Dihydrocapsaicin CAS 19408-84-5

Introduction：Basic information about Dihydrocapsaicin CAS 19408-84-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Dihydrocapsaicin 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: 19408-84-5
• MF: C18H29NO3
• MW: 307.43
• EINECS: 606-308-7
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;Amines;Aromatics;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Natural Products;API;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Elisa Kit-plant ELISA Kit
• Mol File: 19408-84-5.mol

Dihydrocapsaicin Chemical Properties

• Melting point: 62-65 °C(lit.)
• Boiling point: 497.4±35.0 °C(Predicted)
• density: 1.026±0.06 g/cm3(Predicted)
• storage temp.: Sealed in dry,2-8°C
• solubility: H₂O: insoluble
• pka: 9.76±0.20(Predicted)
• form: White to off-white solid.
• color: White to off-white
• BRN: 2815150
• Major Application: cleaning products cosmetics flavors and fragrances food and beverages personal care
• InChI: InChI=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)
• InChIKey: XJQPQKLURWNAAH-UHFFFAOYSA-N
• SMILES: C(NCC1=CC=C(O)C(OC)=C1)(=O)CCCCCCC(C)C
• LogP: 3.556 (est)
• CAS DataBase Reference: 19408-84-5(CAS DataBase Reference)
• EPA Substance Registry System: Dihydrocapsaicin (19408-84-5)

Safety Information

• Hazard Codes: T
• Risk 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
• HS Code: 29399990
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Acute Tox. 2 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Dihydrocapsaicin Usage And Synthesis

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

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.

Uses

Capsaicin (C175680) analog. A VR1 vaniloid receptor agonist.

Definition

ChEBI: Dihydrocapsaicin is a capsaicinoid.

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.

References

[1] PATRíCIA L A NASCIMENTO. Quantification, antioxidant and antimicrobial activity of phenolics isolated from different extracts of Capsicum frutescens (Pimenta Malagueta).[J]. Molecules, 2014, 19 4: 5434-5447. DOI: 10.3390/molecules19045434
[2] CHEOL-HEE CHOI  Seon H O  Yong Keun Jung. Selective induction of catalase-mediated autophagy by dihydrocapsaicin in lung cell lines[J]. Free Radical Biology and Medicine, 2010, 49 2: Pages 245-257. DOI: 10.1016/j.freeradbiomed.2010.04.014
[3] DI WU . Dihydrocapsaicin (DHC) enhances the hypothermia-induced neuroprotection following ischemic stroke via PI3K/Akt regulation in rat[J]. Brain Research, 2017, 1671: Pages 18-25. DOI: 10.1016/j.brainres.2017.06.029
[4] VIKTOR V FEKETA. Shivering and tachycardic responses to external cooling in mice are substantially suppressed by TRPV1 activation but not by TRPM8 inhibition.[J]. American journal of physiology. Regulatory, integrative and comparative physiology, 2013, 305 9: R1040-50. DOI: 10.1152/ajpregu.00296.2013
[5] ELVIRA SONDO. High-Content Screening Identifies Vanilloids as a Novel Class of Inhibitors of NET Formation.[J]. Frontiers in Immunology, 2019: 963. DOI: 10.3389/fimmu.2019.00963