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2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

CAS# 151731-50-9

2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

Catalog No. BCN1675----Order now to get a substantial discount!

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2,2-Dimethyl-8-prenylchromene 6-carboxylic acid: 5mg $886 In Stock
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Quality Control of 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

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Chemical structure

2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

3D structure

Chemical Properties of 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

Cas No. 151731-50-9 SDF Download SDF
PubChem ID 441962 Appearance Powder
Formula C17H20O3 M.Wt 272.3
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,2-dimethyl-8-(3-methylbut-2-enyl)chromene-6-carboxylic acid
SMILES CC(=CCC1=C2C(=CC(=C1)C(=O)O)C=CC(O2)(C)C)C
Standard InChIKey MCQWYGYDCGLCJD-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 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

The herbs of Piper aduncum.

Biological Activity of 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

Description2,2-Dimethyl-8-prenylchromene 6-carboxylic acid showed antioxidative activity.
In vitro

Antioxidative, Antihyaluronidase and Antityrosinase Activities of Some Constituents from the Aerial Part of Piper elongatum VAHL.[Reference: WebLink]

Food Science and Technology Research, 2003, 9(2):197-201.


METHODS AND RESULTS:
Seven known compounds, pyrroside B (1), swertisin (2), isovitexin (3), isoswertiajaponin (4), vomifoliol (blumenol A) (5), (6S,9R)-roseoside (6) and angelicoidenol (7) were isolated from the methanol (MeOH) extract of the aerial part of Piper elongatum VAHL. and their structures were identified on the basis of physical and spectral data. In addition, the antioxidative activity of 1–4 was evaluated by the ferric thiocyanate method.
CONCLUSIONS:
All these compounds showed stronger antioxidative activity than that of α-tocopherol. Furthermore, the scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH), the antihyaluronidase and the antityrosinase activities of 1–4, asebogenin (8), 2′,6′-dihydroxy-4′-methoxydihydrochalcone (9), 3-geranyl-4-methoxybenzoic acid (10), 3-geranyl-4-hydroxybenzoic acid (11), nervogenic acid (12) and 2,2-dimethyl-6-carboxyl-8-prenyl-chromene (2,2-Dimethyl-8-prenylchromene 6-carboxylic acid,13), which were previously isolated from the MeOH extract were evaluated. Compounds 4, 8 and 9 showed higher radical scavenging effect than that of L-cysteine, and 4, 8 and 11 exhibited stronger inhibition effect on the activation of hyaluronidase than that of tranilast. Compound 8 indicated almost the same antityrosinase activity as that of kojic acid.

2,2-Dimethyl-8-prenylchromene 6-carboxylic acid Dilution Calculator

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2,2-Dimethyl-8-prenylchromene 6-carboxylic acid Molarity Calculator

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Preparing Stock Solutions of 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6724 mL 18.3621 mL 36.7242 mL 73.4484 mL 91.8105 mL
5 mM 0.7345 mL 3.6724 mL 7.3448 mL 14.6897 mL 18.3621 mL
10 mM 0.3672 mL 1.8362 mL 3.6724 mL 7.3448 mL 9.1811 mL
50 mM 0.0734 mL 0.3672 mL 0.7345 mL 1.469 mL 1.8362 mL
100 mM 0.0367 mL 0.1836 mL 0.3672 mL 0.7345 mL 0.9181 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 2,2-Dimethyl-8-prenylchromene 6-carboxylic acid

Molecular structure, FT-IR, FT-Raman, NBO, HOMO and LUMO, MEP, NLO and molecular docking study of 2-[(E)-2-(2-bromophenyl)ethenyl]quinoline-6-carboxylic acid.[Pubmed:26142173]

Spectrochim Acta A Mol Biomol Spectrosc. 2015;151:184-97.

The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 2-[(E)-2-(2-bromophenyl)ethenyl]quinoline-6-carboxylic acid have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of the normal modes of vibrations was done using GAR2PED program. (1)H NMR chemical shifts calculations were carried out by using B3LYP functional with SDD basis set. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. MEP was performed by the DFT method and the predicted infrared intensities and Raman activities have also been reported. The calculated geometrical parameters are in agreement with that of similar derivatives. The title compound forms a stable complex with PknB as is evident from the binding affinity values and the molecular docking results suggest that the compound might exhibit inhibitory activity against PknB and this may result in development of new anti-tuberculostic agents.

Regioselective synthesis of 2,8-disubstituted 4-aminopyrido[3,2-d]pyrimidine-6-carboxylic acid methyl ester compounds.[Pubmed:22118529]

J Org Chem. 2012 Jan 6;77(1):243-52.

We report herein the synthesis of 4-amino-2,8-dichloropyrido[3,2-d]pyrimidine derivatives 2 and their regioselective diversification through S(N)Ar and metal-catalyzed cross-coupling reactions. While amination of 2 took place selectively at C-2, the regioselectivity of thiol or thiolate addition depended on the reaction conditions. Selective C-8 addition was obtained in DMF with Hunig's base and C-2 addition in (i)PrOH. These C-2 or C-8 regioselective thiolations provided an opportunistic way to selectively activate either of the two positions toward the metal-catalyzed cross-coupling reaction. The chloride could be efficiently substituted by Suzuki-Miyaura reaction and the sulfanyl group by Liebeskind-Srogl cross-coupling reaction, demonstrating the orthogonality of both reactive centers. The development of regioselective conditions for these different transformations yielded the synthesis of 4-amino-2,6,8-trisubstituted pyrido[3,2-d]pyrimidine derivatives, with various substituents.

Novel lipophilic 7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid derivatives as potential antitumor agents: improved synthesis and in vitro evaluation.[Pubmed:21067931]

Bioorg Med Chem. 2010 Dec 15;18(24):8537-48.

A convenient route for the synthesis of some acyloxymethyl esters and carboxamides of levofloxacin (LV) with modulated lipophilicity is described. The synthesized compounds were evaluated in vitro for their growth inhibitory effect in five human cancer cell lines. The most efficient LV derivatives (ester 2e and amide 4d) displayed IC(50) values in the 0.2-2.2 muM range, while IC(50) values for parent LV ranged between 70 and 622 muM depending on the cell line. The esters displayed no in vivo toxicity up to 80 mg/kg when administered intraperitoneally. This study thus shows that LV analogs displayed antitumor efficacy, at least in vitro, a feature that appeared to be independent from the lipophilicity of the grafted substituent.

7-Amino-2-methylsulfanyl-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylic acid as the dimethylformamide and water monosolvates at 293 K.[Pubmed:20921616]

Acta Crystallogr C. 2010 Oct;66(Pt 10):o503-7.

The molecular structure of 7-amino-2-methylsulfanyl-1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylic acid is reported in two crystal environments, viz. as the dimethylformamide (DMF) monosolvate, C(7)H(7)N(5)O(2)S.C(3)H(7)NO, (I), and as the monohydrate, C(7)H(7)N(5)O(2)S.H(2)O, (II), both at 293 (2) K. The triazolo[1,5-a]pyrimidine molecule is of interest with respect to the possible biological activity of its coordination compounds. While the DMF solvate exhibits a layered structural arrangement through N...O hydrogen-bonding interactions, the monohydrate displays a network of intermolecular O...O and N...O hydrogen bonds assisted by cocrystallized water molecules and weak pi-pi stacking interactions, leading to a different three-dimensional supramolecular architecture. Based on results from topological analyses of the electron-density distribution in X-H...O (X = O, N and C) regions, hydrogen-bonding energies have been estimated from structural information only, enabling the characterization of hydrogen-bond graph energies.

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