| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:06:00 UTC |
|---|
| Update date | 2019-11-26 02:59:39 UTC |
|---|
| Primary ID | FDB003895 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | 3-N-Butyl-4,5-dihydrophthalide |
|---|
| 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. |
|---|
| CAS Number | 62006-39-7 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C12H16O2 |
|---|
| IUPAC name | 3-butyl-1,3,4,5-tetrahydro-2-benzofuran-1-one |
|---|
| 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 |
|---|
| Isomeric SMILES | CCCCC1OC(=O)C2=C1CCC=C2 |
|---|
| Average Molecular Weight | 192.2542 |
|---|
| Monoisotopic Molecular Weight | 192.115029756 |
|---|
| Classification |
|---|
| 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 |
|---|
| Ontology |
|---|
| Ontology | No ontology term |
|---|
| Physico-Chemical Properties - Experimental |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Not Available | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | Not Available | |
|---|
| Melting Point | Not Available | |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| 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 |
|---|
| Spectra | |
|---|
| EI-MS/GC-MS | | Type | Description | Splash Key | View |
|---|
| 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 |
|
|---|
| MS/MS | | Type | Description | Splash Key | View |
|---|
| 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 |
|
|---|
| NMR | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | Not Available |
|---|
| ChEMBL ID | Not Available |
|---|
| KEGG Compound ID | Not Available |
|---|
| Pubchem Compound ID | Not Available |
|---|
| 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 | Not Available |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | 3-N-BUTYL-4,5-DIHYDROPHTHALIDE|SENKYUNOLIDE|SEDANENOLIDE |
|---|
| 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 | rw1588071 |
|---|
| 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 |
|---|
| sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | 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.
|
|
|---|
| Files |
|---|
| MSDS | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| 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]
|
|---|
| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
|---|
