Hexahydrocurcumin

Base Information

• Chemical Name: Hexahydrocurcumin
• CAS No.: 36062-05-2
• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.434
• Hs Code.: 2914509090
• European Community (EC) Number: 924-435-9
• UNII: RNL5XJ2BA7
• DSSTox Substance ID: DTXSID00415731
• Nikkaji Number: J445.265H
• Wikidata: Q27155296
• Metabolomics Workbench ID: 137911
• ChEMBL ID: CHEMBL479650
• Mol file: 36062-05-2.mol

Synonyms:hexahydrocurcumin

Chemical Property of Hexahydrocurcumin

Chemical Property:

• Vapor Pressure: 2.31E-16mmHg at 25°C
• Melting Point: 80-82℃
• Boiling Point: 622.6oC at 760 mmHg
• PKA: 10.02±0.20(Predicted)
• Flash Point: 218.3oC
• PSA: 96.22000
• Density: 1.226g/cm3
• LogP: 3.00050
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), DCM, DMSO
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 374.17293854
• Heavy Atom Count: 27
• Complexity: 442

Purity/Quality:

98%Min ^*data from raw suppliers

Hexahydrocurcumin analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCC(CC(=O)CCC2=CC(=C(C=C2)O)OC)O)O
• Description: Hexahydrocurcumin is a natural product and glucuronide metabolite of curcumin that has anti-inflammatory, antioxidant, and anticancer properties. It reduces prostaglandin E2 (PGE2) production stimulated by phorbol 12-myristate 13-acetate (PMA; ) by 37% in human colonic epithelial cells when used at a concentration of 20 μM. Hexahydrocurcumin (3.125-25 μM) inhibits overproduction of nitric oxide induced by LPS in RAW 264.7 macrophage cells in a concentration-dependent manner. It does not affect LPS-induced cytokine release but inhibits LPS-induced iNOS and COX-2 upregulation and NF-κB activation when used at a concentration of 50 μM. Hexahydrocurcumin prevents the formation of aberrant crypt foci in a dimethylhydrazine rat model of colon cancer and potentiates the effect of 5-fluorouracil .
• Uses: Hexahydrocurcumin is an intermediate in the synthesis of Gingerenone A (G387500) which is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders.

Technology Process of Hexahydrocurcumin

There total 34 articles about Hexahydrocurcumin 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: 84.0%

curcumin (458-37-7) → hexahydrocurcumin (36062-05-2,39886-84-5,93559-28-5,100667-55-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; for 8h;

DOI:10.1016/j.bbadis.2021.166317

Reference yield: 80.0%

(S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(methoxymethoxy)heptan-3-one (1360110-05-9) → (S)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (36062-05-2,93559-28-5,100667-55-8,39886-84-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.010

Reference yield: 69.0%

curcumin (458-37-7) → 1,7-bis(3-hydroxy-4-methoxyphenyl)heptane-3,5-dione (70727-06-9) + hexahydrocurcumin (36062-05-2,39886-84-5,93559-28-5,100667-55-8) + 3,5-dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane (36062-07-4,112494-41-4,135413-63-7)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; ethyl acetate;

DOI:10.1016/j.bmcl.2013.11.039

upstream raw materials:

curcumin

curcumin

4-(2-{2-[4-(4-Benzyloxy-3-methoxy-phenyl)-2-hydroxy-butyl]-[1,3]dioxolan-2-yl}-ethyl)-2-methoxy-phenol

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

Downstream raw materials:

1,7-bis-(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one

(3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane

(3S,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane

Acetic acid 4-[(3S,5R)-3,5-diacetoxy-7-(4-acetoxy-3-methoxy-phenyl)-heptyl]-2-methoxy-phenyl ester

Refernces

• 1、 ?tv?s, Sándor B.,Balogh, Gy?rgy T.,Fül?p, Ferenc,Girst, Gábor,Hunyadi, Attila. "Pharmacokinetics-driven evaluation of the antioxidant activity of curcuminoids and their major reduced metabolites—a medicinal chemistry approach". . . Retrieved 2021/06/30.
• 2、 -. "FOOD COMPOSITION FOR PREVENTING OBESITY, PHARMACEUTICAL COMPOSITION FOR TREATING OBESITY, AND ANIMAL MEDICINE FOR TREATING OBESITY, CONTAINING GINGERNONE A". . . Retrieved 2016/04/10.