Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:20 UTC |
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Update date | 2019-11-26 03:07:32 UTC |
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Primary ID | FDB012752 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Imperatorin |
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Description | Imperatorin, also known as ammidin or marmelosin, belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Imperatorin is found, on average, in the highest concentration within a few different foods, such as parsnips (Pastinaca sativa), lovages (Levisticum officinale), and parsleys (Petroselinum crispum) and in a lower concentration in fennels (Foeniculum vulgare). Imperatorin has also been detected, but not quantified in, several different foods, such as root vegetables, limes (Citrus aurantiifolia), fruits, lemons (Citrus limon), and lambsquarters (Chenopodium album). This could make imperatorin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Imperatorin. |
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CAS Number | 482-44-0 |
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Structure | |
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Synonyms | Synonym | Source |
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8-Isoamylenoxypsoralen | ChEBI | 8-Isopentenyloxypsoralene | ChEBI | 9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g]-1-benzopyran-7-one | ChEBI | Ammidin | ChEBI | Marmelosin | ChEBI | Pentosalen | ChEBI | 5-Hydroxy-8-(1,1-dimethylallyl)psoralen | HMDB | 9-(3-Methyl-2-butenyloxy)-7-oxofuro[3,2-g]chromene | HMDB | 9-(3-Methylbut-2-enyloxy)-7H-furo(3,2-g)chromen-7-one | HMDB | 9-(3-Methylbut-2-enyloxy)furo[3,2-g]chromen-7-one | HMDB | 9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ci | HMDB | 9-[(3-Methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one | HMDB | Marmelide | HMDB | Pentasalen, ban | HMDB | 5-hydroxy-8-(1,1-dimethylallyl)psoralen | biospider | 8-isoamylenoxypsoralen | biospider | 9-[(3-Methyl-2-butenyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9CI | db_source | 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one | biospider | Pentasalen, BAN | db_source |
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Predicted Properties | |
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Chemical Formula | C16H14O4 |
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IUPAC name | 9-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one |
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InChI Identifier | InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 |
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InChI Key | OLOOJGVNMBJLLR-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)=CCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2 |
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Average Molecular Weight | 270.28 |
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Monoisotopic Molecular Weight | 270.089208936 |
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Classification |
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Description | Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Furanocoumarins |
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Direct Parent | Psoralens |
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Alternative Parents | |
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Substituents | - Psoralen
- Benzopyran
- 1-benzopyran
- Benzofuran
- Alkyl aryl ether
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Furan
- Lactone
- Ether
- Oxacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: Biological role: |
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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 71.10%; H 5.22%; O 23.68% | DFC |
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Melting Point | Mp 102° | DFC |
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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 | 301 (e 10600) (MeOH) | DFC |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0udi-3290000000-ccce724ec532a9b1c7ae | 2014-09-20 | View Spectrum | Predicted GC-MS | Imperatorin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0q4l-5490000000-8addd2b7e7d5a89c1657 | Spectrum | Predicted GC-MS | Imperatorin, 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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MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0002-2900000000-a48f50b827aed0c2c74e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-1390000000-a4331e3b6e6ab9ba18c6 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1090000000-25f99a63f2c9348d2805 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-1090000000-205792cde142f77aa94f | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-9080000000-7795cfce5b3fcd729d41 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxu-9540000000-7130c7ebffd168204435 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-6f0805a46d8f54b963d2 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0290000000-cdea20e125d3564dc0ca | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1920000000-a1c90224178c9971284d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0090000000-2e5a86e101fa40f235c9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0190000000-58ef289697c902aee31e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-2950000000-6ffc6c72bc8380498c4d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0gb9-0090000000-e4734d549fe36cc62202 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-3a57f1382615518fb5d1 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uk9-0790000000-eef12a3af90025252e5c | 2021-09-23 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 9797 |
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ChEMBL ID | CHEMBL453805 |
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KEGG Compound ID | C09269 |
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Pubchem Compound ID | 10212 |
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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 | HMDB34376 |
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CRC / DFC (Dictionary of Food Compounds) ID | HKP35-Z:HKP35-Z |
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EAFUS ID | Not Available |
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Dr. Duke ID | IMPERATORIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002477 |
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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 | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Imperatorin |
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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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Anti aflatoxin | 35222 | An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment. | DUKE | Anti-aggregant | | An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots. | DUKE | Anti-alopecic | 52217 | An agent that promotes hair growth and prevents hair loss, commonly used to treat alopecia and other hair-related disorders, by inhibiting dihydrotestosterone (DHT) and stimulating hair follicle growth. | DUKE | Anti convulsant | 52217 | 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-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 leukodermic | | An agent that treats leucoderma (vitiligo), characterized by white skin patches or total loss of pigmentation, promoting skin repigmentation and reducing disease progression, commonly used in dermatology to manage vitiligo and other skin pigmentation disorders. | DUKE | Anti mitotic | | An agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth. | DUKE | Anti-mutagenic | | An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects. | 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 | Antitumor promoter | 35610 | An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis. | DUKE | Anti-vitiligic | | An agent that prevents loss of skin pigmentation, characteristic of vitiligo, promoting melanocyte preservation and repigmentation, used therapeutically to manage vitiligo and other hypopigmentation disorders. | DUKE | Bufocide | | A cardiotonic steroid, bufocide plays a biological role in regulating cardiac function. Therapeutically, it has applications as a cardiostimulant and diuretic. Key medical uses include treating heart failure and edema, with potential in managing certain arrhythmias and hypertension. | DUKE | Calcium antagonist | 48706 | A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Cytochrome-P450 inhibitor | 50183 | An agent that blocks the activity of cytochrome-P450 enzymes, reducing drug metabolism. Therapeutically, it's used to increase the efficacy of certain medications, manage drug interactions, and treat conditions like erectile dysfunction, by inhibiting the breakdown of key drugs, allowing them to remain active in the body for a longer period. | DUKE | Diabetic-macular-edema inhibitor | 35222 | An agent that reduces fluid accumulation in the macula, alleviating vision impairment in diabetic patients. It blocks vascular endothelial growth factor (VEGF) activity, decreasing inflammation and edema, commonly used to treat diabetic macular edema and other retinal disorders. | DUKE | Hepatoprotective | 62868 | An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities. | DUKE | Hepatotoxic | 50908 | An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy. | DUKE | Lipolytic | | An 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 | Molluscicide | 33904 | An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology. | DUKE | Piscicide | | A substance poisonous to fish, used to eliminate dominant or invasive fish species, and combat parasitic fish, allowing for population control and management of aquatic ecosystems. | DUKE | Sedative | 35717 | 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 | Acetylcholinesterase inhibitor | 38462 | An agent that blocks the breakdown of acetylcholine, increasing its concentration and enhancing cholinergic transmission. Therapeutically, it improves cognitive function and muscle contraction, commonly used in managing Alzheimer's disease, myasthenia gravis, and glaucoma. | CHEBI |
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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 | Not Available |
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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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