Dieugenol

CAS# 4433-08-3

Dieugenol

2D Structure

Catalog No. BCX0861----Order now to get a substantial discount!

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Quality Control of Dieugenol

3D structure

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Dieugenol

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Chemical Properties of Dieugenol

Cas No. 4433-08-3 SDF Download SDF
PubChem ID 165225.0 Appearance Powder
Formula C20H22O4 M.Wt 326.39
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(2-hydroxy-3-methoxy-5-prop-2-enylphenyl)-6-methoxy-4-prop-2-enylphenol
SMILES COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)CC=C)OC)O)CC=C
Standard InChIKey KETPSFSOGFKJJY-UHFFFAOYSA-N
Standard InChI InChI=1S/C20H22O4/c1-5-7-13-9-15(19(21)17(11-13)23-3)16-10-14(8-6-2)12-18(24-4)20(16)22/h5-6,9-12,21-22H,1-2,7-8H2,3-4H3
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.

Dieugenol Dilution Calculator

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Dieugenol Molarity Calculator

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Preparing Stock Solutions of Dieugenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0638 mL 15.3191 mL 30.6382 mL 61.2764 mL 76.5955 mL
5 mM 0.6128 mL 3.0638 mL 6.1276 mL 12.2553 mL 15.3191 mL
10 mM 0.3064 mL 1.5319 mL 3.0638 mL 6.1276 mL 7.6595 mL
50 mM 0.0613 mL 0.3064 mL 0.6128 mL 1.2255 mL 1.5319 mL
100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6128 mL 0.766 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 Dieugenol

Crystal structure of De-hydro-dieugenol B methyl ether, a neolignan from Nectandra leucantha Nees and Mart (Lauraceae).[Pubmed:29765758]

Acta Crystallogr E Crystallogr Commun. 2018 Mar 9;74(Pt 4):518-521.

In the title compound, C(21)H(24)O(4) (systematic name: 4,5'-diallyl-2,2',3'-tri-meth-oxy-diphenyl ether), the aromatic rings lie almost perpendicular to each other [dihedral angle = 85.96 (2) degrees ]. The allyl side chains show similar configurations, with C(ar)-C-C=C (ar = aromatic) torsion angles of -123.62 (12) and -115.54 (12) degrees . A possible weak intra-molecular C-Hcdots, three dots, centeredO inter-action is observed. In the crystal, mol-ecules are connected by two C-Hcdots, three dots, centeredO hydrogen bonds, forming undulating layers lying parallel to the bc plane. Weak C-Hcdots, three dots, centeredpi and pi-pi stacking inter-actions also occur.

Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma.[Pubmed:20064974]

Mol Pharmacol. 2010 Apr;77(4):559-66.

Peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists are used for the treatment of type 2 diabetes and metabolic syndrome. However, the currently used PPAR gamma agonists display serious side effects, which has led to a great interest in the discovery of novel ligands with favorable properties. The aim of our study was to identify new PPARgamma agonists by a PPAR gamma pharmacophore-based virtual screening of 3D natural product libraries. This in silico approach led to the identification of several neolignans predicted to bind the receptor ligand binding domain (LBD). To confirm this prediction, the neolignans Dieugenol, tetrahydroDieugenol, and magnolol were isolated from the respective natural source or synthesized and subsequently tested for PPAR gamma receptor binding. The neolignans bound to the PPAR gamma LBD with EC(50) values in the nanomolar range, exhibiting a binding pattern highly similar to the clinically used agonist pioglitazone. In intact cells, Dieugenol and tetrahydroDieugenol selectively activated human PPAR gamma-mediated, but not human PPAR alpha- or -beta/delta-mediated luciferase reporter expression, with a pattern suggesting partial PPAR gamma agonism. The coactivator recruitment study also demonstrated partial agonism of the tested neolignans. Dieugenol, tetrahydroDieugenol, and magnolol but not the structurally related eugenol induced 3T3-L1 preadipocyte differentiation, confirming effectiveness in a cell model with endogenous PPAR gamma expression. In conclusion, we identified neolignans as novel ligands for PPAR gamma, which exhibited interesting activation profiles, recommending them as potential pharmaceutical leads or dietary supplements.

Antioxidant activity of eugenol and related monomeric and dimeric compounds.[Pubmed:11045452]

Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1467-9.

Since the inhibitory effect of eugenol (a), which was isolated as an antioxidative component from plant, Caryopylli flos, on lipid peroxidation was less than that of alpha-tocopherol, we synthesized the eugenol-related compounds Dieugenol (b), tetrahydroDieugenol (c), and dihydroeugenol (d), to find new strong antioxidants and assessed them for their inhibitory effect on lipid peroxidation and scavenging ability for superoxide and hydroxyl radicals. The antioxidative activities were in the order: (b)>(c)>(d)>(a) for the thiobarbituric acid reactive substance (TBARS) formation. These results suggest that the dimerized compounds have higher antioxidant activities than that of the monomers. Electron spin resonance (ESR) spin trapping experiments revealed that eugenol and its dimer, having allyl groups in the structure, scavenged superoxide, and that only eugenol trapped hydroxyl radicals under the conditions used. These finding suggest that eugenol and Dieugenol have a different mechanism of antioxidation, i.e. eugenol may inhibit lipid peroxidation at the level of initiation, however, the related dimeric compounds may inhibit lipid peroxidation at the level of propagation of free radical chain reaction like alpha-tocopherol.

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