Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

Safety Information

M1022

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C18H29NO3
CAS Number:
19408-84-5
Molecular Weight:
307.43
Beilstein:
2815150
MDL number:
MFCD00057794
UNSPSC Code:
12352200
PubChem Substance ID:
24278532
NACRES:
NA.77

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)

Looking for similar products? Visit Product Comparison Guide

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
GHS06

Signal Word

Danger

Hazard Statements

H300,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

JAN Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 6

1 of 6

Capsaicin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1450

Capsaicin

Capsaicin An active constituent of cayenne pepper with excitatory and desensitizing effects on a subset of primary afferent sensory neurons.

Sigma-Aldrich

211275

Capsaicin

Capsaicin European Pharmacopoeia (EP) Reference Standard

Y0000671

Capsaicin

Capsaicin United States Pharmacopeia (USP) Reference Standard

USP

1091108

Capsaicin

N-Vanillylnonanamide phyproof® Reference Substance

PHL89820

N-Vanillylnonanamide

Capsaicin phyproof® Reference Substance

PHL89520

Capsaicin

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)
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
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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service