Nordihydrocapsaicin

Cat. No. FNK-NH100301


Features:

Size: 1 mg
CAS #: 28789-35-7
Molecular Formula: C₁₇H₂₇NO₃
Molecular weight: 293.40
Purity: >99% (HPLC)
Origin: Red pepper
Storage: 4°C, Dark Storage

Product Description
Nordihydrocapsaicin is likely a capsaicinoid compound found in chili peppers. It is probably studied for its potential biological activities and contribution to the pungency of peppers.

Property

• Chemical Formula: C₁₇H₂₇NO₃ 
• Molecular Weight: Approximately 293.40 g/mol
• Appearance: Likely a white to off-white crystalline powder
• Solubility: Probably poorly soluble in water, soluble in organic solvents

Application and Usage

• Research: Used in studies investigating the pungency and biological effects of capsaicinoids
• Food Industry: May be used as a flavoring agent or in the production of spicy foods
• Pharmaceutical Development: Potentially investigated for pain relief applications

Safety and Handling

• Storage: Store in a cool, dry place, protected from light
• Handling: Use appropriate personal protective equipment, including gloves and eye protection
• Safety Measures: Avoid skin and eye contact; may cause irritation

Involved Human Diseases

• Cardiovascular Health
  • Capsaicinoids, including nordihydrocapsaicin, may have beneficial effects on cardiovascular health:
    • They can potentially reduce the risk of heart disease by improving cholesterol levels.
    • These compounds may promote vascular health by increasing the expression and activation of endothelial nitric oxide synthase (eNOS), which enhances endothelium-dependent vasodilation.
    • In animal studies, dietary capsaicin has been shown to slow atherogenesis in atherosclerosis-prone mice.
• Metabolic Disorders
  • Capsaicinoids have demonstrated potential in addressing metabolic disorders:
    • They may help with body weight loss and increased metabolism.
    • Some studies suggest that capsaicinoids could have a positive impact on diabetes management.
• Pain Management
  • One of the most well-established uses of capsaicinoids is in pain management:
    • Capsaicin, and potentially nordihydrocapsaicin, have been used to treat various pain conditions, including neuropathic pain.
    • High-concentration capsaicin patches have shown efficacy in treating post-herpetic neuralgia (PHN) and other neuropathic pain conditions.
• Cancer
  • While more research is needed, capsaicinoids have shown potential anti-cancer properties:
    • Capsaicin has been found to induce apoptosis in various cancer cell types, including prostate, colon, skin, breast, lung, and bladder cancer cells.
    • It may act through multiple pathways, including the activation of TRPV1 receptors and modulation of various signaling pathways involved in cell proliferation and apoptosis.
• Gastrointestinal Disorders
  • Capsaicinoids may have effects on gastrointestinal function:
    • - They can potentially modulate ion transport in the intestine, which could have implications for conditions like diarrhea.
    • - Some studies suggest that capsaicin may have protective effects against gastric ulcers, although more research is needed to confirm this.
• Inflammatory Conditions
  • Capsaicinoids have shown anti-inflammatory properties:
    • They may help in managing inflammatory conditions such as arthritis.
    • The anti-inflammatory effects are thought to be mediated through the desensitization of sensory neurons and modulation of inflammatory mediators.

Cell Signaling Pathways Affected

• TRPV1 Activation
  • Nordihydrocapsaicin, as a capsaicinoid, primarily acts by activating the TRPV1 (transient receptor potential vanilloid 1) receptor. This activation leads to:
    • - Influx of Ca2+ and Na+ ions into cells
    • - Membrane depolarization 
    • - Activation of calcium-dependent signaling cascades
• Downstream Signaling Pathways
  • Activation of TRPV1 by nordihydrocapsaicin triggers several downstream signaling pathways:
    • **Protein Kinase Activation:**
    • - Protein Kinase A (PKA)
    • - Protein Kinase C (PKC) 
    • - CaMKII (Ca2+/calmodulin-dependent protein kinase II)
      • These kinases phosphorylate TRPV1 at multiple sites, leading to sensitization of the channel.
• MAPK Pathway:
  • - Increased phosphorylation of p38 MAPK
  • - Activation of ERK1/2
• PI3K/Akt Pathway:
  • - Activation of PI3K/Akt signaling
• Other Affected Pathways
  • NF-κB Pathway:
    • Capsaicinoids like nordihydrocapsaicin may inhibit the NF-κB pathway by:
    • - Inhibiting phosphorylation of IκBα
    • - Reducing NF-κB activation
  • Calcium Signaling:
    • - Increased intracellular Ca2+ levels
    • - Activation of calmodulin (CaM) and calcineurin (PPP3C)
  • Mitochondrial Effects:
    • - Alteration of NAD+/NADH ratio
    • - Potential effects on oxidative stress and SIRT1 activity
  • Estrogenic Signaling:
    • While lacking cell proliferation activity, nordihydrocapsaicin may affect estrogen-responsive gene expression similarly to other capsaicinoids[6].