Showing Compound Dihydrocurcumin (FDB008164)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:57 UTC

Update date

2020-02-24 19:10:50 UTC

Primary ID

FDB008164

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dihydrocurcumin

Description

Dihydrocurcumin 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. Dihydrocurcumin exists in all living organisms, ranging from bacteria to humans. Dihydrocurcumin is found, on average, in the highest concentration within turmerics (Curcuma longa). Dihydrocurcumin has also been detected, but not quantified in, herbs and spices. This could make dihydrocurcumin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Dihydrocurcumin.

CAS Number

76474-56-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(4Z,6E)-5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one	MeSH
5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4,6-heptadien-3-one, 9ci	HMDB
5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-4,6-heptadien-3-one, 9CI	db_source
Dihydrocurcumin	db_source
Letestuianin b	HMDB, MeSH
Letestuianin B	db_source

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	3.5	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	102.72 m³·mol⁻¹	ChemAxon
Polarizability	38.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H22O6

IUPAC name

(1E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dione

InChI Identifier

InChI=1S/C21H22O6/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/h3,5-7,9-12,24-25H,4,8,13H2,1-2H3/b7-3+

InChI Key

MUYJSOCNDLUHPJ-XVNBXDOJSA-N

Isomeric SMILES

COC1=CC(\C=C\C(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O

Average Molecular Weight

370.3958

Monoisotopic Molecular Weight

370.141638436

Classification

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

Substituents

Curcumin
Gingerdione
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1,3-diketone
Phenol
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enone (CHEBI:67262 )
polyphenol (CHEBI:67262 )
beta-diketone (CHEBI:67262 )
diarylheptanoid (CHEBI:67262 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 68.10%; H 5.99%; O 25.92%	DFC
Melting Point	Mp 179-180°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dihydrocurcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00tb-0931000000-0aef32f9ba1b838b6b8e	Spectrum
Predicted GC-MS	Dihydrocurcumin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fdk-2090310000-a0936717c59264d87b24	Spectrum
Predicted GC-MS	Dihydrocurcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0219000000-06c7320ae4e189b56209	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0923000000-43bf1b1d0b95016c2bbc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004s-2911000000-88a84f0715dc689ca494	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0109000000-9bc993d3ed96a784068a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0729000000-a5d214e2be9886f4d147	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005m-1914000000-5497d1b9173730d18438	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0319000000-ef529cda99b8f857010a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1934000000-288916b47b086fc61574	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001r-1931000000-83daabac7f9c9e011594	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0209000000-3d54c7f6d8d31322eb7e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0945000000-fc4c460aaf95131a8e59	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004r-1933000000-d2b1f6d127a8454affdb	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

8604661

ChEMBL ID

CHEMBL1254325

KEGG Compound ID

Not Available

Pubchem Compound ID

10429233

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31552

CRC / DFC (Dictionary of Food Compounds) ID

HFR53-E:DCY22-Q

EAFUS ID

Not Available

Dr. Duke ID

DIHYDROCURCUMIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Turmeric	5.700 - 5.700 mg/100 g	5.700 mg/100 g	DUKE

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Dihydrocurcumin (FDB008164)

Structure for FDB008164 (Dihydrocurcumin)