| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:39:25 UTC |
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| Updated at | 2020-12-07 19:07:27 UTC |
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| CannabisDB ID | CDB000483 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | (+)-nerolidol |
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| Description | Nerolidol also known as peruviol, belongs to the class of organic compounds known as sesquiterpenoids. 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. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Nerolidol is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is present in neroli, ginger, jasmine, lavender, tea tree, and lemon grass, and is a dominant scent compound in Brassavola nodosa. Nerolidol has also been reported as one of the volatile components detected in cannabis samples (PMID: 26657499 ). The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520 ). Currently it is also under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs ( Ref:DOI ). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | ChEBI | | (S)-cis-Nerolidol | ChEBI | | (+)-cis-Nerolidol | HMDB | | (+)-Nerolidol | HMDB | | (6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | HMDB | | (Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | HMDB | | (Z)-Nerolidol | HMDB | | 3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-ol | HMDB | | 3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-ol | HMDB | | D-Nerolidol | HMDB | | 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | HMDB | | Nerolidol, (Z)-isomer | HMDB | | Nerolidol, (S-(Z))-isomer | HMDB | | Nerolidol | HMDB | | Nerolidol, (e)-isomer | HMDB | | Nerolidol, (S-(e))-isomer | HMDB | | Peruviol | HMDB | | [S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | PhytoBank | | folic alcohol | PhytoBank | | cis-(+)-Nerolidol | PhytoBank | | (3S,6Z)-Nerolidol | PhytoBank | | (±)-Nerolidol | PhytoBank | | Nerodilol | PhytoBank |
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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,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol |
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| Traditional Name | (3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol |
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| CAS Registry Number | 142-50-7 |
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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-QKXCFHHRSA-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 | 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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| 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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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| GC-MS | (+)-nerolidol, non-derivatized, GC-MS Spectrum | splash10-00kf-9100000000-45f6e3893a44769001ce | Spectrum | | GC-MS | (+)-nerolidol, non-derivatized, GC-MS Spectrum | splash10-00kf-9100000000-45f6e3893a44769001ce | Spectrum | | GC-MS | (+)-nerolidol, non-derivatized, GC-MS Spectrum | splash10-00kf-9300000000-5d006438834962306455 | Spectrum | | Predicted GC-MS | (+)-nerolidol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0g4u-9710000000-533a8143456d99d52949 | Spectrum | | Predicted GC-MS | (+)-nerolidol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-009f-9450000000-0e9301ccd24a06b7cb6b | Spectrum | | Predicted GC-MS | (+)-nerolidol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | (+)-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 | splash10-0ab9-0490000000-161e693347ad291e0fbd | 2016-08-02 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0avr-8930000000-9d44e8ed0962b3b4a6e5 | 2016-08-02 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gc0-9200000000-e773e83c3d163f0457dd | 2016-08-02 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-ccfe5910ac69a0881b78 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fk9-0290000000-472fb15ead3e188bca2a | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0q29-8920000000-480ab5d82bb26f770cf2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05gi-9730000000-8f73e6a0f1de3af1ba7d | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001l-9300000000-2b7789b2b428dddd2498 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00l6-9100000000-2f699f362b83b3293a70 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-ab61d8a2af41e6ed2e49 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fk9-0290000000-9251c836633c797793b3 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0v4i-3930000000-8dc35c7845f0ac5d0fe9 | 2021-09-24 | View Spectrum |
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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 ]
- Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
- Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
- 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 ]
- Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
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