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Hydroxy-alpha-sanshool
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
ChemSpider
CC=CC=CC=CCCC=CC(=O)NCC(C)(C)O
Properties
C 16 H 25 N O 2
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).
Chemical compound
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 and
Uzazi .
The term sanshool in the compound's name is derived from the
Japanese term for the
Japanese pepper , sanshō (山椒 ) (literally, mountain pepper), to which was appended the suffix -ol , indicating an
alcohol .
Mechanism
The 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]
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 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%.
[3]
See also
References
^ 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.
TRPA
Activators
4-Hydroxynonenal
4-Oxo-2-nonenal
4,5-EET
12S-HpETE
15-Deoxy-Δ12,14 -prostaglandin J2
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Acrolein
Allicin (
garlic )
Allyl isothiocyanate (
mustard ,
radish ,
horseradish ,
wasabi )
AM404
ASP-7663
Bradykinin
Cannabichromene (
cannabis )
Cannabidiol (
cannabis )
Cannabigerol (
cannabis )
Cinnamaldehyde (
cinnamon )
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Cuminaldehyde (
cumin )
Curcumin (
turmeric )
Dehydroligustilide (
celery )
Diallyl disulfide
Dicentrine (
Lindera spp.)
Farnesyl thiosalicylic acid
Formalin
Gingerols (
ginger )
Hepoxilin A3
Hepoxilin B3
Hydrogen peroxide
Icilin
Isothiocyanate
JT-010
Ligustilide (
celery ,
Angelica acutiloba )
Linalool (
Sichuan pepper ,
thyme )
Methylglyoxal
Methyl salicylate (
wintergreen )
N-Methylmaleimide
Nicotine (
tobacco )
Oleocanthal (
olive oil )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
PF-4840154
Phenacyl chloride
Polygodial (
Dorrigo pepper )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tear gases
Tetrahydrocannabinol (
cannabis )
Tetrahydrocannabiorcol
Thiopropanal S-oxide (
onion )
Umbellulone (Umbellularia californica )
WIN 55,212-2
Blockers
TRPC
TRPM
TRPML
TRPP
TRPV
Activators
2-APB
5',6'-EET
9-HODE
9-oxoODE
12S-HETE
12S-HpETE
13-HODE
13-oxoODE
20-HETE
α-Sanshool (
ginger ,
Sichuan and
melegueta peppers )
Allicin (
garlic )
AM404
Anandamide
Bisandrographolide (
Andrographis paniculata )
Camphor (
camphor laurel ,
rosemary ,
camphorweed ,
African blue basil ,
camphor basil )
Cannabidiol (
cannabis )
Cannabidivarin (
cannabis )
Capsaicin (
chili pepper )
Carvacrol (
oregano ,
thyme ,
pepperwort ,
wild bergamot , others)
DHEA
Diacyl glycerol
Dihydrocapsaicin (
chili pepper )
Estradiol
Eugenol (
basil ,
clove )
Evodiamine (
Euodia ruticarpa )
Gingerols (
ginger )
GSK1016790A
Heat
Hepoxilin A3
Hepoxilin B3
Homocapsaicin (
chili pepper )
Homodihydrocapsaicin (
chili pepper )
Incensole (
incense )
Lysophosphatidic acid
Low
pH (acidic conditions)
Menthol (
mint )
N-Arachidonoyl dopamine
N-Oleoyldopamine
N-Oleoylethanolamide
Nonivamide (PAVA) (
PAVA spray )
Nordihydrocapsaicin (
chili pepper )
Paclitaxel (
Pacific yew )
Paracetamol (acetaminophen)
Phenylacetylrinvanil
Phorbol esters (e.g.,
4α-PDD )
Piperine (
black pepper ,
long pepper )
Polygodial (
Dorrigo pepper )
Probenecid
Protons
RhTx
Rutamarin (
Ruta graveolens )
Resiniferatoxin (RTX) (
Euphorbia resinifera /
pooissonii )
Shogaols (
ginger ,
Sichuan and
melegueta peppers )
Tetrahydrocannabivarin (
cannabis )
Thymol (
thyme ,
oregano )
Tinyatoxin (
Euphorbia resinifera /
pooissonii )
Tramadol
Vanillin (
vanilla )
Zucapsaicin
Blockers