Hydroxy alpha sanshool

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Hydroxy alpha sanshool
HAS-2D.png
Names
IUPAC name
(2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide
Identifiers
3D model (Jmol)
ChemSpider
Properties
C16H25NO2
Molar mass 263.38 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hydroxy-alpha sanshool is a molecule found in plants from the genus Zanthoxylum. It is believed to be responsible for the numbing and tingling sensation caused by eating food cooked with Sichuan peppercorns.

The term sanshool in the compound's name is derived from the Japanese term for the Sichuan pepper, sanshō (山椒?) (literally, Mountain Pepper), to which was appended the suffix -ol, indicating an alcohol.

Mechanism[edit]

Though the chemical structure is similar to that of capsaicin, the mechanism of action by which hydroxy-alpha sanshool induces sensations have been a matter of debate. Although the compound is an agonist at the pain-integrating cation channels TRPV1 and TRPA1 as is capsaicin, newer evidence suggests that the Tandem pore domain potassium channels KCNK3, KCNK9, and KCNK18 are primarily responsible for the molecule's effects.[1]

Hydroxy-alpha sanshool excites D-hair afferent nerve fibers, a distinct subset of the sensitive light touch receptors in the skin, and targets novel populations of Aβ and C-fiber nerve fibers.[2]

References[edit]

  1. ^ Bautista DM, Sigal YM, Milstein AD, Garrison JL, Zorn JA, Tsuruda PR, Nicoll RA, Julius D (July 2008). "Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels". Nat. Neurosci. 11 (7): 772–9. doi:10.1038/nn.2143. PMC 3072296Freely accessible. PMID 18568022. 
  2. ^ Lennertz, Richard C; Tsunozaki, Makoto; Bautista, Diana M; Stucky, Cheryl L (24 Mar 2010). "Physiological basis of tingling paresthesia evoked by hydroxy-α-sanshool". J Neurosci. Society for Neuroscience. 30 (12): 4353–4361. doi:10.1523/JNEUROSCI.4666-09.2010.