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{{chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 407859707 |
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| verifiedrevid = 443880607 |
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| Name = Isoamyl alcohol |
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| Name = Isoamyl alcohol |
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| ImageFile = Isopentanol-2D-skeletal.png |
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| ImageFile = Isoamyl alcohol.svg |
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| ImageFile1 = |
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| ImageFile1 = |
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| IUPACName = 3-methyl-1-butanol |
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| PIN = 3-Methylbutan-1-ol |
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| OtherNames = Isopentyl alcohol, Isopentanol, Isobutylcarbinol |
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| OtherNames = 3-Methyl-1-butanol<br />Isopentyl alcohol<br />Isopentanol<br />Isobutylcarbinol |
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| Reference = <ref name="hand"> |
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| Reference = <ref name="hand"> |
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{{ cite book |
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{{Citation |
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| last = Lide |
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| editor = Lide, David R. |
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| first = David R. |
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| year = 1998 |
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| title = ] |
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| author-link = |
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| last2 = |
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| edition = 87 |
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| publication-place = Boca Raton, Florida |
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| first2 = |
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| publisher = CRC Press |
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| author2-link = |
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| isbn = 0-8493-0487-3 |
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| publication-date = |
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| pages = 3-374, 5-42, 6-188, 8-102, 15-22 |
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| date = |
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| year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| edition = 87 |
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| volume = |
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| series = |
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| publication-place = Boca Raton, FL |
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| place = |
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| publisher = CRC Press |
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| id = |
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| isbn = 0-8493-0594-2 |
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| doi = |
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| oclc = |
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| pages = 3-374, 5-42, 6-188, 8-102, 15-22 |
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| url = |
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| accessdate = |
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}}</ref> |
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}}</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 29000 |
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| ChemSpiderID = 29000 |
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| PubChem = 31260 |
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| PubChem = 31260 |
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| InChI = 1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 |
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| InChI = 1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 |
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| InChIKey = PHTQWCKDNZKARW-UHFFFAOYAW |
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| InChIKey = PHTQWCKDNZKARW-UHFFFAOYAW |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02296 |
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| DrugBank = DB02296 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15837 |
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| ChEBI = 15837 |
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| SMILES = OCCC(C)C |
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| SMILES = OCCC(C)C |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 123-51-3 |
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| CASNo = 123-51-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = |
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| UNII = DEM9NIT1J4 |
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}} |
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| RTECS = |
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| Section2 = {{Chembox Properties |
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}} |
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| Formula = C<sub>5</sub>H<sub>12</sub>O |
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|Section2={{Chembox Properties |
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| MolarMass = 88.148 g/mol |
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| Formula = C<sub>5</sub>H<sub>12</sub>O |
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| Appearance = Clear, colorless liquid |
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| MolarMass = 88.148{{nbsp}}g/mol |
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| Density = 0.8104 g/cm<sup>3</sup> at 20°C |
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| Appearance = Clear, colorless liquid |
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| Solubility = Slightly soluble in water |
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| Odor = Disagreeable odor in high concentrations |
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| MeltingPtC = -117.2 |
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| Density = 0.8104{{nbsp}}g/cm<sup>3</sup> at 20 °C |
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| BoilingPtC = 131.1 |
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| MeltingPtC = −117<ref>Straka, M.; van Genderen, A.; Růžička, K.; Růžička, V. Heat Capacities in the Solid and in the Liquid Phase of Isomeric Pentanols. J. Chem. Eng. Data 2007, 52, 794-802.</ref><ref name=PGCH/> |
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| Viscosity = 3.692 mPa·s |
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| Solubility = 28 g/L |
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| BoilingPtC = 131.1 |
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| Viscosity = 3.692{{nbsp}}mPa·s |
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| SolubleOther = very soluble in ], ], ] |
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| Solubility = Slightly soluble, 28{{nbsp}}g/L |
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}} |
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| SolubleOther = Very soluble in ], ], ] |
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| Section4 = {{Chembox Thermochemistry |
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| VaporPressure = 28{{nbsp}}mmHg (20{{nbsp}}°C)<ref name=PGCH/> |
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| DeltaHf = -356.4 ] (liquid) <br/> -300.7 ] (gas) |
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| MagSus = −68.96·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol |
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| DeltaHc = |
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}} |
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| Entropy = |
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|Section4={{Chembox Thermochemistry |
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| HeatCapacity = 2.382 J·g<sup>-1</sup>·K<sup>-1</sup> |
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| DeltaHf = −356.4{{nbsp}}] (liquid) <br/> −300.7{{nbsp}}] (gas) |
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}} |
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| DeltaHc = |
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| Section7 = {{Chembox Hazards |
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| FlashPt = 43°C |
