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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%

biological source

Capsicum sp.

Quality Level

200

assay

≥85%

storage temp.

2-8°C

SMILES string

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

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)

InChI key

XJQPQKLURWNAAH-UHFFFAOYSA-N

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

M1022-BULK: + M1022PROC: + M1022-1G: + M1022-PM: + M1022-50MG: + M1022-250MG: + M1022-VAR: + M1022-CP:

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Certificates of Analysis (COA)

Lot/Batch Number
106K7039
083K7039
074H7846
036F7305
032K7022

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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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