112494-41-4

Upstream product

• 98885-93-9 curcumin 
• 458-37-7 curcumin 
• 36062-04-1 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione 
• 115945-70-5 glucose 
• 147556-16-9 curcumin 
• 1370262-66-0 (1E,3R,5R,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-diol 
• 1276003-65-6 (1E,3R,5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-diol 
• 1360110-05-9 (S)-1,7-bis(4-hydroxy-3-methoxyphenyl)-5-(methoxymethoxy)heptan-3-one 
• 1360109-97-2 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxypentan-1-one 
• 1360109-98-3 (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-(methoxymethoxy)pentan-1-one 
• 1360110-00-4 (S)-5-(4-(benzyloxy)-3-methoxyphenyl)-3-(methoxymethoxy)pentanal 
• 1360110-02-6 (S)-1,7-bis(4-(benzyloxy)-3-methoxyphenyl)-5-(methoxymethoxy)hept-1-yn-3-one 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 57371-44-5 3-<4-(benzyloxy)-3-methoxyphenyl>propan-1-ol 

Downstream Products

• 138922-33-5 Acetic acid 4-[(3S,5S)-3,5-diacetoxy-7-(4-acetoxy-3-methoxy-phenyl)-heptyl]-2-methoxy-phenyl ester 
• 55094-79-6 (3S,5S)-1,7-Bis-(3,4-dimethoxy-phenyl)-heptane-3,5-diol 

Relevant academic research and scientific papers

Diarylheptanoids from the rhizomes of Zingiber officinale

Seven new diarylheptanoids, i.e., (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane, (3R,5S)-3-acetoxy-5-hydroxy-1,7-bis(4-hydroxy-3- methoxyphenyl)heptane, (3R,5S)-3,5-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)- 7-(4-hydroxy-3-methoxyphenyl)heptane, (5S)-5-acetoxy-1,7-bis(4-hydroxy-3- methoxyphenyl)heptan-3-one, 5-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4- hydroxy-3-methoxyphenyl)heptan-3-one, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7- (3,4-dihydroxy-5-methoxy-phenyl)heptan-3-one and 1,5-epoxy-3-hydroxy-1-(4- hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane were isolated from the rhizomes of Chinese ginger (Zingiber officinale Roscoe), along with 25 known compounds, i.e., 8 diarylheptanoids, 14 gingerol analogs, a diterpene and 2 steroids. Their structures were elucidated by spectroscopic and chemical methods.

Influence of side-chain changes on histone deacetylase inhibitory and cytotoxicity activities of curcuminoid derivatives

Using curcuminoids as lead compounds, fifty-nine curcuminoid derivatives with different side chains at the phenolic moiety were synthesized. All compounds were investigated for their histone deacetylase (HDAC) inhibitory activities. The potent pan-HDAC in

Phenolic and enolic hydroxyl groups in curcumin: Which plays the major role in scavenging radicals?

The aim of this work is to clarify the antioxidant abilities of phenolic and enolic hydroxyl groups in curcumin. 1,7-Bis(4-benzyloxy-3-methoxyphenyl)-1, 6-heptadiene-3,5-dione (BEC), 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol (OHC), 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dlone (THC), and 1,7-bis(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione (BDC) are synthesized to determine the antioxidant activities by using antiradical assays against 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical, galvinoxyl radical, and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cation radical (ABTS?+) and by protecting DNA and erythrocyte against 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) induced oxidation. The phenolic hydroxyl is the main group for curcumin to trap DPPH, galvinoxyl, and ABTS?+ radicals. The conjugative system between enolic and phenolic hydroxyl groups is beneficial for curcumin to protect erythrocytes against hemin-induced hemolysis and to protect DNA against AAPH-lnduced oxidation, but is not beneficial for curcumin to protect erythrocytes against AAPH-induced hemolysis. More hydroxyl groups enhance the antioxidant effectiveness of curcumin in the experimentel systems employed herein. Therefore, curcumin acts as an antioxidant through the phenolic hydroxyl group.

