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(−)-Myrtenal ((1R)-(-)-Myrtenal; (1R)-(−)-Myrtenal; (−)-(1R,5S)-Myrtenal)

(−)-Myrtenal ((1R)-(−)-Myrtenal) is an orally bioavailable terpene with anticancer effect.
(−)-Myrtenal ((1R)-(-)-Myrtenal; (1R)-(−)-Myrtenal; (−)-(1R,5S)-Myrtenal)
(−)-Myrtenal ((1R)-(-)-Myrtenal; (1R)-(−)-Myrtenal; (−)-(1R,5S)-Myrtenal) Chemical Structure CAS No.: 18486-69-6
Product category: Akt
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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Other Forms of (−)-Myrtenal ((1R)-(-)-Myrtenal; (1R)-(−)-Myrtenal; (−)-(1R,5S)-Myrtenal):

  • Myrtenal
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
(−)-Myrtenal ((1R)-(−)-Myrtenal) is an orally bioavailable terpene with anticancer effect. (−)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in skeletal muscle and liver of diabetic rats.
(−)-Myrtenal ((1R)-(−)-Myrtenal) is an orally active terpene with antitumor activity. The compound ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats. With a molecular weight of 150.22 and the formula C10H14O, this natural monoterpene is a valuable research tool for studying metabolic disorders and cancer. (−)-Myrtenal is for research use only and not for human therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
(−)-Myrtenal targets the Akt signaling pathway and GLUT2 glucose transporter. By enhancing GLUT2 through Akt activation, the compound improves glucose uptake in skeletal muscle and liver. This mechanism underlies its hypoglycemic effects in diabetic models. The compound also exhibits antitumor activity, indicating effects on cancer cell proliferation and survival. As an orally active terpene, it is bioavailable for in vivo studies. The compound's mechanism involves modulation of insulin signaling and glucose metabolism.
ln Vitro
(−)-Myrtenal ((1R)-(−)-Myrtenal; 24 hours; 0.1–5 mM has a potent cytotoxic impact (IC50 = 5.3 mM) on human normal colon epithelial cells (CCD 841 CoTr) and human colon carcinoma (HT29)[1].
In vitro studies of (−)-Myrtenal have demonstrated its effects on glucose metabolism and cancer cell lines. The compound enhances GLUT2 expression and activity through Akt activation. As a terpene with antitumor activity, it has been studied for its effects on cancer cell proliferation and survival. The compound's ability to modulate glucose metabolism makes it a valuable research tool for studying metabolic disorders. Detailed in vitro characterization data are available in the primary literature.
ln Vivo
(−)-Myrtenal ((1R)-(−)-Myrtenal; oral; 80 mg/kg/day for 28 days) in diabetic rats induced by a single intraperitoneal injection of Streptozotocin (STZ) (40 mg/kg bw) reveals decreased plasma glucose levels, improved plasma insulin levels, and up-regulation of IRS2, Akt, and GLUT2 in liver and IRS2, Akt, and GLUT4 protein expression in skeletal muscle[2].
In vivo studies demonstrate that (−)-Myrtenal ameliorates hyperglycemia in diabetic rats. Diabetic rats were administered myrtenal at 80 mg/kg body weight for a period of 28 days. The compound enhances GLUT2 through Akt in the skeletal muscle and liver. This leads to improved glucose uptake and reduced blood glucose levels. As an orally active terpene with antitumor activity, it has also been studied for its anticancer effects in preclinical models. The compound's oral bioavailability supports its use in in vivo studies.
Enzyme Assay
For glucose metabolism studies, diabetic rat models are used to assess the hypoglycemic effects of (−)-Myrtenal. Rats are administered the compound orally at 80 mg/kg body weight for 28 days. Blood glucose levels are measured at regular intervals. GLUT2 expression in skeletal muscle and liver is assessed by Western blot or immunohistochemistry. Akt phosphorylation is measured to assess signaling pathway activation. For antitumor studies, cancer cell lines are treated with compound and cell proliferation, apoptosis, and migration are assessed. Assays are performed in replicate with vehicle controls.
Cell Assay
For in vitro cellular assays, cancer cell lines or hepatocytes are cultured in appropriate media under standard conditions (37°C, 5% CO2). (−)-Myrtenal is dissolved in DMSO and diluted in culture medium to desired concentrations. Cells are treated with compound for specified durations. Cell proliferation is assessed using MTT or similar assays. Apoptosis is assessed using flow cytometry or caspase activity assays. Glucose uptake is measured using fluorescent glucose analogs. GLUT2 expression and Akt phosphorylation are assessed by Western blot. Each concentration is tested in replicate wells with vehicle controls.
Animal Protocol
For in vivo animal studies, (−)-Myrtenal is typically administered orally (by gavage) due to its oral activity. In diabetic rat models, animals are made diabetic using streptozotocin (STZ) or other methods. Rats are administered myrtenal at 80 mg/kg body weight for 28 days. Blood glucose levels are monitored regularly. At study termination, skeletal muscle and liver tissues are collected for analysis of GLUT2 expression and Akt phosphorylation by Western blot or immunohistochemistry. Body weight and clinical signs are monitored throughout. All procedures follow institutional animal care and use committee guidelines.
ADME/Pharmacokinetics
Pharmacokinetic properties of (−)-Myrtenal indicate it is orally active. The compound has a molecular weight of 150.22 and formula C10H14O. It is a natural monoterpene with CAS number 18486-69-6. Storage: typically at -20°C for long-term storage; at room temperature for short-term. Solubility: soluble in organic solvents such as ethanol, DMSO, and oils. The compound is an orally active terpene with antitumor activity. Specific pharmacokinetic parameters such as half-life, clearance, and bioavailability are reported in the primary literature.
Toxicity/Toxicokinetics
According to available safety information, (−)-Myrtenal is intended for research use only and not for human therapeutic applications. Standard laboratory safety precautions should be followed when handling this compound, including the use of appropriate personal protective equipment (gloves, lab coat, safety goggles). The compound should be handled in a well-ventilated area. Avoid dust formation and inhalation. In case of skin contact, wash with plenty of soap and water. In case of eye contact, rinse cautiously with water for several minutes. No clinical toxicity data are available.
References

