| Common Name |
Bisdemethoxycurcumin
| Description |
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 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
Bis(4-hydroxycinnamoyl)methaneChEBI
Bis(P-hydroxycinnamoyl)methaneChEBI
Curcumin IIIChEBI
DidemethoxycurcuminChEBI
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)HMDB
Bis-demethoxycurcuminHMDB
| Chemical Formlia |
C19H16O4
| Average Molecliar Weight |
308.3279
| Monoisotopic Molecliar Weight |
308.104859
| IUPAC Name |
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
| Traditional Name |
bisdemethoxycurcumin
| CAS Registry Number |
24939-16-0
| SMILES |
OC1=CC=C(C=CC(=O)CC(=O)C=CC2=CC=C(O)C=C2)C=C1
| InChI Identifier |
InChI=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/h1-12,20-21H,13H2/b11-5+,12-6+
| InChI Key |
PREBVFJICNPEKM-YDWXAUTNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (ferlioyl) chromophores joined by a methylene group.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Diarylheptanoids
| Direct Parent |
Curcuminoids
| Alternative Parents |
Hydroxycinnamic acids and derivatives
Styrenes
Beta-diketones
1-hydroxy-2-unsubstituted benzenoids
Enones
Acryloyl compounds
Ketones
Organic oxides
Hydrocarbon derivatives
| Substituents |
Bis-desmethoxycurcumin
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
1,3-diketone
1,3-dicarbonyl compound
Benzenoid
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
enone (CHEBI:71045 )
polyphenol (CHEBI:71045 )
beta-diketone (CHEBI:71045 )
diarylheptanoid (CHEBI:71045 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Food
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.011 mg/mLALOGPS
logP3.46ALOGPS
logP4.44ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.88 m3·mol-1ChemAxon
Polarizability32.58 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
715
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB011961
| KNApSAcK ID |
Not Available
| Chemspider ID |
4474770
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02114
| Metagene Link |
HMDB02114
| METLIN ID |
Not Available
| PubChem Compound |
5315472
| PDB ID |
Not Available
| ChEBI ID |
269845
Product: Propoxycaine (hydrochloride)
References |
| Synthesis Reference |
Park So-Young; Kim Darrick S H L Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimers disease. Journal of natural products (2002), 65(9), 1227-31. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Chainani-Wu N: Safety and anti-inflammatory activity of curcumin: a component of tumeric (Curcuma longa). J Altern Complement Med. 2003 Feb;9(1):161-8. [PubMed:12676044 ]
|
PMID: 18266975