C1386

Sigma-Aldrich

Curcumin

from Curcuma longa (Turmeric), powder

Synonym(s):
Diferulylmethane, (E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Diferuloylmethane, Natural Yellow 3
Linear Formula:
[HOC6H3(OCH3)CH=CHCO]2CH2
CAS Number:
Molecular Weight:
368.38
Colour Index Number:
75300
Beilstein/REAXYS Number:
2306965
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

Curcuma longa (Turmeric)

vapor density

13 (vs air)

assay

≥65% (HPLC)

form

powder

mp

175  °C

solubility

ethanol: 10 mg/mL
DMSO: >11 mg/mL (lit.)(lit.)
0.5 M NaOH: soluble (then immediately dilute in PBS [lit.])(lit.)

storage temp.

−20°C

SMILES string

COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)c(OC)c2)ccc1O

InChI

1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+

InChI key

VFLDPWHFBUODDF-FCXRPNKRSA-N

Gene Information

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General description

Curcumin is a yellow-colored polyphenol obtained from the rhizome of Curcuma longa L. It constitutes an important part of various diets and herbal medicines, especially in the Asian continent for its various salubrious effects on human health.

Application

Curcumin has been used:
  • to study its effect on the consequences and mechanism involved in the suppression of human homeobox gene NKX3.1 in the prostate cancer cell LNCaP
  • to examine its effect on stress in pigs by having an inhibitory impact on the serum cortisol concentration, hippocampal nitric oxide production, and brain-derived neurotrophic factor expression
  • to study its effect as a dietary supplement on the growth, immunity, antioxidant activity, and disease resistance in Oreochromis niloticus
  • to analyze its protective effect on the organotypic hippocampal slice cultures against the synaptic toxicity caused by amyloid beta peptides (Aβ1–42)
  • to examine the possibility of its non-toxic concentrations to decrease the inflammation caused by interleukin-1beta (IL-1β) in cartilage explant cultures
  • to study its protective impact against intestinal ischemia-reperfusion injury in rats
  • to measure its antibacterial activity in vitro
  • to determine its preventative effects for Alzheimer′s disease (AD) in mice
  • as a bifunctional agent for generation and validation of the erythroid 2-related factor 2 (Nrf2) reporter system
  • to study its in vitro inhibitory effects on human liver glucuronidation activity
  • to evaluate its effects on Parkinson′s disease (PD)-like phenotypes

Packaging

5, 10, 50 g in glass bottle

Biochem/physiol Actions

A natural phenolic compound. Potent anti-tumor agent having anti-inflammatory and anti-oxidant properties. Curcumin has been cited as a potential chemopreventive agent, in addition to its chemotherapeutic activity. Induces apoptosis in cancer cells and inhibits phorbol ester-induced protein kinase C (PKC) activity. Reported to inhibit production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Potent inhibitor of EGFR tyrosine kinase and IκB kinase. Inhibits inducible nitric oxide synthase (iNOS), cycloxygenase and lipoxygenase. Easily penetrates into the cytoplasm of cells, accumulating in membranous structures such as plasma membrane, endoplasmic reticulum and nuclear envelope.
Curcumin possesses anti-inflammatory, cancer prophylactic, and anti-oxidant properties. It also exhibits antagonistic nature towards the cluster of colon, breast, and blood marrow cancer. It does so by means of having an inhibitory effect on the various associated enzymes such as cycloxygenase-2 (COX-2), lipoxygenase and ornithine decarboxylase. It is also postulated to have anti-depressant, anti-stress and neuroprotective effects on humans and other animals. It is being proclaimed to be used as a treatment for Alzheimer′s disease due to its ability to cause synaptic toxicity. Additionally, it also shows anti-fungal, antiviral, anti-microbial, chemosensitizing, radiosensitizing, and wound healing activities.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

In vivo imaging of early signs of dopaminergic neuronal death in an animal model of Parkinson's disease
Rizzi N, et al.
Neurobiology of Disease, 114, 74-84 (2018)
Assessment of diets containing curcumin, epigallocatechin-3-gallate, docosahexaenoic acid and alpha-lipoic acid on amyloid load and inflammation in a male transgenic mouse model of Alzheimer's disease: Are combinations more effective?
Sharman MJ, et al.
Neurobiology of Disease, 124, 505-519 (2019)
Dietary curcumin supplement influence on growth, immunity, antioxidant status, and resistance to Aeromonas hydrophila in Oreochromis niloticus
Mahmoud HK, et al.
Aquaculture (Amsterdam, Netherlands), 475, 16-23 (2017)
Curcumin effectively rescued Parkinson?s disease-like phenotypes in a novel drosophila melanogaster model with dUCH Knockdown
Nguyen TT, et al.
Oxidative Medicine and Cellular Longevity, 2018 (2018)
Curcumin's biphasic hormetic response on proteasome activity and heat-shock protein synthesis in human keratinocytes
Ali RE and Rattan SIS
Annals of the New York Academy of Sciences, 1067(1), 394-399 (2006)
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