or Aversion?

Olfactory Choice for Decomposition Stage in the Burying Beetle Nicrophorus vespilloides: Preference or Aversion?

Biosynthesis of fragrance 2-phenylethanol from sugars by Pseudomonas putida

PRODUCTION OF 2-PHENYLETHANOL IN THE BIOTRANSFORMATION OF CINNAMYL ALCOHOL BY THE PLANT PATHOGENIC FUNGUS <I>Colletotrichum acutatum</I>

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