Dihydrocapsaicin

Base Information

• Chemical Name: Dihydrocapsaicin
• CAS No.: 19408-84-5
• Molecular Formula: C18H29NO3
• Molecular Weight: 307.433
• Hs Code.: 29399990
• UNII: W9BV32M08A
• DSSTox Substance ID: DTXSID4041864
• Nikkaji Number: J126.282C
• Wikipedia: Dihydrocapsaicin
• Wikidata: Q5276422
• NCI Thesaurus Code: C68531
• Metabolomics Workbench ID: 87100
• ChEMBL ID: CHEMBL311158
• Mol file: 19408-84-5.mol

Synonyms:dihydrocapsaicin

Chemical Property of Dihydrocapsaicin

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 1.61E-10mmHg at 25°C
• Melting Point: 62-65 °C(lit.)
• Refractive Index: 1.51
• Boiling Point: 497.4 °C at 760 mmHg
• PKA: 9.76±0.20(Predicted)
• Flash Point: 254.6 °C
• PSA: 58.56000
• Density: 1.026 g/cm³
• LogP: 4.40450
• Storage Temp.: 2-8°C
• Solubility.: H2O: insoluble
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 307.21474379
• Heavy Atom Count: 22
• Complexity: 307

Purity/Quality:

≥98% ^*data from raw suppliers

Dihydro capsaicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-37/38-41-42/43-36/37/38
• Safety Statements: 22-26-28-36/39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• 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.
• Uses: 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. Capsaicin (C175680) analog. A VR1 vaniloid receptor agonist.

Technology Process of Dihydrocapsaicin

There total 27 articles about Dihydrocapsaicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.5%

8-methyl-nonanoyl chloride (205651-88-3) + vanillylamine hydrochloride (7149-10-2) → dihydrocapsaicin (19408-84-5)

Guidance literature:

vanillylamine hydrochloride; With sodium hydrogencarbonate; In water; at 20 ℃; for 0.5h;

8-methyl-nonanoyl chloride; In chloroform; water; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2009.04.046

Reference yield: 88.0%

Vanillylamin (1196-92-5) + 8-methylnonanoic acid (5963-14-4) → dihydrocapsaicin (19408-84-5)

Guidance literature:

With triethyl borate; In toluene; for 4h; Reagent/catalyst; Dean-Stark; Reflux; Green chemistry;

Reference yield: 82.0%

1-iodo-7-methyloctane (10266-06-5) + carbon monoxide (201230-82-2) + vanillylamine hydrochloride (7149-10-2) → dihydrocapsaicin (19408-84-5)

Guidance literature:

1-iodo-7-methyloctane; carbon monoxide; vanillylamine hydrochloride; With potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In benzene; for 16h; under 34200 Torr; Photolysis;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; chloroform; at 20 ℃; for 3h;

DOI:10.1021/ol060123+

upstream raw materials:

Vanillylamin

8-methyl-nonanoyl chloride

capsaicin

cis-capsaicin

Downstream raw materials:

8-methylnonanamide

3-(4-formyl-2-methoxyphenoxy)-4-hydroxy-5-methoxybenzaldehyde

vanillin

2-(4-isobutyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnonanoylamino)-methyl]-phenyl ester