(−)-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.

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)

Biological Activity

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].
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].
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	(-)-Myrtenal has been reported in Forsythia viridissima, Thymus camphoratus, and other organisms with data available.

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. 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.