Hydroxy-alpha-sanshool - CAS 83883-10-7
Catalog number: B0005-008250
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C16H25NO2
Molecular Weight:
263.381
COA:
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Chemical Family:
Other Natural Compounds
Description:
Hydroxy-alpha-sanshool is a compound isolated from the genus Zanthoxylum. It stimulates D-hair afferent nerve fibers.
Ordering Information
Catalog Number Size Price Stock Quantity
B0005-008250 1 mg $298 In stock
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Synonyms:
(2E,6Z,8E,10E)-N-(2-Hydroxy-2-methylpropyl)-2,6,8,10-dodecatetraenamide
MSDS:
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Boiling Point:
471.5±45.0 °C at 760 mmHg
InChIKey:
LHFKHAVGGJJQFF-UEOYEZOQSA-N
InChI:
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+
Canonical SMILES:
CC=CC=CC=CCCC=CC(=O)NCC(C)(C)O
1.Dynamic Proteome Alteration and Functional Modulation of Human Saliva Induced by Dietary Chemosensory Stimuli.
Bader M;Dunkel A;Wenning M;Kohler B;Medard G;Del Castillo E;Gholami A;Kuster B;Scherer S;Hofmann T J Agric Food Chem. 2018 Jun 6;66(22):5621-5634. doi: 10.1021/acs.jafc.8b02092. Epub 2018 May 29.
Saliva flow measurements and SDS-PAGE separation of human whole saliva freshly collected after oral stimulation with citric acid (sour), aspartame (sweet), iso-α-acids (bitter), mono sodium l-glutamate (umami), NaCl (salty), 6-gingerol (pungent), hydroxy-α-sanshool (tingling), and hydroxy-β-sanshool (numbing), followed by tryptic digestion, nano-HPLC-MS/MS, and label-free protein quantitation demonstrated a stimulus- and time-dependent influence of the dietary chemosensates on salivation and the salivary proteome composition. Gene ontology enrichment analysis showed evidence for stimulus-induced alterations of the saliva proteome to boot an efficient molecular defense network of the oral cavity, e.g., 6-gingerol increased salivary lactoperoxidase activity, catalyzing the oxidation of thiocyanate to produce the antimicrobial and antifungal hypothiocyanate, from 0.37 ± 0.02 to 0.91 ± 0.05 mU/mL 45 s after stimulation. In comparison, oral citric acid stimulation induced an increase of myeloperoxidase activity, catalyzing the chloride oxidation to generate antimicrobial hypochloride in saliva, from 0.
2.All-trans-configuration in Zanthoxylum alkylamides swaps the tingling with a numbing sensation and diminishes salivation.
Bader M;Stark TD;Dawid C;Lösch S;Hofmann T J Agric Food Chem. 2014 Mar 26;62(12):2479-88. doi: 10.1021/jf500399w. Epub 2014 Mar 17.
The methanol soluble prepared from a supercritical fluid extract of Szechuan pepper (Zanthoxylum piperitum) was screened for its key tingling and numbing chemosensates by application of taste dilution analysis. Further separation of fractions perceived with the highest sensory impact, followed by LC-TOF-MS, LC-MS, and 1D/2D NMR experiments, led to the structure determination of the known alkylamides hydroxy-γ-sanshool (1), hydroxy-α-sanshool (2), hydroxy-β-sanshool (3), bungeanool (4), isobungeanool (5), and hydroxy-γ-isosanshool (6), as well as hydroxy-ε-sanshool (7), the structure of which has not yet been confirmed by NMR, and hydroxy-ζ-sanshool (8), which has not been previously reported in the literature. Psychophysical half-tongue experiments using filter paper rectangles (1 × 2 cm) as the vehicle revealed amides 1, 2, 4, 5, 7, and 8, showing at least one cis-configured double bond, elicited the well-known tingling and paresthetic orosensation above threshold levels of 3.
3.Quantitative analysis of sanshool compounds in Japanese pepper (Xanthoxylum piperitum DC.) and their pungent characteristics.
Sugai E;Morimitsu Y;Kubota K Biosci Biotechnol Biochem. 2005 Oct;69(10):1958-62.
The distributions of each sanshool in the Japanese pepper plant grown in various regions and the change in composition of sanshools during maturation of the fruit were investigated. The degree of pungency, defined as the amount of a sanshool/the threshold value, was calculated, and the pungent qualities of the products were evaluated and compared. The degree of pungency and amount of a sanshool showed a positive correlation. In young leaves and flowers, the degree of pungency was less than that in the fruits, the main compound being alpha-sanshool, while the two hydroxy sanshools were detected only in trace amounts. The main compound in fruits was hydroxy alpha-sanshool, whose threshold value was higher than that of alpha-sanshool. It is concluded that the pungency of Japanese pepper should be evaluated not only by the threshold values, but also by the pungent qualities, the composition of sanshools, and the usage of each product of Japanese pepper.
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