ChemFOnt: Showing chemical card for 5-5'-Dehydrodiferulic acid (CFc000281234)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:25 UTC

Chemfont ID

CFc000281234

Molecule Identification

Common Name

5-5'-Dehydrodiferulic acid

Definition

5-5'-dehydrodiferulic acid, also known as 8-O-4'-diferulic acid, belongs to biphenyls and derivatives class of compounds. Those are organic compounds containing to benzene rings linked together by a C-C bond. 5-5'-dehydrodiferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-5'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, semolina, and hard wheat, which makes 5-5'-dehydrodiferulic acid a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-{5'-[(1E)-2-carboxyeth-1-en-1-yl]-2',6-dihydroxy-3',5-dimethoxy-[1,1'-biphenyl]-3-yl}prop-2-enoate	Generator
5-5'-Dehydrodiferulate	Generator
8-O-4'-Diferulic acid	MeSH
8-5'-Diferulic acid	MeSH
8-5'-b Diferulic acid	MeSH

Chemical Formula

C₂₀H₁₈O₈

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

IUPAC Name

(2E)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid

Traditional Name

diferulic acid

CAS Registry Number

None

SMILES

COC1=C(O)C(=CC(\C=C\C(O)=O)=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+

InChI Key

LBQZVWQOPFFQJI-GGWOSOGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ferulic acid (CHEBI:27420 )
Neolignans (C10446 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301718)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)
Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)
Hard wheat (FooDB: FOOD00242)

Cereal product

Semolina (FooDB: FOOD00745)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.02	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	39.09 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

External Links

HMDB ID

HMDB0301718

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5-5'-Dehydrodiferulic acid (CFc000281234)

MOL for CFc000281234 (5-5'-Dehydrodiferulic acid)

3D MOL for CFc000281234 (5-5'-Dehydrodiferulic acid)

3D SDF for CFc000281234 (5-5'-Dehydrodiferulic acid)

3D-SDF for CFc000281234 (5-5'-Dehydrodiferulic acid)

PDB for CFc000281234 (5-5'-Dehydrodiferulic acid)

3D PDB for CFc000281234 (5-5'-Dehydrodiferulic acid)

SMILES for CFc000281234 (5-5'-Dehydrodiferulic acid)

INCHI for CFc000281234 (5-5'-Dehydrodiferulic acid)

Structure for CFc000281234 (5-5'-Dehydrodiferulic acid)

3D Structure for CFc000281234 (5-5'-Dehydrodiferulic acid)