tert-Amyl alcohol
| tert-Amyl alcohol | |
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2-Methyl-2-butanol[1] |
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2-Methylbutan-2-ol[1] |
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| Identifiers | |
| CAS number | 75-85-4  |
| PubChem | 6405 |
| ChemSpider | 6165 |
| UNII | 69C393R11Z |
| EC number | 200-908-9 |
| UN number | 1105 |
| KEGG | D02931 |
| MeSH | tert-amyl+alcohol |
| ChEMBL | CHEMBL44658 |
| RTECS number | SC0175000 |
| Beilstein Reference | 1361351 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H12O |
| Molar mass | 88.15 g mol−1 |
| Appearance | Colorless liquid |
| Odor | Camphorous |
| Density | 805 mg cm−3 |
| Melting point |
-9 °C, 264 K, 16 °F |
| Boiling point |
101-103 °C, 374-376 K, 214-217 °F |
| Solubility in water | 120 g dm−3 |
| log P | 1.095 |
| Vapor pressure | 1.6 kPa (at 20 °C) |
| Refractive index (nD) | 1.405 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−380.0–−379.0 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−3.3036–−3.3026 MJ mol−1 |
| Standard molar entropy S |
229.3 J K−1 mol−1 |
| Hazards | |
| MSDS | hazard.com |
| GHS pictograms |   |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H315, H332, H335 |
| GHS precautionary statements | P210, P261 |
| EU Index | 603-007-00-2 |
| EU classification |  F  Xn |
| R-phrases | R11, R20, R37/38 |
| S-phrases | (S2), S46 |
| NFPA 704 |
 3
1
0
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| Flash point | 19 °C (66 °F) |
| Autoignition temperature |
437 °C (819 °F) |
| Explosive limits | 9% |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
tert-Amyl alcohol (TAA), also known as 2-methyl-2-butanol (2M2B), is a speciality pentanol used primarily as a pharmaceutical or pigment solvent. It is a trace component in fermentation ethanol. It is a colorless liquid with a pungent odor of camphor, and soluble with water and other organic solvents.
Contents |
[edit] Natural occurrence
Fusel alcohols including TAA are a grain fermentation byproduct and therefore in most alcoholic beverages.[2] TAA is also found in fried bacon and cassava.[3][4] Trace quantities are in hops used to flavor beer.[5][6]
[edit] Industrial production
The oxo alcohol process is the principal commercial source of TAA. The reaction of 2-methyl-2-butene (also known as isoamylene) with water in the presence of an acid catalyst yields TAA.[7][8] Minor quantities, mainly in Europe, are obtained from separation of fusel alcohols.[citation needed]
[edit] Chemistry
TAA is an isomer of amyl alcohol so it is also known as tert-Amyl alcohol. It is not expected to be susceptible to direct photolysis by sunlight.[9]
[edit] Pharmacology
Tertiary alcohols like TAA cannot be oxidised which makes them useful as drugs because they do not form toxic aldehyde and carboxylic acid metabolites.[10]
TAA produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation, and was previously used in medicine for these purposes.[11] It is active in doses of 2,000-4,000 mg, making it 20 times more potent than ethanol.[12][13] Its hypnotic potency is between chloral hydrate and paraldehyde[14] and between benzodiazepines and ethanol. In humans, TAA is metabolized primarily via gluconoridation and oxidation to 2,3-dihydroxy-2-methylbutane.[15]
[edit] Overdose and toxicity
An overdose produces symptoms similar to alcohol poisoning and is a medical emergency due the sedative/depressant properties of the drug. The oral LD50 in rats is 1000 mg/kg. The subcutaneous LD50 in mice is 2100 mg/kg. [16]
[edit] See also
[edit] References
- ^ a b c d e f "tert-Amyl alcohol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 2011-12-13.
- ^ George Milbry Gould; Richard John Ernst Scott (1919). The Practitioner's Medical Dictionary: Containing All the Words and Phrases Generally Used in Medicine and the Allied Sciences, with Their Proper Pronunciation, Derivation, and Definition. P. Blakiston's. p. 50. Retrieved February 7, 2013.
- ^ Dougan, J.; Robinson, J. M.; Sumar, S.; Howard, G. E.; Coursey, D. G. (1983). "Some flavouring constituents of cassava and of processed cassava products". Journal of the Science of Food and Agriculture 34 (8): 874. doi:10.1002/jsfa.2740340816.
- ^ Ho, C. T.; Lee, K. N.; Jin, Q. Z. (1983). "Isolation and identification of volatile flavor compounds in fried bacon". Journal of Agricultural and Food Chemistry 31 (2): 336. doi:10.1021/jf00116a038.
- ^ "Hops: Humulus lupulus". Retrieved 14 February 09.
- ^ Bourne, Edmund J. (132). "Natural Relief for Anxiety".
- ^ Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V2: 716. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
- ^ http://www.tert-amylalcohol.com/
- ^ http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~PghGgW:1:fate
- ^ Carey, Francis. Organic Chemistry (4 ed.). ISBN 0072905018. Retrieved 2013-02-05.
- ^ Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2.
- ^ Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7.
- ^ D. W. Yandell et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News (Lousville KY: John P. Morton & Co) 5: 88–89.
- ^ F. A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist 17 (3): 58–59.
- ^ Collins, A. S.; Sumner, S. C.; Borghoff, S. J.; Medinsky, M. A. (1999). "A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures". Toxicological sciences : an official journal of the Society of Toxicology 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
- ^ Soehring, K.; Frey, H. H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung 5 (4): 161–165. PMID 14389140.
