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D7696

Sigma-Aldrich

Demethoxycurcumin

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

Synonyme(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

Formule empirique (notation de Hill):
C20H18O5
Numéro CAS:
22608-11-3
Poids moléculaire :
338.35
Numéro MDL:
MFCD03427310
Code UNSPSC :
12352205
ID de substance PubChem :
329798785
Nomenclature NACRES :
NA.77

product name

Demethoxycurcumin, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

orange

Solubilité

DMSO: ≥10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

HJTVQHVGMGKONQ-LUZURFALSA-N

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Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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USP

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USP

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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
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
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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