Asaraldehyde (also called Asaronaldehyde; 2,4,5-trimethoxy-Benzaldehyde), a naturally occuring compound extracted from carrot (Daucus carota L.) seeds, is a potent COX-2 enzyme inhibitor with potential anti-inflammatory activity. It inhibits COX-2 with an IC50 of 100 μg/mL and exhibits 17-fold selectivity for COX-2 over COX-1.

Physicochemical Properties

Molecular Formula	C10H12O4
Molecular Weight	196.2
Exact Mass	196.073
CAS #	4460-86-0
Related CAS #	4460-86-0
PubChem CID	20525
Appearance	White to off-white solid powder
Density	1.1±0.1 g/cm3
Boiling Point	334.7±37.0 °C at 760 mmHg
Melting Point	112-114 °C(lit.)
Flash Point	149.0±26.5 °C
Vapour Pressure	0.0±0.7 mmHg at 25°C
Index of Refraction	1.525
LogP	1.62
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Heavy Atom Count	14
Complexity	183
Defined Atom Stereocenter Count	0
InChi Key	IAJBQAYHSQIQRE-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3
Chemical Name	2,4,5-trimethoxybenzaldehyde
Synonyms	Asaronaldehyde;Asaraldehyde; 2,4,5-trimethoxy-Benzaldehyde
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Asarylaldehyde (2,4,5-TMBA) is a naturally occurring COX-2 inhibitor that was isolated from carrot (Daucus carota L.) seeds. At 100 μg/mL, it significantly inhibits the activity of cyclooxygenase II (COX-2) compared to three commercial nonsteroidal anti-inflammatory drugs (IC50 values: 180, 2.52, and 2.06 μg/mL, respectively). In 3T3-L1 adipocytes, 2,4,5-TMBA, a natural cyclooxygenase-2 inhibitor, inhibits adipogenesis and oromotes lipolysis. It has been shown that at a concentration of 100 μg/mL, 2,4,5-Trimethoxybenzaldehyde (2,4,5-TMBA), which is found in plant roots, seeds, and leaves, significantly inhibits the activity of cyclooxygenase-2 (COX-2). Given that COX-2 is linked to preadipocyte development, the murine 3T3-L1 cells are cultivated with 100 μg/mL of 2,4,5-TMBA both during and after the cells have fully differentiated to examine the impact of the compound on lipolysis and adipogenesis. Oil The formation of lipid droplets during differentiation was found to be inhibited by 2,4,5-TMBA, as demonstrated by Red O staining and triglyceride assay. Additionally, 2,4,5-TMBA down-regulates the protein levels of adipogenic signaling molecules and transcription factors, including MAP kinase kinase (MEK), extracellular signal-regulated kinase (ERK), CCAAT/enhancer binding protein (C/EBP)α, β, and δ, PPAR (peroxisome proliferator-activated receptor)γ, adipocyte determination and differentiation-dependent factor 1 (ADD1), and the rate-limiting enzyme for lipid synthesis, acetyl-CoA carboxylase (ACC). Treatment of completely developed adipocytes with 2,4,5-TMBA for 72 hours resulted in a considerable reduction in lipid accumulation via boosting triglyceride hydrolysis through the up-regulation of hormone-sensitive lipase (HSL) and the suppression of perilipin A (lipid droplet coating protein). Treatment of completely differentiated 3T3-L1 adipocytes with 100 μg/mL of 2,4,5-TMBA for 24, 48, or 72 hours results in a decrease in viability of 8.35, 15.54, and 27.26%, respectively. Premadiocyte cell viability is reduced by 26.46% when they are treated with 100 μg/mL of 2,4,5-TMBA for 24 hours prior to the addition of differentiation medium[1]. The most prevalent component is 2,4,5-trimethoxybenzaldehyde (TMBA), a COX-2 inhibitor that is completely absent from both its natural host, C. kanehirae wood, and its cultured broth. In fruiting bodies, 2,4,5-trimethoxybenzaldehyde (TMBA) is the main component[2].
ln Vivo
Animal Protocol
References	[1]. 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]. Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata. Lett Appl Microbiol. 2007 Apr;44(4):387-92.
Additional Infomation	2,4,5-trimethoxybenzaldehyde is a beige powder. (NTP, 1992) 2,4,5-trimethoxybenzaldehyde is a carbonyl compound. 2,4,5-Trimethoxybenzaldehyde has been reported in Alpinia flabellata, Mosla scabra, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO:39 mg/mL (198.8 mM) Water:<1 mg/mL Ethanol:16 mg/mL (81.5 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 3.75 mg/mL (19.11 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 37.5 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3.75 mg/mL (19.11 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 37.5 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix well. Solubility in Formulation 3: ≥ 2.5 mg/mL (12.74 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 4: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.0968 mL	25.4842 mL	50.9684 mL
	5 mM	1.0194 mL	5.0968 mL	10.1937 mL
	10 mM	0.5097 mL	2.5484 mL	5.0968 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.