Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:11 UTC |
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Update date | 2019-11-26 03:09:47 UTC |
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Primary ID | FDB014294 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one |
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Description | Occurs in peppermint oil, green tea and bergamot oranges (Citrus bergamia)
Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in many foods, some of which are fig, spearmint, citrus, and sweet orange. |
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CAS Number | 488-10-8 |
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Structure | |
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Synonyms | Synonym | Source |
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cis-Jasmone | Kegg | (Z)-Jasmone | HMDB, MeSH | 2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci) | HMDB | 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci) | HMDB | 3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-one | HMDB | cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one | HMDB | Jasmone | MeSH, HMDB | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one | MeSH | 2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8CI) | biospider | 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9CI) | biospider | 2-cyclopenten-1-one, 3-methyl-2-[(2Z)-2-pentenyl]- | biospider | 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, (Z)- | biospider |
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Predicted Properties | |
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Chemical Formula | C11H16O |
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IUPAC name | 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one |
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InChI Identifier | InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4- |
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InChI Key | XMLSXPIVAXONDL-PLNGDYQASA-N |
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Isomeric SMILES | CC\C=C/CC1=C(C)CCC1=O |
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Average Molecular Weight | 164.2441 |
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Monoisotopic Molecular Weight | 164.120115134 |
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Classification |
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Description | Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Cyclic ketones |
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Alternative Parents | |
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Substituents | - Cyclic ketone
- Organic oxide
- Hydrocarbon derivative
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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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 | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 80.44%; H 9.82%; O 9.74% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp12 134-135° | DFC |
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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 | n22D 1.4979 | DFC |
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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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GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrum | splash10-03dl-9700000000-626f6beb94dae241c8a7 | Spectrum | GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrum | splash10-01r6-9600000000-b7842817d55e1ef34cd5 | Spectrum | GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrum | splash10-03dl-9700000000-626f6beb94dae241c8a7 | Spectrum | GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, GC-MS Spectrum | splash10-01r6-9600000000-b7842817d55e1ef34cd5 | Spectrum | Predicted GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4u-6900000000-4ec9a03205a62c5db571 | Spectrum | Predicted GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one, 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 | splash10-014i-1900000000-b3455ba1815cd60172a3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-066r-7900000000-df4da4ed2a4217531361 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxu-9100000000-1ad974119b61c19d8fcb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-54214296816474e67819 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-9e2bcdc11fb8c55163ab | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9800000000-3aa25aca2cc0986b4e11 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0900-5900000000-150eb84c8131eaddd806 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052f-9300000000-4c74719ab790c3d97cb7 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0536-9000000000-eac87e59851b2c86a210 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-defd12a7f890bc945918 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-7005ce6951d5a76167cd | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-066r-4900000000-524d8ff912c0d662ad37 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 1266012 |
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ChEMBL ID | CHEMBL2251602 |
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KEGG Compound ID | C08490 |
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Pubchem Compound ID | 1549018 |
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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 | HMDB35601 |
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CRC / DFC (Dictionary of Food Compounds) ID | JPH11-G:JPJ20-S |
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EAFUS ID | 1955 |
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Dr. Duke ID | JASMONE|CIS-JASMONE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029353 |
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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 | rw1016891 |
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SuperScent ID | 1549018 |
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Wikipedia ID | Jasmone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | |
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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 bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | Anti cariogenic | 52217 | An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health. | 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 | Insectiphile | 24852 | A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration. | DUKE | Nematicide | 25491 | An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health. | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | DUKE | Pesticide | 25944 | 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 | Trichomonicide | | An agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections. | 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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jasmine |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| floral |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| jasmin |
- 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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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