| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:00 UTC |
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| Update date | 2019-11-26 02:59:39 UTC |
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| Primary ID | FDB003895 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 3-N-Butyl-4,5-dihydrophthalide |
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| Description | 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. |
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| CAS Number | 62006-39-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C12H16O2 |
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| IUPAC name | 3-butyl-1,3,4,5-tetrahydro-2-benzofuran-1-one |
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| 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 |
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| InChI Key | ZPIKVDODKLJKIN-UHFFFAOYSA-N |
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| Isomeric SMILES | CCCCC1OC(=O)C2=C1CCC=C2 |
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| Average Molecular Weight | 192.2542 |
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| Monoisotopic Molecular Weight | 192.115029756 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Isobenzofurans |
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| Sub Class | Not Available |
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| Direct Parent | Isobenzofurans |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | Not Available | |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 3-N-Butyl-4,5-dihydrophthalide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004l-9800000000-23619f15e65aaf35ec7b | Spectrum | | Predicted GC-MS | 3-N-Butyl-4,5-dihydrophthalide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-1900000000-a1158f039671b5997791 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000f-4900000000-b662d4b24ab550bdc49e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ktf-9200000000-4895b56617eb5732e535 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-c22a777084b86bdcc0ce | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0007-1900000000-7420f09891f2bf426f6c | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004j-9700000000-45de4fd4ff3df8020719 | 2016-08-03 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | 3-N-BUTYL-4,5-DIHYDROPHTHALIDE|SENKYUNOLIDE|SEDANENOLIDE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | rw1588071 |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference |
- Yi T, Leung KS, Lu GH, Zhang H, Chan K: Identification and comparative determination of senkyunolide A in traditional Chinese medicinal plants Ligusticum chuanxiong and Angelica sinensis by HPLC coupled with DAD and ESI-MS. Chem Pharm Bull (Tokyo). 2005 Nov;53(11):1480-3. Pubmed [Senkyunolide A] [Sructure]
- Qi H, Siu SO, Chen Y, Han Y, Chu IK, Tong Y, Lau AS, Rong J: Senkyunolides reduce hydrogen peroxide-induced oxidative damage in human liver HepG2 cells via induction of heme oxygenase-1. Chem Biol Interact. 2010 Feb 12;183(3):380-9. Epub 2009 Dec 2. Pubmed [Senkyunolide H and I] [Structure]
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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