| Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.
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| InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H |
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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nematicide
A substance used to destroy pests of the phylum Nematoda (roundworms).
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View more via ChEBI Ontology
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2-Hydroxybenzaldehyde
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KEGG COMPOUND
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o-formylphenol
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NIST Chemistry WebBook
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o-Hydroxybenzaldehyde
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KEGG COMPOUND
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salicylal
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NIST Chemistry WebBook
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Salicylaldehyd
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ChEBI
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Salicylaldehyde
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KEGG COMPOUND
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salicylaldehyde
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UniProt
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Salizylaldehyd
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ChEBI
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3273
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Gmelin Registry Number
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Gmelin
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471388
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Reaxys Registry Number
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Reaxys
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90-02-8
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CAS Registry Number
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KEGG COMPOUND
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90-02-8
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CAS Registry Number
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NIST Chemistry WebBook
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90-02-8
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CAS Registry Number
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ChemIDplus
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Caboni P, Aissani N, Cabras T, Falqui A, Marotta R, Liori B, Ntalli N, Sarais G, Sasanelli N, Tocco G (2013)
Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita.
Journal of agricultural and food chemistry 61, 1794-1803 [PubMed:23379671]
[show Abstract]
The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC(50) value of 11 ± 6 mg/L followed by salicylaldehyde (2) and cinnamic aldehyde (3) with EC(50) values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC(50) at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme. The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action. | Montalbano F, Cal PM, Carvalho MA, Gonçalves LM, Lucas SD, Guedes RC, Veiros LF, Moreira R, Gois PM (2013)
Discovery of new heterocycles with activity against human neutrophile elastase based on a boron promoted one-pot assembly reaction.
Organic & biomolecular chemistry 11, 4465-4472 [PubMed:23715243]
[show Abstract]
Herein we demonstrate for the first time that a boron promoted one-pot assembly reaction may be used to discover novel enzyme inhibitors. Inhibitors for HNE were simply assembled in excellent yields, high diastereoselectivities and IC50 up to 1.10 μM, based on components like salicylaldehyde, aryl boronic acids and amino acids. The combination of synthetic, biochemical, analytical and theoretical studies allowed the identification of the 4-methoxy or the 4-diethyl amino substituent of the salicylaldehyde as the most important recognition moiety and the imine alkylation, lactone ring opening as key events in the mechanism of inhibition. | Kim HK, Yun YK, Ahn YJ (2008)
Fumigant toxicity of cassia bark and cassia and cinnamon oil compounds to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
Experimental & applied acarology 44, 1-9 [PubMed:18247142]
[show Abstract]
The toxicity to adults of the American house dust mite, Dermatophagoides farinae, and the European house dust mite, Dermatophagoides pteronyssinus, of cassia bark and cassia and cinnamon oil compounds was examined using residual contact and vapour-phase toxicity bioassays. Results were compared with those of the currently used acaricides: benzyl benzoate and dibutyl phthalate. The acaricidal principles of cassia bark were identified as (E)-cinnamaldehyde and salicylaldehyde. In fabric-circle residual contact bioassays with adult D. farinae, salicylaldehyde (17.3 mg/m(2)) and (E)-cinnamaldehyde (25.8 mg/m(2)) were 2.5 and 1.7 times more toxic than benzyl benzoate (43.7 mg/m(2)), respectively, based on 24-h LD(50) values. The acaricidal activity was more pronounced in benzaldehyde, menthol, alpha-terpineol, and thymol (70.8-234.3 mg/m(2)) than in dibutyl phthalate (281.0 mg/m(2)). Against adult D. pteronyssinus, salicylaldehyde (17.3 mg/m(2)) and (E)-cinnamaldehyde (19.3 mg/m(2)) were 2.4- and 2.2-fold more active than benzyl benzoate (41.9 mg/m(2)). The toxicity of benzaldehyde, menthol, alpha-terpineol, and thymol (75.3-179.2 mg/m(2)) was higher than that of dibutyl phthalate (285.1 mg/m(2)). In vapour-phase toxicity tests with adult D. farinae, the test compounds described were much more effective in closed--but not in open--containers, indicating that the effect of these compounds was largely a result of action in the vapour phase. |
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