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4-Hydroxy-3,5-dimethoxybenzaldehyde

CAS# 134-96-3

4-Hydroxy-3,5-dimethoxybenzaldehyde

2D Structure

Catalog No. BCN6186----Order now to get a substantial discount!

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3D structure

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4-Hydroxy-3,5-dimethoxybenzaldehyde

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Chemical Properties of 4-Hydroxy-3,5-dimethoxybenzaldehyde

Cas No. 134-96-3 SDF Download SDF
PubChem ID 8655 Appearance Powder
Formula C9H10O4 M.Wt 182.2
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-hydroxy-3,5-dimethoxybenzaldehyde
SMILES COC1=CC(=CC(=C1O)OC)C=O
Standard InChIKey KCDXJAYRVLXPFO-UHFFFAOYSA-N
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.
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.
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.

Source of 4-Hydroxy-3,5-dimethoxybenzaldehyde

The herbs of Artemisia annua L.

Biological Activity of 4-Hydroxy-3,5-dimethoxybenzaldehyde

Description4-Hydroxy-3,5-dimethoxybenzaldehyde is an organic compound that occurs naturally in trace amounts, it possesses powerful antioxidant activity, in minimizing DNA damage, and activating survival signal Akt pathway, and it may be of value in the development of radioprotective compounds. It is used in pharmaceuticals, food, cosmetics, textiles, pulp and paper industries, and even in biological control applications.
TargetsDNA-PK | GSK-3 | Akt
In vitro

Radioprotection of 4-hydroxy-3,5-dimethoxybenzaldehyde (VND3207) in culture cells is associated with minimizing DNA damage and activating Akt.[Pubmed: 17981442]

Eur J Pharm Sci. 2008 Jan;33(1):52-9.

Vanillin is a naturally occurring compound and food-flavoring agent with antioxidant and antimutagenic activities.
METHODS AND RESULTS:
In present study, we explored the radioprotective effect of a novel vanillin derivative VND3207 (4-Hydroxy-3,5-dimethoxybenzaldehyde). 4-Hydroxy-3,5-dimethoxybenzaldehyde has a much higher potential in scavenging hydroxyl radical and superoxide radical than vanillin as indicated in the ESR spin-trapping measurement, and it can effectively protect plasmid DNA against 10-50 Gy gamma-ray induced breaks in vitro at the concentrations as low as 10-20 microM. Using human lymphoblastoid AHH-1 cells and human fibroblastoid HFS cells, we demonstrated that 4-Hydroxy-3,5-dimethoxybenzaldehyde at 5-40 microM concentrations significantly attenuated the inhibition of proliferation and occurrence of apoptosis produced by 1-8 Gy gamma-irradiation. In the cultured cells, 4-Hydroxy-3,5-dimethoxybenzaldehyde significantly decreased the initial production and residual level of DNA double-strand breaks (DSBs) induced by 2 or 8 Gy irradiation. Treatment of 4-Hydroxy-3,5-dimethoxybenzaldehyde enhanced the level of DNA-PKcs protein, a critical component of DNA DSB repair pathway in the cells with or without gamma-irradiation. Consistently, the phosphorylation of Akt protein, a mediator of survival signal, as well as its substrate GSK3beta was concurrently increased by 4-Hydroxy-3,5-dimethoxybenzaldehyde.
CONCLUSIONS:
Our results suggest that 4-Hydroxy-3,5-dimethoxybenzaldehyde has radioprotection effect through its capabilities as a powerful antioxidant, in minimizing DNA damage, and activating survival signal Akt pathway, and it may be of value in the development of radioprotective compounds.

Protocol of 4-Hydroxy-3,5-dimethoxybenzaldehyde

Structure Identification
Spectrochim Acta A Mol Biomol Spectrosc. 2005 Oct;61(13-14):3087-96.

