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Merck
CN

P266

Phorbol 12-phenylacetate 13-acetate 20-homovanillate

solid

Synonym(s):

PPAHV

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About This Item

Empirical Formula (Hill Notation):
C39H44O11
CAS Number:
175796-50-6
Molecular Weight:
688.76
UNSPSC Code:
12352200
PubChem Substance ID:
24898345
MDL number:
MFCD06411584

Key Documents

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InChI

1S/C39H44O11/c1-21-14-30-37(45,34(21)44)19-26(20-48-31(42)18-25-12-13-28(41)29(16-25)47-6)15-27-33-36(4,5)39(33,50-23(3)40)35(22(2)38(27,30)46)49-32(43)17-24-10-8-7-9-11-24/h7-16,22,27,30,33,35,41,45-46H,17-20H2,1-6H3/t22-,27+,30-,33-,35-,37-,38-,39-/m1/s1

SMILES string

COc1cc(CC(=O)OCC2=CC3C4C(C)(C)[C@]4(OC(C)=O)[C@H](OC(=O)Cc5ccccc5)[C@@H](C)[C@]3(O)C6C=C(C)C(=O)[C@@]6(O)C2)ccc1O

InChI key

OGRGWTXWAZBJKF-JXWJAAHMSA-N

form

solid

color

white

solubility

DMSO: soluble, H2O: insoluble

Biochem/physiol Actions

Vanilloid receptor agonist.

Legal Information

Sold in France, Germany, Great Britain and Switzerland under license, restricted to research use only, from Procyon Pharmaceuticals, Inc.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
106K1653
129H0786

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L Liu et al.
Neuroscience, 84(2), 569-581 (1998-04-16)
Capsaicin, the vanilloid responsible for the pungent taste of hot peppers, binds to receptors found primarily in polymodal nociceptors. Capsaicin initially stimulates polymodal nociceptors and subsequently inhibits them from responding to a variety of stimuli. This property makes it useful
J S Shin et al.
Neuroscience letters, 299(1-2), 135-139 (2001-02-13)
Heterologously expressed vanilloid receptor 1 (VR1), a cloned cDNA encoding for capsaicin (CAP)-sensitive currents, resembles the native CAP channels in cultured sensory neurons in channel property. But, the pharmacological profile of VR1 to various CAP analogs is not known. The
G Appendino et al.
Journal of medicinal chemistry, 39(16), 3123-3131 (1996-08-02)
A number of phorboid 20-homovanillates were prepared by condensation of phorbol 12,13-diesters and 12-dehydrophorbol 13-esters with Mem-homovanillic acid followed by removal of the protecting group with SnCl4 in THF. These compounds were evaluated for their ability to inhibit [3H]resiniferatoxin (RTX)
A Szallasi et al.
European journal of pharmacology, 299(1-3), 221-228 (1996-03-28)
Capsaicin binds to a specific recognition site, referred to as the vanilloid receptor, which it shares with the natural, ultrapotent agonist resiniferatoxin and with the competitive antagonist capsazepine. Upon binding to its receptor, capsaicin opens a cation channel leading to
Dominic P Geraghty et al.
British journal of pharmacology, 137(6), 919-927 (2002-11-02)
1. Activation of vanilloid receptors on sensory nerve terminals in the commissural nucleus of the solitary tract (cNTS) of rats with capsaicin, produces respiratory slowing. In this study, we used microinjection techniques employing pungent and non-pungent vanilloids to further characterize
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