Record Information |
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Version | 1.0 |
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Created at | 2007-04-12 20:13:40 UTC |
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Updated at | 2022-04-04 18:44:35 UTC |
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NP-MRD ID | NP0000131 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Isobutanol |
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Description | Isobutanol is an aliphatic alcohol. Isobutanol is a colorless, flammable, organic compound with a characteristic smell. Isobutanol is widely used in industry, as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis. Isobutanol is a flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis. Isobutanol is occasionally found as a volatile component of urine and arises from gut microbial metabolism. Isobutanol is used as one of the markers to measure occupational exposure to a mixture of solvents. Aliphatic alcohols levels increase in both diabetes mellitus and insulin-dependent diabetes patients. (PMID:5556886 , 2477620 , 9143482 , 7627316 , 2288731 ). Isobutanol is a microbial metabolite found in Clostridium, Cupriavidus, Escherichia, Geobacillus, Saccharomyces and Synechococcus (PMID:19946322 ). |
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Structure | InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3 |
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Synonyms | Value | Source |
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1-Hydroxymethylpropane | ChEBI | 2-Methyl-1-propanol | ChEBI | 2-Methylpropanol | ChEBI | I-butanol | ChEBI | I-butyl alcohol | ChEBI | IBA | ChEBI | Iso-butyl alcohol | ChEBI | Iso-C4H9OH | ChEBI | Isobutyl alcohol | ChEBI | Isobutylalkohol | ChEBI | Isopropylcarbinol | ChEBI | 2-Methyl propanol | HMDB | 2-Methyl-1-propanyl alcohol | HMDB | 2-Methylpropan-1-ol | HMDB | 2-MethylpropanoI | HMDB | 2-Methylpropanol-1 | HMDB | 2-Methylpropyl alcohol | HMDB | Alcool isobutylique | HMDB | Isopropyl carbitol | HMDB | Methyl-2 propanol-1 | HMDB | Isobutyl alcohol, aluminum salt | HMDB | Isobutyl alcohol, sodium salt | HMDB | Isobutyl alcohol, titanium (+4) salt | HMDB | Isobutanol | MeSH |
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Chemical Formula | C4H10O |
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Average Mass | 74.1216 Da |
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Monoisotopic Mass | 74.07316 Da |
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IUPAC Name | 2-methylpropan-1-ol |
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Traditional Name | isobutanol |
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CAS Registry Number | 78-83-1 |
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SMILES | CC(C)CO |
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InChI Identifier | InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3 |
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InChI Key | ZXEKIIBDNHEJCQ-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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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-04-04 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2022-04-04 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Primary alcohols |
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Alternative Parents | |
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Substituents | - Hydrocarbon derivative
- Primary 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 | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | -108 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 85 mg/mL at 25 °C | Not Available | LogP | 0.76 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
- Bilzer N, Schmutte P, Jehs M, Penners BM: [Kinetics of aliphatic alcohols (methanol, propanol-1 and isobutanol) in the presence of alcohol in the human body]. Blutalkohol. 1990 Nov;27(6):385-409. [PubMed:2288731 ]
- Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. [PubMed:2477620 ]
- Norback D, Bjornsson E, Janson C, Widstrom J, Boman G: Asthmatic symptoms and volatile organic compounds, formaldehyde, and carbon dioxide in dwellings. Occup Environ Med. 1995 Jun;52(6):388-95. [PubMed:7627316 ]
- Kruszewski FH, Walker TL, DiPasquale LC: Evaluation of a human corneal epithelial cell line as an in vitro model for assessing ocular irritation. Fundam Appl Toxicol. 1997 Apr;36(2):130-40. [PubMed:9143482 ]
- Evenepoel P, Meijers BK, Bammens BR, Verbeke K: Uremic toxins originating from colonic microbial metabolism. Kidney Int Suppl. 2009 Dec;(114):S12-9. doi: 10.1038/ki.2009.402. [PubMed:19946322 ]
- Gu P, Liu L, Ma Q, Dong Z, Wang Q, Xu J, Huang Z, Li Q: Metabolic engineering of Escherichia coli for the production of isobutanol: a review. World J Microbiol Biotechnol. 2021 Sep 6;37(10):168. doi: 10.1007/s11274-021-03140-0. [PubMed:34487256 ]
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