19408-84-5 Usage
Description
Dihydrocapsaicin is a terpene alkaloid found in Capsicum and belongs to the capsaicinoid group of compounds, which are responsible for the pungency of capsicum fruits. It is a white solid with diverse biological activities, including antimicrobial, antioxidant, and autophagy-promoting properties.
Uses
Used in Analytical Chemistry:
Dihydrocapsaicin is used as a reference standard for the identification of dihydrocapsaicin in blood and tissue samples by high-performance liquid chromatography (HPLC) combined with tandem mass spectrometry (MS). It is also used in tomato-based salsas by enzyme immunoassay (EIA) and LC with fluorescent detection.
Used in Capsicum Fruit Analysis:
Dihydrocapsaicin is used as a reference standard for the determination of dihydrocapsaicin in Capsicum fruit samples by HPLC equipped with a Surveyor photodiode array (PDA) detector.
Used in Pharmaceutical Research:
Dihydrocapsaicin is used as a Capsaicin analog and a VR1 vaniloid receptor agonist, which has potential applications in the development of new drugs targeting the transient receptor potential vanilloid 1 (TRPV1).
Used in Antimicrobial Applications:
Dihydrocapsaicin is active against various bacteria, including E. faecalis, B. subtilis, S. aureus, P. aeruginosa, K. pneumoniae, E. coli, and C. albicans, making it a potential candidate for antimicrobial agents.
Used in Antioxidant Applications:
Dihydrocapsaicin scavenges DPPH and ABTS radicals in cell-free assays, indicating its potential use as an antioxidant in various industries.
Used in Autophagy and Anticancer Research:
Dihydrocapsaicin increases LC3-II, a marker of autophagy, and catalase levels, and reduces reactive oxygen species (ROS) production in normal WI38 lung fibroblasts and H1299 lung cancer cells, suggesting its potential use in autophagy and anticancer research.
Used in Inflammation and Immune Response:
Dihydrocapsaicin is an agonist of transient receptor potential vanilloid 1 (TRPV1) and inhibits NETosis induced by phorbol 12-myristate 13-acetate (TPA) in isolated human neutrophils, indicating its potential use in modulating inflammation and immune response.
Used in Neuroprotection:
Dihydrocapsaicin induces cortical and systemic hypothermia and reduces infarct volume in a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO) when administered at a dose of 0.5 mg/kg, i.p., suggesting its potential use in neuroprotection and treatment of stroke-related conditions.
Biochem/physiol Actions
VR1 vanilloid receptor agonist.
Check Digit Verification of cas no
The CAS Registry Mumber 19408-84-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,4,0 and 8 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 19408-84:
(7*1)+(6*9)+(5*4)+(4*0)+(3*8)+(2*8)+(1*4)=125
125 % 10 = 5
So 19408-84-5 is a valid CAS Registry Number.
InChI:InChI=1/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)
19408-84-5Relevant articles and documents
Regioselective hydroxylation and dehydrogenation of capsaicin and dihydrocapsaicin by cultured cells of Phytolacca americana
Hamada, Hiroki,Ono, Tsubasa,Shimoda, Kei
, p. 103 - 107 (2022/03/18)
The biotransformations of capsaicin and dihydrocapsaicin were investigated using cultured plant cells of Phytolacca americana as biocatalysts. Four products, ie 15-hydroxycapsaicin, dihydrocapsaicin, 15-hydroxydihydrocapsaicin, and capsaicin 4-β-glucoside
Preparation method of capsaicine and capsaicine prepared by method
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Paragraph 0124-0128, (2021/04/07)
The invention provides a preparation method of capsaicine and capsaicine prepared by the method. The preparation method comprises the following steps: in the presence of an organic solvent and a catalyst, by taking vanillylamine carboxylate and carboxylic acid as reactants, carrying out amidation reaction to obtain a capsaicine reaction liquid. Compared with the prior art, the capsaicine preparation method provided by the invention at least has one of the following beneficial effects: 1) vanillylamine is converted into vanillylamine carboxylate, so that the problem of oxidative discoloration of vanillylamine is avoided, and the problems of purification, drying and storage of intermediate products are solved; 2) the vanillylamine carboxylate can be directly used for the next amidation reaction, other substances are not introduced, and the amidation reaction, operation and post-treatment are not influenced; and 3) after the vanillylamine solid is salified and dissolved, the thorough separation of the Raney Ni catalyst is facilitated, and the catalyst separated by the method can be continuously used after being treated.
Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature
Gallou, Fabrice,Gao, Eugene S.,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.
supporting information, p. 6055 - 6061 (2020/10/14)
Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment. Catalysts new and old are all used under similar conditions that no longer reflect the times. By definition, such reactions are both environmentally irresponsible and dangerous, especially at industrial scales. We now report on a general method for chemoselective and safe hydrogenation of olefins in water using ppm loadings of palladium from commercially available, inexpensive, and recyclable Pd/C, together with hydrogen gas utilized at 1 atmosphere. A variety of alkenes is amenable to reduction, including terminal, highly substituted internal, and variously conjugated arrays. In most cases, only 500 ppm of heterogeneous Pd/C is sufficient, enabled by micellar catalysis used in recyclable water at room temperature. Comparison with several newly introduced catalysts featuring base metals illustrates the superiority of chemistry in water.