Dihydrocapsaicin
CAPSAICINE · N-(3-Methoxy-4-hydroxybenzyl)-8-methylnonanamide · (E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE · FEMA 2787 · FEMA 3404 · CCRIS1589 · (E)-CAPSAICIN · ihydrocapsaicin
Identifikatoren & physikalische Daten
| CAS No. | 19408-84-5 |
|---|---|
| Summenformel | C18H29NO3 |
| Durchschnittliche Molmasse | 307,4 g/mol |
| Monoisotopische Masse | 307,21474379 g/mol |
| SMILES | COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O |
| InChIKey | XJQPQKLURWNAAH-UHFFFAOYSA-N |
| PubChem CID | 107982 |
| ChEMBL | CHEMBL311158 |
| ChEBI | CHEBI:46932 |
| EC No. | 606-308-7 |
| DTXSID | DTXSID4041864 |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 10 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 307 |
| Lipide | Fatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802] |
| Schmelzpunkt | 65.5 - 65.8 °C65.5-65.8 °F62-65 °C(lit.) |
| Physical Description | SolidPure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is found in pepper (C. annum). |
| Collision Cross Section | 164.84 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 497.4±35.0 °C(Predicted) |
| Dichte | 1.026±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Löslichkeit | H2O: insoluble |
| pKa (Säurekonstante) | 9.76±0.20(Predicted) |
| Aggregatzustand | White to off-white solid. |
| Farbe | White to off-white |
| BRN | 2815150 |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal 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 (Verteilungskoeffizient) | 3.556 (est) |
| CAS Datenbank | 19408-84-5(CAS DataBase Reference) |
| EPA chemische Informationen | Dihydrocapsaicin (19408-84-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (97.6%) |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 2 |
| Zollcode | 29399990 |
| RTECS-Nr. | RA8530000 |
| R-Sätze (R) | 25-37/38-41-42/43-36/37/38 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 22-26-28-36/39-45-36/37/39 |
| Gefahrenklasse | 6.1(a)Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.