Guvacine

CAS# 498-96-4

Guvacine

Catalog No. BCN6529----Order now to get a substantial discount!

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Quality Control of Guvacine

Number of papers citing our products

Chemical structure

Guvacine

3D structure

Chemical Properties of Guvacine

Cas No. 498-96-4 SDF Download SDF
PubChem ID 3532 Appearance Powder
Formula C6H9NO2 M.Wt 127.14
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,2,3,6-tetrahydropyridine-5-carboxylic acid
SMILES C1CNCC(=C1)C(=O)O
Standard InChIKey QTDZOWFRBNTPQR-UHFFFAOYSA-N
Standard InChI InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
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 Guvacine

The fruits of Areca catechu

Biological Activity of Guvacine

Descriptionmeso-Hannokinol and (+)-hannokinol can significantly inhibit lipopolysaccharide-induced nitric oxide production in BV2 microglial cells at concentrations ranging from 1 uM to 100 uM.
TargetsNO
In vitro

Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko.[Pubmed: 18523923]

Planta Med. 2008 Jun;74(8):867-9.

A methanolic extract of the fruits of AMOMUM TSAO-KO (Zingiberaceae) significantly attenuated nitric oxide production in lipopolysaccharide-simulated BV2 microglia.
METHODS AND RESULTS:
Two new bicyclic nonanes characterized as 6,7-dihydroxy-indan-4-carbaldehyde ( 1) and 6-hydroxy-indan-4-carbaldehyde ( 2) were isolated with the eleven known compounds 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid ( 3), tsaokoin ( 4), isotsaokoin ( 5), 8-oxogeraniol ( 6), P-menth-1-ene-5,6-diol ( 7), 3alpha-hydroxycarvotagenone ( 8), tsaokoarylone ( 9), 1,7-bis(4-hydroxy-3-methoxyphenyl)-4,6-heptadien-3one ( 10), (+)-hannokinol ( 11), meso-Hannokinol ( 12) and hannokinin ( 13), from the fruits of A. TSAO-KO using bioactivity-guided fractionation.
CONCLUSIONS:
All thirteen compounds significantly inhibited lipopolysaccharide-induced nitric oxide production in BV2 microglial cells at concentrations ranging from 1 microM to 100 microM.

Bioactivity evaluation of ingredients identified from the fruits of Amomum tsaoko Crevost et Lemaire, a Chinese spice.[Pubmed: 24915829]

Food Funct. 2014 Aug;5(8):1747-54.


METHODS AND RESULTS:
In this work, a phytochemical investigation was conducted on Amomum tsaoko Crevost et Lemaire, a traditional Chinese spice. Based on spectroscopic methods including MS, (1)H-NMR, (13)C-NMR, DEPT135 and HMQC spectroscopy, eight main chemical compositions, sitosterol, daucosterol, meso-Hannokinol, quercetin, epicatechin, quercetin-7-O-β-glucoside, quercetin-3-O-β-glucoside, and catechol, were isolated and identified from A. tsaoko, among which quercetin, quercetin-7-O-β-glucoside and quercetin-3-O-β-glucoside were first found in A. tsaoko.
CONCLUSIONS:
Their bioactivities were evaluated by the inhibitory effect on NO production in LPS-stimulated macrophage RAW 264.7 cells, the protective effect on H2O2-induced apoptosis of PC-12 cells and the DPPH radical scavenging assay.

Guvacine Dilution Calculator

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Guvacine Molarity Calculator

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Preparing Stock Solutions of Guvacine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.8653 mL 39.3267 mL 78.6535 mL 157.3069 mL 196.6336 mL
5 mM 1.5731 mL 7.8653 mL 15.7307 mL 31.4614 mL 39.3267 mL
10 mM 0.7865 mL 3.9327 mL 7.8653 mL 15.7307 mL 19.6634 mL
50 mM 0.1573 mL 0.7865 mL 1.5731 mL 3.1461 mL 3.9327 mL
100 mM 0.0787 mL 0.3933 mL 0.7865 mL 1.5731 mL 1.9663 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 Guvacine

Synthesis and Biological Evaluation of Nipecotic Acid and Guvacine Derived 1,3-Disubstituted Allenes as Inhibitors of Murine GABA Transporter mGAT1.[Pubmed:30957949]

ChemMedChem. 2019 Apr 8.

A new class of nipecotic acid and Guvacine derivatives has been synthesized and characterized regarding their inhibitory potency at mGAT1-4 and binding affinity for mGAT1. Compounds of the described class are defined by a four-carbon atom allenyl spacer connecting the nitrogen of the nipecotic acid or Guvacine head with an aromatic residue. Among the compounds investigated, the nipecotic acid derivative 21p, possessing an o-terphenyl residue, was identified as highly selective and most potent mGAT1 inhibitor in this study. For the (R)-nipecotic acid derived form of 21p, the inhibitory potency in [3H]GABA-Uptake-Assays has been determined as pIC50 = 6.78 +/- 0.08 and the binding affinity in MS Binding Assays as pKi = 7.10 +/- 0.12. The synthesis of the designed compounds was carried out by a two-step procedure, generating the allene moiety via allenylation of terminal alkynes that allows a broad variation of the terminal phenyl and biphenyl subunit.

Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with alpha-Methylallenoates.[Pubmed:30246538]

Org Lett. 2018 Oct 5;20(19):6089-6093.

P-Chiral [2.2.1] bicyclic phosphines (HypPhos catalysts) have been applied to reactions between alpha-alkylallenoates and imines, producing Guvacine derivatives. These HypPhos catalysts were assembled from trans-4-hydroxyproline, with the modular nature of the synthesis allowing variations of the exocyclic P and N substituents. Among them, exo-( p-anisyl)-HypPhos was most efficacious for [4 + 2] annulations between ethyl alpha-methylallenoate and imines. Through this method, ( R)-aplexone was identified as being responsible for the decrease in the cellular levels of cholesterol.

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