Isoamyl alcohol

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Isoamyl alcohol^[1]

IUPAC name 3-methyl-1-butanol
Other names Isopentyl alcohol, Isopentanol, Isobutylcarbinol
Identifiers
CAS number	123-51-3^Y
PubChem	31260
ChemSpider	29000^Y
DrugBank	DB02296
KEGG	C07328^Y
ChEBI	CHEBI:15837^Y
ChEMBL	CHEMBL372396^Y
Jmol-3D images	Image 1
SMILES OCCC(C)C
InChI InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3^Y Key: PHTQWCKDNZKARW-UHFFFAOYSA-N^Y InChI=1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 Key: PHTQWCKDNZKARW-UHFFFAOYAW
Properties
Molecular formula	C₅H₁₂O
Molar mass	88.148 g/mol
Appearance	Clear, colorless liquid
Density	0.8104 g/cm³ at 20 °C
Melting point	−117.2 °C; −179.0 °F; 156.0 K
Boiling point	131.1 °C; 268.0 °F; 404.2 K
Solubility in water	28 g/L
Solubility	very soluble in acetone, diethyl ether, ethanol
Viscosity	3.692 mPa·s
Thermochemistry
Std enthalpy of formation Δ_fH^o₂₉₈	-356.4 kJ·mol^-1 (liquid) -300.7 kJ·mol^-1 (gas)
Specific heat capacity, C	2.382 J·g^-1·K^-1
Hazards
Flash point	43 °C; 109 °F; 316 K
Autoignition temperature	350 °C; 662 °F; 623 K
Explosive limits	1.2 – 9%
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Isoamyl alcohol (also known as isopentyl alcohol) is a clear, colorless alcohol with the formula (CH₃)₂CHCH₂CH₂OH. It is one of several isomers of amyl alcohol. It is a main ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. It's also the main ingredient of Kovac's reagent, used for the bacterial diagnostic indole test.

It is also used as an antifoaming agent in the Chloroform:Isomyl Alcohol reagent.^{[citation needed]}

Isoamyl alcohol is used in a Phenol–chloroform extraction mixed with the chloroform to further inhibit RNase activity and prevent solubility of RNAs with long tracts of poly-adenine.^[2]

It is one of the components of the aroma of Tuber melanosporum, the black truffle. It has been identified as a chemical in the pheromone used by hornets to attract other members of the hive to attack.^{[citation needed]}

References

↑ Lide, David R., ed. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 3–374, 5–42, 6–188, 8–102, 15–22. ISBN 0-8493-0487-3.
↑ Green, Michael; Sambrook, Joseph. "Purification of Nucleic Acids: Extraction with Phenol-Chloroform". Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press. ISBN 1936113422.

v t e Alcohols

Straight-chain primary alcohols (1°)	Methanol (C 1) Ethanol (C 2) 1-Propanol (C 3) n-Butanol (C 4) 1-Pentanol (C 5) 1-Hexanol (C 6) 1-Heptanol (C 7) 1-Octanol (C 8) 1-Nonanol (C 9) 1-Decanol (C 10) Undecanol (C 11) Dodecanol (C 12) Tridecan-1-ol (C 13) 1-Tetradecanol (C 14) Pentadecan-1-ol (C 15) Cetyl alcohol (C 16) Heptadecan-1-ol (C 17) Stearyl alcohol (C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol (C 20) Heneicosan-1-ol (C 21) Docosanol (C 22) Tricosan-1-ol (C 23) 1-Tetracosanol (C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol (C 26) 1-Heptacosanol (C 27) 1-Octacosanol (C 28) 1-Nonacosanol (C 29) Triacontanol (C 30) Policosanol

Other primary alcohols	Isobutanol (C 4) Isoamyl alcohol (C 5)

Secondary alcohols (2°)	Isopropanol (C 3) 2-Butanol (C 4) 2-Pentanol (C 5) 2-Hexanol (C 6) 2-Heptanol (C 7) 2-Methyl-1-butanol (C 5) Cyclohexanol (C 6)

Tertiary alcohols (3°)	tert-Butyl alcohol (C 4) tert-Amyl alcohol (C 5) 2-Methyl-2-pentanol (C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol (C 6) 3-Methyloctan-3-ol (C 9)

Biochemical families: carbohydrates alcohols glycoproteins glycosides lipids eicosanoids fatty acids / intermediates phospholipids sphingolipids steroids nucleic acids constituents / intermediates proteins Amino acids / intermediates tetrapyrroles / intermediates

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