[1]. Biological activity of oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour and Fragrance Journal, Volume33, Issue6, November 2018.

[2]. Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats. Chem Biol Interact. 2016 Aug 25;256:161-6.

Additional Infomation
According to reports, (-)-myrtomaldehyde has been found in Forsythia suspensa, camphor thyme, and other organisms with available data.
(−)-Myrtenal ((1R)-(−)-Myrtenal) is an orally active terpene with antitumor activity. It ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats. Diabetic rats were administered the compound at 80 mg/kg for 28 days. The compound has a molecular weight of 150.22 and formula C10H14O. It is for research use only with no clinical development or regulatory approvals reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H14O
Molecular Weight
150.22
Exact Mass
150.104
CAS #
18486-69-6
Related CAS #
Myrtenal;564-94-3
PubChem CID
1201529
Appearance
Colorless to light yellow liquid
Density
0.988 g/mL at 20ºC(lit.)
Boiling Point
220-221ºC(lit.)
Flash Point
174 °F
Index of Refraction
n20/D 1.504
LogP
2.177
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Heavy Atom Count
11
Complexity
225
Defined Atom Stereocenter Count
2
SMILES
O=C([H])C1=C([H])C([H])([H])[C@@]2([H])C([H])([H])[C@@]1([H])C2(C([H])([H])[H])C([H])([H])[H]
InChi Key
KMRMUZKLFIEVAO-IUCAKERBSA-N
InChi Code
InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3/t8-,9-/m0/s1
Chemical Name
(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde
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)
DMSO: 100 mg/mL (665.69 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.64 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 (16.64 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 (16.64 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 6.6569 mL 33.2845 mL 66.5690 mL
5 mM 1.3314 mL 6.6569 mL 13.3138 mL
10 mM 0.6657 mL 3.3285 mL 6.6569 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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.
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