Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:38:33 UTC |
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Updated at | 2021-08-19 23:59:16 UTC |
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NP-MRD ID | NP0002712 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Propargyl alcohol |
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Provided By | BMRB |
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Description | 2-Propyn-1-ol, also known as prop-2-yne-1-ol or 3-propynol, belongs to the class of organic compounds known as acetylides. Acetylides are compounds arising by replacement of one or both hydrogen atoms of acetylene (ethyne) by a metal or other cationic group. E.G. NaC#CH monosodium acetylide. By extension, analogous compounds derived from terminal acetylenes, RC#CH. The class is limited here to derivatives of acetylene where the hydrogen atom is replaced with an element with similar or lower electronegativity that carbon. 2-Propyn-1-ol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Propargyl alcohol is found in Foeniculum vulgare . It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 2-Propyn-1-ol (PMID: 18974778) (PMID: 20151225) (PMID: 23043843) (PMID: 33710232) (PMID: 31635103) (PMID: 28956235). |
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Structure | InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2 |
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Synonyms | Value | Source |
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1-Hydroxy-2-propyne | ChEBI | 1-Propyn-3-ol | ChEBI | 1-Propyn-3-yl alcohol | ChEBI | 2-Propynol | ChEBI | 2-Propynyl alcohol | ChEBI | 3-Hydroxy-1-propyne | ChEBI | 3-Propynol | ChEBI | Acetylene carbinol | ChEBI | Acetylenylcarbinol | ChEBI | Ethynylcarbinol | ChEBI | Ethynylmethanol | ChEBI | NA 1986 | ChEBI | Prop-2-in-1-ol | ChEBI | Prop-2-yne-1-ol | ChEBI | Propargyl alcohol | ChEBI | Propynyl alcohol | ChEBI | Prop-2-yn-1-ol | Kegg | Propargyl alcohol, sodium salt | MeSH | Propargyl alcohol, lithium salt | MeSH |
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Chemical Formula | C3H4O |
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Average Mass | 56.0633 Da |
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Monoisotopic Mass | 56.02621 Da |
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IUPAC Name | prop-2-yn-1-ol |
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Traditional Name | propargyl alcohol |
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CAS Registry Number | Not Available |
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SMILES | OCC#C |
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InChI Identifier | InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2 |
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InChI Key | TVDSBUOJIPERQY-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 acetylides. Acetylides are compounds arising by replacement of one or both hydrogen atoms of acetylene (ethyne) by a metal or other cationic group. E.G. NaC#CH monosodium acetylide. By extension, analogous compounds derived from terminal acetylenes, RC#CH. The class is limited here to derivatives of acetylene where the hydrogen atom is replaced with an element with similar or lower electronegativity that carbon. |
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Kingdom | Organic compounds |
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Super Class | Acetylides |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Acetylides |
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Alternative Parents | |
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Substituents | - Acetylide
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- 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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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Authors unspecified: Toxicology and carcinogenesis studies of propargyl alcohol (CAS No. 107-19-7) in F344/N rats and B6C3F1 mice (inhalation studies). Natl Toxicol Program Tech Rep Ser. 2008 Sep;(552):1-172. [PubMed:18974778 ]
- Tsakiris A, Koutinas AA, Psarianos C, Kourkoutas Y, Bekatorou A: A new process for wine production by penetration of yeast in uncrushed frozen grapes. Appl Biochem Biotechnol. 2010 Oct;162(4):1109-21. doi: 10.1007/s12010-009-8881-8. Epub 2010 Feb 12. [PubMed:20151225 ]
- Pimenta RS, da Silva JF, Buyer JS, Janisiewicz WJ: Endophytic fungi from plums (Prunus domestica) and their antifungal activity against Monilinia fructicola. J Food Prot. 2012 Oct;75(10):1883-9. doi: 10.4315/0362-028X.JFP-12-156. [PubMed:23043843 ]
- Sorbelli D, Segato J, Del Zotto A, Belpassi L, Zuccaccia D, Belanzoni P: The mechanism of the gold(I)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4-endo-dig cyclization. Dalton Trans. 2021 Apr 21;50(15):5154-5160. doi: 10.1039/d1dt00080b. [PubMed:33710232 ]
- Chen Q, Wang Y, Hua R: Base-Promoted Chemodivergent Formation of 1,4-Benzoxazepin-5(4H)-ones and 1,3-Benzoxazin-4(4H)-ones Switched by Solvents. Molecules. 2019 Oct 19;24(20). pii: molecules24203773. doi: 10.3390/molecules24203773. [PubMed:31635103 ]
- Shimada K, Sugawara A, Korenaga T, Kawashima H: Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma. Lipids. 2017 Dec;52(12):1019-1032. doi: 10.1007/s11745-017-4303-9. Epub 2017 Sep 27. [PubMed:28956235 ]
- Shoji T, Nagai D, Tanaka M, Araki T, Ohta A, Sekiguchi R, Ito S, Mori S, Okujima T: Synthesis of 2-Aminofurans by Sequential [2+2] Cycloaddition-Nucleophilic Addition of 2-Propyn-1-ols with Tetracyanoethylene and Amine-Induced Transformation into 6-Aminopentafulvenes. Chemistry. 2017 Apr 11;23(21):5126-5136. doi: 10.1002/chem.201700121. Epub 2017 Mar 23. [PubMed:28191692 ]
- Tan W, Li Q, Dong F, Qiu S, Zhang J, Guo Z: Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property. Carbohydr Polym. 2017 Mar 15;160:163-171. doi: 10.1016/j.carbpol.2016.12.060. Epub 2016 Dec 26. [PubMed:28115090 ]
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