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2,4,5-Trimethoxybenzaldehyde

CAS# 4460-86-0

2,4,5-Trimethoxybenzaldehyde

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Quality Control of 2,4,5-Trimethoxybenzaldehyde

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Chemical structure

2,4,5-Trimethoxybenzaldehyde

3D structure

Chemical Properties of 2,4,5-Trimethoxybenzaldehyde

Cas No. 4460-86-0 SDF Download SDF
PubChem ID 20525 Appearance Yellow powder
Formula C10H12O4 M.Wt 196.2
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Asaronaldehyde; 14374-62-0;Asaraldehyde; 2,4,5-trimethoxy-Benzaldehyde
Solubility H2O : < 0.1 mg/mL (insoluble)
Chemical Name 2,4,5-trimethoxybenzaldehyde
SMILES COC1=CC(=C(C=C1C=O)OC)OC
Standard InChIKey IAJBQAYHSQIQRE-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 2,4,5-Trimethoxybenzaldehyde

The rhizoma of Acorus tatarinowii Schott

Biological Activity of 2,4,5-Trimethoxybenzaldehyde

Description2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA) has anti-adipogenic potential, is a natural cyclooxygenase II (COX-2) inhibitor, suppresses the differentiation of preadipocyts into adipocytes at the concentration of 0.5 mM.
TargetsCOX | MAPK | MEK | PPAR | FAS | ERK
In vitro

2,4,5-trimethoxybenzaldehyde, a bitter principle in plants, suppresses adipogenesis through the regulation of ERK1.[Pubmed: 25222709 ]

J Agric Food Chem. 2014 Oct 8;62(40):9860-7.

We demonstrated that 2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), a bitter principle in plants and a natural cyclooxygenase II (COX-2) inhibitor, suppressed the differentiation of preadipocyts into adipocytes at the concentration of 0.5 mM.
METHODS AND RESULTS:
In this current study, we aimed to investigate the stage during adipogenesis that is critically affected by 2,4,5-Trimethoxybenzaldehyde and the effects of 2,4,5-Trimethoxybenzaldehyde on the time-course expression of signaling molecules MAP kinase kinase (MAPKK, represented by MEK) and extracellular signal-regulated kinase (ERK), transcription factors CCAAT/enhancer binding protein (C/EBP)α, β, and δ and peroxisome proliferator-activated receptor (PPAR)γ, lipogenic enzymes acetyl-CoA carboxylase (ACC) and fatty acid synthase (FAS), and lipid droplet-coating protein perilipin A. When preadipocytes were co-cultured with 2,4,5-Trimethoxybenzaldehyde (0.5 mM) specifically at post-induction days 0-2, 2-4, 4-6, or 6-8 only, relative lipid accumulation was decreased by 67.93, 34.65, 49.56, and 34.32%, respectively. A time-course study showed that treatment of 2,4,5-Trimethoxybenzaldehyde suppressed the phosphorylation of ERK1 at the initial stage of adipogenesis but upregulated the phosphorylation at the late stage, which is opposite to the conditions required for the differentiation process. The overall expression of C/EBPα, β, and δ, PPARγ2, ACC, FAS, and perilipin A in preadipocytes was downregulated by the treatment of 2,4,5-Trimethoxybenzaldehyde.
METHODS AND RESULTS:
Taken together, our findings suggest that 2,4,5-Trimethoxybenzaldehyde suppresses adipogenesis through the regulation of ERK1 phosphorylation. Although results from in vitro studies cannot be directly extrapolated into clinical effects, our study will help to elucidate the anti-adipogenic potential of 2,4,5-Trimethoxybenzaldehyde.

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata.[Pubmed: 17397476]

Lett Appl Microbiol. 2007 Apr;44(4):387-92.

To investigate the active ingredient in fruiting bodies and to produce it with cultured mycelium in Antrodia camphorata (BCRC 35398).
METHODS AND RESULTS:
The volatile components from the fruiting bodies, the liquid cultured broth of A. camphorata and Cinnamomum kanehirae wood were separately isolated by steam distillation-solvent extraction and identified by gas chromatography-mass spectrometry. In the fruiting bodies, a COX-2 inhibitor 2,4,5-Trimethoxybenzaldehyde (TMBA) was found to be the most abundant constituent, but was totally absent in its cultured broth and its natural host, C. kanehirae wood. On feeding with the acid-digested sawdust of C. kanehirae wood or vanillin to the broth for culture, TMBA was produced in both cultured broths.
CONCLUSIONS:
The TMBA identified in fruiting bodies was an active ingredient whose functions consisted with the reported experiences of this mushroom. Feeding vanillin to culture broth could produce TMBA containing mycelium product like its fruiting bodies did. This study found an active ingredient in fruiting bodies of A. camphorata and elucidated this compound derived from digested sawdust of C. kanehirae wood. A feasible method was also developed to produce TMBA containing mycelium by feeding vanillin.

