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(E, E) -Bisdemethoxycurcumin

CAT: 0804-HY-N0007-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0007-01Size:5 mg
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Description
(E, E) -Bisdemethoxycurcumin ((E, E) -Curcumin III) is a curcumin derivative with anti-inflammatory and anticancer activities[1][2][3][4][5][6].
CAS Number
33171-05-0
Product Name Alternative
(E, E) -Curcumin III; (E, E) -Didemethoxycurcumin
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Apoptosis; Autophagy
Type
Natural Products
Related Pathways
Apoptosis; Autophagy
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/e-e-bisdemethoxycurcumin.html
Purity
98.63
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O=C(CC(/C=C/C1=CC=C(O)C=C1)=O)/C=C/C2=CC=C(O)C=C2
Molecular Formula
C19H16O4
Molecular Weight
308.33
Precautions
H315, H319, H335
References & Citations
[1]Lee PJ, et al. Bisdemethoxycurcumin Induces Apoptosis in Activated Hepatic Stellate Cells via Cannabinoid Receptor 2. Molecules. 2015 Jan 14;20 (1) :1277-92.|[2]Chen J, et al. Natural borneol enhances bisdemethoxycurcumin-induced cell cycle arrest in the G2/M phase through up-regulation of intracellular ROS in HepG2 cells. Food Funct. 2014 Dec 24.|[3]Luo C, et al. Bisdemethoxycurcumin attenuates gastric adenocarcinoma growth by inducing mitochondrial dysfunction. Oncol Lett. 2015 Jan;9 (1) :270-274.|[4]Li YB, et al. Bisdemethoxycurcumin Increases Sirt1 to Antagonize t-BHP-Induced Premature Senescence in WI38 Fibroblast Cells. Evid Based Complement Alternat Med. 2013;2013:851714.|[5]Yodkeeree S, et al. Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA. J Nutr Biochem. 2009 Feb;20 (2) :87-95.|[6]Lai CS, et al. Bisdemethoxycurcumin Inhibits Adipogenesis in 3T3-L1 Preadipocytes and Suppresses Obesity in High-Fat Diet-Fed C57BL/6 Mice. J Agric Food Chem. 2016 Feb 3;64 (4) :821-30.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Bisdemethoxycurcumin

Bisdemethoxycurcumin is a beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. It has a role as a metabolite and an EC 3.2.1.1 (alpha-amylase) inhibitor. It is a polyphenol, an enone, a beta-diketone and a diarylheptanoid. It is functionally related to a 4-coumaric acid.

CAS Number33171-05-0
PubChem CID5315472
IUPAC Name(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Molecular FormulaC19H16O4
Molecular Weight308.3
XLogP3.3
Topological Polar Surface Area74.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Heavy Atom Count23
Formal Charge0
Complexity408
SMILES
C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
InChI
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+
InChIKey
PREBVFJICNPEKM-YDWXAUTNSA-N
Chemical Structure
2D Structure
2D structure of Bisdemethoxycurcumin
CAS: 33171-05-0
CID: 5315472
Formula: C19H16O4
MW: 308.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight308.3
XLogP33.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass308.10485899
Monoisotopic Mass308.10485899
Topological Polar Surface Area74.6 Ų
Heavy Atom Count23
Formal Charge0
Complexity408
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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