ChemFOnt: Showing chemical card for 4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan (CFc000283024)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:54 UTC

Chemfont ID

CFc000283024

Molecule Identification

Common Name

4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan

Definition

4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan, also known as 34-divanillyltetrahydrofuran or dv-tetrahydrofuran, is a member of the class of compounds known as 9,9'-epoxylignans. 9,9'-epoxylignans are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan can be found in sesame, which makes 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DV-Tetrahydrofuran	MeSH
34-Divanillyltetrahydrofuran	ChEMBL

Chemical Formula

C₂₀H₂₄O₅

Average Molecular Weight

344.4016

Monoisotopic Molecular Weight

344.162373878

IUPAC Name

4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol

Traditional Name

3,4-divanillyltetrahydrofuran

CAS Registry Number

34730-78-4

SMILES

COC1=CC(CC2COCC2CC2=CC(OC)=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3

InChI Key

ROGUIJKVZZROIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

9,9'-epoxylignans

Alternative Parents

Substituents

9,9p-epoxylignan
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303508)

Food

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.13	ALOGPS
logP	3.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.96	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.78 m³·mol⁻¹	ChemAxon
Polarizability	36.55 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0303508

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015354

KNApSAcK ID

Not Available

Chemspider ID

158474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182210

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan (CFc000283024)

MOL for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

3D MOL for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

3D SDF for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

3D-SDF for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

PDB for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

3D PDB for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

SMILES for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

INCHI for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

Structure for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)

3D Structure for CFc000283024 (4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan)