1.02010-04-08 22:09:55 UTC2019-11-26 03:05:50 UTCFDB011961BisdemethoxycurcuminIsolated from Curcuma zedoaria (zedoary) and Curcuma longa (turmeric)
Bisdemethoxycurcumin is a curcuminoid, a component of tumeric. Tumeric is a spice that comes from the root Curcuma longa, a member of the ginger family, Zingaberaceae. It is bright yellow and has been used as a coloring agent in food in the United States. In India, it has been used for centuries as a spice and a food preservative, and also for its various medicinal properties. In Ayurveda (Indian traditional medicine), tumeric has been used for its medicinal properties for various indications and through different routes of administration. It has been used topically on the skin for wounds, blistering diseases such as pemphigus and herpes zoster, for parasitic skin infections, and for acne. It has been used via oral administration for the common cold, liver diseases, urinary tract diseases, and as a blood purifier. For chronic rhinitis and coryza, it has been used via inhalation. The average intake of tumeric in the diet in India is approximately 2 to 2.5 g in a 60 kg individual. This corresponds to an intake of approximately 60 to 100 mg of curcumin daily. The Food and Drug Administration has classified tumeric among substances Generally Recognized as Safe (GRAS). A large number of in vitro and animal studies have been conducted to evaluate the effect of curcumin on inflammation. It has been found to act at various different levels of the arachadonic acid inflammatory cascade and through effects on various enzymes and cytokines. (PMID: 12676044) [HMDB]. Bisdemethoxycurcumin is found in turmeric and herbs and spices.1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CI1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)Bis-demethoxycurcuminBis(4-hydroxycinnamoyl)methaneBis(p-hydroxycinnamoyl)methaneBisdemethoxycurcuminBisdesmethoxycurcuminCurcumin IIIDidemethoxycurcuminp,p'-DihydroxydicinnamoylmethaneC19H16O4308.3279308.104859(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one24939-16-0O\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-YXAKCQIIROBKOP-HSSGTREWSA-N belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.CurcuminoidsOrganic compoundsPhenylpropanoids and polyketidesDiarylheptanoidsLinear diarylheptanoidsAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoidsAcryloyl compoundsEnolsEnonesHydrocarbon derivativesHydroxycinnamic acids and derivativesKetonesOrganic oxidesStyrenesVinylogous acids1-hydroxy-2-unsubstituted benzenoidAcryloyl-groupAlpha,beta-unsaturated ketoneAromatic homomonocyclic compoundBenzenoidBis-desmethoxycurcuminCarbonyl groupEnolEnoneHydrocarbon derivativeHydroxycinnamic acid or derivativesKetoneMonocyclic benzene moietyOrganic oxideOrganic oxygen compoundOrganooxygen compoundPhenolStyreneVinylogous acidSolidlogp3.50logs-4.35solubility1.38e-02 g/lmelting_pointMp 224°logp4.07pka_strongest_acidic8.64pka_strongest_basic-5.3iupac(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-oneaverage_mass308.3279mono_mass308.104859smilesO\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1formulaC19H16O4inchiInChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-inchikeyYXAKCQIIROBKOP-HSSGTREWSA-Npolar_surface_area77.76refractivity93.2polarizability33.98rotatable_bond_count5acceptor_count4donor_count3physiological_charge0formal_charge0Specdb::MsMs61035Specdb::MsMs61036Specdb::MsMs61037Specdb::MsMs117495Specdb::MsMs117496Specdb::MsMs117497HMDB02114#<Reference:0x000055567567cae8>Herbs and SpicesUnknowngenericTurmericType 1specificCurcuma longa1362171320.4251403.351237.5mg/100 ganti aflatoxin92A substance that diminishes the rate of a chemical reaction.anti Alzheimeran105Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti amyloid-beta109anti angiogenic115An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.anti choleretic179anti inflammatory370A substance that reduces or suppresses inflammation.anti leishmanic388A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti lipoperoxidant407anti mutagenic451anti nitrosating481anti papillomic507A substance that destroys or inhibits replication of viruses.antioxidant502A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.antitumor promoter673A substance that inhibits or prevents the proliferation of neoplasms.DNA-protective887nematicide1141A substance used to destroy pests of the phylum Nematoda (roundworms).nitric-oxide scavenger1168plasmodicide1233quinone-reductase inducer1277sortase-A inhibitor1319A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.topoisomerase-I inhibitor1368A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.topoisomerase-II inhibitor1366A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.