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

Properties

• 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)

Description

Application

Dihydrocapsaicin has been used:

• as a standard to analyze the level of dihydrocapsaicin in endogenous An2 and capsaicin synthase silenced fruits[1]
• as an external standard to determine the variability in capsaicinoid content in different landraces of capsicum[2]
• in the activation or ablation of capsaicin-sensitive primary afferents (CSPA) fibres[3]

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.[4] DHC is capable of reducing body temperature. Hence it is considered as a pharmaceutical-induced hypothermia (PIH) candidate to treat cardiac arrest (CA) patients.[5] 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.[4]

VR1 vanilloid receptor agonist.

Linkage

Capsaicin analog.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300,H315,H319,H335
• pcodes: P261 - P264 - P271 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• 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