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Curcumol

CAS No.
4871-97-0
Chemical Name:
Curcumol
Synonyms
Curcumo;CURCUMOL;Curcumae;(-)-Curcumol;Curcumol USP/EP/BP;5,8-Epoxy-10(14)-guaien-8-ol;(3S,3aS,5S,6R,8aS)-5-Isopropyl-3-methyl-8-methyleneoctahydro-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;6H-3a,6-Epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,3aS,5S,6R,8aS)-;(3s-(3a,3aa,5a,6a,8ab))-octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6h-3a,6-epoxyazulen-6-ol
CBNumber:
CB0701727
Molecular Formula:
C15H24O2
Molecular Weight:
236.35
MDL Number:
MFCD00272163
MOL File:
4871-97-0.mol
MSDS File:
SDS
Last updated:2024-07-24 16:40:20

Curcumol Properties

Melting point 141.0 to 145.0 °C
Boiling point 334.5±42.0 °C(Predicted)
Density 1.06±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility DMSO:55.67(Max Conc. mg/mL);235.54(Max Conc. mM)
DMF:20.0(Max Conc. mg/mL);84.62(Max Conc. mM)
Ethanol:28.5(Max Conc. mg/mL);120.58(Max Conc. mM)
pka 13.02±0.60(Predicted)
form Solid
color White to Light yellow
InChI InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14-,15+/m0/s1
InChIKey QRMPRVXWPCLVNI-YYFQZIEXSA-N
SMILES C1[C@]2([H])[C@@]3(O[C@](O)(CC2=C)[C@H](C(C)C)C3)[C@@H](C)C1
LogP 3.276 (est)
CAS DataBase Reference 4871-97-0
FDA UNII 9190RTN07X

SAFETY

Risk and Safety Statements

WGK Germany  3
HS Code  29321900

Curcumol price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 36236 ( ?)-Curcumol analytical standard 4871-97-0 10mg $269 2022-05-15 Buy
TCI Chemical C3439 Curcumol >98.0%(GC) 4871-97-0 10mg $133 2024-03-01 Buy
TCI Chemical C3439 Curcumol >98.0%(GC) 4871-97-0 50mg $401 2024-03-01 Buy
Cayman Chemical 26849 Curcumol 4871-97-0 50mg $596 2024-03-01 Buy
Cayman Chemical 26849 Curcumol 4871-97-0 100mg $954 2024-03-01 Buy
Product number Packaging Price Buy
36236 10mg $269 Buy
C3439 10mg $133 Buy
C3439 50mg $401 Buy
26849 50mg $596 Buy
26849 100mg $954 Buy

Curcumol Chemical Properties,Uses,Production

Background

Curcumol, a bioactive sesquiterpenoid, has been isolated from numerous plants of family Zingiberaceae. These plants are mostly found in Southeast Asia, China, Indonesia, India, Peru, and West Indies. Curcumol has been isolated from C. longa which is an imperative species of the genus Curcuma and is generally known as common turmeric. Curcumol was also extracted from the rhizome of C. aeruginosae that is effective for antiinflammatory and antioxidant activities. C. aromatic, a well-known natural source of curcumol, has been reported for its antitumor and antimicrobial activities. C. kwangsiensis and C. phaeocaulis are advantageous for their antiproliferative activities against various cancer types. Dried roots of C. zedoary enriched with curcumol are documented for their effective anticancer and antiinflammatory properties. Rhizome of various Curcuma species, a rich source of curcumol, serves as antimicrobial, antifibrotic, and anticancer agent. Besides them, curcumol has also been isolated from the roots of Astragali radix, C. rhizoma, and Fructus gardenia which are traditionally used as anticancer agents.
Curcumol
The above figure provides natural sources of curcumol including Astragali radix, C. aeruginosae, C. aromatica, C. kwangsiensis, C. longa, C. phaeocaulis, C. wenyujin, C. zedoary, Fructus gardenia, and C. trichosantha G[1].

Description

Curcumol, a bioactive sesquiterpenoid, has been isolated from various plants from Zingiberaceae. In recent years, curcumol attracts much attention due to its multiple biological activities and few negative effects. Accumulated studies prove that curcumol shows beneficial effects in protecting against inflammation, oxidative stress, cancer, neurodegeneration and microbial infection. Besides, a number of signaling pathways such as MAPK, PI3K/Akt and NF-κB are influenced by curcumol[2].

