Curcumol

Names

[ Name ]:
Curcumol

[Synonym ]:
6H-3a,6-Epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,3aS,5S,8aS)-
(3S,3aS,5S,8aS)-3-methyl-8-methylidene-5-(propan-2-yl)octahydro-6H-3a,6-epoxyazulen-6-ol
(3S,3aS,5S,6R,8aS)-Octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6H-3a,6-epoxyazulen-6-ol
(1S,2S,5S,9S)-9-Isopropyl-2-methyl-6-methylene-11-oxatricyclo[6.2.1.0]undecan-8-ol

Biological Activity

[Description]:

Curcumol is a sesquiterpene originally isolated from curcuma rhizomes; shows anticancer activities both in vitro and in vivo.IC50 value:Target: Anticancer natural compoundin vitro: Curcumol exhibited time- and concentration-dependent anti-proliferative effects in SPC-A-1 human lung adenocarcinoma cells with cell cycle arrest in the G0/G1 phase while apoptosis-induction was also confirmed with flow cytometry and morphological analyses [1]. Curcumol-induced growth inhibition correlated with apoptosis induction as evidenced by Annexin V staining, and cleavage of caspase-3 and poly (ADP-ribose) polymerase (PARP) in HSC-T6. Suppression of the NF-κB translocation via inhibition of IκB-α phosphorylation by the curcumol led to the inhibition of expression of NF-κB-regulated gene, e.g. Bcl-xL and Bcl-2, in a PI3K-dependent manner, which is upstream of NF-κB activation [2]. Curcumol exhibits an inhibitory effect on receptor activator of nuclear factor kappaB ligand (RANKL)-induced osteoclast differentiation with both bone marrow-derived macrophages and RAW264.7 cells in a dose-dependent manner [3].in vivo: Anti-neoplastic effects of curcumol were also confirmed in tumor bearing mice. Curcumol (60 mg/kg daily) significantly reduced tumor size without causing notable toxicity [1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Tang QL, et al. Curcumol induces apoptosis in SPC-A-1 human lung adenocarcinoma cells and displays anti-neoplastic effects in tumor bearing mice. Asian Pac J Cancer Prev. 2015;16(6):2307-12.

[2]. Chen G, et al. Curcumol induces HSC-T6 cell death through suppression of Bcl-2: involvement of PI3K and NF-κB pathways. Eur J Pharm Sci. 2014 Dec 18;65:21-8.

[3]. Yu M, et al. Curcumol suppresses RANKL-induced osteoclast formation by attenuating the JNK signaling pathway. Biochem Biophys Res Commun. 2014 May 2;447(2):364-70.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
334.5±42.0 °C at 760 mmHg

[ Melting Point ]:
141-142ºC

[ Molecular Formula ]:
C₁₅H₂₄O₂

[ Molecular Weight ]:
236.350

[ Flash Point ]:
134.7±22.1 °C

[ Exact Mass ]:
236.177628

[ PSA ]:
29.46000

[ LogP ]:
3.25

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.526

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
29321900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Isolation and identification of phase 1 metabolites of curcumol in rats.

Drug Metab. Dispos. 38(11) , 2014-22, (2010)

Curcumol is one of the major components of the essential oil of Curcuma wenyujin with the structure of a guaiane-type sesquiterpenoid hemiketal. It exhibits clear antitumor, antihepatic fibrosis, anti...

Subunit-specific inhibition of glycine receptors by curcumol.

J. Pharmacol. Exp. Ther. 343(2) , 371-9, (2012)

Emerging evidence has suggested that inhibitory glycine receptors (GlyRs) are an important molecular target in the treatment of numerous neurological disorders. Rhizoma curcumae is a medicinal plant w...

Chemical constituents from the radix of Curcuma wenyujin.

Fitoterapia 80(6) , 374-6, (2009)

Phytochemical study on the ethanol extract of the radixes of Curcuma wenyujin Y. H. Chen et C. Ling led to the isolation of three new compounds curcuminol F (1) curcuminol G (2) and wenyujinoside (3) ...