View source for Chemistry:Hydroxy alpha sanshool

{{chembox
| ImageFile1 = Hydroxy-alpha-sanshool.svg
| ImageSize1 = 200px
| PIN = (2''E'',6''Z'',8''E'',10''E'')-''N''-(2-Hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide
| OtherNames     = Hydroxy-α-sanshool
| Section1 = {{Chembox Identifiers
|   CASNo = 83883-10-7
|   ChemSpiderID = 39144022
|   PubChem = 10084135
|   SMILES = CC=CC=CC=CCCC=CC(=O)NCC(C)(C)O
  }}
| Section2 = {{Chembox Properties
|   C=16
|   H=25
|   N=1
|   O=2
|   Appearance = 
|   Density = 
|   MeltingPt = 
|   BoilingPt = 
|   Solubility =  
  }}
}}

'''Hydroxy-alpha-sanshool''' is a molecule found in plants from the genus ''[[Biology:Zanthoxylum|Zanthoxylum]]''.
It is believed to be responsible for the [[Unsolved:Paresthesia|numbing and tingling sensation]] caused by eating food cooked with [[Biology:Sichuan pepper|Sichuan pepper]]corns and [[Biology:Uzazi|Uzazi]].

The term ''sanshool'' in the compound's name is derived from the [[Social:Japanese language|Japanese]] term for the [[Biology:Zanthoxylum piperitum|Japanese pepper]], {{nihongo||山椒|sanshō}} (literally, mountain pepper), to which was appended the suffix ''-ol'', indicating an [[Chemistry:Alcohol|alcohol]].

==Mechanism==
{{missing information|section|RA1 afferent fiber, 50Hz [PMID 24026819]|date=October 2021}}
The chemical structure of hydroxy-alpha sanshool is similar to that of [[Chemistry:Capsaicin|capsaicin]], but the [[Chemistry:Mechanism of action|mechanism of action]] by which it induces nerve sensations has been a matter of debate. Although the compound is an agonist at the pain integration channels [[Biology:TRPV1|TRPV1]] and [[Biology:TRPA1|TRPA1]] like capsaicin, newer evidence suggests that the tandem pore domain potassium channels [[Biology:KCNK3|KCNK3]], [[Biology:KCNK9|KCNK9]], and [[Biology:KCNK18|KCNK18]] are primarily responsible for sanshool's effects.<ref name="pmid18568022">{{cite journal |vauthors=Bautista DM, Sigal YM, Milstein AD, Garrison JL, Zorn JA, Tsuruda PR, Nicoll RA, Julius D |title=Pungent agents from Szechuan peppers excite sensory neurons by inhibiting two-pore potassium channels |journal=Nat. Neurosci. |volume=11 |issue=7 |pages=772–9 |date=July 2008 |pmid=18568022 |doi=10.1038/nn.2143 |pmc=3072296}}</ref>

Hydroxy-alpha sanshool excites [[Biology:Mechanosensation#Hair Cells|D-hair]] [[Biology:Afferent nerve fiber|afferent nerve fiber]]s, a distinct subset of the sensitive light touch receptors in the skin, and targets novel populations of Aβ and C-fiber nerve fibers.<ref>{{cite journal |last=Lennertz |first=Richard C |last2=Tsunozaki |first2=Makoto |last3=Bautista |first3=Diana M |last4=Stucky |first4=Cheryl L |date=24 Mar 2010 |title=Physiological basis of tingling paresthesia evoked by hydroxy-α-sanshool |journal=J. Neurosci. |publisher=Society for Neuroscience |volume=30 |issue=12 |pages=4353–4361 |doi=10.1523/JNEUROSCI.4666-09.2010 |pmc=2852189 |pmid=20335471}}<!--|access-date=16 April 2014--></ref>

== Extraction ==
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 35-65% of the alcohol. The solution gets heated up in the process of steam
distillation where the aqueous part evaporates and takes parts of the hydroxy-alpha- sanshool up, too.
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%.<ref>{{cite journal |last=Schlander |first=David |last2=Schleif |first2=Chiara |last3=Schnell |first3=Maxim |last4=Roumeliotis |first4=Paul |title=Hydroxy-alpha-sanshool |url=https://www.chemie.tu-darmstadt.de/media/ak_fessner/damocles_pdf/2019/Hydroxy-alpha-sanshool.pdf |publisher=Technische Universität Darmstadt|pages=2}}<!--|access-date=29 May 2020--></ref>

== See also ==
* Spilanthol

== References ==
{{reflist}}

{{Transient receptor potential channel modulators}}

{{DEFAULTSORT:Hydroxy Alpha Sanshool}}
[[Category:Tertiary alcohols]]
[[Category:Polyenes]]

{{Sourceattribution|Hydroxy alpha sanshool|1}}