Irenolone

CAS# 149184-19-0

Irenolone

Catalog No. BCN7146----Order now to get a substantial discount!

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Quality Control of Irenolone

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Chemical structure

Irenolone

3D structure

Chemical Properties of Irenolone

Cas No. 149184-19-0 SDF Download SDF
PubChem ID 2754650 Appearance Powder
Formula C19H12O3 M.Wt 288.30
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one
SMILES C1=CC2=C3C(=C1)C(=O)C(=CC3=C(C=C2)C4=CC=C(C=C4)O)O
Standard InChIKey UQMKPTIDKHEGFW-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H12O3/c20-13-7-4-11(5-8-13)14-9-6-12-2-1-3-15-18(12)16(14)10-17(21)19(15)22/h1-10,20-21H
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 Irenolone

The fruits of Musa itinerans Cheesm.

Biological Activity of Irenolone

DescriptionIrenolone is a natural product from Musa itinerans Cheesm.
In vitro

Diarylheptanoids and phenylphenalenones from Musa itinerans fruits.[Pubmed: 24766994]

Phytochemistry. 2014 Jul;103:171-177.


METHODS AND RESULTS:
Two diarylheptanoids, musaitinerins A and B, one heterodimeric phenylphenalenone musaitinerone and four known phenylphenalenones, identified as 4-hydroxy-2-methoxy-9-phenyl-1H-phenalen-1-one, musanolone E, hydroxyanigorufone and Irenolone were isolated from the fruits of Musa itinerans Cheesm. Their structures were elucidated using spectroscopic analyses. The antimicrobial activity of these compounds was evaluated against Escherichia coli, Staphylococcus aureus and Candida albicans; the cytotoxic activity of these compounds was also evaluated against human erythromyeloblastoid leukemia (K562) and human alveolar carcinoma epithelial (A549) cell lines, respectively.
CONCLUSIONS:
Musaitinerone and musanolone E exhibited weak effects against the A549 cell line, as compared with adriamycin. However, these two compounds did not exhibit any growth inhibition against K562 cells, S. aureus, E. coli or C. albicans. The other compounds were inactive against all of the tested cell lines and microorganisms, even at concentrations as high as 50 μM.

Changes in the content and biosynthesis of phytoalexins in banana fruit.[Pubmed: 11129580 ]

Biosci Biotechnol Biochem. 2000 Oct;64(10):2089-98.


METHODS AND RESULTS:
Changes in the phytoalexin content in unripe fruit of banana, Musa acuminata, were analyzed after various treatments. The results show that level of hydroxyanigorufone started to increase 1-2 day after either wounding or inoculation with conidia of Colletotrichum musae. Inoculation followed by wounding induced the formation of many other phenylphenalenones. The accumulation of hydroxyanigorufone decreased, after its transient maximum, on ripening by exposure of the wounded fruit to ethylene. The level of production of hydroxyanigorufone in ripe fruit treated by wounding and/or by inoculation was much lower than that in unripe fruit. 2-Aminooxyacetic acid, an inhibitor of phenylalanine ammonia-lyase (PAL), inhibited the accumulation of hydroxyanigorufone in wounded fruit, and the PAL activity increased after wounding and ethylene treatment, respectively.
CONCLUSIONS:
Feeding experiments with [1-(13)C] and [2-(13)C]cinnamic acids, and [2-(13)C]malonate show that two molecules of cinnamic acid and one of malonate were incorporated into each molecule of hydroxyanigorufone. The phytoalexins isolated from fruit to which deuterated hydroxyanigorufone and Irenolone had been administered revealed that 2-(4'-hydroxyphenyl)-1,8-naphthalic anhydride was biosynthesized from hydroxyanigorufone rather than from Irenolone.

Irenolone Dilution Calculator

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Irenolone Molarity Calculator

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Preparing Stock Solutions of Irenolone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4686 mL 17.343 mL 34.6861 mL 69.3722 mL 86.7152 mL
5 mM 0.6937 mL 3.4686 mL 6.9372 mL 13.8744 mL 17.343 mL
10 mM 0.3469 mL 1.7343 mL 3.4686 mL 6.9372 mL 8.6715 mL
50 mM 0.0694 mL 0.3469 mL 0.6937 mL 1.3874 mL 1.7343 mL
100 mM 0.0347 mL 0.1734 mL 0.3469 mL 0.6937 mL 0.8672 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 Irenolone

Diarylheptanoids and phenylphenalenones from Musa itinerans fruits.[Pubmed:24766994]

Phytochemistry. 2014 Jul;103:171-177.

