Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:14 UTC |
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Update date | 2019-11-26 03:03:09 UTC |
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Primary ID | FDB008768 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3-Butylidene-1(3H)-isobenzofuranone |
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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. |
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CAS Number | 551-08-6 |
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Structure | |
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Synonyms | Synonym | Source |
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3-Butylidenephthalide | MeSH | Butylidenephthalide | MeSH | N-Butylidenephthalide | MeSH | (Z)-3-Butylidenephthalide | ChEMBL, HMDB | (e)-3-Butylidenephthalide | HMDB | 3-Butylidene-phthalide | HMDB | 3-Butylidenephthalide, 8ci | HMDB | FEMA 3333 | HMDB | Ligusticum lactone | HMDB | 3-Butylidene-1(3H)-isobenzofuranone | MeSH | 3-Butylidenephthalide, (E)- | biospider | 3-Butylidenephthalide, 8CI | db_source |
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Predicted Properties | |
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Chemical Formula | C12H12O2 |
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IUPAC name | (3E)-3-butylidene-1,3-dihydro-2-benzofuran-1-one |
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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+ |
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InChI Key | WMBOCUXXNSOQHM-DHZHZOJOSA-N |
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Isomeric SMILES | CCC\C=C1\OC(=O)C2=CC=CC=C12 |
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Average Molecular Weight | 188.2225 |
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Monoisotopic Molecular Weight | 188.083729628 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Isocoumarans |
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Sub Class | Isobenzofuranones |
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Direct Parent | Isobenzofuranones |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic 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 | C 76.57%; H 6.43%; O 17.00% | DFC |
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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 | (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 |
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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 | splash10-000i-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 |
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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 | C16924 |
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Pubchem Compound ID | 642376 |
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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 | DWL20-L:DWL20-L |
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EAFUS ID | 415 |
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Dr. Duke ID | BUTYLIDENE-PHTHALIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029489 |
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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 | rw1027291 |
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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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Acaricide | 22153 | An agent that kills mites and ticks, used to control infestations and prevent diseases like scabies and tick-borne illnesses. Therapeutically, acaricides are applied topically or systemically to treat parasitic infections, reducing discomfort and preventing disease transmission. Key medical uses include treating acariasis, demodectic mange, and tick paralysis. | DUKE | Anti anginal | 52217 | An agent that reduces angina symptoms by improving blood flow to the heart, commonly used in managing angina pectoris, coronary artery disease, and other cardiovascular conditions, to alleviate chest pain and prevent cardiac complications. | DUKE | Anti-arrhythmic | 38070 | 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-constrictive | 52217 | 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-inflammatory | 35472 | 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 platelet | | An agent that prevents blood clot formation by inhibiting platelet aggregation, used to treat and prevent heart disease, stroke, and other cardiovascular conditions. | DUKE | Anti-spasmodic | 52217 | 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 | Arteriodilator | | An agent that dilates arteries, increasing blood flow to or from the heart, used therapeutically to manage conditions like hypertension, heart failure, and angina, improving cardiac output and reducing blood pressure. | DUKE | Cyclooxygenase inhibitor | 35544 | An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation. | DUKE | Emmenagogue | | An agent that stimulates blood flow in the pelvic area and uterus, often used to induce or regulate menstruation, treating conditions like amenorrhea and dysmenorrhea. | 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.
| lovage |
- 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.
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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 | Not Available |
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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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