Effects of solvent, pH and beta-cyclodextrin on the photophysical properties of 4-hydroxy-3,5-dimethoxybenzaldehyde: intramolecular charge transfer associated with hydrogen bonding effect.[Pubmed: 16165057]

The photophysical properties of 4-Hydroxy-3,5-dimethoxybenzaldehyde (HDMB) in various solvents, pH and in aqueous beta-cyclodextrin (CD) have been investigated. In non-polar solvents, 4-Hydroxy-3,5-dimethoxybenzaldehyde gives only one emission maxima; whereas, in polar solvents it shows a dual luminescence. The increase in Stokes shift with increase in polarity is much more for longer wavelength (LW) than for a shorter wavelength (SW) band. This behaviour indicates the formation of an intramolecular charge transfer (ICT) state through relaxation from the normal excited state. Especially in water, the ICT emission is further red shifted to 430 nm with the normal emission band at 330 nm and the relative fluorescence intensities between 330 nm and 430 nm emission bands are affected by the excitation wavelength. However, this excitation wavelength dependence is not large in aqueous beta-CD solutions. These results suggest that the ICT state in polar solvents/water is stabilized through exciplex formation by the hydrogen-bonding interaction between the carbonyl group and polar solvents/water. The ground and excited state pK(a) values for the neutral-monoanion equilibrium have been measured and discussed. 4-Hydroxy-3,5-dimethoxybenzaldehyde forms a 1:1 inclusion complex with beta-CD. A mechanism is proposed to explain the inclusion process.

J Fluoresc. 2014 May;24(3):695-707.

Spectral and molecular modeling studies on hydroxybenzaldehydes with native and modified cyclodextrins.[Pubmed: 24310479]

The inclusion complexation of 2-hydroxy-3-methoxybenzaldehyde (2HMB), 4-hydroxy-3-methoxybenzaldehyde (4HMB), 3,4-dimethoxybenzaldehyde (DMB) and 4-Hydroxy-3,5-dimethoxybenzaldehyde (HDMB) with α-CD, β-CD, HP-α-CD and HP-β-CD were carried out by UV-Visible, steady-state and time-resolved fluorescence and PM3 methods. All the benzaldehydes shows dual fluorescence in aqueous and CD mediums and 1:1 inclusion complexes were formed with CDs. PM3 geometry optimizations results indicate that the 4-Hydroxy-3,5-dimethoxybenzaldehyde /CD complex is significantly more favorable than the other complexes. The negative enthalpy changes suggest that the inclusion complexation processes are spontaneous. The geometry of the most stable complex shows that methoxy/OH group of HMBs is entrapped in the less polar CD cavities, while the aldehyde group present in the upper part of the CDs cavities.

4-Hydroxy-3,5-dimethoxybenzaldehyde Dilution Calculator

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Preparing Stock Solutions of 4-Hydroxy-3,5-dimethoxybenzaldehyde

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.4885 mL 27.4424 mL 54.8847 mL 109.7695 mL 137.2119 mL
5 mM 1.0977 mL 5.4885 mL 10.9769 mL 21.9539 mL 27.4424 mL
10 mM 0.5488 mL 2.7442 mL 5.4885 mL 10.9769 mL 13.7212 mL
50 mM 0.1098 mL 0.5488 mL 1.0977 mL 2.1954 mL 2.7442 mL
100 mM 0.0549 mL 0.2744 mL 0.5488 mL 1.0977 mL 1.3721 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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References on 4-Hydroxy-3,5-dimethoxybenzaldehyde

Radioprotection of 4-hydroxy-3,5-dimethoxybenzaldehyde (VND3207) in culture cells is associated with minimizing DNA damage and activating Akt.[Pubmed:17981442]

Eur J Pharm Sci. 2008 Jan;33(1):52-9.

