AFCDB: 3-Butyl-1(3H)-isobenzofuranone (FDB011862)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:52 UTC

Update date

2019-11-26 03:05:37 UTC

Primary ID

FDB011862

Secondary Accession Numbers

FDB008773

Chemical Information

FooDB Name

3-Butyl-1(3H)-isobenzofuranone

Description

(S)-3-Butyl-1(3H)-isobenzofuranone, also known as 3-N-butylphthalide or L-NBP CPD, belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone (S)-3-Butyl-1(3H)-isobenzofuranone is a celery and herbal tasting compound (S)-3-Butyl-1(3H)-isobenzofuranone is found, on average, in the highest concentration within wild celeries (Apium graveolens) and lovages (Levisticum officinale) (S)-3-Butyl-1(3H)-isobenzofuranone has also been detected, but not quantified in, several different foods, such as celeriacs (Apium graveolens var. rapaceum), celery stalks (Apium graveolens var. dulce), dills (Anethum graveolens), and parsleys (Petroselinum crispum). This could make (S)-3-butyl-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-3-Butyl-1(3H)-isobenzofuranone.

CAS Number

3413-15-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.065 g/L	ALOGPS
logP	3	ALOGPS
logP	3.36	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	-6.9	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	54.78 m³·mol⁻¹	ChemAxon
Polarizability	21.29 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

Chemical Formula

C12H14O2

IUPAC name

3-butyl-1,3-dihydro-2-benzofuran-1-one

InChI Identifier

InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3

InChI Key

HJXMNVQARNZTEE-UHFFFAOYSA-N

Isomeric SMILES

CCCCC1OC(=O)C2=C1C=CC=C2

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

Classification

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Phthalide
Benzofuranone
Isocoumaran
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 75.76%; H 7.42%; O 16.82%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.80	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-3-Butyl-1(3H)-isobenzofuranone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9700000000-a60db6c280b6eaa60eb1	Spectrum
Predicted GC-MS	(S)-3-Butyl-1(3H)-isobenzofuranone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-d904c229292bb1e0158f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-5900000000-eaf37a164a20b7e34633	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-9100000000-91e07caebaab8b4c09f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-2146ee7ffa48beef55f9	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-0900000000-51103c4450b69b0a893b	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f97-3900000000-0a47a98e87c08ae044bb	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-f778b0a41733b7c667b1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-87c178dc0d4e990c1b99	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-5900000000-a54a8ddd5cde35355e32	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-00db18150d760fe6b576	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-5900000000-8734ee9e85c67c76ae91	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0690-9200000000-20cd801d5d09a00b292e	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

55293

ChEMBL ID

Not Available

KEGG Compound ID

C17854

Pubchem Compound ID

61361

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32064

CRC / DFC (Dictionary of Food Compounds) ID

HBG01-I:HBG01-I

EAFUS ID

429

Dr. Duke ID

3-N-BUTYL-PHTHALIDE|BUTYL-PHTHALIDE|N-BUTYLPHTHALIDE|3-BUTYLPHTHALIDE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1013781

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti constrictive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti uterocontractant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypocholesterolemic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
lipolytic			DUKE
myorelaxant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
tracheorelaxant			DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
celery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

3-Butyl-1(3H)-isobenzofuranone (FDB011862)

Structure for FDB011862 (3-Butyl-1(3H)-isobenzofuranone)