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| Entropy = |
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| HeatCapacity = 2.382{{nbsp}}J/g·K |
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| ExploLimits = 1.2 – 9% |
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}} |
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| Autoignition = 350°C |
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|Section7={{Chembox Hazards |
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| EUClass = |
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| MainHazards = Flammable, moderately toxic |
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| NFPA-H = |
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| NFPA-F = |
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| FlashPtC = 43 |
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| NFPA-R = |
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| ExploLimits = 1.2–9% |
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| NFPA-O = |
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| AutoignitionPtC = 350 |
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| RPhrases = |
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| NFPA-H = 1 |
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| SPhrases = |
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| NFPA-F = 2 |
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| NFPA-R = 0 |
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}} |
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| NFPA-S = |
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| Section8 = {{Chembox Related |
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| GHSPictograms = {{GHS02|Flammable}}{{GHS05|Corrosive}}{{GHS07|Irritant}} |
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| Function = |
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| OtherFunctn = |
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| GHSSignalWord = DANGER |
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| HPhrases = {{H-phrases|226|302|305|315|318|332|335}} |
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| OtherCpds = }} |
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| PPhrases = {{P-phrases|P210|P233|P240|P241|P242|P243|P261|P264|P270|P271|P280|P301+P312|P302+P352|P303+P361+P353|P304+P312|P304+P340|P305+P351+P338|P310|P312|P321|P330|P332+P313|P337+P313|P362|P370+P378|P403+P233|P403+P235|P405|P501}} |
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| PEL = TWA 100{{nbsp}}ppm (360{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0348}}</ref> |
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| IDLH = 500{{nbsp}}ppm<ref name=PGCH/> |
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| REL = TWA 100{{nbsp}}ppm (360{{nbsp}}mg/m<sup>3</sup>), ST 125{{nbsp}}ppm (450{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH/> |
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| LD50 = 1453{{nbsp}}mg/kg (rabbit, oral)<br/>1300{{nbsp}}mg/kg (rat, oral)<ref>{{IDLH|123513|Isoamyl alcohol}}</ref> |
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}} |
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|Section8={{Chembox Related |
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| OtherFunction_label = |
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| OtherFunction = |
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| OtherCompounds = |
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}} |
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'''Isoamyl alcohol''' (also known as isopentyl alcohol) is a clear, colourless ] with the formula (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>OH. It is one of several ]s of ]. It is a main ingredient in the production of ], an ] found in nature and also produced as a flavouring in industry. |
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'''Isoamyl alcohol''' is a colorless liquid with the formula {{chem|C|5|H|12|O}}, specifically (H<sub>3</sub>C–)<sub>2</sub>CH–CH<sub>2</sub>–CH<sub>2</sub>–OH. It is one of several ]s of ] (pentanol). It is also known as '''isopentyl alcohol''', '''isopentanol''', or (in the ] recommended nomenclature) '''3-methyl-butan-1-ol'''. An obsolete name for it was '''isobutyl carbinol'''.<ref name=EB1911/> |
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Isoamyl alcohol is an ingredient in the production of ], an ] found in nature and also produced as a flavouring in industry. It is a common ], produced as a major by-product of ethanol fermentation. |
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==References== |
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{{reflist}} |
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==Occurrence== |
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{{alcohol-stub}} |
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Isoamyl alcohol is one of the components of the aroma of '']'', the black truffle. |
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]s like isoamyl alcohol are grain fermentation byproducts, and therefore trace amounts of isoamyl are present in ]. |
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The compound has also been identified as a chemical in the ] used by ]s to attract other members of the hive to attack.<ref>Wilson, Calum & Davies, Noel & Corkrey, Ross & J. Wilson, Annabel & M. Mathews, Alison & C. Westmore, Guy. (2017). Receiver Operating Characteristic curve analysis determines association of individual potato foliage volatiles with onion thrips preference, cultivar and plant age. PLOS ONE. 12. e0181831. 10.1371/journal.pone.0181831.</ref> |
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==Extraction from fusel oil== |
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Isoamyl alcohol can be separated from fusel oil by either of two methods: shaking with strong ] solution and separating the oily layer from the brine layer; ] it and collecting the fraction that boils between 125 and 140 °C. Further purification is possible with this procedure: shaking the product with hot ], separating the oily layer, drying the product with ], and distilling it, collecting the fraction boiling between 128 and 132 °C.<ref name=EB1911>{{EB1911|inline=y|wstitle=Amyl Alcohols|volume=1|page=900}}</ref> |
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==Synthesis== |
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Isoamyl alcohol can be synthesized by condensation of ] and ] which produces ], then ]. It is a colourless liquid of density 0.8247 g/cm<sup>3</sup> (0 °C), boiling at 131.6 °C, slightly soluble in water, and easily dissolved in organic solvents. It has a characteristic strong smell and a sharp burning taste. On passing the vapour through a red-hot tube, it decomposes into ], ], ], and other compounds. It is ] by ] to ], and it forms ]s ]s with calcium chloride and ].<ref name=EB1911/> |
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==Uses== |
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Besides its use in the synthesis of banana oil, isoamyl alcohol is also an ingredient of ], used for the bacterial diagnostic ]. |
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It is also used as an ] in the chloroform isoamyl alcohol reagent.<ref>{{cite web|last1=Zumbo|first1=P.|title=Phenol-chloroform Extraction|url=http://physiology.med.cornell.edu/faculty/mason/lab/zumbo/files/PHENOL-CHLOROFORM.pdf|publisher=WEILL CORNELL MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E. MASON, PH.D|access-date=19 June 2014}}</ref> |
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Isoamyl alcohol is used in a ] mixed with the chloroform to further inhibit ] activity and prevent solubility of RNAs with long tracts of poly-].<ref>{{cite book |last1=Green |first1=Michael |last2=Sambrook |first2=Joseph |title=Molecular Cloning: A Laboratory Manual |url=http://www.molecularcloning.com/ |section=Purification of Nucleic Acids: Extraction with Phenol-Chloroform |publisher=Cold Spring Harbor Laboratory Press |isbn=1936113422 }}</ref> |
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===Drugs=== |
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IAA is also used as the reactant in the synthesis of the following list of drugs: |
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== References == |
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{{reflist}} |
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{{Use dmy dates|date=March 2018}} |
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] |
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{{Alcohols}} |
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