(−)-Myrtenal

Names

[ Name ]:
(−)-Myrtenal

[Synonym ]:
(1R,5S)-6,6-dimethyl-bicyclo[3.3.1]hept-2-en-2-carbaldehyde
FEMA 3395
l-Myrtenal
(R)-6,6-dimethylbicyclo[3.3.1]hept-2-en-2-carboxaldehyde
(-)-(1R,5S)-Myrtenal
(-)-Myrtenal
(1R)-6,6-DIMETHYLBICYCLO[3.1.1]HEPT-2-EN-2-CARBOXAL-DEHYDE
(-)-1R-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxaldehyde
(1R)-2-PINEN-10-AL
MYRTENAL,-(-)-(SG)
(R)-mirtenal
MYRTENAL,-(-)

Biological Activity

[Description]:

(−)-Myrtenal ((1R)-(−)-Myrtenal) is an orally active terpene with antitumour activity. (−)-Myrtenal ameliorates hyperglycemia by enhancing GLUT2 through Akt in the skeletal muscle and liver of diabetic rats[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

(−)-Myrtenal ((1R)-(−)-Myrtenal; 0.1-5 mM; for 24 h) exerts strong cytotoxic effect (IC50 = 5.3 mM) on human colon tumour (HT29) and human normal colon epithelial cells (CCD 841 CoTr)[1].

[In Vivo]

(−)-Myrtenal ((1R)-(−)-Myrtenal; orally; 80 mg/kg/day for 28 days) reveals decreased the levels of plasma glucose, improved the plasma insulin levels, up-regulation of IRS2, Akt and GLUT2 in liver and IRS2, Akt and GLUT4 protein expression in skeletal muscle in diabetic rats induced by single intraperitoneal injection of Streptozotocin (STZ) (40 mg/kg bw)[2].

[References]

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

[2]. Ayyasamy Rathinam, et al. 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.

Chemical & Physical Properties

[ Density]:
0.988 g/mL at 20ºC(lit.)

[ Boiling Point ]:
220-221ºC(lit.)

[ Molecular Formula ]:
C₁₀H₁₄O

[ Molecular Weight ]:
150.22

[ Flash Point ]:
174 °F

[ Exact Mass ]:
150.10400

[ PSA ]:
17.07000

[ LogP ]:
2.17770

[ Appearance of Characters ]:
Liquid | Clear colorless to yellow

[ Index of Refraction ]:
n20/D 1.504

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Safety Phrases ]:
23-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DT5180000

Articles

Synthesis of stable thromboxane A2 analogs: pinane thromboxane A2 (PTA2) and carbocyclic thromboxane A2 (CTA2).

Meth. Enzymol. 86 , 400, (1982)

Organoleptic Characteristics of Flavor Materials Mosciano, G.

Perfum. Flavor. 8th ed., 30 , 41, (2005)

Mosciano, G.

Perfum. Flavor. 7th ed., 30 , 56, (2005)

Related Compounds

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