Vanillin is a naturally occurring compound and food-flavoring agent with antioxidant and antimutagenic activities. In present study, we explored the radioprotective effect of a novel vanillin derivative VND3207 (4-Hydroxy-3,5-dimethoxybenzaldehyde). VND3207 has a much higher potential in scavenging hydroxyl radical and superoxide radical than vanillin as indicated in the ESR spin-trapping measurement, and it can effectively protect plasmid DNA against 10-50 Gy gamma-ray induced breaks in vitro at the concentrations as low as 10-20 microM. Using human lymphoblastoid AHH-1 cells and human fibroblastoid HFS cells, we demonstrated that VND3207 at 5-40 microM concentrations significantly attenuated the inhibition of proliferation and occurrence of apoptosis produced by 1-8 Gy gamma-irradiation. In the cultured cells, VND3207 significantly decreased the initial production and residual level of DNA double-strand breaks (DSBs) induced by 2 or 8 Gy irradiation. Treatment of VND3207 enhanced the level of DNA-PKcs protein, a critical component of DNA DSB repair pathway in the cells with or without gamma-irradiation. Consistently, the phosphorylation of Akt protein, a mediator of survival signal, as well as its substrate GSK3beta was concurrently increased by VND3207. Our results suggest that VND3207 has radioprotection effect through its capabilities as a powerful antioxidant, in minimizing DNA damage, and activating survival signal Akt pathway, and it may be of value in the development of radioprotective compounds.

Effects of solvent, pH and beta-cyclodextrin on the photophysical properties of 4-hydroxy-3,5-dimethoxybenzaldehyde: intramolecular charge transfer associated with hydrogen bonding effect.[Pubmed:16165057]

Spectrochim Acta A Mol Biomol Spectrosc. 2005 Oct;61(13-14):3087-96.

The photophysical properties of 4-Hydroxy-3,5-dimethoxybenzaldehyde (HDMB) in various solvents, pH and in aqueous beta-cyclodextrin (CD) have been investigated. In non-polar solvents, HDMB gives only one emission maxima; whereas, in polar solvents it shows a dual luminescence. The increase in Stokes shift with increase in polarity is much more for longer wavelength (LW) than for a shorter wavelength (SW) band. This behaviour indicates the formation of an intramolecular charge transfer (ICT) state through relaxation from the normal excited state. Especially in water, the ICT emission is further red shifted to 430 nm with the normal emission band at 330 nm and the relative fluorescence intensities between 330 nm and 430 nm emission bands are affected by the excitation wavelength. However, this excitation wavelength dependence is not large in aqueous beta-CD solutions. These results suggest that the ICT state in polar solvents/water is stabilized through exciplex formation by the hydrogen-bonding interaction between the carbonyl group and polar solvents/water. The ground and excited state pK(a) values for the neutral-monoanion equilibrium have been measured and discussed. HDMB forms a 1:1 inclusion complex with beta-CD. A mechanism is proposed to explain the inclusion process.

Spectral and molecular modeling studies on hydroxybenzaldehydes with native and modified cyclodextrins.[Pubmed:24310479]

J Fluoresc. 2014 May;24(3):695-707.

The inclusion complexation of 2-hydroxy-3-methoxybenzaldehyde (2HMB), 4-hydroxy-3-methoxybenzaldehyde (4HMB), 3,4-dimethoxybenzaldehyde (DMB) and 4-Hydroxy-3,5-dimethoxybenzaldehyde (HDMB) with alpha-CD, beta-CD, HP-alpha-CD and HP-beta-CD were carried out by UV-Visible, steady-state and time-resolved fluorescence and PM3 methods. All the benzaldehydes shows dual fluorescence in aqueous and CD mediums and 1:1 inclusion complexes were formed with CDs. PM3 geometry optimizations results indicate that the HDMB/CD complex is significantly more favorable than the other complexes. The negative enthalpy changes suggest that the inclusion complexation processes are spontaneous. The geometry of the most stable complex shows that methoxy/OH group of HMBs is entrapped in the less polar CD cavities, while the aldehyde group present in the upper part of the CDs cavities.

Description

Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL. Anti-hyperglycemic and anti-inflammatory activities

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