Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:58 UTC |
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Update date | 2019-11-26 03:09:15 UTC |
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Primary ID | FDB013900 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | (S)-5,6,7,7alpha-Tetrahydro-4,4,7alpha-trimethyl-2(4H)-benzofuranone |
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Description | Dihydroactinidiolide is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Dihydroactinidiolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroactinidiolide is a red fruit, ripe apricot, and woody tasting compound found in coffee and coffee products, fruits, and tea, which makes dihydroactinidiolide a potential biomarker for the consumption of these food products. Dihydroactinidiolide exists in all eukaryotes, ranging from yeast to humans. Dihydroactinidiolide is a volatile terpene. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangos, silver vine (Actinidia polygama), and tobacco. It has also been prepared synthetically . |
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CAS Number | 17092-92-1 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic acid lactone | HMDB | 4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-4H-benzofuran-2-one | HMDB | 4,5,7,7a-tetrahydro-4,4,7a-Trimethyl-2(6H)benzofuranone | HMDB | 2-Hydroxy-2,6,6-trimethylcyclohexylideneacetic acid gamma-lactone | MeSH, HMDB | (S)-5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone | Generator | (S)-5,6,7,7Α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzofuranone | Generator | 5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone | biospider | Dihydroactindiolide | biospider |
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Predicted Properties | |
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Chemical Formula | C11H16O2 |
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IUPAC name | 4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one |
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InChI Identifier | InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3 |
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InChI Key | IMKHDCBNRDRUEB-UHFFFAOYSA-N |
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Isomeric SMILES | CC12CCCC(C)(C)C1=CC(=O)O2 |
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Average Molecular Weight | 180.2435 |
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Monoisotopic Molecular Weight | 180.115029756 |
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Classification |
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Description | Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzofurans |
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Sub Class | Not Available |
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Direct Parent | Benzofurans |
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Alternative Parents | |
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Substituents | - Benzofuran
- 2-furanone
- Dihydrofuran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- 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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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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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 73.30%; H 8.95%; O 17.75% | DFC |
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Melting Point | Mp 71-72° (40-41°) | 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 | [a]22D +122.7 (CHCl3) (synthetic) | DFC |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-03di-5900000000-875f4155f7a4044b0a2a | 2015-03-01 | View Spectrum | Predicted GC-MS | Dihydroactinidiolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-007c-6900000000-27116463eaa31cd838f5 | Spectrum | Predicted GC-MS | Dihydroactinidiolide, 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 | splash10-001i-0900000000-b0a7c2689f1ca5d0ae35 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-4900000000-9f6cefae5043b00a2ca8 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00l6-9000000000-ea0ae11d0ba2410fe44c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-71187b755914bfd750bf | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004r-0900000000-e3790c89f994eda416fc | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05nr-2900000000-c550c1933884677823ea | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-ed614b6bd089f6f9641a | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fb9-0900000000-732e641af33d2bb8a042 | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0900000000-a68e0eac4bebe698e071 | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-fa414fe3da96b61b2fda | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-3900000000-a38dd3a7eff08112fb9a | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9500000000-f3a71ce8b3e13f563ab8 | 2021-09-25 | View Spectrum |
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NMR | |
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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 | JJR15-S:JJR17-U |
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EAFUS ID | Not Available |
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Dr. Duke ID | DIHYDROACTINIDIOLIDE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000319 |
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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 | rw1547981 |
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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 | Not Available |
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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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musk |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| coumarin |
- 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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