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Curcumol

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-C2006

  • Specification : 98%

  • CAS number : 4871-97-0

  • Formula : C15H24O2

  • Molecular Weight : 236.35

  • PUBCHEM ID : 14240392

  • Volume : 20mg

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Catalogue Number

BF-C2006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

236.35

Appearance

White crystalline powder

Botanical Source

Curcuma phaeocaulis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CCC2C13CC(C(O3)(CC2=C)O)C(C)C

Synonyms

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

IUPAC Name

(1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-propan-2-yl-11-oxatricyclo[6.2.1.01,5]undecan-8-ol

Density

1.1±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

134.7±22.1 °C

Boiling Point

334.5±42.0 °C at 760 mmHg

Melting Point

141-142ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:4871-97-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31400785

Abstract

Phytophthora capsici is a plant oomycete pathogen, which causes many devastating diseases on a broad range of hosts. Zedoary turmeric oil (ZTO) is a kind of natural plant essential oil that has been widely used in pharmaceutical applications. However, the antifungal activity of ZTO against phytopathogens remains unknown. In this study, we found ZTO could inhibit P. capsici growth and development in vitro and in detached cucumber and Nicotiana benthamiana leaves. Besides, ZTO treatment resulted in severe damage to the cell membrane of P. capsici, leading to the leakage of intracellular contents. ZTO also induced a significant increase in relative conductivity, malondialdehyde concentration and glycerol content. Furthermore, we identified 50 volatile organic compounds from ZTO, and uncovered Curcumol, β-elemene, curdione and curcumenol with strong inhibitory activities against mycelial growth of P. capsici. Overall, our results not only shed new light on the antifungal mechanism of ZTO, but also imply a promising alternative for the control of phytophthora blight caused by P. capsici.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Antifungal activity; Cell membrane injury; Essential oil; Phytophthora capsici; Zedoary turmeric oil

Title

Antifungal activity of zedoary turmeric oil against Phytophthora capsici through damaging cell membrane.

Author

Wang B1, Liu F1, Li Q2, Xu S1, Zhao X1, Xue P1, Feng X3.

Publish date

2019 Sep

PMID

30811964

Abstract

AIMS:
The purpose of this study was to demonstrate how curcumol affected the expression of miR-21 and whether its effects on miR-21 was associated with the activation of PTEN/PI3K/Akt pathways in CRC cells.

MAIN METHODS:
MTT and xenograft assay were used to examine how curcumol inhibits colorectal cancer (CRC) cells’ growth. Q-PCR and western blot analysis were employed to test the role of miR-21 in the inhibition of curcumol on proliferation and PTEN/PI3K/Akt pathways of CRC cells.

KEY FINDINGS:
We found that curcumol effectively inhibited CRC cells from proliferating via the PTEN/PI3K/Akt pathways and reduced expression of miR-21 both in vitro and in vivo. miR-21 mimics were found to decrease the protein level of PTEN and increase the expression of PI3K, phospho-Akt (p-Akt) and NF-κB, while miR-21 sponge (miR-21-SP) enhanced the expression of PTEN and reduced the activity of PI3K, Akt and NF-κB. Furthermore, miR-21-SP strengthened the role of curcumol in up-regulating PTEN and inhibiting PI3K/Akt pathways, but miR-21 reversed the effect of curcumol on the PTEN/PI3K/Akt pathways.

SIGNIFICANCE:
Our research demonstrated that curcumol reduced the proliferation of CRC cells through PTEN/PI3K/Akt by targeting miR-21 and miR-21 could be a target molecule of curcumol for CRC treatment.

Copyright © 2019. Published by Elsevier Inc.

KEYWORDS

Colorectal cancer; Curcumol; PTEN/PI3K/Akt; Proliferation; miR-21

Title

Curcumol inhibits colorectal cancer proliferation by targeting miR-21 and modulated PTEN/PI3K/Akt pathways.

Author

Liu H1, Wang J2, Tao Y3, Li X1, Qin J1, Bai Z4, Chi B5, Yan W6, Chen X7.

Publish date

2019 Mar 15

PMID

30658235

Abstract

In this paper, the mechanism of orobanone analogues formation via aromatization rearrangement of curcumol was minutely explored. Aromatization of curcumol with acetone under acidic condition was selected as the model reaction. The formation of a stable aromatic system was the driving force for this reaction. Based on the model reaction, other four new orobanone analogues were prepared through curcumol reacting with different carbonyl compounds. The results showed that the stability of carbocation, which was generated from the carbonyl compounds, and the steric hindrance were main factors affecting the aromatization. We also synthesized the analogue of aromaticane B using compound 2. In vitro anti-proliferative activity of some derivatives were tested by MTT assay. Two derivatives showed weak anti-tumor effect on two cancer cell lines (HepG2 and MCF7) under normoxia. Four orobanone analogue 2, 5, 6 and 9 significantly inhibited hypoxia-induced HIF-1 luciferase reporter activity in HeLa cells with the IC50 values of 13.6, 6.6, 2.4 and 18.2 μM, respectively.

Copyright © 2019 Elsevier Inc. All rights reserved.

KEYWORDS

Acid catalysis; Aromatization; Curcumol; HIF-1 transcription; Orobanone

Title

Orobanone analogues from acid-promoted aromatization rearrangement of curcumol inhibit hypoxia-inducible factor-1 (HIF-1) in cell-based reporter assays.

Author

Li YQ1, Li GZ2, Dong Y1, Ma X1, Dong HJ1, Wu QQ1, Zhao WJ3.

Publish date

2019 Apr


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].