Isolongifolene

Names

[ Name ]:
Isolongifolene

[Synonym ]:
2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-
2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S,4aR)-
(1R)-2,2,7,7-Tetramethyltricyclo[6.2.1.01.6]undec-5-ene
EINECS 214-494-2
(1R,8S)-2,2,7,7-Tetramethyltricyclo[6.2.1.0]undec-5-ene
2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S,4aR)-(-)-
2,2,7,7-Tetramethyltricyclo[6.2.1.0]undec-5-ene
trans-Isolongifolene
1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyI-2H-2,4a-methanonaphthalene
MFCD00042616
UNII:PX6N25M90H
iso-Longifolene

Biological Activity

[Description]:

Isolongifolene ((-)-Isolongifolene) is a tricyclic sesquiterpene isolated from Murraya koenigii. Isolongifolene attenuates Rotenone-induced oxidative stress, mitochondrial dysfunction and apoptosis through the regulation of P13K/AKT/GSK-3β signaling pathways. Isolongifolene has antioxidant, anti-inflammatory, anticancer and neuroprotective properties[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[In Vitro]

Isolongifolene (0-50 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment significantly alleviates Rotenone-induced cytotoxicity in SH-SY5Y cells in a dose-dependent manner[1]. Isolongifolene (10 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment attenuates Rotenone-induced apoptosis in SH-SY5Y cells[1]. Isolongifolene (10 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment attenuates Rotenone induced toxicity by down-regulating Bax, caspases-3, 6, 8 and 9 expression and up-regulating of Bcl-2 expression. Furthermore regulation of p-P13K, p-AKT and p-GSK-3β expression by Isolongifolene[1]. Cell Viability Assay[1] Cell Line: SH-SY5Y neuroblastoma cells Concentration: 0 μM, 1 μM, 2.5 μM, 5 μM, 10 μM, 20 μM and 50 µM Incubation Time: 26 hours Result: Significantly alleviated Rotenone-induced cytotoxicity in SH-SY5Y cells. Apoptosis Analysis[1] Cell Line: SH-SY5Y neuroblastoma cells Concentration: 10 µM Incubation Time: 26 hours Result: Attenuated Rotenone-induced apoptosis in SH-SY5Y cells. Western Blot Analysis[1] Cell Line: SH-SY5Y neuroblastoma cells Concentration: 10 µM Incubation Time: 26 hours Result: Attenuated rotenone induced toxicity by down-regulating Bax, caspases-3, 6, 8 and 9 expression and up-regulating of Bcl-2 expression. Prevented the rotenone-induced decreased phosphorylation of GSK-3β.

[References]

[1]. Balakrishnan R, et al. Isolongifolene attenuates rotenone-induced mitochondrial dysfunction, oxidative stress and apoptosis. Front Biosci (Schol Ed). 2018 Jan 1;10:248-261.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
266.5±7.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₄

[ Molecular Weight ]:
204.351

[ Flash Point ]:
102.6±13.0 °C

[ Exact Mass ]:
204.187805

[ LogP ]:
6.36

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.518

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
F+

[ Risk Phrases ]:
R10

[ RIDADR ]:
UN 2319 3/PG 3

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
3.2

[ HS Code ]:
2902199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2902199090

[ Summary ]:
2902199090 other cyclanes, cyclenes and cyclotherpenes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%

Related Compounds

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