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9-Hydroxycanthin-6-one

CAS# 138544-91-9

9-Hydroxycanthin-6-one

Catalog No. BCN3105----Order now to get a substantial discount!

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Chemical structure

9-Hydroxycanthin-6-one

3D structure

Chemical Properties of 9-Hydroxycanthin-6-one

Cas No. 138544-91-9 SDF Download SDF
PubChem ID 10263500 Appearance Yellow powder
Formula C14H8N2O2 M.Wt 236.2
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES C1=CC2=C3C=CNC4=C3N(C2=CC1=O)C(=O)C=C4
Standard InChIKey YMNACIYZMIKRMM-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 9-Hydroxycanthin-6-one

The barks of Ailanthus altissima

Biological Activity of 9-Hydroxycanthin-6-one

Description1. 9-Hydroxycanthin-6-one inhibits Wnt signaling through the activation of GSK3β independent of CK1α. 2. 9-Hydroxycanthin-6-one might be the active component that contributed to the aphrodisiac effect of E. longifolia by antagonizing the smooth muscle tone of CC as well as SV probably through interfering with Ca2+ mobilization.
TargetsCalcium Channel | Potassium Channel | GSK-3 | Wnt/β-catenin

9-Hydroxycanthin-6-one Dilution Calculator

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9-Hydroxycanthin-6-one Molarity Calculator

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Preparing Stock Solutions of 9-Hydroxycanthin-6-one

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.2337 mL 21.1685 mL 42.337 mL 84.674 mL 105.8425 mL
5 mM 0.8467 mL 4.2337 mL 8.4674 mL 16.9348 mL 21.1685 mL
10 mM 0.4234 mL 2.1169 mL 4.2337 mL 8.4674 mL 10.5843 mL
50 mM 0.0847 mL 0.4234 mL 0.8467 mL 1.6935 mL 2.1169 mL
100 mM 0.0423 mL 0.2117 mL 0.4234 mL 0.8467 mL 1.0584 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 9-Hydroxycanthin-6-one

9-hydroxycanthin-6-one induces penile erection and delays ejaculation.[Pubmed:21569213]

J Sex Med. 2012 Apr;9(4):1027-36.

INTRODUCTION: Eurycoma longifolia Jack (Simaroubaceae) has the reputation as a male aphrodisiac because it is claimed to increase virility and sexual prowess. Nevertheless, whether or not E. longifolia regulates directly the muscle tone of corpus cavernosa and/or seminal vesicle (SV) remains unclear. Even until now, the compositions that could account for its aphrodisiac property are still unknown AIM: We examined the effect of 9-Hydroxycanthin-6-one (9-HC-6-one), a beta-carboline alkaloid isolated from E. longifolia, on penile erection and ejaculation, and further elucidated the mechanism of action. MAIN OUTCOME MEASURES: 9-HC-6-one induces penile erection and delays ejaculation. METHODS: Drug's effect was studied on rat corpus cavernosum (CC) and SV in vitro, and on the changes in intracavernosal pressure (ICP) after IC injection and intraluminal pressure (ILP) of the SV after hypogastric nerve stimulation (HNS), respectively. RESULTS: 9-HC-6-one relaxed significantly phenylephrine (PE)-precontracted CC. Such response was not attenuated by endothelium disruption, N(G) -nitro-L-arginine methyl ester, or 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one treatment, suggesting that a nitric oxide/cyclic guanosine monophosphate-dependent pathway was precluded. 9-HC-6-one attenuated PE-induced contraction by blocking cell surface and internal calcium channels with a higher potency for internal calcium release. This compound also antagonized calcium-evoked contraction in Ca2+ -free, high K+ -depolarizing condition, suggesting that interfering with the entry of calcium through voltage-dependent channels also contributed to 9-HC-6-one-induced corporal relaxation. After IC application of 9-HC-6-one, a significant rise in ICP was observed as compared with the application of normal saline. 9-HC-6-one relaxed significantly norepinephrine (NE)- and KCl-precontracted SV, and antagonized NE-induced oscillatory contraction as potent as clomipramine. Finally, the HNS-evoked increase in ILP was dose-dependently repressed after challenge by 9-HC-6-one. CONCLUSION: 9-HC-6-one might be the active component that contributed to the aphrodisiac effect of E. longifolia by antagonizing the smooth muscle tone of CC as well as SV probably through interfering with Ca2+ mobilization.

Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia.[Pubmed:1800638]

J Nat Prod. 1991 Sep-Oct;54(5):1360-7.

By bioactivity-directed fractionation, five cytotoxic constituents have been characterized from the roots of Eurycoma longifolia collected in Kalimantan, Indonesia. Four canthin-6-one alkaloids, namely, 9-methoxycanthin-6-one, 9-methoxycanthin-6-one-N-oxide, 9-Hydroxycanthin-6-one, and 9-Hydroxycanthin-6-one-N-oxide, and one quassinoid, eurycomanone, were found to be cytotoxic principles. Each of these compounds was evaluated against a panel of cell lines comprising a number of human cancer cell types [breast, colon, fibrosarcoma, lung, melanoma, KB, and KB-V1 (a multi-drug resistant cell line derived from KB)] and murine lymphocytic leukemia (P-388). The canthin-6-ones 1-4 were found to be active with all cell lines tested except for the KB-V1 cell line. Eurycomanone was inactive against murine lymphocytic leukemia (P-388) but was significantly active against the human cell lines tested. Two additional isolates, the beta-carboline alkaloids beta-carboline-1-propionic acid and 7-methoxy-beta-carboline-1-propionic acid, were not significantly active with these cultured cells. However, compounds 5 and 7 were found to demonstrate significant antimalarial activity as judged by studies conducted with cultured Plasmodium falciparum strains. The structures of the novel compounds 2-4 and 7 were established by spectral and chemical methods.

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