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

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2025-11-18 23:31:41 UTC
Primary IDFDB011862
Secondary Accession Numbers
  • FDB008773
Chemical Information
FooDB Name3-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 Number3413-15-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(S)-(-)-3-ButylphthalideMeSH
3-N-ButylphthalideMeSH
N-ButylphthalideMeSH
L-NBP CPDMeSH
ColforsinHMDB
ForskolinHMDB
1(3H)-Isobenzofuranone, 3-butyl-biospider
3-Butyl-phthalidebiospider
3-Butylphthalidebiospider
3-Butylphthalide, 8CIdb_source
3-n-Butylphthalidebiospider
Butylphthalidebiospider
FEMA 3334db_source
N-butylphthalidebiospider
NBPbiospider
Phthalide, 3-butyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP3ALOGPS
logP3.36ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.78 m³·mol⁻¹ChemAxon
Polarizability21.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H14O2
IUPAC name3-butyl-1,3-dihydro-2-benzofuran-1-one
InChI IdentifierInChI=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 KeyHJXMNVQARNZTEE-UHFFFAOYSA-N
Isomeric SMILESCCCCC1OC(=O)C2=C1C=CC=C2
Average Molecular Weight190.2384
Monoisotopic Molecular Weight190.099379692
Classification
Description Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentBenzofuranones
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.76%; H 7.42%; O 16.82%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.80HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-3-Butyl-1(3H)-isobenzofuranone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9700000000-a60db6c280b6eaa60eb1Spectrum
Predicted GC-MS(S)-3-Butyl-1(3H)-isobenzofuranone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-d904c229292bb1e0158f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5900000000-eaf37a164a20b7e346332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9100000000-91e07caebaab8b4c09f12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-2146ee7ffa48beef55f92016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0900000000-51103c4450b69b0a893b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f97-3900000000-0a47a98e87c08ae044bb2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-f778b0a41733b7c667b12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-87c178dc0d4e990c1b992021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-5900000000-a54a8ddd5cde35355e322021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-00db18150d760fe6b5762021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-5900000000-8734ee9e85c67c76ae912021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-9200000000-20cd801d5d09a00b292e2021-09-25View Spectrum
NMRNot Available
ChemSpider ID55293
ChEMBL IDCHEMBL248594
KEGG Compound IDC17854
Pubchem Compound ID61361
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32064
CRC / DFC (Dictionary of Food Compounds) IDHBG01-I:HBG01-I
EAFUS ID429
Dr. Duke ID3-N-BUTYL-PHTHALIDE|BUTYL-PHTHALIDE|N-BUTYLPHTHALIDE|3-BUTYLPHTHALIDE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1013781
SuperScent IDNot Available
Wikipedia IDButylphthalide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-arrhythmic38070 An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.DUKE
Anti-constrictive52217 An agent that relaxes and dilates blood vessels, airways, or other smooth muscle tissues, reducing constriction and improving blood flow or breathing. Therapeutically, it's used to manage conditions like hypertension, asthma, and angina, helping to alleviate symptoms and prevent complications.DUKE
Anti convulsant52217 An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-stress52217 An agent that reduces stress symptoms, commonly used in managing anxiety disorders, promoting relaxation, and mitigating the biological effects of stress on the body, such as hypertension and immune suppression, with therapeutic applications in mental health and key medical uses in cardiology and neurology.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti uterocontractant52217 An agent that relaxes the uterus, preventing contractions. It is used therapeutically to manage preterm labor, cervical ripening, and other obstetric conditions, helping to prolong pregnancy and reduce complications.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
Hypoglycemic35526 An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
LipolyticAn agent that stimulates hydrolysis of fats into fatty acids and glycerol, playing a key biological role in fat metabolism. Therapeutically, lipolytics have applications in managing obesity and hypertriglyceridemia, with medical uses including weight loss and improving lipid profiles.DUKE
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
TracheorelaxantAn agent that relaxes tracheal smooth muscle, easing breathing by reducing airway resistance, commonly used to treat respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD).DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
celery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).