ChemFOnt: Showing chemical card for 3-N-Butyl-4,5-dihydrophthalide (CFc000333315)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:17 UTC

Chemfont ID

CFc000333315

Molecule Identification

Common Name

3-N-Butyl-4,5-dihydrophthalide

Definition

3-n-butyl-4,5-dihydrophthalide, also known as nbpa or sedanenolide, is a member of the class of compounds known as isobenzofurans. Isobenzofurans are organic aromatic compounds containing an isobenzofuran moiety. 3-n-butyl-4,5-dihydrophthalide is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-n-butyl-4,5-dihydrophthalide is a herbal tasting compound found in dill, lovage, parsley, and wild celery, which makes 3-n-butyl-4,5-dihydrophthalide a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
NBPA	MeSH
3-N-Butyl-4,5-dihydrophthalide, (S)-isomer	MeSH
Senkyunolide	MeSH
Sedanenolide	MeSH
Senkyunolide a	MeSH

Chemical Formula

C₁₂H₁₆O₂

Average Molecular Weight

192.2542

Monoisotopic Molecular Weight

192.115029756

IUPAC Name

3-butyl-1,3,4,5-tetrahydro-2-benzofuran-1-one

Traditional Name

3-butyl-4,5-dihydro-3H-2-benzofuran-1-one

CAS Registry Number

62006-39-7

SMILES

CCCCC1OC(=O)C2=C1CCC=C2

InChI Identifier

InChI=1S/C12H16O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7,11H,2-4,6,8H2,1H3

InChI Key

ZPIKVDODKLJKIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Odor

Herbal

Disposition

Source

Exogenous

Exogenous (FooDB: )

Food

Vegetable

Root vegetable

Celeriac (FooDB: FOOD00214)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Dill (FooDB: FOOD00013)
Parsley (FooDB: FOOD00131)
Lovage (FooDB: FOOD00100)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (FooDB: )

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.45 g/L	ALOGPS
logP	3.47	ALOGPS
logP	3.07	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.49	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.55 m³·mol⁻¹	ChemAxon
Polarizability	21.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0258235

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003895

KNApSAcK ID

Not Available

Chemspider ID

151725

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 3-N-Butyl-4,5-dihydrophthalide (CFc000333315)

MOL for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

3D MOL for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

3D SDF for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

3D-SDF for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

PDB for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

3D PDB for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

SMILES for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

INCHI for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

Structure for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)

3D Structure for CFc000333315 (3-N-Butyl-4,5-dihydrophthalide)