ChemFOnt: Showing chemical card for 5-8'-Dehydrodiferulic acid (CFc000281235)

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

CFc000281235

Molecule Identification

Common Name

5-8'-Dehydrodiferulic acid

Definition

5-8'-dehydrodiferulic acid is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 5-8'-dehydrodiferulic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-8'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, rye, and semolina, which makes 5-8'-dehydrodiferulic acid a potential biomarker for the consumption of these food products. 8,5'-Diferulic acid is a non cyclic type of diferulic acid. It is the predominant diferulic acid in sugar beet pulp. It is also found in barley, in maize bran and rye. 8-5'-Diferulic acid has also been identified to be covalently linked to carbohydrate moieties of the arabinogalactan-protein fraction of gum arabic .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-2-[5-(2-Carboxyeth-1-en-1-yl)-2-hydroxy-3-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate	Generator
5-8'-Dehydrodiferulate	Generator

Chemical Formula

C₂₀H₁₈O₈

Average Molecular Weight

386.3521

Monoisotopic Molecular Weight

386.100167552

IUPAC Name

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

Traditional Name

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

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4-,14-8+

InChI Key

DEPVSDIYICBTJE-FGDQGFBNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
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

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301719)

Food

Cereal and cereal product

Cereal

Cereal product

Semolina (FooDB: FOOD00745)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.04	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.85	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	101.4 m³·mol⁻¹	ChemAxon
Polarizability	37.5 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

HMDB0301719

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000264

KNApSAcK ID

Not Available

Chemspider ID

59696645

KEGG Compound ID

Not Available

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 5-8'-Dehydrodiferulic acid (CFc000281235)

MOL for CFc000281235 (5-8'-Dehydrodiferulic acid)

3D MOL for CFc000281235 (5-8'-Dehydrodiferulic acid)

3D SDF for CFc000281235 (5-8'-Dehydrodiferulic acid)

3D-SDF for CFc000281235 (5-8'-Dehydrodiferulic acid)

PDB for CFc000281235 (5-8'-Dehydrodiferulic acid)

3D PDB for CFc000281235 (5-8'-Dehydrodiferulic acid)

SMILES for CFc000281235 (5-8'-Dehydrodiferulic acid)

INCHI for CFc000281235 (5-8'-Dehydrodiferulic acid)

Structure for CFc000281235 (5-8'-Dehydrodiferulic acid)

3D Structure for CFc000281235 (5-8'-Dehydrodiferulic acid)