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| Names | |
|---|---|
| Preferred IUPAC name (2E,6Z,8E,10E)-N-(2-Hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide | |
| Other names Hydroxy-α-sanshool | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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| |
| Properties | |
| C16H25NO2 | |
| Molar mass | 263.381 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Hydroxy-α-sanshool (/-sænʃoʊ.ɒl/), also known as simplysanshool[1] is a molecule found in plants from the genusZanthoxylum. It is believed to be responsible for thenumbing and tingling sensation caused by eating food cooked withSichuan peppercorns andUzazi.
The termsanshool in the compound's name is derived from theJapanese term for theJapanese pepper,sanshō (山椒) (lit. 'mountain pepper'), to which was appended the suffix-ol, indicating analcohol.
The chemical structure of hydroxy-alpha-sanshool resemblescapsaicin as both arefatty acid amides, but themechanism 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 channelsTRPV1 andTRPA1; however, evidence suggests that the inhibition oftandem pore domain potassium channelsKCNK3,KCNK9, andKCNK18 are primarily responsible for sanshool's effects.[2]
Hydroxy-alpha-sanshool excitesD-hairafferent nerve fibers, a distinct subset of the sensitivelight touch receptors in the skin, and targets novel populations of Aβ and C-fiber nerve fibers.[3]
To 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%.[4]
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