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Merck
CN

SML3479

Hydroxy-α-sanshool

≥95% (HPLC)

Synonym(s):

(2E,6Z,8E,10E)-N-(2-Hydroxy-2-methylpropyl)-2,6,8,10-dodecatetraenamide, 2E,6Z,8E,10E-Dodecatetraenoic acid N-(2-hydroxy-2-methylpropyl)amide

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About This Item

Empirical Formula (Hill Notation):
C16H25NO2
CAS Number:
83883-10-7
Molecular Weight:
263.38
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD17779317

Key Documents

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SMILES string

N(CC(O)(C)C)C(=O)\C=C\CC\C=C/C=C/C=C/C

InChI

1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4+,7-6+,9-8-,13-12+

InChI key

LHFKHAVGGJJQFF-UEOYEZOQSA-N

assay

≥95% (HPLC)

form

powder

storage condition

protect from light, under inert gas

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Biochem/physiol Actions

Hydroxy-α-sanshool is an active ingredient in Szechuan peppers (also present in other Zanthoxylum plants) that produces a tingling paresthesia or numbing effects. Hydroxy-α-sanshool is a potent agonist of TRPV1/TRPA1 as well as antagonist/blocker of KCNK3/KCNK9/KCNK18 channels. It induces colonic motor activity in rat proximal colon.
Potent agonist of TRPV1/TRPA1 as well as antagonist/blocker of KCNK3/KCNK9/KCNK18 channels

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000514783
0000514782
0000514782
0000514783
0000225121

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Kunitsugu Kubota et al.
American journal of physiology. Gastrointestinal and liver physiology, 308(7), G579-G590 (2015-01-31)
Various colonic motor activities are thought to mediate propulsion and mixing/absorption of colonic content. The Japanese traditional medicine daikenchuto (TU-100), which is widely used for postoperative ileus in Japan, accelerates colonic emptying in healthy humans. Hydroxy-α sanshool (HAS), a readily
Sanshool on The Fingertip Interferes with Vibration Detection in a Rapidly-Adapting (RA) Tactile Channel
PLoS ONE, 11(12), e0165842-e0165842 (2016)
Diana M Bautista et al.
Nature neuroscience, 11(7), 772-779 (2008-06-24)
In traditional folk medicine, Xanthoxylum plants are referred to as 'toothache trees' because their anesthetic or counter-irritant properties render them useful in the treatment of pain. Psychophysical studies have identified hydroxy-alpha-sanshool as the compound most responsible for the unique tingling

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