19408-84-5

Basic information

• Product Name: Dihydrocapsaicin
• Synonyms: CAPSAICINE;CAPSAICIN, NATURAL;(E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE;(E)-CAPSAICIN;(E)-N-([4-HYDROXY-3-METHOXYPHENYL]METHYL)8-METHYL-6-NONEAMIDE;FEMA 3404;FEMA 2787;N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6E-NONENAMIDE
• CAS NO: 19408-84-5
• Molecular Formula: C₁₈H₂₉NO₃
• Molecular Weight: 307.43
• EINECS: 206-969-8
• Product Categories: Miscellaneous Natural Products;Amines;Aromatics;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;API
• Mol File: 19408-84-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 497.4 °C at 760 mmHg
• Flash Point: 254.6 °C
• Appearance: White to off-white solid
• Density: 1.026 g/cm³
• Vapor Pressure: 1.61E-10mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: 2-8°C
• Solubility: H2O: insoluble
• PKA: 9.76±0.20(Predicted)
• BRN: 2815150
• CAS DataBase Reference: Dihydrocapsaicin(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrocapsaicin(19408-84-5)
• EPA Substance Registry System: Dihydrocapsaicin(19408-84-5)

Safety Data

• Hazard Codes: T
• Statements: 25-37/38-41-42/43-36/37/38
• Safety Statements: 22-26-28-36/39-45-36/37/39
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: RA8530000
• F: 10-21
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 19408-84-5(Hazardous Substances Data)

Usage

Description

Dihydrocapsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities. It is active against E. faecalis, B. subtilis, S. aureus, P. aeruginosa, K. pneumoniae, E. coli, and C. albicans (MICs = 0.6-10 μg/ml). Dihydrocapsaicin scavenges DPPH and ABTS radicals in cell-free assays. It increases LC3-II, a marker of autophagy, and catalase levels and reduces reactive oxygen species (ROS) production in normal WI38 lung fibroblasts and H1299, but not A549 or H460, lung cancer cells when used at a concentration of 200 μM. 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. It 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.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 19408-84-5 differently. You can refer to the following data:
1. Dihydrocapsaicin has been 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) and in tomato-based salsas by enzyme immunoassay (EIA) and LC with fluorescent detection. It may be used as a reference standard for the determination of dihydrocapsaicin in Capsicum fruit samples by HPLC equipped with a Surveyor photodiode array (PDA) detector and in rat plasma by HPLC-triple quadrupole MS with electrospray ionization (ESI) in selected reaction monitoring (SRM) mode.
2. Capsaicin (C175680) analog. A VR1 vaniloid receptor agonist.

General Description

Dihydrocapsaicin belongs to the capsaicinoid group of compounds which are responsible for the pungency of capsicum fruits.

Biochem/physiol Actions

VR1 vanilloid receptor agonist.

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)

Upstream product

• 55277-54-8 8-Methyl-7-oxononanoic acid 
• 205651-88-3 8-methyl-nonanoyl chloride 
• 7149-10-2 vanillylamine hydrochloride 
• 404-86-4 capsaicin 
• 4547-43-7 methyl 6-hydroxycaproate 
• 59320-77-3 trans-8-methyl-6-nonenoic acid 
• 6654-36-0 methyl 6-oxohexanoate 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 5963-14-4 8-methylnonanoic acid 
• 10266-06-5 1-iodo-7-methyloctane 
• 201230-82-2 carbon monoxide 
• 64-17-5 ethanol 
• 7553-53-9 capsaicin 
• 1196-92-5 Vanillylamin 

Downstream Products

• 404-86-4 capsaicin 

Related news

Simultaneous determination of capsaicin and Dihydrocapsaicin (cas 19408-84-5) for vegetable oil adulteration by immunoaffinity chromatography cleanup coupled with LC–MS/MS08/21/2019

Capsaicin and dihydrocapsaicin were selected as adulteration markers to authenticate vegetable oils. In this study, a method of immunoaffinity chromatography (IAC) combined with liquid chromatography–tandem mass spectrometry was established for the determination of capsaicin and dihydrocapsaici...detailed

A validated HPLC-FLD method for analysis of intestinal absorption and metabolism of capsaicin and Dihydrocapsaicin (cas 19408-84-5) in the rat08/20/2019

A sensitive and selective reverse-phase high performance liquid chromatographic method with fluorescence detection has been developed for determination of capsaicin (8-methyl-N-vanillyl-(trans)-6-nonenamid) and dihydrocapsaicin (8-methyl-N-vanillylnonanamide) in samples generated in rat small in...detailed

Study of electrochemical determination of capsaicin and Dihydrocapsaicin (cas 19408-84-5) at carbon paste electrodes modified by β-cyclodextrin08/19/2019

In this work, we showed electrochemical evidences that α-, β-, and γ-cyclodextrins (CDs) form inclusion complex in a solution with capsaicin (CP). The electrochemical behavior of CP was evaluated on carbon paste electrodes modified with CDs. The modified electrodes exhibited a markedly enhanc...detailed

Rapid and sensitive LC-MS/MS method for simultaneous quantification of capsaicin and Dihydrocapsaicin (cas 19408-84-5) in microdialysis samples following dermal application08/17/2019

A bioanalytical LC–MS/MS method was developed and validated for the simultaneous quantification of capsaicin (CAPS) and dihydrocapsaicin (D-CAPS) in dermal microdialysis samples from rats. Capsaicinoids were separated by using a C18 column, with a mobile phase of water and acetonitrile, both wi...detailed

Relevant articles and documents

Regioselective hydroxylation and dehydrogenation of capsaicin and dihydrocapsaicin by cultured cells of Phytolacca americana

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

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

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.