2-Hydroxy-4-methoxybenzaldehydeCAS# 673-22-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 673-22-3 | SDF | Download SDF |
| PubChem ID | 69600 | Appearance | Powder |
| Formula | C8H8O3 | M.Wt | 152.14 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 50 mg/mL (328.62 mM) H2O : 2 mg/mL (13.14 mM; Need ultrasonic) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 2-hydroxy-4-methoxybenzaldehyde | ||
| SMILES | COC1=CC(=C(C=C1)C=O)O | ||
| Standard InChIKey | WZUODJNEIXSNEU-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 2-Hydroxy-4-methoxybenzaldehyde is an excellent antimicrobial agent with additional antiaflatoxigenic potency. 2-Hydroxy-4-methoxybenzaldehyde has antioxidant and high antimycotic potency, it possesses chemosensitizing capability to magnify the efficacy of monoterpenoid phenols, which improves target-based (viz., cell wall disruption) antifungal intervention. |
| Targets | MAPK | Antifection |
| In vitro | Augmenting the Activity of Monoterpenoid Phenols against Fungal Pathogens Using 2-Hydroxy-4-methoxybenzaldehyde that Target Cell Wall Integrity.[Pubmed: 26569223]Int J Mol Sci. 2015 Nov 10;16(11):26850-70.Disruption of cell wall integrity system should be an effective strategy for control of fungal pathogens. Antioxidant property of Decalepis hamiltonii Wight & Arn.[Pubmed: 17131914]Indian J Exp Biol. 2006 Oct;44(10):832-7.Aromatic edible root of D. hamiltonii was subjected to the extraction of the antioxidant rich fraction. |
| In vivo | Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.[Pubmed: 26986086 ]Eur J Med Chem. 2016 May 23;114:209-19.In our earlier study, we have reported that a phenolic compound 2-Hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. |
| Structure Identification | J Agric Food Chem. 2017 Oct 11;65(40):8773-8778.Antiaflatoxigenic and Antimicrobial Activities of Schiff Bases of 2-Hydroxy-4-methoxybenzaldehyde, Cinnamaldehyde, and Similar Aldehydes.[Pubmed: 28942637 ]2-Hydroxy-4-methoxybenzaldehyde (HMBA) is a nontoxic phenolic flavor from dietary source Decalipus hamiltonii and Hemidesmus indicus. HMBA is an excellent antimicrobial agent with additional antiaflatoxigenic potency. On the other hand, cinnamaldehyde from cinnamon is a widely employed flavor with significant antiaflatoxigenic activity. |
2-Hydroxy-4-methoxybenzaldehyde Dilution Calculator
2-Hydroxy-4-methoxybenzaldehyde Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 6.5729 mL | 32.8645 mL | 65.7289 mL | 131.4579 mL | 164.3223 mL |
| 5 mM | 1.3146 mL | 6.5729 mL | 13.1458 mL | 26.2916 mL | 32.8645 mL |
| 10 mM | 0.6573 mL | 3.2864 mL | 6.5729 mL | 13.1458 mL | 16.4322 mL |
| 50 mM | 0.1315 mL | 0.6573 mL | 1.3146 mL | 2.6292 mL | 3.2864 mL |
| 100 mM | 0.0657 mL | 0.3286 mL | 0.6573 mL | 1.3146 mL | 1.6432 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Augmenting the Activity of Monoterpenoid Phenols against Fungal Pathogens Using 2-Hydroxy-4-methoxybenzaldehyde that Target Cell Wall Integrity.[Pubmed:26569223]
Int J Mol Sci. 2015 Nov 10;16(11):26850-70.
