| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:32:25 UTC |
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| Updated at | 2020-12-07 19:07:23 UTC |
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| CannabisDB ID | CDB000351 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | (±)-trans-Nerolidol |
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| 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 ). | Read more...
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| Structure | |
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| Synonyms | | Value | Source |
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| (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 |
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| Chemical Formula | C15H26O |
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| Average Molecular Weight | 222.37 |
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| Monoisotopic Molecular Weight | 222.1984 |
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| IUPAC Name | (3S,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol |
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| Traditional Name | nerolidol |
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| CAS Registry Number | 1119-38-6 |
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| SMILES | CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C |
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| 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 |
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| InChI Key | FQTLCLSUCSAZDY-ATGUSINASA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesquiterpenoids |
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| Direct Parent | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Farsesane sesquiterpenoid
- Sesquiterpenoid
- Tertiary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | (±)-trans-Nerolidol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | (±)-trans-Nerolidol, 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 | 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 |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | Not Available |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| 8-Ball Kush | Detected and Quantified | 0.293 mg/g dry wt | | details | | 9 Lb Hammer | Detected and Quantified | 0.381 mg/g dry wt | | details | | 97 Sage | Detected and Quantified | 0.264 mg/g dry wt | | details | | Adonis | Detected and Quantified | 0.512 mg/g dry wt | | details | | Alien Dawg (Indica dominant) | Detected and Quantified | 0.85 +/- 0.01 mg/g dry wt | | details | | Alien Sour Apple | Detected and Quantified | 0.24 mg/g dry wt | | details | | Alien Sour Apple | Detected and Quantified | 0.240 mg/g dry wt | | details | | Black Boss | Detected and Quantified | 0.311 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.353 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.414 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.794 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.8 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.800 mg/g dry wt | | details | | Bob Marley | Detected and Quantified | 0.264 mg/g dry wt | | details | | Chemdawg | Detected and Quantified | 0.639 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 0.551 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 1.004 mg/g dry wt | | details | | Cookies and Cream | Detected and Quantified | 0.293 mg/g dry wt | | details | | Cosmic Lotus | Detected and Quantified | 0.282 mg/g dry wt | | details | | Dairy Queen | Detected and Quantified | 0.134 mg/g dry wt | | details | | Dark Shadow Haze | Detected and Quantified | 0.547 mg/g dry wt | | details | | FLO | Detected and Quantified | 0.491 mg/g dry wt | | details | | Goji OG | Detected and Quantified | 0.268 mg/g dry wt | | details | | Golden Cobra | Detected and Quantified | 0.212 mg/g dry wt | | details | | Golden Sage | Detected and Quantified | 0.357 mg/g dry wt | | details | | Gorilla Glue | Detected and Quantified | 0.906 mg/g dry wt | | details | | Gorilla Glue #4 | Detected and Quantified | 0.693 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 0.193 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 0.29 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 0.290 mg/g dry wt | | details | | Grizzly Kush | Detected and Quantified | 0.374 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 0.526 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 0.57 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 0.570 mg/g dry wt | | details | | Hemlock | Detected and Quantified | 0.294 mg/g dry wt | | details | | Island Honey | Detected and Quantified | 1.1 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 0.496 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 1.266 mg/g dry wt | | details | | Jack Herer | Detected and Quantified | 0.529 mg/g dry wt | | details | | Kandy Kush | Detected and Quantified | 0.363 mg/g dry wt | | details | | Kush Puppy | Detected and Quantified | 0.519 mg/g dry wt | | details | | La Choco | Detected and Quantified | 0.486 mg/g dry wt | | details | | Lemon Balm | Detected and Quantified | 0.484 mg/g dry wt | | details | | Lemon Goji | Detected and Quantified | 0.110 mg/g dry wt | | details | | Lemon Goji | Detected and Quantified | 0.11 mg/g dry wt | | details | | Lemon OG | Detected and Quantified | 0.258 mg/g dry wt | | details | | Lemon Sherbet | Detected and Quantified | 0.202 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.530 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.274 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.53 mg/g dry wt | | details | | Liberty Haze | Detected and Quantified | 0.116 mg/g dry wt | | details | | Lohan | Detected and Quantified | 0.158 mg/g dry wt | | details | | Lucky Charms | Detected and Quantified | 0.829 mg/g dry wt | | details | | Maui Haze | Detected and Quantified | 0.876 mg/g dry wt | | details | | Moby Dick | Detected and Quantified | 0.445 mg/g dry wt | | details | | Moonshine Ghost Trane Haze | Detected and Quantified | 0.131 mg/g dry wt | | details | | Nightmare Cookie | Detected and Quantified | 0.215 mg/g dry wt | | details | | Orange Skunk | Detected and Quantified | 0.476 mg/g dry wt | | details | | Pineapple Skunk | Detected and Quantified | 0.351 mg/g dry wt | | details | | Pipe Dream | Detected and Quantified | 0.558 mg/g dry wt | | details | | Platinum Delight | Detected and Quantified | 0.354 mg/g dry wt | | details | | Purple Eclipse | Detected and Quantified | 0.614 mg/g dry wt | | details | | Rocket Fuel | Detected and Quantified | 0.888 mg/g dry wt | | details | | Rollex OG | Detected and Quantified | 0.590 mg/g dry wt | | details | | Rollex OG | Detected and Quantified | 0.59 mg/g dry wt | | details | | Rosetta Stone | Detected and Quantified | 1.068 mg/g dry wt | | details | | Satori | Detected and Quantified | 0.112 mg/g dry wt | | details | | Sensi Star (Pure Indica) | Detected and Quantified | 0.82 +/- 0.00 mg/g dry wt | | details | | Skunk Haze | Detected and Quantified | 0.781 mg/g dry wt | | details | | Skywalker OG | Detected and Quantified | 0.629 mg/g dry wt | | details | | Spectrum | Detected and Quantified | 0.243 mg/g dry wt | | details | | Star Bud | Detected and Quantified | 0.972 mg/g dry wt | | details | | Star Killer | Detected and Quantified | 0.410 mg/g dry wt | | details | | Star Killer | Detected and Quantified | 0.41 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 0.341 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 0.385 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 0.482 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 0.644 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 1.09 mg/g dry wt | | details | | Tangerine Dream (Sativa dominant) | Detected and Quantified | 0.82 +/- 0.00 mg/g dry wt | | details | | The Sauce | Detected and Quantified | 0.798 mg/g dry wt | | details | | Venom OG | Detected and Quantified | 0.491 mg/g dry wt | | details | | White Widow | Detected and Quantified | 0.152 mg/g dry wt | | details | | Wonder Woman | Detected and Quantified | 0.096 mg/g dry wt | | details |
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| External Links |
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| HMDB ID | HMDB0041629 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB021837 |
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| KNApSAcK ID | C00003166 |
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| Chemspider ID | 4444858 |
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| KEGG Compound ID | C09704 |
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| BioCyc ID | CPD-12568 |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 5281525 |
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| PDB ID | Not Available |
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| ChEBI ID | 59958 |
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| References |
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| 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 ]
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