BIS(4-HYDROXYCINNAMOYL)METHANE Chemical Properties

Melting point:

221-223 ºC

Boiling point:

551.3±45.0 °C(Predicted)

Density 

1.285

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

8.50±0.46(Predicted)

form 

solid

color 

Orange to Dark Orange

BRN 

3149384

Stability:

Light Sensitive

LogP

3.155 (est)

Safety Information

WGK Germany 

3

HS Code 

29145090

BIS(4-HYDROXYCINNAMOYL)METHANE Usage And Synthesis

Uses

Bisdemethoxycurcumin is one of the three major forms of curcuminoids found in the rhizomes of turmeric. Bisdemethoxycurcumin displays antioxidant, anti-inflammatory as well as chemotherapeutic activit y. Bisdemethoxycurcumin acts as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes .

Uses

Bisdemethoxycurcumin has been used:

• to test its inhibitory effect on cell cycle and mitochondrial function in gastric adenocarcinoma cells
• to test it neuroprotective role against lead (Pb) induced toxicity in dopaminergic and noradrenergic systems of Meriones shawi
• as a standard for calibration curve generation to quantify plasma curcuminoids using high-performance liquid chromatography-diode array detection (HPLC-DAD) and ultraviolet (UV)

Definition

ChEBI: 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 beta-diketone, a polyphenol, an enone and a diarylheptanoid. It is functionally related to a 4-coumaric acid.

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

Bisdemethoxycurcumin (BDMC) is a derivative or curcumin, and represents one of the major active components of curcumin products isolated from Curcumae sp. BDMC shares similar anti-inflammatory properties with demethoxycurcumin. It inhibits LPS-induced nitric oxide (NO) production and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. BDMC also displays unique properties in that it enhances Abeta clearance by upregulating expression MGAT3 and TLR genes. BDMC potently inhibits AKR1B10.

BIS(4-HYDROXYCINNAMOYL)METHANE(33171-05-0)Related Product Information

• 4-Methoxybenzoic acid
• Octyl 4-methoxycinnamate
• 5"-MethoxyhexahydrocurcuMin
• DihydrocurcuMin
• FLLL31
• ASC-J9
• (3S,5S)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)HEPTANE-3,5-DIOL
• HEXAHYDROCURCUMIN
• Tetrahydrocurcumin
• DEMETHOXYCURCUMIN
• 1,4-HEXADIENE
• BIS(4-HYDROXYCINNAMOYL)METHANE,BIS-(PARA-HYDROXYCINNAMOYL)METHANE
• DEMETHOXYCURCUMIN
• Curcumin