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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Supachai Yodkeeree et al.
European journal of pharmacology, 627(1-3), 8-15 (2009-10-13)
Demethoxycurcumin (DMC) is one of the main active compounds of curcuminoids found in turmeric powder, which is used as a spice in Asian cooking and traditional medicine. Recent studies reveal that DMC has several biological activities including anti-inflammation and anti-cancer
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
Mathanaporn Boonrao et al.
Archives of pharmacal research, 33(7), 989-998 (2010-07-28)
Matrix metalloproteinase-3 (MMP-3) is a key enzyme with important implications in the invasion and metastasis of breast cancer cells. Curcumin (Cur), demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC) are major forms of curcuminoids found in turmeric powder with reported anticancer activity. This
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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