| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2020-03-19 00:32:25 UTC |
|---|
| Updated at | 2020-12-07 19:07:23 UTC |
|---|
| CannabisDB ID | CDB000351 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Cannabis Compound Identification |
|---|
| Common Name | (±)-trans-Nerolidol |
|---|
| Description | (±)-Trans-nerolidol, also known simply as Trans-nerolidol or penetrol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 7640522 ). However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. With regard to the production of nerolidol, (E)-nerolidol synthase was recently found to be responsible for the conversion of farnesyl diphosphate (FDP), the universal precursor of sesquiterpenes to (3S)-(E)-nerolidol. Trans-nerolidol is a also member of the class of compounds known as acyclic sesquiterpenoids. Acyclic sesquiterpenoids are sesquiterpenes that do not contain a cycle. There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. (±)-Trans-nerolidol is a neutral, hydrophobic molecule that is practically insoluble in water. It exists as a pale, yellow liquid oil. (±)-Trans-nerolidol has a woody, fruity citrus aroma reminiscent of citrus, apples and roses. Industrially is used as a food flavoring agen and, a perfuming agent (in shampoos and perfumes). It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520 ). Statistics have shown that the global usage of nerolidol per annum ranges from 10 to 100 metric tonnes. Trans-nerolidol is being tested as a skin penetration enhancer for the transdermal delivery of therapeutic drugs (PMID: 15855481 , 27136520 ). Trans-nerolidol is a naturally occurring compound found in many plants, foods and spices including ginger, hyssop, lemongrass, jasmine, tea tree, ginger and neroli (an essential oil distilled from bitter orange flowers). As with many terpenoids, it plays a very active role in the defense system of some plants. Trans-nerolidol has been traditionally used for its relaxing, slightly sedative effects. It appears to have anti-parasitic, antifungal and anti-bacterial properties (PMID: 15855481 , 27136520 ). These findings are consistent with the traditional use of orange oil as a natural disinfectant. Trans-nerolidol has been shown to sensitize pathogenic bacteria to the effects of conventional antibiotics by enhancing the permeability of the bacterial membrane (PMID: 14506058 ). It has also been shown to reduce Leishmaniasis infection by 95% (PMID: 15855481 ). Trans-nerolidol has also been shown to have anti-ulcer and anti-cancer activity (PMID: 27136520 ). Trans-Nerolidol is one of more than 140 terpenoids that are known in cannabis plants (PMID: 6991645 ). |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (S-(e))-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol | ChEBI | | Nerolidol | HMDB | | Nerolidol, (e)-isomer | HMDB | | Nerolidol, (S-(e))-isomer | HMDB | | 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | HMDB | | Nerolidol, (S-(Z))-isomer | HMDB | | Peruviol | HMDB | | Nerolidol, (Z)-isomer | HMDB | | (+)-trans-Nerolidol | HMDB | | (3S)-(e)-Nerolidol | HMDB | | (3S)-trans-Nerolidol | HMDB | | (3S,6E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | HMDB | | (3S,e)-Nerolidol | HMDB | | (S)-(+)-trans-Nerolidol | HMDB | | (S)-trans-Nerolidol | HMDB | | (S,e)-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol | HMDB | | (S,e)-Nerolidol | HMDB | | trans-(+)-Nerolidol | HMDB | | (3S,6E)-Nerolidol | HMDB |
|
|---|
| Chemical Formula | C15H26O |
|---|
| Average Molecular Weight | 222.37 |
|---|
| Monoisotopic Molecular Weight | 222.1984 |
|---|
| IUPAC Name | (3S,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol |
|---|
| Traditional Name | nerolidol |
|---|
| CAS Registry Number | 1119-38-6 |
|---|
| SMILES | CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C |
|---|
| InChI Identifier | InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+/t15-/m1/s1 |
|---|
| InChI Key | FQTLCLSUCSAZDY-ATGUSINASA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Sesquiterpenoids |
|---|
| Direct Parent | Sesquiterpenoids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Farsesane sesquiterpenoid
- Sesquiterpenoid
- Tertiary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
|
| Role | Industrial application: |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
|
|---|
| Predicted Properties | [] |
|---|
| MS/MS | | Type | Description | Splash Key | View |
|---|
| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-ab61d8a2af41e6ed2e49 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-4390000000-1e6703c26890b0ed7c60 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006t-8910000000-f204944da3e1544896d6 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00e9-6920000000-ad48f7ac5c3e7a13b831 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-008a-9500000000-2a007f295fe4ebe9dfb6 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00o3-9100000000-9e89155500d705ca9581 | 2021-09-23 | View Spectrum |
|
|---|
| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- Chan WK, Tan LT, Chan KG, Lee LH, Goh BH: Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Molecules. 2016 Apr 28;21(5). pii: molecules21050529. doi: 10.3390/molecules21050529. [PubMed:27136520 ]
- Arruda DC, D'Alexandri FL, Katzin AM, Uliana SR: Antileishmanial activity of the terpene nerolidol. Antimicrob Agents Chemother. 2005 May;49(5):1679-87. doi: 10.1128/AAC.49.5.1679-1687.2005. [PubMed:15855481 ]
- Brehm-Stecher BF, Johnson EA: Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother. 2003 Oct;47(10):3357-60. doi: 10.1128/aac.47.10.3357-3360.2003. [PubMed:14506058 ]
|
|---|
