Monodemethylcurcumin

Base Information

• Chemical Name: Monodemethylcurcumin
• CAS No.: 149732-51-4
• Molecular Formula: C20H18O6
• Molecular Weight: 354.359
• NSC Number: 687844
• UNII: 422O27405E
• DSSTox Substance ID: DTXSID00420209
• Nikkaji Number: J877.766G
• Wikidata: Q27258483
• Metabolomics Workbench ID: 121260
• ChEMBL ID: CHEMBL103410
• Mol file: 149732-51-4.mol

Synonyms:(1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione;demethylcurcumin;monodemethylcurcumin

Chemical Property of Monodemethylcurcumin

Chemical Property:

• Melting Point: 183-187°C (dec.)
• Boiling Point: 617.5±55.0 °C(Predicted)
• PKA: 8.14±0.46(Predicted)
• PSA: 104.06000
• Density: 1.350±0.06 g/cm3(Predicted)
• LogP: 3.06690
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 540

Purity/Quality:

99% ^*data from raw suppliers

Demethyl Curcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC(=C(C=C2)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
• Uses: A metabolite of Curcumin (C838500) with potent activity against Trypanosoma and Leishmania species.

Technology Process of Monodemethylcurcumin

There total 9 articles about Monodemethylcurcumin 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: 60.0%

curcumin (458-37-7) → 1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione (149732-51-4) + bisdemethylcurcumin (60831-46-1)

Guidance literature:

With pyridine; aluminium trichloride; In dichloromethane; for 24h; Heating;

DOI:10.1021/jm970190x

Reference yield:

→ (1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (869789-09-3) + bisdemethoxycurcumin (22608-12-4,24939-16-0,33171-05-0,91884-88-7) + 1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione (149732-51-4) + bisdemethylcurcumin (60831-46-1)

Guidance literature:

With pyridine; aluminum (III) chloride; In ethyl acetate; at 0 ℃; for 7.25h; Purification / work up; Heating / reflux;

Reference yield:

vanillin (121-33-5,8014-42-4) → 1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione (149732-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) boric anhydride, 2.) a) tributyl borate, b) n-butylamine, 3.) 10percent HCl

2: 15 percent / AlCl₃, pyridine / CH₂Cl₂ / 24 h / Heating

With pyridine; hydrogenchloride; boron trioxide; aluminium trichloride; boric acid tributyl ester; N-butylamine; In dichloromethane;

DOI:10.1021/jm970190x

upstream raw materials:

curcumin

vanillin

acetylacetone

Downstream raw materials:

bisdemethylcurcumin

mono-O'-acetyldemethoxycurcumin

di-O-acetyldemethoxycurcumin

1-(3,4-dihydroxyphenyl)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)heptan-3-one

Refernces

• 1、 Lammer, Aaron D.,Thiabaud, Grégory,Brewster, James T.,Alaniz, Julie,Bender, Jon A.,Sessler, Jonathan L.. "Lanthanide Texaphyrins as Photocatalysts". . p. 3458 - 3464. Retrieved 2018.
• 2、 Tocharus, Jiraporn,Jamsuwan, Sataporn,Tocharus, Chainarong,Changtam, Chatchawan,Suksamrarn, Apichart. "Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells". body text. p. 400 - 405. Retrieved 2012/09/10.