Uses

Curcumol is a potential treatment for advanced hepatocellular carcinoma (HCC). It can be used as a chemotherapeutic sensitiser in order to enhance the anti-tumour effect of chemotherapeutic drugs. Studies have shown that it promotes HCC cell apoptosis in vitro and inhibits HCC tumour growth in vivo. It combined with lenvatinib can induce more autolysosome formation, which can enhance the anti-tumour effect of lenvatinib on hepatocellular carcinoma cells.

Definition

ChEBI: Curcumol is a sesquiterpenoid.

Biological Activity

Curcumol is a biologically active sesquiterpene with many pharmacological activities such as anticancer, antimicrobial, antifungal, antiviral and anti-inflammatory. It efficiently induces apoptosis in many cancer cells by targeting key signaling pathways such as MAPK/ERK, PI3K/Akt and NF-κB, which are often dysregulated in several cancers.

Pharmacokinetics

Curcumol is rapidly absorbed and eliminated in rats following oral administration of 10, 40 and 80 mg/kg curcumol. Its oral and intravenous bioavailability ranges from 9.2% ~ 13.1%. Maximum concentration is reached within 0.5-1.0 hours. In addition, high protein binding of curcumin was observed in rat plasma, ranging from 85.6% to 93.4%.

in vitro

Curcumol ((-)-Curcumol) is the major component extracted from root of Rhizoma Curcumae . Curcumol exerts anticancer effect in cholangiocarcinoma cells via down-regulating CDKL3. It induces cell cycle arrest in colon cancer cells via reactive oxygen species and Akt/ GSK3β/cyclin D1 pathway. It suppresses breast cancer cell metastasis by inhibiting MMP-9 via JNK1/2 and Akt-dependent NF-κB signaling pathways.

References

[1] Wei Wei. “Curcumol: From Plant Roots to Cancer Roots.” International Journal of Biological Sciences 27 1 (2019): 1600–1609.
[2] Ying Liu. “Curcumol ameliorates neuroinflammation after cerebral ischemia-reperfusion injury via affecting microglial polarization and Treg/Th17 balance through Nrf2/HO-1 and NF-κB signaling.” Cell Death Discovery 10 1 (2024): 300.

Curcumol Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 245)Suppliers
Supplier Tel Email Country ProdList Advantage
DSHare Pharmaceutical Science Technology Co.Ltd.
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Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873 sales@chemdad.com China 39916 58

View Lastest Price from Curcumol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Curcumol pictures 2023-02-24 Curcumol
4871-97-0
US $0.00 / mg 5mg ≥98%(HPLC) 10 g Shanghai Standard Technology Co., Ltd.
Curcumol pictures 2023-02-13 Curcumol
4871-97-0
US $110.00 / kg 1kg 99% 100MT Hebei baicao biology science and technology co., ltd
Curcumol pictures 2019-07-06 Curcumol
4871-97-0
US $150.00 / KG 1KG 99% 1000kg Career Henan Chemical Co
  • Curcumol pictures
  • Curcumol
    4871-97-0
  • US $0.00 / mg
  • ≥98%(HPLC)
  • Shanghai Standard Technology Co., Ltd.
  • Curcumol pictures
  • Curcumol
    4871-97-0
  • US $110.00 / kg
  • 99%
  • Hebei baicao biology science and technology co., ltd
  • Curcumol pictures
  • Curcumol
    4871-97-0
  • US $150.00 / KG
  • 99%
  • Career Henan Chemical Co

Curcumol Spectrum

6H-3a,6-Epoxyazulen-6-ol, octahydro-3-methyl-8-methylene-5-(1-methylethyl)-, (3S,3aS,5S,6R,8aS)- (3S,3aS,5S,6R,8aS)-Octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6H-3a,6-epoxyazulen-6-ol CURCUMOL (3s-(3a,3aa,5a,6a,8ab))-octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6h-3a,6-epoxyazulen-6-ol 5,8-Epoxy-10(14)-guaien-8-ol (3S-(3alpha,3Aalpha,5alpha,6alpha,8abeta))-octahydro-3-methyl-8-methylene-5-(1-methylethyl)-6H-3A,6-epoxyazulen-6-ol Curcumae Curcumol USP/EP/BP Curcumo (-)-Curcumol (3S,3aS,5S,6R,8aS)-5-Isopropyl-3-methyl-8-methyleneoctahydro-6H-3a,6-epoxyazulen-6-ol 4871-97-0 chemical reagent Inhibitors pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract Miscellaneous Natural Products