Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-03-18 23:24:04 UTC |
---|
Updated at | 2020-12-07 19:07:04 UTC |
---|
CannabisDB ID | CDB000081 |
---|
Secondary Accession Numbers | Not Available |
---|
Cannabis Compound Identification |
---|
Common Name | Citronellol |
---|
Description | Citronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID: 6991645 ). Citronellol occurs in many essential oils as either – or + enantiomers. -Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral leathery waxy rose citrus odor ( Ref:DOI ). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID: 2862274 ). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID: 30453001 ) against human lung cancer (PMID: 31280209 ), against induced rat breast cancer (PMID: 31313341 ), has antifungal activity against Candida species (PMID: 32150884 ) and has anti-hypertensive properties (PMID: 26872991 ). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(-)-3,7-Dimethyloct-6-en-1-ol | ChEBI | (-)-Citronellol | ChEBI | (S)-3,7-Dimethyl-6-octen-1-ol | ChEBI | L-Citronellol | ChEBI | (-)-(S)-Citronellol | HMDB | (-)-beta-Citronellol | HMDB | (-)-β-Citronellol | HMDB | (3S)-3,7-Dimethyl-6-octen-1-ol | HMDB | (S)-(-)-Citronellol | HMDB | (S)-(-)-beta-Citronellol | HMDB | (S)-(-)-β-Citronellol | HMDB | (S)-Citronellol | HMDB | (S)-beta-Citronellol | HMDB | (S)-β-Citronellol | HMDB | l-Citronellol | HMDB | (-)-3,7-Dimethyl-6-octen-1-ol | PhytoBank | 3,7-Dimethyl-6-octen-1-ol | PhytoBank | (±)-3,7-Dimethyl-6-octen-1-ol | PhytoBank | (±)-Citronellol | PhytoBank | (±)-beta-Citronellol | PhytoBank | (±)-β-Citronellol | PhytoBank | 1-Hydroxy-3,7-dimethyl-6-octene | PhytoBank | 2,3-Dihydrogeraniol | PhytoBank | 2,6-Dimethyl-2-octen-8-ol | PhytoBank | dl-Citronellol | PhytoBank | Dihydrogeraniol | PhytoBank | beta-Citronellol | PhytoBank | β-Citronellol | PhytoBank |
|
---|
Chemical Formula | C10H20O |
---|
Average Molecular Weight | 156.27 |
---|
Monoisotopic Molecular Weight | 156.1514 |
---|
IUPAC Name | (3S)-3,7-dimethyloct-6-en-1-ol |
---|
Traditional Name | (-)-citronellol |
---|
CAS Registry Number | 7540-51-4 |
---|
SMILES | C[C@H](CCO)CCC=C(C)C |
---|
InChI Identifier | InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m0/s1 |
---|
InChI Key | QMVPMAAFGQKVCJ-JTQLQIEISA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Monoterpenoids |
---|
Direct Parent | Acyclic monoterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Acyclic monoterpenoid
- Fatty alcohol
- Fatty acyl
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | 225 °C | Wikipedia | Water Solubility | Not Available | Not Available | logP | Not Available | Not Available |
|
---|
Predicted Properties | [] |
---|
Spectra |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
Predicted GC-MS | Citronellol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Citronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-1900000000-9f559c6b6bae07c69978 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-8900000000-f8c3d1ff7e6f87d6e43d | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-066u-9100000000-8ae7fa4f01b76f1eed16 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-82f8313ff8eb7c68242b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056r-0900000000-de94d5335c77bdb5afcf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6u-9800000000-b04acf4b20ad46274796 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05o0-9200000000-e66f9e249b523e6771bb | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053r-9000000000-6e0012cc1ab177db56c0 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-97567d47518fef28ec28 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-f6034c6a8245c68a37ac | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ab9-0900000000-4432dcd3f704b4a61b30 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-9400000000-fe45ce059cb434ed5e0c | 2021-09-25 | View Spectrum |
|
---|
NMR | Not Available |
---|
Pathways |
---|
Pathways | Not Available |
---|
Protein Targets |
---|
Enzymes | Not Available |
---|
Transporters | Not Available |
---|
Metal Bindings | Not Available |
---|
Receptors | Not Available |
---|
Transcriptional Factors | Not Available |
---|
Concentrations Data |
---|
| Not Available |
---|
External Links |
---|
HMDB ID | HMDB0035094 |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FoodDB ID | FDB013723 |
---|
KNApSAcK ID | C00000844 |
---|
Chemspider ID | 7505 |
---|
KEGG Compound ID | C11386 |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Citronellol |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 7793 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 88 |
---|
References |
---|
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 ]
- Taylor WG, Schreck CE: Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol. J Pharm Sci. 1985 May;74(5):534-9. doi: 10.1002/jps.2600740508. [PubMed:2862274 ]
- Santos PL, Matos JPSCF, Picot L, Almeida JRGS, Quintans JSS, Quintans-Junior LJ: Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food Chem Toxicol. 2019 Jan;123:459-469. doi: 10.1016/j.fct.2018.11.030. Epub 2018 Nov 16. [PubMed:30453001 ]
- Yu WN, Lai YJ, Ma JW, Ho CT, Hung SW, Chen YH, Chen CT, Kao JY, Way TD: Citronellol Induces Necroptosis of Human Lung Cancer Cells via TNF-alpha Pathway and Reactive Oxygen Species Accumulation. In Vivo. 2019 Jul-Aug;33(4):1193-1201. doi: 10.21873/invivo.11590. [PubMed:31280209 ]
- Rajendran J, Pachaiappan P, Subramaniyan S: Dose-dependent chemopreventive effects of citronellol in DMBA-induced breast cancer among rats. Drug Dev Res. 2019 Sep;80(6):867-876. doi: 10.1002/ddr.21570. Epub 2019 Jul 16. [PubMed:31313341 ]
- Silva D, Diniz-Neto H, Cordeiro L, Silva-Neta M, Silva S, Andrade-Junior F, Leite M, Nobrega J, Morais M, Souza J, Rosa L, Melo T, Souza H, Sousa A, Rodrigues G, Oliveira-Filho A, Lima E: (R)-(+)-beta-Citronellol and (S)-(-)-beta-Citronellol in Combination with Amphotericin B against Candida Spp. Int J Mol Sci. 2020 Mar 5;21(5). pii: ijms21051785. doi: 10.3390/ijms21051785. [PubMed:32150884 ]
- Ribeiro-Filho HV, de Souza Silva CM, de Siqueira RJ, Lahlou S, dos Santos AA, Magalhaes PJ: Biphasic cardiovascular and respiratory effects induced by beta-citronellol. Eur J Pharmacol. 2016 Mar 15;775:96-105. doi: 10.1016/j.ejphar.2016.02.025. Epub 2016 Feb 9. [PubMed:26872991 ]
|
---|