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MilliporeSigma

08511

Supelco

Curcumin

analytical standard

Sinónimos:

(E,E)-1,7-bis(4-Hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Diferuloylmethane, Diferulylmethane, Natural Yellow 3

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About This Item

Fórmula lineal:
[HOC6H3(OCH3)CH=CHCO]2CH2
Número de CAS:
Peso molecular:
368.38
Colour Index Number:
75300
Beilstein/REAXYS Number:
2306965
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
E Number:
E100
NACRES:
NA.24

grade

analytical standard

Quality Level

vapor density

13 (vs air)

assay

≥98.0% (HPLC)

form

powder

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

2-8°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

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General description

Curcumin is an anti-inflammatory agent extracted from the roots of Curcuma longa Linn.

application

Curcumin may be used as a reference standard for the determination of curcumin in rat plasma by high-performance liquid chromatography method.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

This compound is commonly found in plants of the genus: curcuma

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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A rapid and simple HPLC method for the determination of curcumin in rat plasma: assay development, validation and application to a pharmacokinetic study of curcumin liposome.
Li J, et al.
Biomedical Chromatography, 23(11), 1201-1207 (2009)
Oxygen radical scavenging activity of curcumin.
Kunchandy E and Rao MNA
International Journal of Pharmaceutics, 58(3), 237-240 (1990)
Phase I clinical trial of curcumin, a chemopreventive agent, in patients with highrisk or pre-malignant lesions.
Hsieh CY.
Anticancer Research, 21, 2895-2900 (2001)
Michal Heger et al.
Pharmacological reviews, 66(1), 222-307 (2013-12-26)
This review addresses the oncopharmacological properties of curcumin at the molecular level. First, the interactions between curcumin and its molecular targets are addressed on the basis of curcumin's distinct chemical properties, which include H-bond donating and accepting capacity of the
Stefanie Engleitner et al.
International journal of oncology, 56(4), 1034-1044 (2020-04-23)
Metastatic cancer cells cross endothelial barriers and travel through the blood or lymphatic fluid to pre‑metastatic niches, leading to their colonisation. 'S' stereoisomer 12S‑hydroxy‑5Z,8Z,10E,14Z‑eicosatetraenoic acid [12(S)‑HETE] is secreted by a variety of cancer cell types and has been indicated to

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