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
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. |
Computed Descriptors for BIS(4-HYDROXYCINNAMOYL)METHANE
New Products
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