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M1022 Sigma-Aldrich

Dihydrocapsaicin

from Capsicum sp., ≥85%

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

  • CAS Number 19408-84-5

  • Empirical Formula (Hill Notation) C18H29NO3

  • Molecular Weight 307.43

  •  Beilstein/REAXYS Number 2815150

  •  MDL number MFCD00057794

  •  PubChem Substance ID 24278532

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, DIG-DY,
Quality Level   200
biological source   Capsicum sp.
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)

Description

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

Packaging

1 g in glass bottle

250 mg in glass bottle

50 mg in poly bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Linkage

Capsaicin analog.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
RA5998000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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