Record Information |
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Version | 1.0 |
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Created at | 2022-09-08 19:39:00 UTC |
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Updated at | 2022-09-08 19:39:00 UTC |
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NP-MRD ID | NP0272843 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | β-santalene |
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Description | (-)-Beta-santalene, also known as β-santalene or alpha-santalene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. β-santalene is found in Artemisia xerophytica, Asarum macranthum, Atalantia buxifolia, Cinnamomum camphora, Citrus latifolia, Daphne genkwa, Dysoxylum spectabile, Erigeron canadensis, Gackstroemia magellanica, Gossypium hirsutum, Hamamelis virginiana, Gymnomitrion alpinum, Ophrys arachnitiformis, Osyris quadripartita, Piper aduncum, Rhaponticum carthamoides, Santalum album, Santalum spicatum and Smallanthus uvedalia. It was first documented in 2019 (PMID: 30922222). Based on a literature review a significant number of articles have been published on (-)-beta-santalene (PMID: 35933050) (PMID: 33121934) (PMID: 31930246) (PMID: 30576771). |
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Structure | CC(C)=CCC[C@]1(C)[C@H]2CC[C@H](C2)C1=C InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15+/m1/s1 |
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Synonyms | Value | Source |
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(1S-exo)-2-Methyl-3-methylene-2-(4-methyl-3-pentenyl)bicyclo[2.2.1]heptane | ChEBI | beta-Santalene | ChEBI | b-Santalene | Generator | Β-santalene | Generator | (-)-b-Santalene | Generator | (-)-Β-santalene | Generator | alpha-Santalene | MeSH |
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Chemical Formula | C15H24 |
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Average Mass | 204.3570 Da |
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Monoisotopic Mass | 204.18780 Da |
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IUPAC Name | (1S,2R,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane |
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Traditional Name | β-santalene |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC[C@]1(C)[C@H]2CC[C@H](C2)C1=C |
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InChI Identifier | InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15+/m1/s1 |
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InChI Key | PGBNIHXXFQBCPU-ILXRZTDVSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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 | - Sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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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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General References | - Chen X, Zhang Y, Yan H, Niu M, Xiong Y, Zhang X, Li Y, Teixeira da Silva JA, Ma G: Cloning and functional analysis of 1-deoxy-D-xylulose-5-phosphate synthase (DXS) in Santalum album L. Gene. 2022 Aug 3:146762. doi: 10.1016/j.gene.2022.146762. [PubMed:35933050 ]
- Di Girolamo A, Durairaj J, van Houwelingen A, Verstappen F, Bosch D, Cankar K, Bouwmeester H, de Ridder D, van Dijk ADJ, Beekwilder J: The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase. Arch Biochem Biophys. 2020 Nov 30;695:108647. doi: 10.1016/j.abb.2020.108647. Epub 2020 Oct 26. [PubMed:33121934 ]
- Najera C, Foubelo F, Sansano JM, Yus M: Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes. Org Biomol Chem. 2020 Feb 19;18(7):1232-1278. doi: 10.1039/c9ob02419k. [PubMed:31930246 ]
- Zhang X, Niu M, Teixeira da Silva JA, Zhang Y, Yuan Y, Jia Y, Xiao Y, Li Y, Fang L, Zeng S, Ma G: Identification and functional characterization of three new terpene synthase genes involved in chemical defense and abiotic stresses in Santalum album. BMC Plant Biol. 2019 Mar 28;19(1):115. doi: 10.1186/s12870-019-1720-3. [PubMed:30922222 ]
- Ogunwande IA, Avoseh ON, Olasunkanmi KN, Lawal OA, Ascrizzi R, Flamini G: Chemical composition, anti-nociceptive and anti-inflammatory activities of essential oil of Bougainvillea glabra. J Ethnopharmacol. 2019 Mar 25;232:188-192. doi: 10.1016/j.jep.2018.12.017. Epub 2018 Dec 18. [PubMed:30576771 ]
- LOTUS database [Link]
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