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| Targets |
Cardanol monoene targets tyrosinase, a copper-containing enzyme involved in melanin biosynthesis, with an IC50 of 56 μM. The compound also induces mitochondria-associated apoptosis in human melanoma cells, suggesting that it may target mitochondrial pathways involved in apoptosis. As a phenolic lipid, it may interact with various cellular targets through its phenolic hydroxyl group and hydrophobic alkyl chain. The compound's mechanism of action in melanoma cells involves mitochondrial dysfunction leading to apoptosis.
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| ln Vitro |
Cardanol monoene induces mitochondria-associated apoptosis in human melanoma cells. It reversibly inhibits tyrosinase with an IC50 of 56 μM in vitro. As a phenolic compound found in cashew nut shell liquid, it has potential applications in cancer research and as a tyrosinase inhibitor. The compound's ability to induce apoptosis in melanoma cells suggests potential for anticancer research. It is also used in the production of resins, coatings, and adhesives.
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| ln Vivo |
In vivo activity data for cardanol monoene are not extensively documented. The compound has been studied for its ability to induce apoptosis in melanoma cells, suggesting potential antitumor activity in vivo. As a natural product, it may have favorable safety and efficacy profiles. However, specific in vivo efficacy studies in animal models are not specified in the public domain. The compound is intended for research use only.
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| Enzyme Assay |
The in vitro enzyme assay for cardanol monoene typically involves measuring its inhibition of tyrosinase activity. Mushroom tyrosinase is incubated with varying concentrations of cardanol monoene (typically 1-1000 μM) in the presence of a substrate such as L-DOPA or tyrosine. The enzymatic activity is measured by monitoring the formation of dopachrome spectrophotometrically at 475 nm. The IC50 value is determined by plotting the percentage of inhibition against compound concentration. The compound is dissolved in DMSO or ethanol and diluted in assay buffer.
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| Cell Assay |
In vitro cellular assays for cardanol monoene typically involve treating human melanoma cells with the compound at concentrations ranging from 1 to 100 μM for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or CellTier-Glo assays. Apoptosis is assessed by Annexin V/PI staining, caspase activity assays, or DNA fragmentation analysis. Mitochondrial function is assessed by measuring mitochondrial membrane potential using JC-1 dye or by measuring ATP levels. The compound is dissolved in DMSO as a stock solution and diluted in cell culture medium.
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| Animal Protocol |
In vivo animal studies for cardanol monoene are not extensively documented. For potential in vivo applications, the compound could be administered to mice via oral gavage or intraperitoneal injection at doses determined from preliminary studies. Melanoma xenograft models could be used to evaluate antitumor efficacy. Tumor growth is monitored by caliper measurements. Apoptosis in tumors is assessed by TUNEL staining or caspase activity assays. The compound's pharmacokinetics and pharmacodynamics would be evaluated in these models.
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| ADME/Pharmacokinetics |
Cardanol monoene has a molecular weight of 302.50 g/mol and formula C21H34O. It has a density of 0.953-0.965 and is a phenolic lipid. Recommended storage is at -20°C. The compound is soluble in organic solvents such as ethanol, DMSO, and chloroform. Detailed PK parameters such as half-life, Cmax, AUC, and bioavailability would require experimental determination. The compound is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
Toxicity data for cardanol monoene are not extensively reported. The compound is intended for research use only and is not approved for human therapeutic applications. As a naturally occurring compound, it may have a favorable safety profile, but appropriate safety precautions should be taken when handling. Standard toxicity assessments would include acute toxicity, genotoxicity, and repeated-dose toxicity studies. The compound's ability to induce apoptosis suggests potential cytotoxicity at high concentrations.
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| References | |
| Additional Infomation |
(15:1)-Cardanophenol belongs to the phenolic class of compounds. Cardanomonene has been reported in cashew nuts (Anacardium occidentale), ginkgo (Ginkgo biloba), and Brazilian pepperwood (Schinus terebinthifolia), and relevant data are available. See also: Cardanomonene (note moved to).
Cardanol monoene (CAS 501-26-8) is a naturally occurring monounsaturated phenolic lipid found in cashew nut shell liquid. It has a molecular weight of 302.50 g/mol and formula C21H34O. The compound induces mitochondria-associated apoptosis in human melanoma cells and reversibly inhibits tyrosinase with an IC50 of 56 μM. It is also known as Cardanol C15:1 and (15:1)-Cardanol. The compound is not approved for clinical use. |
| Molecular Formula |
C21H34O
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|---|---|
| Molecular Weight |
302.49406
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| Exact Mass |
302.261
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| CAS # |
501-26-8
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| PubChem CID |
5281854
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| Appearance |
Colorless to light yellow ointment
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| Density |
0.919g/cm3
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| Boiling Point |
435.4ºC at 760 mmHg
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| Flash Point |
196.6ºC
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| Index of Refraction |
1.507
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| Source |
Originated from plants: Anacardiaceae Anacardium occidentaleL.
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| LogP |
6.801
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
22
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| Complexity |
259
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCC=CCCCCCCCC1=CC(=CC=C1)O
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| InChi Key |
YLKVIMNNMLKUGJ-FPLPWBNLSA-N
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| InChi Code |
InChI=1S/C21H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h7-8,15,17-19,22H,2-6,9-14,16H2,1H3/b8-7-
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| Chemical Name |
3-[(Z)-pentadec-8-enyl]phenol
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~330.6 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.26 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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 (8.26 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3059 mL | 16.5295 mL | 33.0589 mL | |
| 5 mM | 0.6612 mL | 3.3059 mL | 6.6118 mL | |
| 10 mM | 0.3306 mL | 1.6529 mL | 3.3059 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.
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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