Bisdemethoxycurcumin

Base Information

• Chemical Name: Bisdemethoxycurcumin
• CAS No.: 24939-16-0
• Deprecated CAS: 91884-88-7,85801-92-9,104024-29-5,22608-12-4,104024-29-5,85801-92-9
• Molecular Formula: C₁₉H₁₆O₄
• Molecular Weight: 308.334
• Hs Code.: 2914500000
• European Community (EC) Number: 607-464-9,881-423-5
• NSC Number: 687839
• UNII: 2EFO1BP34R
• DSSTox Substance ID: DTXSID00872663
• Nikkaji Number: J468.370F,J877.763B
• Wikipedia: Bisdemethoxycurcumin
• Wikidata: Q4917168
• Pharos Ligand ID: KMR9SJSX4M5P
• Metabolomics Workbench ID: 38028
• ChEMBL ID: CHEMBL105350
• Mol file: 24939-16-0.mol

Synonyms:Bisdemethoxycurcumin;33171-05-0;24939-16-0;Curcumin III;Didemethoxycurcumin;(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione;Bis(4-hydroxycinnamoyl)methane;Bis-demethoxycurcumin;Bisdemethoxycucurmin;bisdesmethoxycurcumin;Bis(p-hydroxycinnamoyl)methane;(E,E)-Bisdemethoxycurcumin;1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-;BHCMT;NSC687839;UNII-2EFO1BP34R;2EFO1BP34R;1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;CHEMBL105350;CHEBI:71045;1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione;22608-12-4;1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-;p,p'-Dihydroxydicinnamoylmethane;Curcumin Lll;Curcuminoid A;Bisdemethoxy Curcumin;di-p-coumaroylmethane;Dide Methoxycurcu Min;INS NO.100(III);SCHEMBL428638;INS-100(III);SCHEMBL13521971;cid_5324473;HY-N0007A;DTXSID00872663;E-100(III);(1E,6E)-1,7-Bis(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione;ZAA93916;1,3-Di(4-hydroxystyryl)propanedial;BIS-DEMETHOXYCURCUMIN [INCI];BDBM50059989;MFCD03419284;BISDESMETHOXYCURCUMIN [USP-RS];AKOS015902102;CCG-207959;CCG-208635;NSC-687839;Bisdemethoxycurcumin, analytical standard;AC-24239;AC-34720;ADAMANTAN-1-YL-ACETICACIDHYDRAZIDE;AS-57295;AS-68737;B3347;Bisdemethoxycurcumin, >=98% (HPLC), solid;CS-0018287;S3938;A14544;A875406;Q-100322;Q4917168;BRD-K37445107-001-01-9;1,7-bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione(E,E);(1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione;1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3,6-heptatrien-5-one;1,7-BIS-(4-HYDROXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE;(1E,6E)-1,7-Bis-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione;1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (E,E)-;5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one;(1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one

Chemical Property of Bisdemethoxycurcumin

Chemical Property:

• Vapor Pressure: 9.17E-13mmHg at 25°C
• Melting Point: 91-93℃
• Refractive Index: 1.68
• Boiling Point: 551.3 °C at 760 mmHg
• PKA: 8.67±0.46(Predicted)
• Flash Point: 301.3 °C
• PSA: 74.60000
• Density: 1.285 g/cm³
• LogP: 3.35270
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 308.10485899
• Heavy Atom Count: 23
• Complexity: 408

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bisdemethoxycurcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O

Technology Process of Bisdemethoxycurcumin

There total 15 articles about Bisdemethoxycurcumin 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: 85.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + acetylacetone (123-54-6,81235-32-7) → bisdemethoxycurcumin (22608-12-4,24939-16-0,33171-05-0,91884-88-7)

Guidance literature:

4-hydroxy-benzaldehyde; acetylacetone; With boron trioxide; boric acid tributyl ester; In ethyl acetate; at 50 ℃; for 0.0833333h; Inert atmosphere;

With N-butylamine; In ethyl acetate; at 50 - 80 ℃; for 4.25h; Inert atmosphere;

With hydrogenchloride; In water; ethyl acetate; for 0.5h; Inert atmosphere;

DOI:10.3390/molecules16021888

Reference yield: 70.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + acetylacetone (123-54-6,81235-32-7) → bisdemethoxycurcumin (22608-12-4,24939-16-0,33171-05-0,91884-88-7)

Guidance literature:

With 1,2,3,4-tetrahydroisoquinoline; boric acid; acetic acid; In N,N-dimethyl-formamide; for 4h; Heating;

Reference yield: 64.93%

acetylacetone boric oxide + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → bisdemethoxycurcumin (22608-12-4,24939-16-0,33171-05-0,91884-88-7)

Guidance literature:

acetylacetone boric oxide; 4-hydroxy-benzaldehyde; for 0.666667h;

With N-butylamine; for 16h;

upstream raw materials:

4-hydroxy-benzaldehyde

acetylacetone

acetone

vanillin

Downstream raw materials:

1,7-bis(4-hydroxyphenyl)heptane-3,5-dione

di-O-acetylbisdemethoxycurcumin

di-O-acetyldemethoxycurcumin

C₂₆H₂₀O₅

Refernces

• 1、 Kazantzis,Koutsonikoli,Mavroidi,Zachariadis,Alexiou,Pelecanou,Politopoulos,Alexandratou,Sagnou. "Curcumin derivatives as photosensitizers in photodynamic therapy: Photophysical properties and: In vitro studies with prostate cancer cells". . p. 193 - 206. Retrieved 2020/03/03.
• 2、 Li, Yanci,Gu, Zhenyu,Zhang, Can,Li, Shenghui,Zhang, Liang,Zhou, Guoqiang,Wang, Shuxiang,Zhang, Jinchao. "Synthesis, characterization and ROS-mediated antitumor effects of palladium(II) complexes of curcuminoids". . p. 662 - 671. Retrieved 2018/01/01.