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HomeProduct name listBIS(4-HYDROXYCINNAMOYL)METHANE

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: 2024-04-02 16:26:50
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)
ghs
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.

Computed Descriptors for BIS(4-HYDROXYCINNAMOYL)METHANE

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