Showing Compound 3-Butylidene-1(3H)-isobenzofuranone (FDB008768)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:14 UTC

Update date

2019-11-26 03:03:09 UTC

Primary ID

FDB008768

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Butylidene-1(3H)-isobenzofuranone

Description

3-Butylidene-1(3H)-isobenzofuranone, also known as 3-butylidenephthalide, belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position. 3-Butylidene-1(3H)-isobenzofuranone is a celery, herbal, and lovage tasting compound. 3-Butylidene-1(3H)-isobenzofuranone is found, on average, in the highest concentration within lovages (Levisticum officinale). 3-Butylidene-1(3H)-isobenzofuranone has also been detected, but not quantified in, celery stalks (Apium graveolens var. dulce) and wild celeries (Apium graveolens). This could make 3-butylidene-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Butylidene-1(3H)-isobenzofuranone.

CAS Number

551-08-6

Structure

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

Synonyms

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Synonym	Source
(e)-3-Butylidenephthalide	HMDB
(Z)-3-Butylidenephthalide	ChEMBL, HMDB
3-Butylidene-1(3H)-isobenzofuranone	MeSH
3-Butylidene-phthalide	HMDB
3-Butylidenephthalide	MeSH
3-Butylidenephthalide, (E)-	biospider
3-Butylidenephthalide, 8ci	HMDB
3-Butylidenephthalide, 8CI	db_source
Butylidenephthalide	MeSH
FEMA 3333	HMDB

Showing 1 to 10 of 12 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.38	ALOGPS
logP	3.02	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-7.1	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	2	ChemAxon
Refractivity	56.28 m³·mol⁻¹	ChemAxon
Polarizability	20.37 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

C12H12O2

IUPAC name

(3E)-3-butylidene-1,3-dihydro-2-benzofuran-1-one

InChI Identifier

InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+

InChI Key

WMBOCUXXNSOQHM-DHZHZOJOSA-N

Isomeric SMILES

CCC\C=C1\OC(=O)C2=CC=CC=C12

Average Molecular Weight

188.2225

Monoisotopic Molecular Weight

188.083729628

Classification

Description

Belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Isobenzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Benzenoid
Enol ester
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

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 76.57%; H 6.43%; O 17.00%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(Z)-Butylidenephthalide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002f-6900000000-732e96716c41a04fb3fa	Spectrum
Predicted GC-MS	(Z)-Butylidenephthalide, 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	splash10-000i-2900000000-8ae9e1a01eaa6fecf1b4	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5900000000-f3bbe4d26792fe9d6533	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9100000000-3c7f96234901b9d9e933	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-95d702d187abea157d2e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-0900000000-551a78bdb3bd751e3988	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-3900000000-f234896ae771c1f4eb20	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-0efd5563391c35d6cf2a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-03cc6cd126f49f632654	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2900000000-fe566d20babcbcbca0ce	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-18975ec6e59c754be61e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0900000000-6eebf85402bef8698a16	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar9-9600000000-82c62a98392b22d4237c	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C16924

Pubchem Compound ID

642376

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

DWL20-L:DWL20-L

EAFUS ID

415

Dr. Duke ID

BUTYLIDENE-PHTHALIDE

BIGG ID

Not Available

KNApSAcK ID

C00029489

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1027291

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

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Food	Content Range	Average	Reference

Celery stalks	Expected but not quantified	Not Available	Jian Tang, Yuangang Zhang, Thomas G. Hartman, Robert T. Rosen, and Chi Tang Ho. Free and glycosidically bound volatile compounds in fresh celery (Apium graveolens L.). J. Agric. Food Chem. 1990, 38, 10, 1937-1940
Lovage	84.400 - 84.400 mg/100 g	84.400 mg/100 g	DUKE
Wild celery	Expected but not quantified	Not Available	DUKE

Showing 1 to 3 of 3 entries

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
anti anginal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti platelet			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
arteriodilator			DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
emmenagogue			DUKE

Showing 1 to 10 of 10 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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