Two diarylheptanoids, musaitinerins A and B, one heterodimeric phenylphenalenone musaitinerone and four known phenylphenalenones, identified as 4-hydroxy-2-methoxy-9-phenyl-1H-phenalen-1-one, musanolone E, hydroxyanigorufone and Irenolone were isolated from the fruits of Musa itinerans Cheesm. Their structures were elucidated using spectroscopic analyses. The antimicrobial activity of these compounds was evaluated against Escherichia coli, Staphylococcus aureus and Candida albicans; the cytotoxic activity of these compounds was also evaluated against human erythromyeloblastoid leukemia (K562) and human alveolar carcinoma epithelial (A549) cell lines, respectively. Musaitinerone and musanolone E exhibited weak effects against the A549 cell line, as compared with adriamycin. However, these two compounds did not exhibit any growth inhibition against K562 cells, S. aureus, E. coli or C. albicans. The other compounds were inactive against all of the tested cell lines and microorganisms, even at concentrations as high as 50 muM.

[Active compounds from rhizomes of Musa basjoo].[Pubmed:21141492]

Zhongguo Zhong Yao Za Zhi. 2010 Sep;35(18):2424-7.

OBJECTIVE: To study the active compounds from the rhizomes of Musa basjoo. METHOD: Antioxidant and alpha-glucosidase inhibitory activity of different extracts were tested. Using bioassay-guided fractionation, the chemical constituents in EtOAC extracts were isolated by column chromatography and identified by MS and NMR spectroscopy. RESULT: Five compounds were isolated and identified as 2',3, 4'-trihydroxyflavone (1), 3,3'-bis-hydroxyanigorufone (2), Irenolone (3), 4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone (4) and 3,4-dihydroxybenzaldehyde (5). Compound 1(IC50 8.61 mg x L(-1)), 3 (IC50 19.55 mg x L(-1)) and 5 (IC50 1.1 mg x L(-1)) had antioxidant activity. Compound 2 (IC50 24.15 mg x L(-1)) and 4(IC50 2.81 mg x L(-1)) had alpha-glucosidase inhibitory activity. Compound 5 showed MIC of 0.078, 0.313, 0.039 microg/disc against SA, MRSA and ESBLs, respectively. CONCLUSION: Compound 1-5 were isolated from this plant for the first time. Compound 5 was isolated from the genus Musa for the first time. All compound except 5 were first reported about activity.

Changes in the content and biosynthesis of phytoalexins in banana fruit.[Pubmed:11129580]

Biosci Biotechnol Biochem. 2000 Oct;64(10):2089-98.

Changes in the phytoalexin content in unripe fruit of banana, Musa acuminata, were analyzed after various treatments. The results show that level of hydroxyanigorufone started to increase 1-2 day after either wounding or inoculation with conidia of Colletotrichum musae. Inoculation followed by wounding induced the formation of many other phenylphenalenones. The accumulation of hydroxyanigorufone decreased, after its transient maximum, on ripening by exposure of the wounded fruit to ethylene. The level of production of hydroxyanigorufone in ripe fruit treated by wounding and/or by inoculation was much lower than that in unripe fruit. 2-Aminooxyacetic acid, an inhibitor of phenylalanine ammonia-lyase (PAL), inhibited the accumulation of hydroxyanigorufone in wounded fruit, and the PAL activity increased after wounding and ethylene treatment, respectively. Feeding experiments with [1-(13)C] and [2-(13)C]cinnamic acids, and [2-(13)C]malonate show that two molecules of cinnamic acid and one of malonate were incorporated into each molecule of hydroxyanigorufone. The phytoalexins isolated from fruit to which deuterated hydroxyanigorufone and Irenolone had been administered revealed that 2-(4'-hydroxyphenyl)-1,8-naphthalic anhydride was biosynthesized from hydroxyanigorufone rather than from Irenolone.

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