Dihydrocapsaicin

Cayman Chemical Item Number 92355

(CAS 19408-84-5)

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Description

Capsaicin is the primary active component of the heat and pain-eliciting lipid soluble fraction of the Capsicum pepper.1 Capsaicin is found in natural hot pepper extracts along with a number of impurities, including dihydrocapsaicin and several lesser impurities. Separation by HPLC is required in order to obtain pure dihydrocapsaicin.2 Dihydrocapsaicin represents about 10% of the compound present in commercial preparations purporting to be pure capsaicin. VR1 (vanilloid receptor 1) is a heat activated calcium ion channel which functions as a part of the normal nociceptive pain pathway. Capsaicin elicits a sensation of burning pain by activation of VR1 on small, non-myelinated polymodal C-type nociceptive nerve fibers.3 The potency of dihydrocapsaicin at VR1 appears equivalent to capsaicin.

1. Gannett, P.M., Nagel, D.L., Reilly, P.J., et al. The capsaicinoids: Their separation, synthesis, and mutagenicity. J Org Chem 53(5) 1064-1071 (1988).

2. Hoffman, P.G., Lego, M.C., and Galetto, W.G. Separation and quantitation of red pepper major heat principles by reverse-phase high-pressure liquid chromatography. J Agric Food Chem 31(6) 1326-1330 (1983).

3. Caterina, M.J., Schumacher, M.A., Tominaga, M., et al. The capsaicin receptor: A heat-activated ion channel in the pain pathway. Nature 389 816-824 (1997).

Formal Name N-​[(4-​hydroxy-​3-​methoxyphenyl)methyl]-​8-​methyl-​nonanamide
CAS Number 19408-84-5
Molecular Formula C18H29NO3
Formula Weight 307.4
Formulation A crystalline solid
Purity ≥98%
λmax 230, 281 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COc1cc(CNC(=O)​CCCCCCC(C)​C)​ccc1O
InCHI Code
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​1S/C18H29NO3/c1-14(2)​8-6-4-5-7-9-18(21)​19-13-15-10-11-16(20)​17(12-15)​22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)​
InCHI Key
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XJQPQKLURWNAAH-UHFFFAOYSA-N

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Dihydrocapsaicin is available in the following screening library:

Size Price Quantity Subtotal
5 mg $22.00 $0.00
10 mg $42.00 $0.00
50 mg $176.00 $0.00
100 mg $308.00 $0.00
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