BIS(4-HYDROXYCINNAMOYL)METHANE

Synonym(s):(E,E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione;Bisdesmethoxycurcumin;Curcumin III;Didemethoxycurcumin

CAS NO.：33171-05-0
Empirical Formula: C19H16O4
Molecular Weight: 308.33
MDL number: MFCD03419284
EINECS: 1312995-182-4
SAFETY DATA SHEET (SDS)
Update Date: 2026-01-20 19:14:41

BIS(4-HYDROXYCINNAMOYL)METHANE Structural

What is BIS(4-HYDROXYCINNAMOYL)METHANE?

The Uses of BIS(4-HYDROXYCINNAMOYL)METHANE

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 .

The Uses of BIS(4-HYDROXYCINNAMOYL)METHANE

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.

Properties of BIS(4-HYDROXYCINNAMOYL)METHANE

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)
form	solid
pka	8.50±0.46(Predicted)
color	Orange to Dark Orange
BRN	3149384
Stability:	Light Sensitive

Safety information for BIS(4-HYDROXYCINNAMOYL)METHANE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.