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

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

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.

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

• 1196-92-5 Vanillylamin 
• 205651-88-3 8-methyl-nonanoyl chloride 
• 404-86-4 capsaicin 
• 5963-14-4 8-methylnonanoic acid 
• 7149-10-2 vanillylamine hydrochloride 
• 66086-06-4 methyl 4,7-dione-8-methylnonanoate 
• 17678-19-2 2-(2-hydroxyacetyl)furan 
• 563-80-4 3-methyl-butan-2-one 
• 4196-97-8 1-(2-furyl)-1-pentene-4-methyl-3-one 
• 112375-54-9 methyl (E)-8-methyl-6-nonenoate 
• 112375-42-5 methyl (6Z)-8-methylnon-6-enoate 
• 95636-02-5 (E)-8-Methylnon-6-enoic acid chloride 
• 31467-61-5 (Z)-8-Methyl-non-6-enoyl chloride 
• 31467-60-4 (6Z)-8-methyl-6-nonaneneoic acid 

Downstream Products

• 1224428-95-8 2-(4-isobutyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnonanoylamino)-methyl]-phenyl ester 
• 1224428-91-4 2-(6-methoxy-naphthalen-2-yl)-propionic acid 2-methoxy-4-[(8-methyl-nonanoylamino)-methyl]-phenyl ester 
• 1224428-88-9 [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid 2-methoxy-4-[(8-methyl-nonanoylamino)-methyl]-phenyl ester 
• 1224428-99-2 2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnonanoylamino)-methyl]-phenyl ester 
• 1224429-03-1 (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 2-methoxy-4-[(8-methyl-nonanoylamino)-methyl]-phenyl ester 
• 1236876-25-7 3-[2-(4-isobutylphenyl)propionylamino]propionic acid 2-methoxy-4-[(8-methylnonanoylamino)methyl]phenyl ester 
• 1236876-17-7 [2-(4-isobutylphenyl)propionylamino]acetic acid 2-methoxy-4-[(8-methylnonanoylamino)methyl]phenyl ester 
• 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 capsaicin and capsaicin prepared by using method

The invention relates to a capsaicin preparation method and capsaicin prepared by the method. The preparation method comprises the steps that: in the presence of an organic solvent and a catalyst, vanillylamine and carboxylic acid serve as reactants, after amidation reaction, capsaicin reaction liquid is obtained, and the catalyst comprises a boric acid ester compound. Compared with the prior art, the capsaicin preparation method provided by the invention has the following beneficial effects: 1) a large amount of water is not generated in the reaction process, violent reflux for water separation is not needed, the production cost is reduced, and the production safety is improved; 2) boric acid is replaced by the boric acid ester compound, so that the reaction time can be shortened, the reaction yield can be improved, and the product purity is very high; and 3) the boric acid ester compound can be recycled after proper treatment after the reaction, so that the production cost is saved, and green production is realized.

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.

Vanilla amide synthesis method

The invention discloses a vanilla amide synthesis method, which comprises the following step: by taking alcohol and vanilla amide as raw materials, or aldehyde and vanilla amide as raw materials, inorganic ferric salt and inorganic indium salt as a composite catalyst and oxygen as an oxidant, carrying out one-pot reaction in an organic solvent to generate vanilla amide. The synthesis raw materials adopted by the synthesis method are wide in source, a large amount of chemical reaction waste can be avoided in the whole reaction process, and the synthesis method is clean and environmentally friendly, has the advantages of mild and controllable reaction conditions, simple operation, convenience in product separation and purification, high product yield, wide universality of reaction substrates and the like, and is a method suitable for industrial production.

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.

Preparation method of dihydrocapsaicine and dihydrocapsaicine ester

The invention relates to a preparation method of dihydrocapsaicine and dihydrocapsaicine ester. The preparation method specifically comprises the following steps: (1) condensing furfural and methyl isopropyl ketone under an alkaline condition to obtain a condensation product A; (2) carrying out ring opening on the condensation product A in water or alcohol under an acidic condition to obtain 4,7-diketo-8-methylnonanoic acid or 4,7-diketo-8-methyl nonanoate; (3) carrying out hydrodeoxygenation on 4,7-diketo-8-methylnonanoic acid or 4,7-diketo-8-methyl nonanoate, hydrogen, trifluoromethanesulfonate and a hydrogenation catalyst to obtain 8-methylnonanoic acid; and (4) reacting the 8-methylnonanoic acid with vanillamine or vanillol under the action of a catalyst to generate dihydrocapsaicine or dihydrocapsaicine ester. The method is good in atom economy, high in product yield, high in product purity, small in environmental pollution, simple in process route, convenient to operate and suitable for industrial large-scale production; the dihydrocapsaicine and the dihydrocapsaicine ester are wide in application scope and good in market prospect; raw materials are widely available and cheap; and the method is simple to operate, low in cost and suitable for industrial production.

Capsaicin preparation method and the preparation method of the capsaicin (by machine translation)

The present invention provides a capsaicin preparation method and the preparation method of the capsaicin. The capsaicin preparation method comprises: to vanilla amine free base and carboxylic acid as raw materials, the use of SiO2 - H3 BO3 Catalyst, in the acylation reaction is carried out in a solvent, to obtain the capsaicin reaction solution. The present invention provides capsaicin preparation method, compared with the prior art, has the following advantages: 1) with carboxylic acid as the raw material, to avoid the preparation of the acyl chloride and a large number of strong corrosive organic waste liquid generation; 2) SiO for2 - H3 BO3 Catalyst instead of boric acid as catalyst, can realize the repeated use of the catalyst, and the cost is reduced, significantly reduces the production of waste water containing boron; 3) can effectively shorten the reaction time, reduce energy consumption. (by machine translation)

Preparation method for high-purity dihydrocapsaicin monomer

The invention provides a preparation method for a high-purity dihydrocapsaicin monomer. The preparation method is characterized by comprising the following steps: putting natural capsaicinoid in a polar protic solvent, stirring the mixture for 1-3 hours at room temperature to obtain a natural capsaicinoid solution; adding a catalyst into the natural capsaicinoid solution, carrying out a hydrogenation reaction for 6-12 hours under a normal pressure and at room temperature, filtering and concentrating the mixture to obtain a colorless oily product; dissolving the colorless oily product with a refining agent at 30-55 DEG C, pouring the dissolved product into a crystallizer, carrying out standing for crystallizing, wherein the crystallization temperature is -20 DEG C to -10 DEG C; and filtering and separating precipitated crystals, pressing a filter cake, and drying the filter cake to obtain the white spicy dihydrocapsaicin monomer product. According to the preparation method, the content of a dihydrocapsaicin monomer component in the natural capsaicinoid is effectively enriched and greatly improved, and therefore the purpose of preparing the high-purity dihydrocapsaicin monomer product is further reached by refining and purifying the new product taking the dihydrocapsaicin monomer as a main component. Accordingly, the separation preparation efficiency of the dihydrocapsaicin monomer is obviously improved.

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.

Effective acceleration of atom transfer carbonylation of alkyl iodides by metal complexes. Application to the synthesis of the hinokinin precursor and dihydrocapsaicin

Atom transfer carbonylation (ATC) of alkyl iodides leading to carboxylic acid esters is effectively accelerated by Pd(PPh3)4 and Mn2(CO)10 under photoirradiation conditions. In the presence of amines, Pd(0) complexes affected double carbonylations leading to α-keto amides, whereas Mn2(CO)10 accelerated only a single carbonylation reaction leading to the corresponding amides. The Pd(0)-accelerated ATC system was successfully applied to the synthesis of hinokinin and dihydrocapsaicin.