2-Hydroxy-4-Methoxybenzaldehyde, an Astounding Food Flavoring Metabolite: A Review

Rathi, Neelima; Harwalkar, Keerthana; Jayashree, .; Sharma, Ashwani; Rao, Nagashree N

doi:10.22159/ajpcr.2017.v10i10.19729

Cited by 12 publications

(4 citation statements)

References 49 publications

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“…They were cleaned with water and stored under shade awaiting extraction. The roots were chopped into small pieces and subjected to isolation using the established procedures [25]. The white crystalline compound [10 g, mp 41-43 °C] was obtained from 1000 g (10% yield) of the roots and confirmed to be 2-hydroxy-4-methoxybenzaldehyde ( 1 ) from NMR and ESI-MS data [22].…”

Section: Methodsmentioning

confidence: 99%

Ovicidal Activity of 2-Hydroxy-4-Methoxybenzaldehyde, Derivatives and Structural Analogues on Anopheles gambiae eggs

Omolo

Andati

Ndiege

2021

Preprint

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Background Effective remedies for disrupting Anopheles gambiae metamorphosis at the egg stage are crucial in suppression of the malaria vector populations that result in the reduction of disease burden. 2-Hydroxy-4-methoxybenzaldehyde (the major component of Mondia whytei roots), its derivatives, structural analogues and their blends were evaluated against the eggs of An. gambiae in the search for ovicidal compounds with potential use in mosquito control programs. Methods Mature roots were harvested from Mondia whytei plants grown in the Center for African Medicinal & Nutritional Flora and Fauna (CAMNFF) herbal medicinal garden and cleaned with distilled water. 2-Hydroxy-4-methoxybenzaldehyde ( 1 ) was isolated by steam distillation of the chopped roots. The selected derivatives and/or analogues were prepared using established chemical procedures and their structures confirmed by NMR spectroscopy and ESI-MS. Ovicidal activity of the pure compounds, derivatives, structural analogues and/or formulated blends was tested at 1, 10, 25 and 50 ppm on An. gambiae eggs. . Results Eleven mono-substituted ( 3-7 ), di-substituted ( 8-10 ), tri-substituted ( 1-2 ) aromatic compounds were assayed for ovicidal activity against Anopheles gambiae eggs singly or as blends. Benzaldehyde ( 4 ) and 4-methoxybenzaldehyde ( 9 ) were further converted into 2-hydroxy-1, 2-diphenylethanone ( 11 ), 1, 5-diphenylpenta-1, 4-diene-3-one ( 12 ) and 1, 5- bis (4-methoxyphenyl) penta-1, 4-diene-3-one ( 13 ) and evaluated for ovicidal activity individually or as blends. Of the thirteen compounds evaluated individually, 2-hydroxy-4-methoxybenzaldehyde ( 1 ) exhibited the highest ovicidal activity at LC 50 0.7075 ppm while anisole had the lowest activity at LC 50 40.342 ppm. The derivatives exhibited moderate activity: 2-hydroxy-1, 2-diphenylethanone (LC 50 10.599 ppm), 1, 5-diphenylpenta-1, 4-diene-3-one (LC 50 9.019 ppm) and 1, 5-bis (4-methoxyphenyl) penta-1, 4-diene-3-one (LC 50 15.642 ppm). The blends exhibited intriguingly high ovicidal efficacy with the mixture of benzaldehyde and phenol showing the highest (LC 50 0.332 ppm) while phenol and anisole exhibited the lowest activity (LC 50 9.9909 ppm). Conclusion From the activity of the blends, it is evident that anisole is antagonistic to the efficacy of phenol and benzaldehyde. It is also apparent that aldehyde and hydroxyl groups, when directly attached to the phenyl ring, provide the critical structural characteristics that contribute to the ovicidal activity of the aromatic compounds.

