| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:15:05 UTC |
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| Update date | 2020-09-17 15:32:27 UTC |
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| Primary ID | FDB020535 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | trans-Linalool 3,6-oxide |
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| Description | (±)-trans-Linalyl oxide, also known as (E)-linalool oxide or trans-Linalool oxide is an oxidized derivative of Linalool which is a terpene alcohol common in various flowers and spice plants. It belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. From a biosynthetic point of view, trans-Linalool oxide is a monoterpenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Linalool oxide occurs in two distinctly different structural guises in nature. The most common structural form is based on a five member, furan-like ring structure. The less common form is based on a six member, pyran-like structure. Both types of linalool oxide exist as cis- and trans- isomers. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance. The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. It is used as a perfuming agent and a flavoring agent. trans-Linalool oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. (±)-trans-Linalyl oxide is found within tea and ceylon cinnamons and has also been detected, but not quantified in, several different foods, such as common oregano, sweet basils, garden tomatoes, gingers, and tarragons. |
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| CAS Number | 34995-77-2 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C10H18O2 |
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| IUPAC name | 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol |
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| InChI Identifier | InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1 |
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| InChI Key | BRHDDEIRQPDPMG-WCBMZHEXSA-N |
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| Isomeric SMILES | CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C |
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| Average Molecular Weight | 170.2487 |
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| Monoisotopic Molecular Weight | 170.13067982 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Tetrahydrofurans |
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| Sub Class | Not Available |
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| Direct Parent | Tetrahydrofurans |
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| Alternative Parents | |
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| Substituents | - Tetrahydrofuran
- Tertiary alcohol
- Oxacycle
- Ether
- Dialkyl ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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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 70.55%; H 10.66%; O 18.80% | 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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| GC-MS | trans-Linalool 3,6-oxide, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-e8c8defcb13d413ce23b | Spectrum | | GC-MS | trans-Linalool 3,6-oxide, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-e8c8defcb13d413ce23b | Spectrum | | Predicted GC-MS | trans-Linalool 3,6-oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-9100000000-d76b0d8bd5839f5bad93 | Spectrum | | Predicted GC-MS | trans-Linalool 3,6-oxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-003r-9720000000-d7880141bef77c136d15 | Spectrum | | Predicted GC-MS | trans-Linalool 3,6-oxide, 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 | splash10-00di-1900000000-3717374e13c0e4e46e01 | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fl0-7900000000-1a57b949dcbd663fc1eb | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbi-9000000000-29f24016ec67ee4e749b | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-92d23807ba882368b9c5 | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1900000000-9591ca26dd3aa91ec77b | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00m0-9400000000-adb5d889f7dfc0e0d558 | 2016-09-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-efbd93a1a83feefc94df | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aor-3900000000-6b8e798821e4115bf1d0 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9100000000-ace0a44f890d3bb40734 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-8900000000-a536912550058a32831e | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0f7p-9100000000-b3759eefd18d5faed102 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kc6-9000000000-369ce7815f6cf7814da3 | 2021-09-22 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 4937513 |
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| ChEMBL ID | CHEMBL2252947 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 6432254 |
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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 | HMDB40727 |
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| CRC / DFC (Dictionary of Food Compounds) ID | JVB43-D:MTJ99-F |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | TRANS-LINALOOL-OXIDE|TRANS-LINALOL-OXIDE|LINALOOL-OXIDE-(TRANS-FURANOID)|LINALOOL-OXIDE-A|LINALOOL-OXIDE-II |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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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 | 34995-77-2 |
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| GoodScent ID | rw1384891 |
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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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| flower |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| | floral |
- 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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