149579-07-7

Basic information

• Product Name: TETRAHYDRODEMETHOXYDIFERULOYLMETHANE
• Synonyms: TETRAHYDRODEMETHOXYDIFERULOYLMETHANE
• CAS NO: 149579-07-7
• Molecular Formula: C20H22O5
• Molecular Weight: 342.38568
• Mol File: 149579-07-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 543.821°C at 760 mmHg
• Flash Point: 192.417°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: TETRAHYDRODEMETHOXYDIFERULOYLMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDRODEMETHOXYDIFERULOYLMETHANE(149579-07-7)
• EPA Substance Registry System: TETRAHYDRODEMETHOXYDIFERULOYLMETHANE(149579-07-7)

Safety Data

• Hazardous Substances Data: 149579-07-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H22O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-3,6-8,11-12,21,24H,4-5,9-10,13H2,1H3

Upstream product

• 22608-11-3 demethoxycurcumin 
• 1924-25-0 (5E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione 
• 98885-92-8 demethoxycurcumin 

Downstream Products

• 908094-05-3 5-hydroxy-7-(4-hydroxyl-3-methoxyphenyl)-1-(4-hydroxylphenyl)-3-heptanone 
• 138870-92-5 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptan-3-one 
• 648916-74-9 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hept-4-en-3-one 

Relevant articles and documents

Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells

The chemically modified analogs, the demethy-lated analogs 4-6, the tetrahydro analogs 7-9 and the hexahydro analogs 10-12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O- demethyldemethoxycurcumin (6) are the two most potent compounds that inhibited NO production. The analogs 5 and 6 were twofold and almost twofold more active than the parent curcuminoids 1 and 2, respectively. Moreover, the mRNA expression level of inducible NO synthase was inhibited by these two compounds. The strong neuroprotective activity of analogs 5 and 6 provide potential alternative compounds to be developed as therapeutics for neurological disorders associated with activated microglia. The Japanese Society of Pharmacognosy and Springer 2011.

A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 °C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain.