Dimethylcurcumin

Base Information

• Chemical Name: Dimethylcurcumin
• CAS No.: 52328-98-0
• Molecular Formula: C23H24O6
• Molecular Weight: 396.44
• NSC Number: 734923
• DSSTox Substance ID: DTXSID10200352
• Nikkaji Number: J845.478G,J2.427.915D,J3.606.945G
• Wikipedia: Dimethylcurcumin
• Wikidata: Q76390125
• Metabolomics Workbench ID: 123206
• ChEMBL ID: CHEMBL128748
• Mol file: 52328-98-0.mol

Synonyms:ASC-J9;52328-98-0;Dimethylcurcumin;917813-54-8;(1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one;1,7-Bis-(3,4-dimethoxy-phenyl)-5-hydroxy-hepta-1,4,6-trien-3-one;ASCJ-9;1,7-Bis-(3,4-dimethoxyphenyl)-5-hydroxy-hepta-1,4,6-trien-3-one;GO-Y-025;UNII-D60XLY608D;Go-Y025;(1E,4E,6E)-1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one;1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one;(1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-1,4,6-heptatrien-3-one;1,4,6-Heptatrien-3-one, 1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-, (1E,4Z,6E)--;1,4,6-Heptatrien-3-one, 1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-, (Z,E,E)-;115851-85-9;GO-Y025;CHC 004;Di-O-methylcurcumin;Dimethylcurcumin (ASC-J9);GO-Y025ASC-J9;SCHEMBL3487103;DTXSID10200352;EX-A927;(1E,4E,6E)-1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxy-1,4,6-heptatrien-3-one;ZMGUKFHHNQMKJI-CIOHCNBKSA-N;AMY15692;MFCD12912341;MFCD22123809;NSC734923;s6630;AKOS015891371;AKOS025311328;CS-0533;DB06133;NSC-734923;AC-31058;AS-82881;DS-14720;HY-15194;ASC-J9,CAS:52328-98-0;J3.606.945G;ASC J9;GO Y025;1, 4-dimethoxyphenyl)-1, 6-heptadiene-3,5-dione;(1E,6E)-1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxy-1,4,6-heptatriene-3-one;1,7-Bis-(3,4-dimethoxy-phenyl)- 5-hydroxy-hepta-1,4,6-trien-3-one;(1E,4Z,6E)-1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxy-1,4,6-heptatriene-3-one;(1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxy-hepta-1,4,6-trien-3-one

Chemical Property of Dimethylcurcumin

Chemical Property:

• Melting Point: 129-130℃
• Boiling Point: 588.6±50.0 °C(Predicted)
• PKA: 8.34±0.60(Predicted)
• PSA: 74.22000
• Density: 1.191
• LogP: 4.45860
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥16.65 mg/mL in DMSO
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 396.15728848
• Heavy Atom Count: 29
• Complexity: 596

Purity/Quality:

≥98% ^*data from raw suppliers

Dimethylcurcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=CC(=O)C=CC2=CC(=C(C=C2)OC)OC)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=C/C(=O)/C=C/C2=CC(=C(C=C2)OC)OC)/O)OC
• Recent ClinicalTrials: Topical ASC-J9 Cream for Acne
• Uses: Dimethylcurcumin selectively enhances the degradation of androgen receptor. Dimethylcurcumin is a related compound of Curcumin (C838500).

Technology Process of Dimethylcurcumin

There total 20 articles about Dimethylcurcumin 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: 95.0%

2,2-difluoro-4,6-bis[β-(3,4-dimethoxystyryl)]-1,3,2-dioxaborine → O,O-dimethyl-curcumin (52328-98-0,917813-54-8)

Guidance literature:

With sodium oxalate; In methanol; water; at 140 ℃; for 0.1h; Microwave irradiation; Sealed tube;

DOI:10.1016/j.jfluchem.2016.09.009

Reference yield: 90.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + acetylacetone (123-54-6,81235-32-7) → O,O-dimethyl-curcumin (52328-98-0,917813-54-8)

Guidance literature:

acetylacetone; With boron trioxide; In ethyl acetate; at 70 ℃; for 3h;

3,4-dimethoxy-benzaldehyde; With boric acid tributyl ester; N-butylamine; In ethyl acetate; at 70 ℃; for 24h;

With hydrogenchloride; In ethyl acetate; at 60 ℃; for 0.5h; pH=5; Further stages.;

DOI:10.1016/j.bmc.2008.07.054

Reference yield: 77.2%

curcumin (98885-93-9,115851-80-4,147556-16-9) + dimethyl sulfate (77-78-1) → O,O-dimethyl-curcumin (52328-98-0,917813-54-8)

Guidance literature:

With sodium hydroxide; In water; Heating;

upstream raw materials:

3,4-dimethoxy-benzaldehyde

acetylacetone

curcumin

dimethyl sulfate

Downstream raw materials:

(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-((5-methylfuran-2-yl)methylene)hepta-1,6-diene-3,5-dione

(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-(4-fluorobenzylidene)hepta-1,6-diene-3,5-dione

(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxybenzylidene)hepta-1,6-diene-3,5-dione

(1E,6E)-1,7-bis(3,4-dimethoxyphenyl)-4-(4-hydroxybenzylidene)hepta-1,6-diene-3,5-dione

Refernces

• 1、 Li, Zhengyi,Yan, Jinbei,Yin, Yue,Zhang, Zhihui,Wang, Zhiming,Xu, Defeng,Sun, Xiaoqiang. "A Fluorescent Chemosensor for Al3+Based on C O Isomerization Derivated from Curcumin". . p. 657 - 661. Retrieved 2016.
• 2、 Abonia, Rodrigo,Bunge, Scott D.,Laali, Kenneth K.,Raja Somu, Dawn,Wang, Esther C.. "A Flexible Strategy for Modular Synthesis of Curcuminoid-BF2/Curcuminoid Pairs and Their Comparative Antiproliferative Activity in Human Cancer Cell Lines". . . Retrieved 2020/02/05.
• 3、 Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.. "Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin". supporting information. p. 854 - 865. Retrieved 2017/12/13.