AFCDB: Eriodictyol (FDB000688)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-04-21 18:01:53 UTC

Primary ID

FDB000688

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Eriodictyol

Description

3',4',5,7-Tetrahydroxyflavanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. 3',4',5,7-Tetrahydroxyflavanone is an extremely weak basic (essentially neutral) compound (based on its pKa). 3',4',5,7-Tetrahydroxyflavanone has been detected, but not quantified in, several different foods, such as common oregano, common thymes, parsley, sweet basils, and tarragons. This could make 3',4',5,7-tetrahydroxyflavanone a potential biomarker for the consumption of these foods.

CAS Number

552-58-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	2.15	ALOGPS
logP	2.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.27 m³·mol⁻¹	ChemAxon
Polarizability	28.22 Å³	ChemAxon
Number of Rings	3	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

C15H12O6

IUPAC name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2

InChI Key

SBHXYTNGIZCORC-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=C(O)C=C1

Average Molecular Weight

288.255

Monoisotopic Molecular Weight

288.063388106

Classification

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Catechol
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 62.50%; H 4.20%; O 33.30%	DFC
Melting Point	Mp 267°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.07 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.02	PERRISSOUD,D & TESTA,B (1986)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	326 (e 140) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Eriodictyol, 5 TMS, GC-MS Spectrum	splash10-00o3-2964120000-760c54cbe3d97e214b89	Spectrum
GC-MS	Eriodictyol, 1 MEOX; 4 TMS, GC-MS Spectrum	splash10-05i4-3982160000-16d59df001928b3a3494	Spectrum
Predicted GC-MS	Eriodictyol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0imi-2530190000-6bcd43fd8b42301ed166	Spectrum
Predicted GC-MS	Eriodictyol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0bti-0590000000-341ad13558335b7f1c83	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0390000000-0dc39ca84a3e57cc4553	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0980000000-1ccfe66899ea0c7d03a3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fa9-4900000000-df7958810e2c56540877	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0190000000-a7838f78d4cef436da5f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0390000000-adb9e4c67817a09b2fd0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0apr-5940000000-9fb4bafc0204f514e65f	2016-08-03	View Spectrum