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Details

Stereochemistry ACHIRAL
Molecular Formula C19H16O4
Molecular Weight 308.3279
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BISDEMETHOXYCURCUMIN

SMILES

OC1=CC=C(C=C1)\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2

InChI

InChIKey=PREBVFJICNPEKM-YDWXAUTNSA-N
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

HIDE SMILES / InChI

Molecular Formula C19H16O4
Molecular Weight 308.3279
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description

Bisdemethoxycurcumin (BDMC) is a minor constituent (approximately 3%) of curcuminoids that has been shown to be more stable than the other two main curcuminoids, that is, curcumin and desmethoxycurcumin. Bisdemethoxycurcumin inhibits the proliferation and survival of several types of tumor cells including colon cancer cells, breast cancer cells, leukemia cells, and glioma cells. In addition, Bisdemethoxycurcumin suppresses cancer invasion and has the highest anti-metastatic potency in HT1080 human fibrosarcoma cells among the three curcuminoids. Bisdemethoxycurcumin has been reported to possess anti-oxidant and anti-inflammatory activities. However, the underlying molecular mechanisms responsible for the inhibitory action of Bisdemethoxycurcumin on tumor invasion and migration have remained largely unknown. More interestingly, the anti-cancer effects of Bisdemethoxycurcumin are comparable to and sometimes more potent than those of curcumin in different conditions.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Mice were treated with Bisdemethoxycurcumin as a dose of either 1 or 5 g/kg diet for 15 weeks.
Route of Administration: Oral
In Vitro Use Guide
NCI-H460 cells at a density of 5Ч105 cells/ml were maintained on 12-well plates with RPMI-1640 medium for 24 h and then incubated with or without 35 μM of Bisdemethoxycurcumin for 24 h. At the end of incubation, cells were collected from each treatment and total RNA was extracted by using the Qiagen RNeasy Mini Kit (Qiagen, Inc, Valencia, CA, USA)
Substance Class Chemical
Record UNII
2EFO1BP34R
Record Status Validated (UNII)
Record Version