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Record Information
Version	2.0
Creation Date	2012-10-10 12:20:21 -0600
Update Date	2015-09-13 15:15:34 -0600
Secondary Accession Numbers	ECMDB23171
Identification
Name:	Tetrahydrocurcumin
Description	Tetrahydrocurcumin (THC), is a product of the metabolism of curcumin by the enzyme NADPH-dependent curcumin reductase. Curcumin is a yellow, polyphenolic pigment, derived from the rhizomes of a plant (Curcuma longa Linn). It is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family and is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods. In E. coli curcumin is a substrate for the enzyme NADPH-dependent curcumin reductase which catalyzes the metal-independent reduction of curcumin to dihydrocurcumin (DHC) as an intermediate product, followed by further reduction to tetrahydrocurcumin (THC) as an end product. Tetrahydrocurcumin (THC) exhibits many of the same physiologic and pharmacological activities as curcumin and in some systems may exert greater antioxidant activity than curcumin [PMID:21467222]
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0x5e0c16c> Close
Synonyms:	1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione
Chemical Formula:	C21H24O6
Weight:	Average: 372.4117 Monoisotopic: 372.1572885
InChI Key:	LBTVHXHERHESKG-UHFFFAOYSA-N
InChI:	InChI=1S/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3
CAS number:	36062-04-1
IUPAC Name:	1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Traditional IUPAC Name:	tetrahydrocurcumin
SMILES:	COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O
Chemical Taxonomy
Description	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.
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Diarylheptanoids
Sub Class	Linear diarylheptanoids
Direct Parent	Curcuminoids
Alternative Parents	Gingerdiones Phenoxy compounds Methoxybenzenes Anisoles Beta-diketones Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Ketones Organic oxides Hydrocarbon derivatives
Substituents	Curcumin Gingerdione Methoxyphenol Anisole Phenoxy compound Phenol ether Methoxybenzene Phenol 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether 1,3-diketone Benzenoid 1,3-dicarbonyl compound Monocyclic benzene moiety Ketone Ether Organooxygen compound Organic oxygen compound Carbonyl group Hydrocarbon derivative Organic oxide Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	polyphenol (CHEBI:67263 ) beta-diketone (CHEBI:67263 ) diarylheptanoid (CHEBI:67263 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	95 - 97 C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0056 g/L ALOGPS logP 3.51 ALOGPS logP 3.96 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 9.31 ChemAxon pKa (Strongest Basic) -4.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 93.06 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 101.62 m³·mol⁻¹ ChemAxon Polarizability 39.42 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	Tetrahydrocurcumin + 2 NADP > curcumin +2 NADPH Dihydrocurcumin + Hydrogen ion + NADPH + Dihydrocurcumin + NADPH > Tetrahydrocurcumin + NADP
SMPDB Pathways:	curcumin degradation PW001896
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-004r-0910000000-fa5f9c88947d04535eb3 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-0umr-9410140000-19c50b651dca5f38ec3c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-0209000000-7dfd4c091aad667f4f26 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00bi-0922000000-4172923a1d3dfd5cefd5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004r-1911000000-8ecd77e0bdc5eeb2914c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0109000000-cc999937febfc38f47c1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00di-0639000000-3347b9d7105791a849f6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-05ru-5986000000-5bfd0dc38ca2bb0b9efe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-1049000000-140fb262cdbb389db98d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00ks-6962000000-30302cd971363baba315 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000i-3930000000-7ddc098840a945474666 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-0219000000-9f478fd39c93a8ba2530 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0935000000-5253debe0acf5be8a731 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1921000000-1003e2c392e655b3af0f View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Hassaninasab, A., Hashimoto, Y., Tomita-Yokotani, K., Kobayashi, M. (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108:6615-6620. Pubmed: 21467222 Heath DD, Pruitt MA, Brenner DE, Begum AN, Frautschy SA, Rock CL: Tetrahydrocurcumin in plasma and urine: quantitation by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 25;824(1-2):206-12. Pubmed: 16061427
Synthesis Reference:	Lampe, W.; Smolinska, J. Ability of the two methyl groups of the quaternary base of 3,5-dimethylisoxazole to couple. III. Bull. acad. polon. sci., Ser. sci. chim., geol. et geograph (1958), 6 481-6.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 67263 HMDB ID HMDB05789 Pubchem Compound ID 124072 Kegg ID Not Available ChemSpider ID 110569 Wikipedia ID Not Available BioCyc ID Not Available