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Merck
CN

SML0726

Sigma-Aldrich

Panepoxydone

from Lentinus conatus, ≥95% (HPLC)

Synonym(s):

(1S,5R,6S)-5-Hydroxy-3-[(1S)-1-hydroxy-3-methyl-2-buten-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

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About This Item

Empirical Formula (Hill Notation):
C11H14O4
CAS Number:
31298-54-1
Molecular Weight:
210.23
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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biological source

Lentinus conatus

Assay

≥95% (HPLC)

form

powder

storage condition

protect from light

solubility

DMSO: soluble 10 mg/mL

storage temp.

−20°C

InChI

1S/C11H14O4/c1-5(2)3-7(12)6-4-8(13)10-11(15-10)9(6)14/h3-4,7-8,10-13H,1-2H3/t7?,8-,10+,11-/m1/s1

InChI key

MBXKEYXHJAZKBP-VQZXEUHYSA-N

Biochem/physiol Actions

Panepoxydone is a fungal metabolite that inhibits NF-κB transcription factor by preventing IκB phosphorylation, thus inhibiting the release of NF-κB from the IκB : NF-κB complex and its translocation into the nucleus. Panepoxydone also has antimalarial, cytotoxic activities and anti-parasitic activity against Trypanosoma cruzi.
Panepoxydone is a fungal metabolite that inhibits NF-κB transcription factor.

Preparation Note

Soluble in ethyl acetate, ethanol, and DMSO (10mg/ml). The product is soluble, but not stable in water and methanol.

Other Notes

Store the product sealed at -20 °C, protect from light. Under these conditions, the product is stable for at least 2 years.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
044M4118V
14140216
32140202
32140201

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J Brad Shotwell et al.
Bioorganic & medicinal chemistry letters, 12(23), 3463-3466 (2002-11-07)
A number of inhibitors of NF-kappaB signaling arising from our recent syntheses of isopanepoxydone and panepoxydone have been identified. Structure-activity data have been correlated to allow the design and synthesis of an affinity reagent for the isolation and identification of
E M Souza-Fagundes et al.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas, 43(11), 1054-1061 (2010-11-23)
Hypnophilin and panepoxydone, terpenoids isolated from Lentinus strigosus, have significant inhibitory activity on Trypanosoma cruzi trypanothione reductase (TR). Although they have similar TR inhibitory activity at 10 μg/mL (40.3 μM and 47.6 μM for hypnophilin and panepoxydone, respectively; ~100%), hypnophilin
Z Y Jiang et al.
Placenta, 33(1), 1-7 (2011-11-04)
To date, the relationship between inflammatory cytokines and progesterone receptors (PRs) has been little studied, although both mediate the mechanism of parturition in human deciduas. Thus, the aim of study was to investigate the role of an inflammatory cytokine, tumor

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