CAS Number4460-86-0
Synonyms2,4,5-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
Molecular Formula(CH3O)3C6H2CHO
Molecular Weight196.20
Purity≥95.0 (GC)%
Density1.1±0.1 g/cm3
Boiling Point334.7±37.0 °C at 760 mmHg
Melting Point112-114 °C (lit.)
Appearancecrystals
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 4460-86-0 |
| Catalog No. | 2A-9001766 |
| Chinese Name | 2,4,5-三甲氧基苯甲醛 |
| 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 |
| Molecular Formula | (CH3O)3C6H2CHO |
| Molecular Weight | 196.20 |
| Purity | ≥95.0 (GC) |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 334.7±37.0 °C at 760 mmHg |
| Melting Point | 112-114 °C (lit.) |
| Appearance | crystals |
| Water Solubility | <0.1 g/100 mL at 22 ºC |
| Storage Condition | Keep away from light, ventilated and dry, sealed |
| Application | Asarylaldehyde is a natural COX-2 inhibitor isolated from carrot (Daucus carota L.) seeds that significantly inhibits cyclooxygenase II (COX-2) activity with an IC50 value of 100 μg/mL. |
| HTC | 2912499000 |
| MDL Number | MFCD00003312 |
| SMILES | [H]C(=O)c1cc(OC)c(OC)cc1OC |
| InChI | 1S/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3 |
| InChI Key | IAJBQAYHSQIQRE-UHFFFAOYSA-N |
| Beilstein/REAXYS | 1951403 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | Transport |
| MSDS | msds/1766_1_4460_86_0.pdf |
| Bioactivity | 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 Research Areas >> Inflammation/Immunology Natural Products >> Acids and Aldehydes 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 InChIKey IAJBQAYHSQIQRE-UHFFFAOYSA-N SMILES COc1cc(OC)c(OC)cc1C=O Storage condition 2-8°C Water Solubility <0.1 g/100 mL at 22 ºC |
| Use of | 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. Properties Articles13 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 Research Areas >> Inflammation/Immunology Natural Products >> Acids and Aldehydes 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 Molecular Formula C10H12O4 Exact Mass 196.073563 PSA 44.76000 Index of Refraction 1.525 InChIKey IAJBQAYHSQIQRE-UHFFFAOYSA-N |
| Tax Rebate | 9.0% |
| Supervision | None. MFN tariff: 5.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: Purity: 0.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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