IsovelleralAn irritant fungal terpenoid that inhibits the TRPV1 channel

Isovelleral (CAS 37841-91-1)

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Synonym: TRPV1 antagonist
Application: An irritant fungal terpenoid that inhibits the TRPV1 channel
CAS Number: 37841-91-1
Purity: ≥99%
Molecular Weight: 232.3
Molecular Formula: C15H20O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Isovelleral is an irritant fungal terpenoid that inhibits the TRPV1 (transient receptor potential vanilloid-1) channel. TRPV1 is a Capsaicin receptor that behaves as a non-selective cation channel that is mainly found in the sensory neurons, and specifically detects painful stimuli, low pH and heat. Research shows that out of twenty unsaturated sesquiterpene dialdehydes tested for cytotoxic and antimicrobial activity, Isovelleral was one of the most potent compounds. The compound has been shown to activate the ion channel, TRPA1, which is associated in the signaling of inflammatory pain. Isovelleral is an inhibitor of VR1 and an activator of ANKTM1.


References

1. Anke, H. and Sterner, O. 1999. Planta Med. 57: 344-346. PMID: 1775575
2. Jonassohn, M., et al. 1997. Bioorg. Med. Chem. 5: 1363-1367. PMID: 9377096
3. Ralevic, V., et al. 2003. Biochem. Pharmacol. 65: 143-151. PMID: 12473388
4. Escalera, J., et al. 2008. J. Biol. Chem. 283: 24136-24144. PMID: 18550530
5. Schumacher, M.A. and Eilers, H. 2010. Front. Biosci. 15: 872-882. PMID: 20515731

Appearance :
Crystalline
Physical State :
Solid
Solubility :
Soluble in organic solvents. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
101.85° C (Predicted)
Boiling Point :
322.79° C at 760 mmHg (Predicted)
Density :
1.21 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
EDG-6: IC50 = 253 nM (human); GPR55: IC50 = 500 nM (human); Heat shock factor protein 1: IC50 = 530 nM (mouse); XBP-1: IC50 = 2.35 µM (human); EDG-1: IC50 = 4.96 µM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GZ2245000
PubChem CID :
37839
MDL Number :
MFCD01735881
Beilstein Registry :
2506661
SMILES :
C[C@]12C[C@]1(C(=C[C@H]3[C@@H]2CC(C3)(C)C)C=O)C=O

Download SDS (MSDS)

Certificate of Analysis

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