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Merck

M1022

Dihydrocapsaicin

from Capsicum sp., ≥85% (HPLC), powder, VR1 vanilloid receptor agonist

Synonym(s):

6,7-Dihydrocapsaicin, 8-Methyl-N-vanillylnonanamide, N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonenamide

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About This Item

Empirical Formula (Hill Notation):
C18H29NO3
CAS Number:
19408-84-5
Molecular Weight:
307.43
NACRES:
NA.77
PubChem Substance ID:
24278532
UNSPSC Code:
12352200
MDL number:
MFCD00057794
Beilstein/REAXYS Number:
2815150
Assay:
≥85%
Quality level:
200

Key Documents

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Product Name

Dihydrocapsaicin, from Capsicum sp., ≥85%

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)

SMILES string

COc1cc(CNC(=O)CCCCCCC(C)C)ccc1O

InChI key

XJQPQKLURWNAAH-UHFFFAOYSA-N

biological source

Capsicum sp.

assay

≥85%

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... TRPV1(7442)
rat ... Trpv4(66026)

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Application

Dihydrocapsaicin has been used:
  • as a standard to analyze the level of dihydrocapsaicin in endogenous An2 and capsaicin synthase silenced fruits
  • as an external standard to determine the variability in capsaicinoid content in different landraces of capsicum
  • in the activation or ablation of capsaicin-sensitive primary afferents (CSPA) fibres

Biochem/physiol Actions

Dihydrocapsaicin/8-methyl-N-vanillylnonanamide; N-[−4-hydroxy-3-methoxybenzyl] 8-methylnonanamide (DHC) is an active component of capsaicinoids in chili peppers. DHC is capable of reducing body temperature. Hence it is considered as a pharmaceutical-induced hypothermia (PIH) candidate to treat cardiac arrest (CA) patients. It may possess anti-cancer, anti-inflammation, antioxidant, anti-obesity properties. DHC might help in the reduction of oxidative stress and inflammation in ischemia and reperfusion (I/R) injury. DHC can repress nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling pathway.
VR1 vanilloid receptor agonist.

Other Notes

Capsaicin analog.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6952V
WXBD3669V
WXBD2450V
WXBD1341V
SLCC9716

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Variability in capsaicinoid content in different landraces of Capsicum cultivated in north-eastern India
Islam Md A, et al.
Sci. Hortic., 183, 66-71 (2015)
Harnessing anthocyanin-rich fruit: a visible reporter for tracing virus-induced gene silencing in pepper fruit
Kim J, et al.
Plant methods, 13(1), 1-10 (2017)
Upregulation of proinflammatory cytokines and nerve growth factor by intraplantar injection of capsaicin in rats
Saadee NE, et al.
The Journal of Physiology, 545(1), 241-253 (2002)
Dihydrocapsaicin-induced Hypothermia after Asphyxial Cardiac Arrest in Rats
He J, et al.
Conference proceedings : Annual International Conference of the IEEE Engineering in Medicine and Biology Society, 2016, 1858-1858 (2016)
Dihydrocapsaicin Attenuates Blood Brain Barrier and Cerebral Damage in Focal Cerebral Ischemia/Reperfusion via Oxidative Stress and Inflammatory
Janyou A, et al.
Scientific Reports, 7 (2017)
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