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Section: Methodsmentioning

confidence: 99%

Ovicidal Activity of 2-Hydroxy-4-Methoxybenzaldehyde, Derivatives and Structural Analogues on Anopheles gambiae eggs

Omolo

Andati

Ndiege

2021

Preprint

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“…As a result, HMB is recognized as a propitious anti-virulence candidate against MRSA [30]. Moreover, it was found to have antibacterial, antifungal, antipyretic and antioxidant properties [31]. A previous study was carried out on the safety profile of HMB to determine the possibility of being added in and on food as a new flavoring agent.…”

Section: Pogostemon Heyneanus and Cinnamomum Tamala Essential Oilsmentioning

confidence: 99%

Staphyloxanthin as a Potential Novel Target for Deciphering Promising Anti-Staphylococcus aureus Agents

et al. 2022

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Staphylococcus aureus is a fatal Gram-positive pathogen threatening numerous cases of hospital-admitted patients worldwide. The emerging resistance of the pathogen to several antimicrobial agents has pressurized research to propose new strategies for combating antimicrobial resistance. Novel strategies include targeting the virulence factors of S. aureus. One of the most prominent virulence factors of S. aureus is its eponymous antioxidant pigment staphyloxanthin (STX), which is an auspicious target for anti-virulence therapy. This review provides an updated outline on STX and multiple strategies to attenuate this virulence factor. The approaches discussed in this article focus on bioprospective and chemically synthesized inhibitors of STX, inter-species communication and genetic manipulation. Various inhibitor molecules were found to exhibit appreciable inhibitory effect against STX and hence would be able to serve as potential anti-virulence agents for clinical use.

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“…2‐Hydroxy‐4‐methoxybenzaldehyde has been identified in plants, which are used in some Asian countries as ‘plant‐based traditional medicines’ (Rathi et al., 2017 ).…”

Section: Assessmentmentioning

confidence: 99%

Scientific opinion on flavouring group evaluation 414 (FGE.414): 2‐hydroxy‐4‐methoxybenzaldehyde

Younes¹,

Aquilina²,

Castle³

et al. 2021

EFS2

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The EFSA Panel on Food Additives and Flavourings (FAF) was requested to evaluate the safety of the substance 2-hydroxy-4-methoxybenzaldehyde as a new flavouring substance, in accordance with Regulation (EC) No 1331/2008. 2-Hydroxy-4-methoxybenzaldehyde belongs to chemical group 23 (Commission Regulation (EC) No 1565/2000) and is structurally related to the hydroxy-and alkoxy-ring substituted benzyl derivatives evaluated in FGE.52 and in FGE.20Rev4. The Panel considered the structural/metabolic similarity sufficient to evaluate the candidate substance following a group-based approach according to the EFSA Guidance on the data required for the risk assessment of flavourings to be used in or on foods. The information provided on the manufacturing process, the composition and the stability of ] was considered sufficient. From studies carried out with this substance, the Panel concluded that there is no concern with respect to genotoxicity. Based on QSAR evaluation of possible metabolism, and based on information from structurally related substances, various metabolic routes can be anticipated, which only result in the formation of innocuous metabolites. The exposure estimates for [FL-no: 05.229] (24 and 60 lg/person per day for children and adults, respectively) were below the Threshold of Toxicological Concern (TTC) for its structural class (I). Accordingly, toxicity studies are not required and the Panel concluded at step A3 of the Procedure that 2-hydroxy-4-methoxybenzaldehyde is not of safety concern when used as a flavouring substance at the intended uses and use levels. Cumulative exposure estimates for 2-hydroxy-4-methoxybenzaldehyde and three structurally related substances (2.4 and 6.2 mg/kg body weight (bw) per day for adults and children, respectively) are above the TTC for structural class I, but below the ADI (acceptable daily intake) of 0-10 mg/kg bw per day for vanillin, which is one of these structurally related substances. Therefore, the cumulative exposure to these four substances 05.018, 05.229 and 09.749] also does not raise a safety concern.

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2-Hydroxy-4-Methoxybenzaldehyde, an Astounding Food Flavoring Metabolite: A Review

Cited by 12 publications

References 49 publications

Ovicidal Activity of 2-Hydroxy-4-Methoxybenzaldehyde, Derivatives and Structural Analogues on Anopheles gambiae eggs

Ovicidal Activity of 2-Hydroxy-4-Methoxybenzaldehyde, Derivatives and Structural Analogues on Anopheles gambiae eggs

Staphyloxanthin as a Potential Novel Target for Deciphering Promising Anti-Staphylococcus aureus Agents

Scientific opinion on flavouring group evaluation 414 (FGE.414): 2‐hydroxy‐4‐methoxybenzaldehyde

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