Isoprocurcumenol

Modify Date: 2024-01-16 15:42:56

Isoprocurcumenol Structure
Isoprocurcumenol structure
Common Name Isoprocurcumenol
CAS Number 102130-90-5 Molecular Weight 234.334
Density 1.1±0.1 g/cm3 Boiling Point 360.3±41.0 °C at 760 mmHg
Molecular Formula C15H22O2 Melting Point 99.5-100.5 ºC (hexane )
MSDS N/A Flash Point 153.7±20.2 °C

 Use of Isoprocurcumenol


Isoprocurcumenol is a guaiane type sesquiterpene, that can be isolated from Curcuma comosa. Isoprocurcumenol can activate EGFR signaling. Isoprocurcumenol increases the phosphorylation of ERK and Akt. Isoprocurcumenol promotes the proliferation of keratinocytes[1][2][3].

 Names

Name iso-Procurcumenol
Synonym More Synonyms

 Isoprocurcumenol Biological Activity

Description Isoprocurcumenol is a guaiane type sesquiterpene, that can be isolated from Curcuma comosa. Isoprocurcumenol can activate EGFR signaling. Isoprocurcumenol increases the phosphorylation of ERK and Akt. Isoprocurcumenol promotes the proliferation of keratinocytes[1][2][3].
Related Catalog
Target

ERK

Akt

In Vitro Isoprocurcumenol (10 μM, 0-1 h) 可促进 ERK 和 AKT 的磷酸化[3]。 Isoprocurcumenol (0-200 μM, 24 or 48 h) 诱导角质形成细胞 HaCaT 细胞增殖[3]。 Isoprocurcumenol (1 μM, 1 h) 通过激活 EGFR 信号通路增加细胞生长和增殖相关基因的表达,例如 c-fos、c-jun、c-myc 和 egr-1[ 3]。 Isoprocurcumenol 诱导细胞恢复和伤口愈合[3]。 Western Blot Analysis[3] Cell Line: HaCaT cells (human keratinocyte cell) Concentration: 10 μM Incubation Time: 10, 30, or 60 min Result: Induced the phosphorylation of ERK and AKT after 10 min and this was sustained for 1 h. Cell Proliferation Assay[3] Cell Line: HaCaT cells (human keratinocyte cell) Concentration: 0 nM, 1 nM, 10 nM, 100 nM, 1 μM, 10 μM, 25 μM, 50 μM, 100 μM, or 200 μM Incubation Time: 24 or 48 h Result: Showed a significant increase in the proliferation of cells at most of the Isoprocurcumenol concentrations, starting at 10 nM. RT-PCR[3] Cell Line: HaCaT cells (human keratinocyte cell) Concentration: 1 μM Incubation Time: 1 h Result: Increased the expression of genes related to cell growth and proliferation, such as c-myc, c-jun, c-fos, and egr-1.
References

[1]. Qu Y, et al. Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4.  

[2]. Anuchapreeda S, et al. Cytotoxicity and inhibition of leukemic cell proliferation by sesquiterpenes from rhizomes of Mah-Lueang (Curcuma cf. viridiflora Roxb.). Bioorg Med Chem Lett. 2018 Feb 1;28(3):410-414.  

[3]. Kwon PK, et al. Isoprocurcumenol Supports Keratinocyte Growth and Survival through Epidermal Growth Factor Receptor Activation. Int J Mol Sci. 2021 Nov 22;22(22):12579.  

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 360.3±41.0 °C at 760 mmHg
Melting Point 99.5-100.5 ºC (hexane )
Molecular Formula C15H22O2
Molecular Weight 234.334
Flash Point 153.7±20.2 °C
Exact Mass 234.161987
LogP 2.59
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.523
Water Solubility Very slightly soluble (0.82 g/L) (25 ºC)

 Synonyms

(1S,3aR,8aS)-1-Hydroxy-7-isopropylidene-1-methyl-4-methyleneoctahydro-6(1H)-azulenone
iso-Procurcumenol
6(1H)-Azulenone, octahydro-1-hydroxy-1-methyl-4-methylene-7-(1-methylethylidene)-, (1S,3aR,8aS)-
Isoprocurcumenol
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