Hydroxy-α-sanshool (/-sænʃoʊ.ɒl/) 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 and Uzazi.
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| Names | |
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| Preferred IUPAC name
(2E,6Z,8E,10E)-N-(2-Hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide | |
| Other names
Hydroxy-α-sanshool
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C16H25NO2 | |
| Molar mass | 263.381 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The term sanshool in the compound's name is derived from the Japanese term for the Japanese pepper, sanshō (山椒) (lit. 'mountain pepper'), to which was appended the suffix -ol, indicating an alcohol.
Mechanism
editThe chemical structure of hydroxy-alpha-sanshool resembles capsaicin as both are fatty acid amides, but the mechanism of action by which it induces nerve sensations has been a matter of debate. Like capsaicin, hydroxy-alpha-sanshool is an agonist at the pain integration channels TRPV1 and TRPA1; however, evidence suggests that the inhibition of tandem pore domain potassium channels KCNK3, KCNK9, and KCNK18 are primarily responsible for sanshool'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]
Extraction
editTo isolate the molecule from the pepper in form of an extract, steam distillation can be used: Dried peels of the fruit are immersed in a mixture of lower alcohols (for example ethanol) and water with a mass percentage between 35% and 65% of the alcohol. The solution is heated up in the process of steam distillation, where the aqueous part evaporates and takes parts of the hydroxy-alpha- sanshool up as well.
The distillate separates in two phases: the aqueous ethanol phase and the oil phase which contains the desired molecule.
Steam distillation extraction methods demonstrate yields of approximately 60%.[3]
See also
editReferences
edit- ^ 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 3072296. PMID 18568022.
- ^ 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. 30 (12). Society for Neuroscience: 4353–4361. doi:10.1523/JNEUROSCI.4666-09.2010. PMC 2852189. PMID 20335471.
- ^ Schlander, David; Schleif, Chiara; Schnell, Maxim; Roumeliotis, Paul. "Hydroxy-alpha-sanshool" (PDF). Technische Universität Darmstadt: 2.
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