| Identification | More | [Name]
Dihydrocapsaicin | [CAS]
19408-84-5 | [Synonyms]
8-METHYL-N-VANILLYL-6-NONENAMIDE
8-METHYL-N-VANILLYL-6-NONENEAMIDE
8-METHYL-N-VANILLYL-TRANS-6-NONENAMIDE
CAPSAICIN
CAPSAICINE
CAPSAICIN, NATURAL
(E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE
(e)-8-methyl-n-vanillyl-6-nonenamide
(E)-CAPSAICIN
(E)-N-([4-HYDROXY-3-METHOXYPHENYL]METHYL)8-METHYL-6-NONEAMIDE
(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
FEMA 2787
FEMA 3404
N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6E-NONENAMIDE
N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE
TRANS-8-METHYL-N-VANILLYL-6-NONENAMIDE
6,7-dihydrocapsaicin
8-methyl-n-vanillyl-nonanamid
8-methyl-N-vanillylnonanamide approx.*90% from ca
8-METHYL-N-VANILLYLNONANAMIDE APPROX.*90 % FROM CAPS | [EINECS(EC#)]
206-969-8 | [Molecular Formula]
C18H29NO3 | [MDL Number]
MFCD00017259 | [Molecular Weight]
307.43 | [MOL File]
19408-84-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
62-65 °C(lit.)
| [Boiling point ]
497.4±35.0 °C(Predicted) | [density ]
1.026±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
H2O: insoluble
| [form ]
White to off-white solid. | [pka]
9.76±0.20(Predicted) | [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]
19408-84-5(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H315-H319-H335 | [Precautionary statements ]
P261-P301+P310-P305+P351+P338 | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R42/43:May cause sensitization by inhalation and skin contact .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/39:Wear suitable protective clothing and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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 |
| Hazard Information | Back Directory | [Description]
Dihydrocapsaicin is a terpene alkaloid that has been found in Capsicum and has diverse biological activities.1,2,3 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).1 Dihydrocapsaicin scavenges DPPH (Item No. 14805) and ABTS (Item No. 27317) 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.2 Dihydrocapsaicin is an agonist of transient receptor potential vanilloid 1 (TRPV1) and inhibits NETosis induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in isolated human neutrophils.4,5 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.3 | [Chemical Properties]
White Solid | [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 |
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