Demethoxycurcumin

Base Information

• Chemical Name: Demethoxycurcumin
• CAS No.: 24939-17-1
• Deprecated CAS: 33171-16-3,85801-93-0,91884-87-6,1281950-91-1,1281950-91-1,85801-93-0,91884-87-6
• Molecular Formula: C20H18O5
• Molecular Weight: 338.36
• Hs Code.: 2914500000
• European Community (EC) Number: 607-465-4,663-429-8
• NSC Number: 687841
• UNII: W2F8059T80
• DSSTox Substance ID: DTXSID00873751
• Nikkaji Number: J468.369B,J877.764K
• Wikipedia: Desmethoxycurcumin
• Wikidata: Q5264607
• Metabolomics Workbench ID: 64104
• ChEMBL ID: CHEMBL105360
• Mol file: 24939-17-1.mol

Synonyms:4-hydroxycinnamoyl(feroyl)methane;curcumin II;demethoxy-curcumin;demethoxycurcumin;monodemethoxycurcumin

Chemical Property of Demethoxycurcumin

Chemical Property:

• Vapor Pressure: 1.17E-13mmHg at 25°C
• Refractive Index: 1.659
• Boiling Point: 571.4 °C at 760 mmHg
• PKA: 8.59±0.46(Predicted)
• Flash Point: 205.5 °C
• PSA: 83.83000
• Density: 1.282 g/cm³
• LogP: 3.36130
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 338.11542367
• Heavy Atom Count: 25
• Complexity: 502

Purity/Quality:

99% ^*data from raw suppliers

Desmethoxycurcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
• Uses: Desmethoxycurcumin is a derivative of Curcumin (C838500) that regulates anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. It attenuates the Wnt/β-catenin pathway through down-regulation of the transcriptional coactivator p300.

Technology Process of Demethoxycurcumin

There total 10 articles about Demethoxycurcumin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-hexa-3,5-dien-2-one + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → demethoxycurcumin (22608-11-3,24939-17-1,33171-16-3,91884-87-6)

Guidance literature:

4-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-hexa-3,5-dien-2-one; With boron trioxide; In ethyl acetate; at 50 ℃; for 0.5h;

4-hydroxy-benzaldehyde; With boric acid tributyl ester; at 50 ℃; for 0.5h; Further stages;

DOI:10.3390/molecules16021888

Reference yield: 54.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + vanillin (121-33-5,8014-42-4) + acetylacetone (123-54-6,81235-32-7) → demethoxycurcumin (22608-11-3,24939-17-1,33171-16-3,91884-87-6)

Guidance literature:

acetylacetone; With boron trioxide; boric acid tributyl ester; In N,N-dimethyl-formamide; at 65 ℃; for 0.25h;

4-hydroxy-benzaldehyde; vanillin; With 1,2,3,4-tetrahydroisoquinoline; acetic acid; In N,N-dimethyl-formamide; at 95 ℃; for 4h;

With acetic acid; In water; N,N-dimethyl-formamide; at 70 ℃; for 1h;

DOI:10.1016/j.bmc.2005.06.050

Reference yield:

C29H32O6 + C30H34O7 → bisdemethoxycurcumin (22608-12-4,24939-16-0,33171-05-0,91884-88-7) + demethoxycurcumin (22608-11-3,24939-17-1,33171-16-3,91884-87-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 20 ℃;

upstream raw materials:

4-hydroxy-benzaldehyde

vanillin

acetylacetone

di-O-acetylbisdemethoxycurcumin

Downstream raw materials:

di-O-methyldemethoxycurcumin

di-O-acetylbisdemethoxycurcumin

di-O-acetyldemethoxycurcumin

Refernces

• 1、 -. "METHOD TO PREPARE PURE CURCUMIN". Page/Page column 4-5. . Retrieved 2010/03/31.
• 2、 Venkateswarlu, Somepalli,Ramachandra, Marellapudi S.,Subbaraju, Gottumukkala V.. "Synthesis and biological evaluation of polyhydroxycurcuminoids". . p. 6374 - 6380. Retrieved 2007/10/03.