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D7696

Sigma-Aldrich

Demethoxycurcumin

≥98% (HPLC)

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Synonym(s):
(E,E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, Curcumin II, Desmethoxycurcumin, Monodemethoxycurcumin
Empirical Formula (Hill Notation):
C20H18O5
CAS Number:
Molecular Weight:
338.35
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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1 of 4

This Item
C7727C1386B6938
Demethoxycurcumin ≥98% (HPLC)

D7696

Demethoxycurcumin

Curcumin ≥94% (curcuminoid content), ≥80% (Curcumin)

C7727

Curcumin

Curcumin from Curcuma longa (Turmeric), powder

C1386

Curcumin

Bisdemethoxycurcumin ≥98% (HPLC), solid

B6938

Bisdemethoxycurcumin

assay

≥98% (HPLC)

assay

≥80% (Curcumin), ≥94% (curcuminoid content)

assay

-

assay

≥98% (HPLC)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

DMSO: ≥10 mg/mL

solubility

ethanol: 1 mg/mL, DMSO: >11 mg/mL, 0.5 M NaOH: soluble (then immediately diluted in PBS)

solubility

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

solubility

DMSO: ≥20 mg/mL

storage condition

protect from light

storage condition

-

storage condition

-

storage condition

-

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


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Curcumin

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)(•))
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
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
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

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