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22608-11-3

22608-11-3 Structure

22608-11-3 Structure
IdentificationBack Directory
[Name]

DEMETHOXYCURCUMIN
[CAS]

22608-11-3
[Synonyms]

Demethoxycurcumin
Curcumin Desmethoxy
DEMETHOXYCURCUMIN(SH)
MonodeMethoxycurcuMin
Z/E-Desmethoxycurcumin
(2E)-DeMethoxy CurcuMin
(1E,6E)-Demethoxycurcumin
DEMETHOXYCURCUMIN USP/EP/BP
p-HydroxycinnaMoylferuloylMethane
Feruloyl-P-hydroxycinnnamoylmethane
DeMethoxyCurcuMin(DesMethoxycurcuMin)
Demethoxycurcumin, 98%, from Curcuma longa L.
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
1-(4-Hydroxy-3-Methoxyphenyl)-7-(p-hydroxyphenyl)-1,6-heptadiene-3,5-dione
1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-
(1E,6E)-1-(4-Hydroxyphenyl)-7-(4-hydroxy-3-Methoxyphenyl)-1,6-heptadiene-3,5-d
(E,E)-1-(4-Hydroxy-3-Methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1E,6E)-
[Molecular Formula]

C20H18O5
[MDL Number]

MFCD03427310
[MOL File]

22608-11-3.mol
[Molecular Weight]

338.35
Chemical PropertiesBack Directory
[Melting point ]

166~170℃
[Boiling point ]

571.4±50.0 °C(Predicted)
[density ]

1.282±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: ≥10mg/mL
[form ]

powder
[pka]

8.31±0.46(Predicted)
[color ]

orange
[Cosmetics Ingredients Functions]

ANTIOXIDANT
[LogP]

3.113 (est)
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

50
[Safety Statements ]

61
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

2
[HS Code ]

29145090
Hazard InformationBack Directory
[Chemical Properties]

Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from turmeric rhizomes.
[Uses]

Demethoxycurcumin (DMC) is a natural demethoxy derivative of curcumin. More stable than curcumin in physiological media, DMC suppresses proliferation in cancer cells at 50-100 μM. It down-regulates the transcriptional coactivator p300, suppressing the Wnt/β-catenin pathway, and inhibits lipopolysaccharide induction of iNOS.
[Uses]

The demethoxy derivative of Curcumin (C838500) that regulates anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. It attenuates the Wnt/β-catenin pathway through do wn-regulation of the transcriptional coactivator p300.
[Definition]

ChEBI: Demethoxycurcumin is a beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior. It has a role as a metabolite, an antineoplastic agent and an anti-inflammatory agent. It is a polyphenol, a beta-diketone, an enone and a diarylheptanoid.
[General Description]

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
[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.
[in vivo]

Demethoxycurcumin (3-30 mg/kg/day for 5 days or 20 days, i.p.) regulates the expression of inflammatory and apoptotic genes in the hippocampus and frontal cortex of rat models infused with Aβ + Ibotenic acid (HY-N2311) and helps to improve Alzheimer's disease[3].
Demethoxycurcumin (10 mg/kg/day for 28 days, p.o.) can enhance cognition and enhance choline acetyltransferase (ChAT) activity in mice induced by Scopolamine (HY-N0296) [4].

Animal Model:Male ICR mice (6 weeks old) weighing 30–35 g, memory impairment induced by Scopolamine[5]
Dosage:10 mg/kg/day for 28 days
Administration:Oral gavage (p.o.)
Result:Significantly improved scopolamine induced passive avoidance task learning disabilities and memory impairments in Morris Water Maze.
The activity of choline acetyltransferase (ChAT) was significantly increased to 33.03%.
[IC 50]

ChAT; iNOS
[storage]

Store at RT
Spectrum DetailBack Directory
[Spectrum Detail]

DEMETHOXYCURCUMIN(22608-11-3)1HNMR
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