Myrcene (β-Myrcene) is a naturally occurring monoterpene with anti-invasive effects. It is an aromatic volatile hydrocarbon compound that can suppress TNFα-induced NF-κB activity.
Physicochemical Properties
| Molecular Formula | C10H16 |
| Molecular Weight | 136.23404 |
| Exact Mass | 136.125 |
| CAS # | 123-35-3 |
| Related CAS # | 29463-45-4 |
| PubChem CID | 31253 |
| Appearance | Colorless to light yellow liquid |
| Density | 0.8±0.1 g/cm3 |
| Boiling Point | 167.0±0.0 °C at 760 mmHg |
| Melting Point |
< -10 °C < -10 °C |
| Flash Point | 39.4±0.0 °C |
| Vapour Pressure | 2.3±0.1 mmHg at 25°C |
| Index of Refraction | 1.450 |
| LogP | 4.58 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 10 |
| Complexity | 145 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C=CC(=C)CCC=C(C)C |
| InChi Key | UAHWPYUMFXYFJY-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3 |
| Chemical Name | 7-methyl-3-methylideneocta-1,6-diene |
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), 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) |
Biological Activity
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion In a pharmacokinetic study, blood levels as high as 14.1+/- 3.0 ug/mL beta-myrcene (peak value) were detected sixty minutes after oral administration of 1.0 g/kg bw (7300 umol/kg bw) beta-myrcene to female rats. ... The compound was concentrated in adipose tissue and in many organs, including the brain, liver, kidneys, and testes. Metabolism / Metabolites Metabolites isolated from the urine of rats after oral administration of beta-myrcene were: 10-hydroxylinalool, 7-methyl-3-methylene-oct-6-ene-1,2-diol, 1-hydroxymethyl-4-isopropenyl cyclohexanol, 10-carboxylinalool and 2-hydroxy-7-methyl-3-methylene-oct-6-enoic acid. Liver microsomes prepared from phenobarbital-treated rats convert beta-myrcene to 10-hydroxylinalool in the presence of NADPH and oxygen. NADH neither supported this reaction nor did it show any synergistic effect. The rate of conversion was significantly greater in microsomes prepared from phenobarbital-treated rats than from 3-methylcholanthrene-treated or control microsomal preparations. The formation of 10-hydroxylinalool was inhibited by metyrapone, carbon monoxide, SKF-525A, p-chloromercuric benzoate (p-CMB) and cytochrome c. ... Biological Half-Life ... After oral administration of 1.0 g/kg bw (7300 umol/kg bw) beta-myrcene to female rats, the elimination half-life of beta-myrcene at this concentration was 285 min. ... |
| References |
[1]. Myrcene, an Aromatic Volatile Compound, Ameliorates Human Skin Extrinsic Aging via Regulation of MMPs Production. Am J Chin Med. 2017;45(5):1113-1124. [2]. Anti-invasive effect of β-myrcene, a component of the essential oil from Pinus koraiensis cones, in metastatic MDA-MB-231 human breast cancer cells. Journal of the Korean Society for Applied Biological Chemistry volume 58, pages563–569. |
| Additional Infomation |
beta-Myrcene can cause cancer according to The National Toxicology Program. Myrcene, [liquid] appears as a yellow oily liquid with a pleasant odor. Flash point below 200 °F. Insoluble in water and less dense than water. Beta-myrcene is a monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, an anabolic agent, a fragrance, a flavouring agent and a volatile oil component. Myrcene has been reported in Camellia sinensis, Artemisia thuscula, and other organisms with data available. 7-Methyl-3-methylene-1,6-octadiene is found in allspice. 7-Methyl-3-methylene-1,6-octadiene is found in many essential oils, e.g. hop oil. 7-Methyl-3-methylene-1,6-octadiene is a flavouring agent. Myrcene is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Mandarin oil (part of); Juniper Berry Oil (part of); Caraway Oil (part of) ... View More ... |
Solubility Data
| Solubility (In Vitro) |
Ethanol :≥ 100 mg/mL (~734.05 mM) DMSO : ~100 mg/mL (~734.05 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.35 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 (18.35 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (18.35 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 | 7.3405 mL | 36.7026 mL | 73.4053 mL | |
| 5 mM | 1.4681 mL | 7.3405 mL | 14.6811 mL | |
| 10 mM | 0.7341 mL | 3.6703 mL | 7.3405 mL |