ChemicalBook CAS DataBase List 19408-84-5

19408-84-5

Name	Dihydrocapsaicin
CAS	19408-84-5
EINECS(EC#)	206-969-8
Molecular Formula	C18H29NO3
MDL Number	MFCD00017259
Molecular Weight	307.43
MOL File	19408-84-5.mol

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

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.	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

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 . less more
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 . less more
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

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 (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. 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. 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

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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