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33171-05-0

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33171-05-0 Usage

Description

BIS(4-HYDROXYCINNAMOYL)METHANE, also known as Bisdemethoxycurcumin, is one of the three major forms of curcuminoids found in the rhizomes of turmeric. It is a primary reference substance with assigned absolute purity, considering chromatographic purity, water, residual solvents, and inorganic impurities. Bisdemethoxycurcumin exhibits antioxidant, anti-inflammatory, and chemotherapeutic activities, making it a promising compound for various applications.

Uses

Used in Pharmaceutical Industry:
BIS(4-HYDROXYCINNAMOYL)METHANE is used as a chemotherapeutic agent for its antioxidant, anti-inflammatory, and chemotherapeutic properties. It has been tested for its inhibitory effect on cell cycle and mitochondrial function in gastric adenocarcinoma cells, demonstrating potential in cancer treatment.
Used in Diabetes Management:
BIS(4-HYDROXYCINNAMOYL)METHANE is used as an inhibitor of human pancreatic α-amylase, a target for type-2 diabetes, indicating its potential application in managing and treating diabetes.
Used in Neuroprotection:
Bisdemethoxycurcumin has been tested for its neuroprotective role against lead (Pb) induced toxicity in dopaminergic and noradrenergic systems of Meriones shawi, suggesting its potential use in protecting the nervous system from harmful substances.
Used in Analytical Chemistry:
BIS(4-HYDROXYCINNAMOYL)METHANE is used as a standard for calibration curve generation to quantify plasma curcuminoids using high-performance liquid chromatography-diode array detection (HPLC-DAD) and ultraviolet (UV), making it a valuable tool in analytical chemistry and research.
Source:
This substance is produced by PhytoLab GmbH & Co. KG, ensuring the quality and purity of the compound for various applications.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 33171-05-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,1,7 and 1 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 33171-05:
(7*3)+(6*3)+(5*1)+(4*7)+(3*1)+(2*0)+(1*5)=80
80 % 10 = 0
So 33171-05-0 is a valid CAS Registry Number.
InChI:InChI=1/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+

33171-05-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (90594)  Bisdemethoxycurcumin  analytical standard

  • 33171-05-0

  • 90594-10MG

  • 2,552.94CNY

  • Detail

33171-05-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Bisdemethoxycurcumin

1.2 Other means of identification

Product number -
Other names BIS(4-HYDROXYCINNAMOYL)METHANE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:33171-05-0 SDS

33171-05-0Relevant articles and documents

Preparation method 1,7 - di (4 -hydroxy) heptyl -3-5 - glycol ester

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Paragraph 0026; 0035; 0037; 0039-0040, (2021/01/30)

The invention discloses a preparing method of 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester. The method includes the following steps of firstly, conducting a -C=C- reduction reaction with bisdemethoxycurcumin as the raw material to obtain a product 3; secondly, conducting a reduction reaction of carbonyl on the premise of protecting hydroxyl on a benzene ring to obtain a product 5; secondly,conducting an esterification reaction on the product 5 to obtain a product 6, and conducting a protecting group removing reaction on the product 6 to obtain the final product, namely 1,7-bis(4-benzenehydroxyl)heptyl-3,5-glycol ester. By means of the method, through the reduction reaction, the reaction of protecting hydroxyl on the benzene ring, the reaction of reducing carbonyl, the esterification reaction and the protecting group removing reaction, 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester can be obtained; the reaction process is simple, operation is simple, applied raw materials are low in cost, yield is high, and the method is suitable for industrially producing 1,7-bis(4-benzene hydroxyl)heptyl-3,5-glycol ester on a large scale.

Method for artificially synthesizing curcumin and derivatives thereof

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Paragraph 0026-0027; 0031-0032; 0050-0052, (2020/05/30)

The invention provides a method for artificially synthesizing curcumin and derivatives thereof. The method comprises the following steps: reacting acetylacetone with boron oxide under a weakly acidiccondition to generate a complex, protecting methylene groups between two ketocarbonyl groups, adding a catalyst, reacting the complex with vanillin (benzaldehyde derivative) to obtain a curcumin derivative intermediate (I), and hydrolyzing the intermediate to obtain the curcumin derivative. The selectivity of the reaction is far higher than that of a preparation reaction in an alkaline system, andis macroscopically and specifically embodied in the yield of curcumin and derivatives thereof: in the existing two-pot reaction, the yield of curcumin in the whole process is about 60%; the yield ofthe preparation method can reach 80-90%. Therefore, the method provided by the invention reduces the waste of raw materials and the generation of byproducts; and complete hydrolysis can be realized only at normal temperature, insoluble substances included in the product are almost zero, and the obtained product is pure.

Synthesis, spectral characterization and thermal analysis of rubrocurcumin and its analogues

John, Jeena,Devi, R. Sudha,Balachandran,Babu, K. V. Dinesh

, p. 2301 - 2314 (2017/10/06)

Rubrocurcumin and its analogues were synthesized and characterized by UV, IR, NMR and FT-MS spectral data. Thermal analysis of compounds has been carried out using TG-DTG techniques using non-isothermal heating conditions. Flynn–Wall–Ozawa and Kissinger–Akahira–Sunose isoconversional methods were used to determine the apparent activation energies (Ea) for the thermal decomposition rubrocurcumin and its analogues. The Ea values obtained using these methods were used as reference to determine the most suitable kinetic model using Coats–Redfern method. A possible mechanism is suggested to explain the thermal decomposition process. From the TG-DTG data, kinetic parameters have been calculated and were used to evaluate the thermal stability of compounds and the substituent effect on its thermal stability.

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