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Myrcene

Cat No.:V10478 Purity: ≥90%
Myrcene(β-Myrcene) is a naturally occurring monoterpene withanti-invasiveeffects.
Myrcene
Myrcene Chemical Structure CAS No.: 123-35-3
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
10g
25g
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Product Description

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.

Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
In a pharmacokinetic study, after oral administration of 1.0 g/kg body weight (7300 μmol/kg body weight) of β-myrcene to female rats 60 minutes later, a blood concentration of β-myrcene was detected as high as 14.1 +/- 3.0 ug/mL (peak). This compound was primarily enriched in adipose tissue and multiple organs, including the brain, liver, kidney, and testes. Metabolisms/Metabolites Metabolites isolated from the urine of rats following oral administration of β-myrcene included: 10-hydroxylinalool, 7-methyl-3-methylene-oct-6-en-1,2-diol, 1-hydroxymethyl-4-isopropenylcyclohexanol, 10-carboxylinalool, and 2-hydroxy-7-methyl-3-methylene-oct-6-enoic acid. Phenobarbital-treated rat liver microsomes can convert β-myrcene to 10-hydroxylinalool in the presence of NADPH and oxygen. NADH neither participates in this reaction nor shows any synergistic effect. The conversion rate in rat microsomes treated with phenobarbital was significantly higher than that in the 3-methylcholanthrene-treated or control groups. The formation of 10-hydroxylinalool could be inhibited by metheprone, carbon monoxide, SKF-525A, p-chloromercuric benzoate (p-CMB), and cytochrome c. …
Biological half-life
… After oral administration of 1.0 g/kg body weight (7300 μmol/kg body weight) of β-myrcene to female rats, the elimination half-life of β-myrcene at this concentration was 285 minutes. …
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
According to the National Toxicology Program (NTP) in the United States, β-myrcene may be carcinogenic. Myrcene (liquid) is a yellow, oily liquid with a pleasant odor. Its flash point is below 200°F (93°C). It is insoluble in water and has a density less than water. β-Myrcene is a monoterpene, octyl-1,6-diene, with methylene and methyl substituents at positions 3 and 7, respectively. It is a plant metabolite with anti-inflammatory, anabolic, spice, flavoring, and volatile oil components. Myrcene has been reported in tea trees (Camellia sinensis), artemisia (Artemisia thanscula), and several other organisms with relevant data. 7-Methyl-3-methylene-1,6-octadiene is found in allspice. 7-Methyl-3-methylene-1,6-octadiene is also found in many essential oils, such as hop oil. 7-Methyl-3-methylene-1,6-octadiene is a flavoring agent. Myrcene is a metabolite found or produced in Saccharomyces cerevisiae. See also: Citrus oil (one of the ingredients); Juniper berry oil (one of the ingredients); Caraway oil (one of the ingredients)... See more...
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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.

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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

*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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  • 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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  • 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
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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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05432284 Not yet recruiting Drug: THC
Drug: Beta-Myrcene
Cannabis Use Johns Hopkins University May 2024 Phase 1
NCT04451863 Recruiting Drug: High THC
Drug: Low Myrcene
Pain
Abuse, Drug
University of California, Los Angeles December 15, 2021 Phase 1
NCT04290312 Completed Other: Mastiha oil Absorption Harokopio University February 1, 2018 Not Applicable
NCT05316597 Recruiting Behavioral: Forest bathing Monoterpene Exposure During
a Forest Bathing Intervention
University of Washington July 12, 2022 Not Applicable
Biological Data
  • A comparison of the chromatogram of the essential oil (red) obtained at 254 nm (A), 230 nm (B, C), and 210 nm (D) with an authentic sample (blue); α-pinene (A), β-myrcene (B), d-limonene (C), and 3-carene (D). The inset figures show the ultraviolet spectra of the peak observed in the chromatogram of the EOPC (red) and the authentic sample (blue). x-axis, retention time (min); y-axis, UV absorbance
  • Effect of major EOPC constituents on MMP-9 promoter activity. A MMP-9 promoter activity assay. MDA-MB-231 cells were transiently transfected with pMMP9(−925/+13)_Luc. At 48 h post-transfection, the cells were either left untreated or treated with 10 ng/mL TNFα in the absence or presence of EOPC components (100 μM). B Cytotoxicity assay. MDA-MB-231 cells were treated with TNFα or EOPC components as in (A) for 24 h. The data shown represent the mean ± SD of three independent experiments performed in triplicate. **p < 0.01
  • Effect of β-myrcene on the inhibition of TNFα-induced NF-κB activity. A Immunoblot analysis. B NF-κB-dependent transcriptional activity assay. The data shown represent the mean ± SD of three independent experiments performed in triplicate. **p < 0.01 versus TNFα-only treatment (n = 9). C Immunofluorescence microscopic analysis using Alexa Fluor 488-conjugated (green signal) or Alexa Fluor 555-conjugated (red signal) secondary antibody. Nuclear DNA was stained with 1 μg/mL Hoechst 33,258 (blue signal)
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