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Description: Non-pungent vanilloid receptor agonist
Alternative Names: Phorbol 12-phenylacetate 13-acetate 20-homovanillate
Chemical Name: [(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-9-[phenylacetyl)oxy]-1H-cyclopropa[3,4]benz[1,2-e]azulen-3-yl]methyl ester benzeneacetic acid
Purity: ≥98% (HPLC)
Biological Activity
Non-pungent vanilloid TRPV1 (VR1) receptor agonist (Ki = 3.1 μM) that displays non-cooperative binding. Induces apoptosis via a non-VR1 mechanism in Jurkat cells and causes vasoconstriction in vivo.
Technical Data
| M. Wt | 688.77 |
| Formula | C39H44O11 |
| Storage | Desiccate at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 175796-50-6 |
| PubChem ID | 3035862 |
| InChI Key | OGRGWTXWAZBJKF-JXWJAAHMSA-N |
| Smiles | O=C1C(C)=C[C@]2([H])[C@@](O)1CC(COC(CC5=CC(OC)=C(O)C=C5)=O)=C[C@]3([H])[C@@](O)2[C@H](C)[C@@H](OC(CC6=CC=CC=C6)=O)[C@]4(OC(C)=O)[C@]([H])3C(C)4C |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data
| Solubility | Soluble in DMSO and in ethanol |
Product Datasheets
References
References are publications that support the biological activity of the product.
Griffiths et al (2000) Functional and desensitizing effects of the novel synthetic vanilloid-like agent 12-phenylacetate 13-acetate 20-homovanillate (PPAHV) in the perfused rat hindlimb. Br.J.Pharmacol. 131 1408 PMID: 11090114
Macho et al (2000) Phorboid 20-homovanillates induce apoptosis through a VR1-independent mechanism. Chem.Biol. 7 483 PMID: 10903936
Szallasi et al (1996) A novel agonist, phorbol 12-phenylacetate 13-acetate 20-homovanillate, abolishes positive cooperativity of binding by the vanilloid receptor. Eur.J.Pharmacol. 299 221 PMID: 8901026
If you know of a relevant reference for PPAHV, please let us know.
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Keywords: PPAHV, PPAHV supplier, Non-pungent, vanilloid, receptor, agonists, Receptors, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, Phorbol12, phenylacetate13, acetate20, homovanillate, Phorbol, 12-phenylacetate, 13-acetate, 20-homovanillate, 1466, Tocris Bioscience
Citations for PPAHV
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Pain Research Product Guide
A collection of over 280 products for pain research, the guide includes research tools for the study of:
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Peripheral sensitization is the reduction in the threshold of excitability of sensory neurons that results in an augmented response to a given external stimulus. This poster outlines the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. The role of ion channels, GPCRs, neurotrophins, and cytokines in sensory neurons are also described.