Cinnamic Acid, Cinnamaldehyde, and Cinnamyl Alcohol

Eilerman, Robert G.; Staff, Updated by

doi:10.1002/0471238961.0309141405091205.a01.pub2

Cited by 8 publications

(7 citation statements)

References 17 publications

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“…CA is well known to oxidize to CAcid by air oxidation ,− (Figure ), and a part of CA is oxidized to epoxy cinnamaldehyde , (Figure ). In fact, when CA is stored at room temperature, CAcid was produced over the time course (Figure ).…”

Section: Discussionmentioning

confidence: 99%

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

Fujita

Yamamoto

Watanabe

et al. 2021

Chem. Res. Toxicol.

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Aldehydes comprise a major portion of skin sensitizers because they can react with both cysteine and lysine. Moreover, cinnamaldehyde (CA) is a typical moderate sensitizer and is often used in an alternative test method for skin sensitization. The amino acid derivative reactivity assay (ADRA) is an in chemico test method that evaluates the reactivity of cysteine derivatives (N-(2-(1naphthyl)acetyl)-L-cysteine, NAC) and lysine derivatives with the test chemicals and uses CA as a proficiency substance. We found that NAC depletion for CA was only 10−20% when CA was used directly from the reagent bottle, although it increased to almost 100% when stored after being aliquoted from the reagent bottle. It was also found that this was due to the air oxidation of NAC itself rather than the reaction of NAC with CA, indicating that this result simply shows an increase in apparent reactivity. Aldehydes are known to produce active species, such as radicals, during air oxidation. Therefore, we investigated whether radicals were generated under storage conditions using the radical scavenger OH-TEMPO. LC/MS/MS analysis revealed that CA and OH-TEMPO complexes were produced during the air oxidation of CA. In the results of five aldehydes, similar to CA, active species were not generated as significantly as CA. Collectively, during the evaluation of the aldehydes, it can be seen that careful measures need to be taken to prevent the aldehydes from oxidizing during storage, indicating that assessment without preventing air oxidation carries an increased risk of overestimation compared with the intrinsic skin sensitization potency.

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Section: Discussionmentioning

confidence: 99%

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

Fujita

Yamamoto

Watanabe

et al. 2021

Chem. Res. Toxicol.

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“…As this model is more complex, much more reliable parameters compared to the EQ stage model [5] are required and convergence problems often occur. This problem can be overcome by building the EQ stage model of each column first to use its results as a very good initial guess of stage temperature, liquid phase composition and vapor phase composition for the NEQ stage model [37,41]. Initial column parameters such as the number of theoretical stages (N), reactive zone (N R ), feed stage position (f ), reflux ratio (R), column type and internals were adopted from literature [4,5].…”

Section: Equipment Modelmentioning

confidence: 99%

“…In case of reactive distillation columns, esterification chemical reaction (3) was allowed in the reactive zone (N R ); its reaction rate is expressed by Equation (4). The reactive zone was determined by acetic acid as a homogeneous catalyst (sulfuric acid) was fed to the column together with acetic acid [10,41].…”

Section: Equipment Modelmentioning

confidence: 99%

Multi-Objective Assessment of Heat Pump-Assisted Ethyl Acetate Production

et al. 2021

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Multi-objective (energy–economic–safety) assessment of ethyl acetate production involving a heat pump is presented in this paper. The heat pump is designed to intensify ethyl acetate separation and to reduce the total operating cost. Two ethyl acetate production pathways are upgraded using a heat pump, conventional process and reactive distillation column with a separation unit. Detailed process models including the heat pump environment have been compiled and optimized in the Aspen Plus software. Both benefits and drawbacks of including the heat pump in the processes are evaluated using three different points of view: process energy, economics, and safety. As a result, using a heat pump is highly recommended in both conventional process and reactive distillation column with a separation unit. As a higher level of process integration is achieved using a heat pump, economic aspects are improved; however, safety aspects deteriorate. The final decision on the suitability of using a heat pump depends on whether it is proposed for an existing plant, or a completely new plant is designed. In a new plant, the concept of a thermally coupled process (reactive distillation column with a stripper column) has been proven to be the most promising.

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“…Cinnamic derivatives are substances whose isolation and identification as odor-producing constituents are associated with a variety of botanical extracts. Many products are commercialized containing these chemicals, including flavors, fragrances, agrochemicals, pharmaceuticals, and polymers . In the similarity maps, the fragments of the molecules colored in red are predicted to make major contributions to the sensitizing activity, whereas the fragments colored in green contribute negatively to the sensitizing activity (Figure ).…”

Section: Case Studymentioning

confidence: 99%

Pred-Skin: A Web Portal for Accurate Prediction of Human Skin Sensitizers

Borba

Braga²,

Alves

et al. 2020

Chem. Res. Toxicol.

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Safety assessment is an essential component of the regulatory acceptance of industrial chemicals. Previously, we have developed a model to predict the skin sensitization potential of chemicals for two assays, the human patch test and murine local lymph node assay, and implemented this model in a web portal. Here, we report on the substantially revised and expanded freely available web tool, Pred-Skin version 3.0. This up-to-date version of Pred-Skin incorporates multiple quantitative structure–activity relationship (QSAR) models developed with in vitro, in chemico, and mice and human in vivo data, integrated into a consensus naïve Bayes model that predicts human effects. Individual QSAR models were generated using skin sensitization data derived from human repeat insult patch tests, human maximization tests, and mouse local lymph node assays. In addition, data for three validated alternative methods, the direct peptide reactivity assay, KeratinoSens, and the human cell line activation test, were employed as well. Models were developed using open-source tools and rigorously validated according to the best practices of QSAR modeling. Predictions obtained from these models were then used to build a naïve Bayes model for predicting human skin sensitization with the following external prediction accuracy: correct classification rate (89%), sensitivity (94%), positive predicted value (91%), specificity (84%), and negative predicted value (89%). As an additional assessment of model performance, we identified 11 cosmetic ingredients known to cause skin sensitization but were not included in our training set, and nine of them were accurately predicted as sensitizers by our models. Pred-Skin can be used as a reliable alternative to animal tests for predicting human skin sensitization.

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Cinnamic Acid, Cinnamaldehyde, and Cinnamyl Alcohol

Cited by 8 publications

References 17 publications

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

Cause Clarification of Cysteine Oxidation by Active Species Generated during the Oxidation Process of Cinnamaldehyde and Impact on an In Chemico Alternative Method for Skin Sensitization Using a Nucleophilic Reagent Containing Cysteine

Multi-Objective Assessment of Heat Pump-Assisted Ethyl Acetate Production

Pred-Skin: A Web Portal for Accurate Prediction of Human Skin Sensitizers

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