Disruption of cell wall integrity system should be an effective strategy for control of fungal pathogens. To augment the cell wall disruption efficacy of monoterpenoid phenols (carvacrol, thymol), antimycotic potency of benzaldehyde derivatives that can serve as chemosensitizing agents were evaluated against strains of Saccharomyces cerevisiae wild type (WT), slt2Delta and bck1Delta (mutants of the mitogen-activated protein kinase (MAPK) and MAPK kinase kinase, respectively, in the cell wall integrity pathway). Among fourteen compounds investigated, slt2Delta and bck1Delta showed higher susceptibility to nine benzaldehydes, compared to WT. Differential antimycotic activity of screened compounds indicated "structure-activity relationship" for targeting the cell wall integrity, where 2-Hydroxy-4-methoxybenzaldehyde (2H4M) exhibited the highest antimycotic potency. The efficacy of 2H4M as an effective chemosensitizer to monoterpenoid phenols (viz., 2H4M + carvacrol or thymol) was assessed in yeasts or filamentous fungi (Aspergillus, Penicillium) according to European Committee on Antimicrobial Susceptibility Testing or Clinical Laboratory Standards Institute M38-A protocols, respectively. Synergistic chemosensitization greatly lowers minimum inhibitory or fungicidal concentrations of the co-administered compounds. 2H4M also overcame the tolerance of two MAPK mutants (sakADelta, mpkCDelta) of Aspergillus fumigatus to fludioxonil (phenylpyrrole fungicide). Collectively, 2H4M possesses chemosensitizing capability to magnify the efficacy of monoterpenoid phenols, which improves target-based (viz., cell wall disruption) antifungal intervention.
Antioxidant property of Decalepis hamiltonii Wight & Arn.[Pubmed:17131914]
Indian J Exp Biol. 2006 Oct;44(10):832-7.
Aromatic edible root of D. hamiltonii was subjected to the extraction of the antioxidant rich fraction. Different parts of root namely whole tuber, peel, tuber without peel and medullary portion were extracted with dichloromethane (European Patent No. W02005063272). The extract was found to contain flavor compound 2-Hydroxy-4-methoxybenzaldehyde (2H4MB), which was identified by TLC and GC. Medullary portion was found to be rich in 2H4MB, (73.73 mg g(-1) dry tissue) followed by peel, containing 68.34 mg g(-1) 2H4MB. Different concentration of dichloromethane extracts were subjected for antioxidant assay by DPPH (1,1 dihydroxy 2-picryl hydrazyl) method, this has shown 44, 46.7% radical scavenging activity in case of medullary, peel extracts and 67.3% in case of pure 2-Hydroxy-4-methoxybenzaldehyde at 100 ppm concentration, whereas ascorbic acid used as standard showed 94.3% activity. In beta-carotene linoleate model system (b-CLAMS) 43.46 and 45.7% antioxidant activity was observed in medullary and peel extracts at 100 ppm concentrations respectively, whereas standard 2-Hydroxy-4-methoxybenzaldehyde exhibited 69.64% at 100 ppm and BHA (butylated hydroxyl anisole) 90.1% activity also at 100-ppm level. Similarly hydroxyl radical scavenging activity was found to be 48.36, 46.86, 48.26 and 73.60% in whole tuber, medullary, peel and standard 2-hydroxy-4-methoxy benzaldehyde respectively at 100 ppm levels. This is the first report on the antioxidant activity of D. hamiltonii. Results have shown that 2H4MB is one of the major constituents responsible for antioxidant activity. Hence the extract of D. hamiltonii can be utilized for the production of antioxidant rich fractions required for various health benefits.
Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.[Pubmed:26986086]
Eur J Med Chem. 2016 May 23;114:209-19.
In our earlier study, we have reported that a phenolic compound 2-Hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-Hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.
Antiaflatoxigenic and Antimicrobial Activities of Schiff Bases of 2-Hydroxy-4-methoxybenzaldehyde, Cinnamaldehyde, and Similar Aldehydes.[Pubmed:28942637]
J Agric Food Chem. 2017 Oct 11;65(40):8773-8778.
2-Hydroxy-4-methoxybenzaldehyde (HMBA) is a nontoxic phenolic flavor from dietary source Decalipus hamiltonii and Hemidesmus indicus. HMBA is an excellent antimicrobial agent with additional antiaflatoxigenic potency. On the other hand, cinnamaldehyde from cinnamon is a widely employed flavor with significant antiaflatoxigenic activity. We have attempted the enhancement of antiaflatoxigenic and antimicrobial properties of HMBA, cinnamaldehyde, and similar molecules via Schiff base formation accomplished from condensation reaction with amino sugar (d-glucamine). HMBA derived Schiff bases exhibited commendable antiaflatoxigenic activity at the concentration 0.1 mg/mL resulting in 9.6 +/- 1.9% growth of Aspergillus flavus and subsequent 91.4 +/- 3.9% reduction of aflatoxin B1 with respect to control.
