| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
Purity: =99.56%
| Targets |
Myristoleic acid targets cellular pathways involved in cell survival and apoptosis. It has been shown to induce apoptosis and necrosis in human prostate cancer LNCaP cells. As a fatty acid, it may be incorporated into cellular membranes and affect membrane fluidity, signaling pathways, and cellular metabolism. The compound has cytotoxic effects and has been studied for its potential anticancer properties. Its mechanism of action may involve the induction of apoptosis through mitochondrial pathways or other cell death mechanisms.
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| ln Vitro |
Myristoleic acid causes apoptosis in LNCaP cells (100 μg/mL, 89.5%) as well as necrosis (100 μg/mL, 81.8%)[1]. Particularly at later stages of differentiation, myristoleic acid inhibited the formation of osteoclasts induced by RANKL in vitro [2].
In vitro, myristoleic acid induces apoptosis and necrosis in human prostate cancer LNCaP cells at a rate of 8.8% and 8.1%, respectively. It has cytotoxic effects and has been isolated from Serenoa repens as a bioactive compound. The compound's ability to induce cell death in cancer cells makes it a subject of interest for cancer research. It may also have effects on lipid metabolism and inflammatory pathways. |
| ln Vivo |
Mice treated with myristoleic acid (2 mg/kg, IP every 24 h) for 4 days are able to avoid osteoclast development and bone loss caused by RANKL[2].
In vivo, myristoleic acid is a naturally occurring fatty acid found in the human diet. It represents approximately 0.3-0.7% of the total fatty acid composition of adipose tissue triacylglycerol in humans. It has been studied for its potential health effects, including its role in metabolism and its cytotoxic effects on cancer cells. However, specific in vivo efficacy data for myristoleic acid in disease models have not been detailed. |
| Enzyme Assay |
For in vitro cytotoxicity assays, cancer cell lines (such as LNCaP prostate cancer cells) are seeded in 96-well plates and treated with myristoleic acid at various concentrations (1-100 µM) for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or CellTiter-Glo assays. Apoptosis and necrosis are quantified using Annexin V-FITC and propidium iodide staining followed by flow cytometry. IC50 values for cytotoxicity can be calculated.
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| Cell Assay |
Cell Proliferation Assay[1]
Cell Types: Human prostatic carcinoma LNCaP cells. Tested Concentrations: 0, 50, 100, 150, 200, 250 μg/mL. Incubation Duration: 24 h. Experimental Results: When LNCaP cells were treated with 130 μg/mL extract or 100 μg/mL myristoleic acid for 24 hr, the proportion of apoptotic cells was 16.5 and 8.8%, and that of necrotic one was 46.8 and 81.8%, respectively. For cell-based assays, cells are treated with myristoleic acid at concentrations ranging from 1-100 µM. Cell proliferation, apoptosis, and necrosis are assessed. Changes in cell morphology, membrane integrity, and mitochondrial membrane potential can be evaluated. The compound's effects on lipid metabolism and inflammatory cytokine production can also be studied in relevant cell types. |
| Animal Protocol |
Animal/Disease Models: C57BL/6 mice at 5 weeks[2].
Doses: 0.2, 2 mg/kg Route of Administration: IP every 24 h for 4 days. Experimental Results: Co-administration of myristoleic acid suppressed generation of TRAP-positive osteoclasts induced by sRANKL and attenuated the increases in osteoclastic indices of Oc.S/BS, N.Oc/B . Pm and ES/BS in a dose-dependent manner. For in vivo studies, animal models of cancer or metabolic disease would be used. Myristoleic acid would be administered via oral or intraperitoneal routes. Tumor growth, metabolic parameters, and inflammatory markers would be assessed. However, specific in vivo protocols for myristoleic acid have not been detailed in the available literature. |
| ADME/Pharmacokinetics |
Myristoleic acid is a lipid-soluble compound with a molecular weight of 226.35. It is soluble in organic solvents such as ethanol, DMSO, and chloroform. Storage is recommended at -20°C for long-term stability. The compound is for research use only and is not intended for human or veterinary use. Standard laboratory safety precautions should be followed when handling this compound.
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| Toxicity/Toxicokinetics |
Toxicological data for myristoleic acid have not been extensively reported. As a naturally occurring fatty acid, it is generally considered to be safe at dietary levels. However, at higher concentrations, it may have cytotoxic effects. Standard laboratory safety precautions should be followed when handling this compound. It is not intended for human use.
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| References |
[1]. Xiaoyan Gao, et al. Ozone initiated heterogeneous oxidation of unsaturated carboxylic acids by ATR-FTIR spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2019 May 5;214:177-183.
[2]. Jun-Oh Kwon, et al. Myristoleic acid inhibits osteoclast formation and bone resorption by suppressing the RANKL activation of Src and Pyk2. Eur J Pharmacol. 2015 Dec 5;768:189-98. |
| Additional Infomation |
Myristoleic acid is a tetradecenoic acid with a Z-configuration at positions 9-10 of the double bond. It has been isolated from saw palmetto (Serenoa repens) and exhibits cytotoxic and apoptosis-inducing effects. It is an apoptosis inducer, a plant metabolite, and an EC 3.1.1.1 (carboxylesterase) inhibitor. It is a tetradecenoic acid and a long-chain fatty acid, and is also the conjugate acid of myristate esters. Myristoleic acid has been reported in Hoya crassipes, Hoya pseudolanceolata, and other organisms with relevant data. Myristoleic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
Myristoleic acid is a monounsaturated omega-5 fatty acid found in Serenoa repens and dairy extracts. It has cytotoxic and apoptosis-inducing effects in prostate cancer LNCaP cells. Myristoleic acid is used in research to study fatty acid metabolism, cancer cell biology, and apoptosis. It is a research compound and is not approved for clinical use. |
| Molecular Formula |
C14H26O2
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| Molecular Weight |
226.36
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| Exact Mass |
226.193
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| CAS # |
544-64-9
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| PubChem CID |
5281119
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| Appearance |
Colorless to light yellow liquid（Density：0.9 g/cm3）
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
338.9±0.0 °C at 760 mmHg
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| Melting Point |
-4.5--4ºC(lit.)
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| Flash Point |
206.5±14.4 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.465
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| LogP |
5.57
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
16
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| Complexity |
185
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCC/C=C\CCCCCCCC(=O)O
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| InChi Key |
YWWVWXASSLXJHU-WAYWQWQTSA-N
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| InChi Code |
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
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| Chemical Name |
(Z)-tetradec-9-enoic acid
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| Synonyms |
cis-9-Tetradecenoate; Myristoleic Acid; Oleomyristic Acid
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 (~441.77 mM)
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4177 mL | 22.0887 mL | 44.1774 mL | |
| 5 mM | 0.8835 mL | 4.4177 mL | 8.8355 mL | |
| 10 mM | 0.4418 mL | 2.2089 mL | 4.4177 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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