2,4,5-Trimethoxybenzaldehyde

Modify Date: 2024-01-02 20:25:40

2,4,5-Trimethoxybenzaldehyde Structure
2,4,5-Trimethoxybenzaldehyde structure
 Common Name 2,4,5-Trimethoxybenzaldehyde
CAS Number 4460-86-0 Molecular Weight 196.200
Density 1.1±0.1 g/cm3 Boiling Point 334.7±37.0 °C at 760 mmHg
Molecular Formula C10H12O4 Melting Point 112-114 °C(lit.)
MSDS USA Flash Point 149.0±26.5 °C

 Use of 2,4,5-Trimethoxybenzaldehyde


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.

 Names

Name 2,4,5-Trimethoxybenzaldehyde
Synonym More Synonyms

 2,4,5-Trimethoxybenzaldehyde Biological Activity

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.
Related Catalog
Target

COX-2
In Vitro Asarylaldehyde (2,4,5-TMBA) is a natural COX-2 inhibitor, which isolated from carrot (Daucus carota L.) seeds significantly inhibits cyclooxygenase II (COX-2) activity at the concentration of 100 μg/mL compared to three commercial nonsteroidal anti-inflammatory drugs Aspinin, Ibuprofen, and Naproxen at their IC50 values 180, 2.52, and 2.06 μg/mL, respectively. 2,4,5-TMBA, a natural inhibitor of cyclooxygenase-2, suppresses adipogenesis and oromotes lipolysis in 3T3-L1 adipocytes. 2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA) present in plant roots, seeds, and leaves is reported to be a significant inhibitor of cyclooxygenase-2 (COX-2) activity at the concentration of 100 μg/mL. Because COX-2 is associated with differentiation of preadipocytes, the murine 3T3-L1 cells are cultured with 100 μg/mL of 2,4,5-TMBA during differentiation and after the cells are fully differentiated to study the effect of 2,4,5-TMBA on adipogenesis and lipolysis. Oil Red O staining and triglyceride assay revealed that 2,4,5-TMBA inhibited the formation of lipid droplets during differentiation; moreover, 2,4,5-TMBA down-regulated the protein levels of adipogenic signaling molecules and transcription factors MAP kinase kinase (MEK), extracellular signal-regulated kinase (ERK), CCAAT/enhancer binding protein (C/EBP)α, β, and δ, peroxisome proliferator-activated receptor (PPAR)γ, adipocyte determination and differentiation-dependent factor 1 (ADD1), and the rate-limiting enzyme for lipid synthesis acetyl-CoA carboxylase (ACC). In fully differentiated adipocytes, treatment with 2,4,5-TMBA for 72 h significantly decreased lipid accumulation by increasing the hydrolysis of triglyceride through suppression of perilipin A (lipid droplet coating protein) and up-regulation of hormone-sensitive lipase (HSL). When treated with 100 μg/mL of 2,4,5-TMBA for 24, 48, or 72 h, the viability of fully differentiated 3T3-L1 adipocytes is decreased by 8.35, 15.54, and 27.26%, respectively. When the preadiocytes are treated with 100 μg/mL of 2,4,5-TMBA for 24 h before differentiation medium is supplemented, the cell viability is decreased by 26.46%[1]. A COX-2 inhibitor 2,4,5-trimethoxybenzaldehyde (TMBA) is found to be the most abundant constituent, but is totally absent in its cultured broth and its natural host, C. kanehirae wood. 2,4,5-trimethoxybenzaldehyde (TMBA) is the major constituent in fruiting bodies[2].
Cell Assay 3T3-L1 preadipocytes are seeded into 6-well plates at a concentration of 105/well and cultured in DMEM supplemented with 10% bovine calf serum at 37°C in a humidified atmosphere containing 5% CO2. Two days after confluence, cells are cultured in FBS-containing DMEM (10%, v/v) with the addition of adipogenic factors (0.5 mM IBMX, 1 μM DEX, 5 μg/mL insulin) to induce differentiation (Day 0). Two days later (Day 2), the medium is changed to DMEM supplemented with 10% FBS and 5 μg/mL insulin for another two days. Afterward (Day 4), the medium is changed to DMEM supplemented with 10% FBS only. For the coculture study, 2,4,5-TMBA (0.1 g dissolved in 2 mL of DMSO) is added to the medium from Day 0 to Day 8 (final concentration 100 μg/mL). Control samples are prepared by adding isovolumetric DMSO to the culture medium. For the postculture study, 2,4,5-TMBA is added to the medium on Day 8 (when the cells are fully differentiated) at a final concentration of 100 μg/mL, followed by another 72 h culture. 3T3-L1 cells are seeded in 96-well plates at a concentration of 104/well. Twenty-four hours after seeding, the cells are treated with 100 μg/mL of 2,4,5-TMBA for 24 h or for the whole 8-day differentiation period. Fully differentiated adipocytes are also treated with 100 μg/mL of 2,4,5-TMBA for 24-72 h to test the cytotoxicity. At the end of treatment, cells are cultured with MTT at a final concentration of 0.5 mg/mL for another 4 h. The purple MTT formazan is dissolved by DMSO and the absorbance at 570 nm is taken with a spectrophotometer. The absorbance is proportional to the viability of adipocytes[1].
References

[1]. Wu MR, et al. 2,4,5-TMBA, a natural inhibitor of cyclooxygenase-2, suppresses adipogenesis and promotes lipolysis in 3T3-L1 adipocytes. J Agric Food Chem. 2012 Jul 25;60(29):7262-9.

[2]. Chen CC, et al. Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata. Lett Appl Microbiol. 2007 Apr;44(4):387-92.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 334.7±37.0 °C at 760 mmHg
Melting Point 112-114 °C(lit.)
Molecular Formula C10H12O4
Molecular Weight 196.200
Flash Point 149.0±26.5 °C
Exact Mass 196.073563
PSA 44.76000
LogP 1.62
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.525
Storage condition 2-8°C
Water Solubility <0.1 g/100 mL at 22 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CU8460000
CHEMICAL NAME :
Benzaldehyde, 2,4,5-trimethoxy-
CAS REGISTRY NUMBER :
4460-86-0
BEILSTEIN REFERENCE NO. :
1951403
LAST UPDATED :
199701
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C10-H12-O4
MOLECULAR WEIGHT :
196.22

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - wild bird species
DOSE/DURATION :
422 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - mouse Lymphocyte
DOSE/DURATION :
900 mg/L
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 12,85,1988

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes C: Corrosive;
Risk Phrases R36/37/38
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS CU8460000
HS Code 2912499000

 Synthetic Route

 Customs

HS Code 2912499000
Summary 2912499000. other aldehyde-ethers, aldehyde-phenols and aldehydes with other oxygen function. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0%

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 Synonyms

2,4,5-Trimethoxybenzolcarbaldehyd
2,4,5-Trimethoxy
2,4,5-Trimethoxybenzaldehyde
ASARONALDEHYDE
EINECS 224-713-3
2,4,5-Trimethoxybenz
Azarylaldehyde
2,4,5-Trimethoxy benzaldehyde
ASARALDEHYDE
2,4,5-tris-methoxy benzaldehyde
Gazarin
Asarylaldehyde
2,4,5-trimethyl ether
MFCD00003312
Benzaldehyde, 2,4,5-trimethoxy-
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