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(-)-Fenchone ((-)-fenchone)

Alias: l-alpha-Fenchone; L-Fenchone; CCRIS 8093
Cat No.:V64322 Purity: ≥98%
(-)-Fenchone is a bicyclic monoterpene that is widely distributed in plants and is present in the essential oil of fennel.
(-)-Fenchone ((-)-fenchone)
(-)-Fenchone ((-)-fenchone) Chemical Structure CAS No.: 7787-20-4
Product category: Terpenoids
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
(-)-Fenchone is a bicyclic monoterpene that is widely distributed in plants and is present in the essential oil of fennel. (-)-Fenchone is oxidized in liver microsomes by CYP2A6 and CYP2B6 to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone, and 10-hydroxyfenchone derivatives.
(-)-Fenchone is a bicyclic monoterpenoid widely distributed in plants, such as Foeniculum vulgare (fennel) and Peumus boldus. It exhibits a wide range of biological activities, including antioxidant, anti-inflammatory, antifungal, wound healing, antidiarrheal, and bronchodilator effects. It has intestinal anti-inflammatory activity and is a potential anti-tumor compound.
Biological Activity I Assay Protocols (From Reference)
Targets
(-)-Fenchone targets multiple pathways involved in inflammation, oxidative stress, and infection. It acts as an antioxidant by scavenging free radicals. It has immunomodulatory effects. It shows antifungal activity, particularly against Candida albicans, and antidiarrheal activity via antimotility mechanisms.
ln Vitro
In vitro, (-)-fenchone exhibits antifungal activity, with a MIC90 of 8 µg/mL and MFC of 16 µg/mL, including against micronazole-resistant C. albicans isolates. It has antioxidant and immunomodulatory properties.
ln Vivo
In vivo, (-)-fenchone (75, 150, and 300 mg/kg) has shown antidiarrheal activity, with a significant decrease in the evacuation index. It prevents duodenal ulcers and enhances gastric healing. It has intestinal anti-inflammatory activity related to cytoprotection of the intestinal barrier.
Enzyme Assay
Non-cellular assays for (-)-fenchone typically involve measuring its antioxidant activity using DPPH or ABTS radical scavenging assays. Its antifungal activity is assessed using standard broth microdilution methods to determine MIC and MFC values.
Cell Assay
Cellular assays for (-)-fenchone are conducted using immune cells to assess its immunomodulatory effects. It may be tested on macrophages or other cell types to measure cytokine production and inflammatory mediator release.
Animal Protocol
In vivo animal experiments for (-)-fenchone are conducted in models of colitis, diarrhea, and ulcers. The compound is administered orally, and its effects on inflammation, intestinal motility, and tissue integrity are assessed.
ADME/Pharmacokinetics
Pharmacokinetic properties of (-)-fenchone are not well-characterized. As a small, lipophilic monoterpenoid, it is likely absorbed and metabolized. Its bioavailability and tissue distribution depend on the route of administration.
Toxicity/Toxicokinetics
Toxicological data for (-)-fenchone indicate that it exhibits low toxicity. It is considered safe at the doses used in research studies. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Metabolism of (-)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. Xenobiotica. 2007;37(2):194-204.

Additional Infomation
(1R,4S)-Fenone is a fenone with a (1R,4S)- stereochemical configuration. It is a component of anise essential oil and a plant metabolite. It is the enantiomer of (1S,4R)-Fenone. (-)-Fenone has been reported in Magnolia officinalis and Thuja occidentalis, and relevant data are available.
(-)-Fenchone is a bioactive monoterpenoid with potential therapeutic applications. Its wide range of biological activities makes it a compound of interest for in vitro and in vivo pharmacological research. It is being studied for its potential in treating inflammatory bowel disease, fungal infections, and other conditions.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H16O
Molecular Weight
152.23
Exact Mass
152.12
Elemental Analysis
C, 78.90; H, 10.59; O, 10.51
CAS #
7787-20-4
PubChem CID
82229
Appearance
Colorless to light yellow liquid
Density
1.0±0.1 g/cm3
Boiling Point
193.5±0.0 °C at 760 mmHg
Melting Point
5ºC
Flash Point
52.8±0.0 °C
Vapour Pressure
0.5±0.3 mmHg at 25°C
Index of Refraction
1.485
LogP
2.13
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Heavy Atom Count
11
Complexity
217
Defined Atom Stereocenter Count
2
SMILES
CC1(C)[C@H]2CC[C@](C)(C2)C1=O
InChi Key
LHXDLQBQYFFVNW-OIBJUYFYSA-N
InChi Code
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
Chemical Name
(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Synonyms
l-alpha-Fenchone; L-Fenchone; CCRIS 8093
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)
DMSO: 100 mg/mL (656.90 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (16.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.5690 mL 32.8450 mL 65.6901 mL
5 mM 1.3138 mL 6.5690 mL 13.1380 mL
10 mM 0.6569 mL 3.2845 mL 6.5690 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.

Calculator

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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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  • 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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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