2,4,5-Trimethoxybenzaldehyde Dilution Calculator

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Preparing Stock Solutions of 2,4,5-Trimethoxybenzaldehyde

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.0968 mL 25.4842 mL 50.9684 mL 101.9368 mL 127.421 mL
5 mM 1.0194 mL 5.0968 mL 10.1937 mL 20.3874 mL 25.4842 mL
10 mM 0.5097 mL 2.5484 mL 5.0968 mL 10.1937 mL 12.7421 mL
50 mM 0.1019 mL 0.5097 mL 1.0194 mL 2.0387 mL 2.5484 mL
100 mM 0.051 mL 0.2548 mL 0.5097 mL 1.0194 mL 1.2742 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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Background on 2,4,5-Trimethoxybenzaldehyde

Asaraldehyde is a natural COX-2 inhibitor, exhibiting 17-fold selectivity over COX-1.

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References on 2,4,5-Trimethoxybenzaldehyde

[Chemical constituents from rhizomes of Acorus tatarinowii].[Pubmed:23713285]

Zhongguo Zhong Yao Za Zhi. 2013 Feb;38(4):569-73.

Fifteen compounds were isolated from the rhizomes of Acorus tatarinowii by means of various chromatographic techniques such as silica gel, ODS, Sephadex LH-20 and preparative HPLC, and their structures were elucidated as tatanone A (1), calamusenone (2), acoronene (3), 2-acetyloxyacoronene (4), acorenone (5), alpha-asarone (6), beta-asarone (7), 1,2-dimethoxy-4-(1'Z-propenyl) benzene (8), methyleugenol (9), asarylaldehyde (10), acoramone (11), gamma-asarone (12), 5-hydroxymethyl-2-furaldehyde (13), galgravin (14) and eudesmin (15) on the basis of spectroscopic data analysis. Compound 1 was a new compound, and compounds 3-5 were separated from Acorus species for the first time.

Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata.[Pubmed:17397476]

Lett Appl Microbiol. 2007 Apr;44(4):387-92.

AIMS: To investigate the active ingredient in fruiting bodies and to produce it with cultured mycelium in Antrodia camphorata (BCRC 35398). METHODS AND RESULTS: The volatile components from the fruiting bodies, the liquid cultured broth of A. camphorata and Cinnamomum kanehirae wood were separately isolated by steam distillation-solvent extraction and identified by gas chromatography-mass spectrometry. In the fruiting bodies, a COX-2 inhibitor 2,4,5-Trimethoxybenzaldehyde (TMBA) was found to be the most abundant constituent, but was totally absent in its cultured broth and its natural host, C. kanehirae wood. On feeding with the acid-digested sawdust of C. kanehirae wood or vanillin to the broth for culture, TMBA was produced in both cultured broths. CONCLUSION: The TMBA identified in fruiting bodies was an active ingredient whose functions consisted with the reported experiences of this mushroom. Feeding vanillin to culture broth could produce TMBA containing mycelium product like its fruiting bodies did. SIGNIFICANCE AND IMPACT OF THE STUDY: This study found an active ingredient in fruiting bodies of A. camphorata and elucidated this compound derived from digested sawdust of C. kanehirae wood. A feasible method was also developed to produce TMBA containing mycelium by feeding vanillin.

2,4,5-trimethoxybenzaldehyde, a bitter principle in plants, suppresses adipogenesis through the regulation of ERK1.[Pubmed:25222709]

J Agric Food Chem. 2014 Oct 8;62(40):9860-7.

Because of the prevalence of obesity, there is particular interest in finding potential therapeutic targets. In a previous study, we demonstrated that 2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), a bitter principle in plants and a natural cyclooxygenase II (COX-2) inhibitor, suppressed the differentiation of preadipocyts into adipocytes at the concentration of 0.5 mM. In this current study, we aimed to investigate the stage during adipogenesis that is critically affected by 2,4,5-TMBA and the effects of 2,4,5-TMBA on the time-course expression of signaling molecules MAP kinase kinase (MAPKK, represented by MEK) and extracellular signal-regulated kinase (ERK), transcription factors CCAAT/enhancer binding protein (C/EBP)alpha, beta, and delta and peroxisome proliferator-activated receptor (PPAR)gamma, lipogenic enzymes acetyl-CoA carboxylase (ACC) and fatty acid synthase (FAS), and lipid droplet-coating protein perilipin A. When preadipocytes were co-cultured with 2,4,5-TMBA (0.5 mM) specifically at post-induction days 0-2, 2-4, 4-6, or 6-8 only, relative lipid accumulation was decreased by 67.93, 34.65, 49.56, and 34.32%, respectively. A time-course study showed that treatment of 2,4,5-TMBA suppressed the phosphorylation of ERK1 at the initial stage of adipogenesis but upregulated the phosphorylation at the late stage, which is opposite to the conditions required for the differentiation process. The overall expression of C/EBPalpha, beta, and delta, PPARgamma2, ACC, FAS, and perilipin A in preadipocytes was downregulated by the treatment of 2,4,5-TMBA. Taken together, our findings suggest that 2,4,5-TMBA suppresses adipogenesis through the regulation of ERK1 phosphorylation. Although results from in vitro studies cannot be directly extrapolated into clinical effects, our study will help to elucidate the anti-adipogenic potential of 2,4,5-TMBA.

Description

Asarylaldehyde is a natural COX-2 inhibitor, which isolated from carrot (Daucus carota L.) seeds significantly inhibits cyclooxygenase II (COX-2) activity at IC50 value 100 μg/mL.

Keywords:

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