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Homocapsaicin II

Alias: Homocapsaicin II
Cat No.:V62757 Purity: ≥98%
Homocapsaicin II is a pungent compound extracted from the fruits of Capsicum annuum L.
Homocapsaicin II
Homocapsaicin II Chemical Structure CAS No.: 71240-51-2
Product category: Phenols
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
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Product Description
Homocapsaicin II is a pungent compound isolated from the fruits of Capsicum annuum L.
Homocapsaicin II is a pungent compound that can be isolated from the fruits of Capsicum annuum L. Its molecular formula is C19H29NO3 with a molecular weight of 319.44 g/mol. Homocapsaicin II is a capsaicinoid that accounts for about 1% of the total capsaicinoids mixture in chili peppers and has approximately half the pungency of capsaicin. It displays significant potential to act as an effective inhibitor of cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2). The compound is useful for its anti-inflammatory activities.
Biological Activity I Assay Protocols (From Reference)
Targets
Homocapsaicin II targets cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes. By inhibiting these enzymes, it reduces the synthesis of prostaglandins, which are mediators of inflammation and pain. This mechanism is similar to that of non-steroidal anti-inflammatory drugs (NSAIDs). The compound's ability to inhibit COX enzymes makes it a subject of interest for anti-inflammatory research.
ln Vitro
In vitro, Homocapsaicin II has been shown to inhibit COX-1 and COX-2 activity. Its inhibitory activity can be assessed by measuring the production of prostaglandins in cell-based or cell-free enzyme assays. The compound's IC50 values for COX-1 and COX-2 inhibition can be determined. Its anti-inflammatory activity is a key area of research.
ln Vivo
Homocapsaicin II is useful for its anti-inflammatory activities. As a COX-1 and COX-2 inhibitor, it may exhibit in vivo anti-inflammatory effects similar to those of other NSAIDs. Its potential therapeutic applications include the treatment of inflammatory conditions. However, specific in vivo study details are not extensively documented in general references.
Enzyme Assay
The inhibitory activity of Homocapsaicin II on COX-1 and COX-2 can be assessed using an in vitro enzyme assay. Purified COX enzymes are incubated with arachidonic acid and varying concentrations of the compound. The production of prostaglandins is measured, and the IC50 values are determined. The compound's selectivity for COX-1 versus COX-2 can also be evaluated.
Cell Assay
Homocapsaicin II is used in cell-based assays to evaluate its anti-inflammatory activity. Cells such as macrophages are treated with the compound and stimulated with inflammatory agents. The production of pro-inflammatory mediators, including prostaglandins and cytokines, is measured. The compound's ability to reduce inflammation in cell culture models can be assessed.
Animal Protocol
The in vivo efficacy of Homocapsaicin II can be studied in animal models of inflammation. The compound is administered to animals, and its effects on inflammatory markers and tissue damage are assessed. However, specific animal study protocols are not detailed in general references. The compound is primarily used in research settings to study its anti-inflammatory properties.
ADME/Pharmacokinetics
Homocapsaicin II has a molecular weight of 319.44 g/mol and a molecular formula of C19H29NO3. It is a lipophilic, colorless, odorless crystalline to waxy compound. The compound is typically stored at room temperature and is soluble in organic solvents. As a capsaicinoid, its pharmacokinetic properties would be characteristic of this class of compounds.
Toxicity/Toxicokinetics
Toxicological data for Homocapsaicin II are not extensively detailed, as it is a research compound. It is not intended for human or veterinary use. Standard laboratory safety precautions, including the use of personal protective equipment (PPE), should be followed when handling the compound. Its safety profile would be established through dedicated toxicology studies if it were to be developed further.
References

[1]. Nachweis und Identifizierung neuer Scharfstoffe in Capsicum-Früchten [Detection and identification of new pungent compounds in fruits of Capsicum (author's transl)]. Planta Med. 1979 May;36(1):61-7. German.

Additional Infomation
Homocapsaicin II has been reported in chili peppers and data are available.
Homocapsaicin II is a pungent compound isolated from the fruits of Capsicum annuum L. It is a capsaicinoid that accounts for about 1% of the total capsaicinoids mixture in chili peppers and has approximately half the pungency of capsaicin. The compound displays significant potential to act as an effective inhibitor of COX-1 and COX-2 and is useful for its anti-inflammatory activities. It is a research-grade compound not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H29NO3
Molecular Weight
319.44
Exact Mass
319.215
CAS #
71240-51-2
PubChem CID
11674147
Appearance
Typically exists as solid at room temperature
LogP
4.57
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
10
Heavy Atom Count
23
Complexity
357
Defined Atom Stereocenter Count
0
SMILES
OC1C=CC(CNC(=O)CCCC/C=C/C(C)CC)=CC=1OC
InChi Key
MLJGZARGNROKAC-VQHVLOKHSA-N
InChi Code
InChI=1S/C19H29NO3/c1-4-15(2)9-7-5-6-8-10-19(22)20-14-16-11-12-17(21)18(13-16)23-3/h7,9,11-13,15,21H,4-6,8,10,14H2,1-3H3,(H,20,22)/b9-7+
Chemical Name
(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyldec-6-enamide
Synonyms
Homocapsaicin II
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1305 mL 15.6524 mL 31.3048 mL
5 mM 0.6261 mL 3.1305 mL 6.2610 mL
10 mM 0.3130 mL 1.5652 mL 3.1305 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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