Hydroxy alpha sanshool

Hydroxy alpha sanshool
IUPAC name

(2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide
Identifiers
CAS number 83883-10-7
PubChem 10084135
ChemSpider 39144022
Jmol-3D images Image 1
Properties
Molecular formula C16H25NO2
Molar mass 263.19 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Hydroxy-alpha sanshool is a bioactive component of plants from the Xanthoxylum genus, including the Sichuan pepper. It is believed to be responsible for the numbing, tingling sensation (paresthesia) caused by eating food cooked with Sichuan peppercorns.

The molecular mechanisms by which hydroxy-alpha sanshool induces these sensations have been a matter of debate. Although the compound is an agonist at the pain-integrating cation channels TRPV1 and TRPA1, newer evidence suggests that the two-pore domain potassium channels KCNK3, KCNK9, and KCNK18 are primarily responsible for hydroxy-alpha sanshool's effects.[1]

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 a chemical alcohol.

See also

References

  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. PMID 18568022.