Pharmacokinetics-driven evaluation of the antioxidant activity of curcuminoids and their major reduced metabolites—a medicinal chemistry approach

Curcuminoids are the main bioactive components of the well-known Asian spice and traditional medicine turmeric. Curcuminoids have poor chemical stability and bioavailability; in vivo they are rapidly metabolized to a set of bioreduced derivatives and/or glucuronide and sulfate conjugates. The reduced curcuminoid metabolites were also reported to exert various bioactivities in vitro and in vivo. In this work, we aimed to perform a comparative evaluation of curcuminoids and their hydrogenated metabolites from a medicinal chemistry point of view, by determining a set of key pharmacokinetic parameters and evaluating antioxidant potential in relation to such properties.Reduced metabolites were prepared from curcumin and demethoxycurcumin through continuous-flow hydrogenation. As selected pharmacokinetic parameters, kinetic solubility, chemical stability, metabolic stability in human liver microsomes, and parallel artificial membrane permeability assay (PAMPA)-based gastrointestinal and blood-brain barrier permeability were determined. Experimentally determined logP for hydrocurcumins in octanol-water and toluene-water systems provided valuable data on the tendency for intramolecular hydrogen bonding by these compounds. Drug likeness of the compounds were further evaluated by a in silico calculations. Antioxidant properties in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and oxygen radical absorbance capacity (ORAC) assays were comparatively evaluated through the determination of ligand lipophilic efficiency (LLE). Our results showed dramatically increased water solubility and chemical stability for the reduced metabolites as compared to their corresponding parent compound. Hexahydrocurcumin was found the best candidate for drug development based on a complex pharmacokinetical comparison and high LLE values for its antioxidant properties. Development of tetrahydrocurcumin and tetrahydro-demethoxycurcumin would be limited by their very poor metabolic stability, therefore such an effort would rely on formulations bypassing first-pass metabolism.

Use of curcumin derivative

The invention provides the use of a curcumin derivative. The use of the curcumin derivative shown in a formula I (please see the specification for the formula), or salts of the curcumin derivative inthe preparation of drugs of anti-inflammatory diseases and/or a COX inhibitor is particularly provided. The curcumin derivative has good COX inhibitory activity and anti-inflammatory activity and canbe used for preparing the COX inhibitor and anti-inflammatory drugs. Compound 6 and compound 7 have the best effects on COX-2 inhibitory activity and anti-inflammatory activity and can be used for preparing a COX-2 inhibitor and the anti-inflammatory drugs.

A PERSONAL CARE COMPOSITION

Disclosed is a personal care composition and a method of providing antiperspirant and anti-inflammation using certain curcuminoid derivatives. The composition comprises: (i) a compound of the Formula 1 Ar-CHnCHn-X.C(R)2-X.CHnCHn-Ar (Formula 1) wherein Ar is a substituted or unsubstituted phenyl group; R is H or CH3; X is CH(OH) group or C=O group; n has the value 1 or 2; and, (ii) a topically acceptable base comprising at least 0.1% of a fragrance wherein, when n=1, the compound of (Formula 1) is 1E,6E)-1,7-bis(3,4- dimethoxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione (Formula 2), and when n=2, the compound of (Formula 1) is 1,7-bis(4-hydroxy-3- methoxyphenyl) heptane-3,5-diol (Formula 4) or is 1,7-bis (3,4-dimethoxyphenyl)-4,4-dimethylheptane-3,5-diol (Formula 5).

Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1

To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp2 carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation.

Synthesis of gingerol and diarylheptanoids

The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.

Microbial conversion of curcumin into colorless hydroderivatives by the endophytic fungus Diaporthe sp. associated with Curcuma longa

We investigated the microbial conversion of curcumin (1) using endophytic fungi associated with the rhizome of Curcuma longa (Zingiberaceae). We found that Diaporthe sp., an endophytic filamentous fungus, converts curcumin (1) into four colorless derivatives, namely (3R,5R)-tetrahydrocurcumin (2), a novel (3R,5S)-hexahydrocurcumin (3) named neohexahydrocurcumin, (3S,5S)- octahydrocurcumin (4) and meso-octahydrocurcumin (5).

Microbial transformation of curcumin by Rhizopus chinensis

Curcumin (1) is a potent antioxidant and antitumor natural product. In spite of its efficacy and safety, its clinical use is hindered mainly by poor water solubility and bioavailability. Structural modification to introduce hydrophilic functions is a promising approach to resolve this problem. In the present study we first found that curcumin could be efficiently converted into glucosides by filamentous fungi including Rhizopus chinensis IFFI 03043, Absidia coerulea AS 3.3389 and Cunninghamella elegans AS 3.1207. Curcumin 4′-O-β-d-glucoside (2), together with hexahydrocurcumin (3), was isolated from a preparative-scale biotransformation with R. chinensis IFFI 03043 and characterized fully by NMR and MS. A time-course study revealed that curcumin could be efficiently converted into curcumin 4′-O-β-d- glucoside within 8 h when administered at 0.05 mmol L-1 and the productivity was 57%. Additionally, the biotransformation products of curcumin by different fungal strains were analyzed by LC/MS. At least 15 metabolites were detected, and the predominant biotransformation reaction was glucosylation. This study provides a simple, efficient and less expensive approach for the preparation of curcumin glucosides. The introduction of the glucosyl function might be able to enhance the bioavailability of curcumin.