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Product name: Homodihydrocapsaicin II
Synonym name: N-(4-Hydroxy-3-methoxybenzyl)-8-methyldecanamide
Catalogue No.: BP5043
Cas No.: 71239-21-9
Formula: C19H31NO3
Mol Weight: 321.461
Botanical Source:
Type of Compound: Alkaloids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Homodihydrocapsaicin II
NMR of Homodihydrocapsaicin II
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
58.5600
4.5496
4.5484
.0223
2.6334
8.0488
High
93.8768
2.4177
No
No
Yes
No
No
No
0.0
No
No
No
No
Homodihydrocapsaicin II (CAS No.: 71239-21-9) is a natural capsaicin compound, mainly found in the fruits of chili peppers (Capsicum spp.). As an important member of the capsaicin family, high dihydrocapsaicin II has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique molecular structure and significant biological activity. Research shows that hyperdihydrocapsaicin II not only has the spicy sensation of classic capsaicin but also demonstrates good analgesic and anti-inflammatory effects, especially showing potential application value in the treatment of inflammatory diseases and neuropathic pain.
Capsaicin compounds participate in the regulatory mechanisms of pain transmission and inflammatory responses by modulating various ion channels and receptors. As a derivative of capsaicin, the unique molecular structure of hyper-dihydrocapsaicin II gives it high bioactivity and good pharmacokinetic properties. This paper will systematically review the chemical structure and physicochemical properties of high dihydrocapsaicin II, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and finally explore its clinical application prospects and future research directions, providing a reference for researchers in related fields.
The molecular formula of high dihydrocapsaicin II is C20H33NO3, with a molecular weight of 321.4610. Its chemical structure belongs to the capsaicin compounds, with a core structure consisting of an aromatic ring connecting a long-chain fatty acid acamide. Compared to capsaicin, hyper-dihydrocapsaicin II has higher saturation in the fatty acid chain, making its chemical properties more stable and its metabolic pathways in organisms may differ.
In terms of physicochemical properties, the LogP value of high dihydrocapsaicin II is 4.5496, indicating strong lipid solubility that facilitates crossing of cell membranes and the blood-brain barrier. Its polar surface area (TPSA) is 58.56 Ų, indicating moderate polarity that facilitates binding with biomacromolecules. Low water solubility (0.0223 mg/mL), consistent with its high lipid solubility, suggests that it may require suitable carriers or formulation technologies in vivo to improve bioavailability.
Additionally, hyper-dihydrocapsaicin II did not show hERG channel inhibition, reducing the risk of cardiotoxicity; The Ames test result was 0.0, indicating no significant genotoxicity and relatively high safety. Its molecular structure and physicochemical properties provide a solid foundation for its role as a candidate drug molecule.
High dihydrocapsaicin II is mainly found in the fruits of Capsicum species, especially varieties such as Capsicum annuum and Capsicum frutescens. During the ripening process of chili fruits, the content of capsaicin compounds gradually increases, and different varieties and growth environments significantly influence their content and composition.
Traditional methods for extracting high dihydrocapsaicin II typically use organic solvent extraction such as ethanol, methanol, or ethyl acetate, combined with ultrasound-assisted extraction or reflux extraction technologies to improve extraction efficiency. The extract undergoes concentration, liquid-liquid separation, and column chromatography purification, and is finally identified and purified using techniques such as high-performance liquid chromatography (HPLC) or gas chromatography-mass spectrometry (GC-MS).
In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have also been applied to the extraction of capsaicin-type substances, offering advantages such as low solvent residue, environmental friendliness, and high extraction efficiency. For the extraction of high dihydrocapsaicin II, optimizing extraction conditions and purification processes is key to achieving its large-scale production and application.
The pharmacological activity of hyperdihydrocapsaicin II mainly focuses on analgesic and anti-inflammatory aspects. Multiple in vivo and in vitro experiments have shown that this compound can effectively alleviate inflammatory and neuropathic pain, with mechanisms involving multiple molecular targets.
Hyperdihydrocapsaicin II exerts its analgesic effect by activating and modulating the TRPV1 (transient receptor potential vanillic acid receptor 1) channel. TRPV1 is an important ion channel at sensory nerve endings, involved in the transmission and regulation of pain signals. High dihydrocapsaicin II can bind to TRPV1, inducing its desensitization and thereby reducing pain sensation.
Additionally, hyper-dihydrocapsaicin II affects neurotransmitter receptors such as CNR1 (cannabinoid receptor 1), OPRD1 (δ-opioid receptor), OPRM1 (μ-opioid receptor), and OPRK1 (κ-opioid receptor), regulating pain transmission pathways in the central nervous system. Its regulatory effect on multiple opioid receptors suggests it may have effects similar to opioid analgesics but with fewer side effects.
