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M1022

Sigma-Aldrich

Dihydrocapsaicin

from Capsicum sp., ≥85%

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Synonym(s):
6,7-Dihydrocapsaicin, 8-Methyl-N-vanillylnonanamide, N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnonenamide
Empirical Formula (Hill Notation):
C18H29NO3
CAS Number:
Molecular Weight:
307.43
Beilstein/REAXYS Number:
2815150
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Capsicum sp.

Quality Level

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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1 of 4

This Item
M2028PHR26271200600
vibrant-m

M1022

Dihydrocapsaicin

vibrant-m

M2028

Capsaicin

vibrant-m

PHR2627

Dihydrocapsaicin

vibrant-m

1200600

Dihydrocapsaicin

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-30°C

storage temp.

-

biological source

Capsicum sp.

biological source

Capsicum sp.

biological source

-

biological source

-

Gene Information

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

Gene Information

human ... CYP1A2(1544), TRPV1(7442)
rat ... Trpv1(83810), Trpv4(66026)

Gene Information

-

Gene Information

-

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.

Linkage

Capsaicin analog.

pictograms

Skull and crossbones

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_germany

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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Capsaicin

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)
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)
Y J Surh et al.
Life sciences, 56(16), PL305-PL311 (1995-03-10)
A new metabolic oxidation pathway of capsaicin (N-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-methyl-(E)-6 -nonenamide), a major pungent and pharmacologically active principle of hot peppers, was investigated. Incubation of capsaicin with phenobarbital-induced rat liver postmitochondrial supernatant enriched with NADPH-generating system produced N-(4,5-dihydroxy-3-methoxybenzyl)-(E)-6 -nonenylamide and a more
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)

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