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D7696

Sigma-Aldrich

Demethoxycurcumin

≥98% (HPLC), powder, LPS-induced nitric oxide (NO) production inhibitor

Synonym(s):

(E,E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, Curcumin II, Desmethoxycurcumin, Monodemethoxycurcumin

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About This Item

Empirical Formula (Hill Notation):
C20H18O5
CAS Number:
22608-11-3
Molecular Weight:
338.35
MDL number:
MFCD03427310
UNSPSC Code:
12352205
PubChem Substance ID:
329798785
NACRES:
NA.77

product name

Demethoxycurcumin, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

orange

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)cc2)ccc1O

InChI

1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+

InChI key

HJTVQHVGMGKONQ-LUZURFALSA-N

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Biochem/physiol Actions

Demethoxycurcumin (DMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. DMC inhibits LPS-induced nitric oxide (NO) production, and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. DMC also inhibits NF-kB dependent iNOS, TNFα and IL-1β expression in LPS-treated rat microglial cells. DMC suppresses expression of MMPs and ICAM-1 in MDA-MB-231 human breast cancer cells by inhibition of NF-kB.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Lijia Zhang et al.
International immunopharmacology, 10(3), 331-338 (2009-12-19)
Our previous report has showed that demethoxycurcumin (DMC), a natural derivative of curcumin (Cur), exhibited stronger inhibitory activity on nitric oxide (NO) and tumor necrosis factor-alpha (TNF-alpha) production compared with Cur in lipopolysaccharide (LPS) activated rat primary microglia. In the
T Ahmed et al.
Neuroscience, 169(3), 1296-1306 (2010-06-12)
Alzheimer's disease (AD) is a neurodegenerative disease. There are a limited number of therapeutic options available for the treatment of AD. Curcuminoids (a mixture of bisdemethoxycurcumin, demethoxycurcumin and curcumin) is the main chemical constituent found in turmeric, a well known
Hye Jin Kim et al.
Phytochemical analysis : PCA, 20(5), 372-377 (2009-06-18)
The new ion source technique, direct analysis in real time (DART) atmospheric pressure ionisation, allows high resolution mass measurements of gas, liquid and solid samples. As DART-MS produces [M + H](+) molecular ions of most compounds, relatively simple and clear
R Douglas Shytle et al.
Current Alzheimer research, 6(6), 564-571 (2009-09-01)
Inhibition of beta-amyloid (A beta) accumulation and A beta fibril (fA beta) formation from A beta are attractive therapeutic targets for the treatment of Alzheimer's disease (AD). While previous studies have shown anti-amyloidogenic effects of curcumin in vitro and in
Umang Singh et al.
Free radical research, 45(3), 317-325 (2010-11-03)
Three curcumin analogues viz., bisdemethoxy curcumin, monodemethoxy curcumin, and dimethoxycurcumin that differ at the phenolic substitution were synthesized. These compounds have been subjected for free radical reactions with DPPH radicals, superoxide radicals (O(2)(•-)), singlet oxygen ((1)O(2)) and peroxyl radicals (CCl(3)O(2)(•))
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