Research on hyper-dihydrocapsaicin II in anti-inflammatory research shows that it can inhibit the activities of PTGS1 (cyclooxygenase-1) and PTGS2 (cyclooxygenase-2), reduce the synthesis of inflammatory mediators such as prostaglandins, and alleviate inflammatory responses. Its regulation of TRPA1 (transient receptor potential vanillic acid receptor subfamily A1) channel also contributes to the relief of inflammatory pain.
Additionally, hyper-dihydrocapsaicin II indirectly affects the neuroregulatory processes of inflammation and pain by modulating neurotransmitter systems such as SLC6A4 (serotonin transporter) and DRD2 (dopamine receptor D2). Overall, the multi-target mechanism of hyperdihydrocapsaicin II makes it a potential candidate for treating complex pain and inflammatory diseases.
The pharmacological effects of hyper-dihydrocapsaicin II depend on its interactions with various molecular targets and mainly include the following aspects:
TRPV1 is one of the main targets of hyperdihydrocapsaicin II. This receptor is a non-selective cation channel widely distributed among sensory neurons and participates in the transduction of pain signals triggered by heat perception and chemical stimuli. Hypercapsaicin II achieves analgesic effects by activating TRPV1, inducing its desensitization and endocytosis, and reducing neuronal excitability.
Monodihydrocapsaicin II binds to three opioid receptors: δ, μ, and κ, modulating the endogenous opioid system and exerting analgesic effects. Unlike traditional opioid analgesics, hyper-dihydrocapsaicin II may reduce the risk of addiction and resistance by partially stimulating or modulating receptor activity.
CNR1 receptors are primarily distributed in the central nervous system and are involved in pain regulation, mood, and inflammatory responses. The regulatory effect of hyper-dihydrocapsaicin II on CNR1 helps alleviate neuropathic pain and inflammation-related symptoms.
PTGS1 and PTGS2 are key enzymes for prostaglandin synthesis and are involved in regulating inflammatory responses. High dihydrocapsaicin II inhibits the activity of these two enzymes, reduces the production of inflammatory mediators, and exerts anti-inflammatory effects.
TRPA1 receptors are closely related to inflammatory pain, and hypercapsaicin II regulates TRPA1 activity to reduce inflammation-induced pain. SLC6A4 and DRD2 are involved in neurotransmission of serotonin and dopamine, regulating mood and pain perception. The regulation of these targets by high-dihydrocapsaicin II helps alleviate pain and improve patients' quality of life.
High dihydrocapsaicin II shows good medicinal properties:
Pharmacokinetics, although specific in vivo metabolic and clearance data are not yet complete, based on its physicochemical properties and structure, it is speculated that hyperdihydrocapsaicin II may undergo biological transformation through the hepatic metabolic enzyme system, exhibiting good in vivo stability and central distribution capability. In the future, further in vivo pharmacokinetic studies are needed to clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics, providing a basis for clinical development.
High dihydrocapsaicin II has broad clinical application prospects due to its remarkable analgesic and anti-inflammatory activities. It has particular potential in the following areas:
Treatment of inflammatory diseases: such as rheumatoid arthritis and inflammatory bowel disease. Hyperdihydrocapsaicin II is expected to relieve symptoms and improve patients' quality of life by inhibiting the synthesis of inflammatory mediators and modulating neuroinflammatory responses.
Neuropathic pain management: For difficult-to-treat pain such as diabetic neuropathy and postherpetic neuralgia, hyperdihydrocapsaicin II may become a new type of non-opioid analgesic through a multi-target mechanism, reducing the side effects of traditional analgesics.
Adjunctive therapy for central nervous system diseases: Its excellent blood-brain barrier penetration gives it potential value in treating pain related to neuroinflammation and neurodegenerative diseases.
Future research should focus on in-depth analysis of the pharmacodynamic mechanisms, pharmacokinetic optimization, and safety evaluation of hyper-dihydrocapsaicin II, combined with modern drug delivery technologies such as nanocarriers and sustained-release formulations to enhance its clinical feasibility and efficacy.
Moreover, the implementation of preclinical and clinical trials will be key to advancing the pharmacization of hyperdihydrocapsaicin II, especially in dosage optimization, toxicological evaluation, and long-term safety monitoring.
As a natural capsaicin compound, high dihydrocapsaicin II demonstrates significant analgesic and anti-inflammatory potential due to its unique chemical structure and multi-target pharmacological effects. Its excellent druggability parameters and safety characteristics provide a solid foundation for developing novel natural-origin analgesic and anti-inflammatory drugs. In the future, through in-depth mechanistic research and clinical validation, hyperdihydrocapsaicin II is expected to become an effective drug for treating inflammatory diseases and neuropathic pain, offering patients new treatment options.
With continuous advances in natural product pharmacology and modern drug development technologies, the prospects for research and application of hyperdihydrocapsaicin II will become even broader, warranting sustained attention and investment from the scientific research and pharmaceutical communities.
Shenshuai
Wenjing
Hedandan
