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Identification
YMDB IDYMDB00573
Nameisobutanol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionIsobutanol is a colorless, flammable liquid with a characteristic smell. Its isomers include n-butanol, 2-butanol, and tert-butanol. Isobutanol is produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter. This alcohol tends to increase in content during wine aging. It is the final product of the catabolism of valine in S. cerevisiae.
Structure
Thumb
Synonyms
  • 1-Hydroxymethylpropane
  • 1-Propanol, 2-methyl-
  • 2-Methyl propanol
  • 2-Methyl-1-propanol
  • 2-methyl-1-propanyl alcohol
  • 2-Methylpropan-1-ol
  • 2-methylpropanoI
  • 2-Methylpropanol
  • 2-Methylpropanol-1
  • 2-Methylpropyl alcohol
  • Alcohol
  • Alcool isobutylique
  • Butanol-iso
  • Fermentation butyl alcohol
  • I-butanol
  • I-butyl alcohol
  • IBA
  • Iso-butyl alcohol
  • iso-C4H9OH
  • isobutanol
  • Isobutanol or isobutyl alcohol
  • Isobutyl alcohol
  • Isobutylalkohol
  • Isopropyl carbitol
  • Isopropylcarbinol
  • Methyl-2 propanol-1
  • Propanol, 2-methyl-
  • Isobutyl alcohol, aluminum salt
  • Isobutyl alcohol, sodium salt
  • Isobutyl alcohol, titanium (+4) salt
CAS number78-83-1
WeightAverage: 74.1216
Monoisotopic: 74.073164942
InChI KeyZXEKIIBDNHEJCQ-UHFFFAOYSA-N
InChIInChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
IUPAC Name2-methylpropan-1-ol
Traditional IUPAC Nameisobutanol
Chemical FormulaC4H10O
SMILESCC(C)CO
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-108 °C
Experimental Properties
PropertyValueReference
Water Solubility85 mg/mL at 25 oC [VALVANI,SC et al. (1981)]PhysProp
LogP0.76 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility140 g/LALOGPS
logP0.6ALOGPS
logP0.73ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)17.33ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.01 m³·mol⁻¹ChemAxon
Polarizability9.07 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BitterFDB030942
EtherFDB030942
SolventFDB030942
WineFDB030942
SMPDB Pathways
Valine DegradationPW002489 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
isobutyraldehyde + NADH + hydronisobutanol + NAD
KEGG Reactions
Acetyl-CoA + isobutanolisobutyl acetate + Coenzyme A
NADH + isobutyraldehyde + hydronNAD + isobutanol
isobutyraldehyde + NADPH + hydronNADP + isobutanol
isobutyl acetate + waterAcetic acid + isobutanol + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
  • Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). "Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry." Proc Natl Acad Sci U S A 104:2193-2198.17287358
  • Fukuda, K., Kiyokawa, Y., Yanagiuchi, T., Wakai, Y., Kitamoto, K., Inoue, Y., Kimura, A. (2000). "Purification and characterization of isoamyl acetate-hydrolyzing esterase encoded by the IAH1 gene of Saccharomyces cerevisiae from a recombinant Escherichia coli." Appl Microbiol Biotechnol 53:596-600.10855721
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
  • Larroy, C., Pares, X., Biosca, J. A. (2002). "Characterization of a Saccharomyces cerevisiae NADP(H)-dependent alcohol dehydrogenase (ADHVII), a member of the cinnamyl alcohol dehydrogenase family." Eur J Biochem 269:5738-5745.12423374
  • Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
  • Larroy, C., Fernandez, M. R., Gonzalez, E., Pares, X., Biosca, J. A. (2002). "Characterization of the Saccharomyces cerevisiae YMR318C (ADH6) gene product as a broad specificity NADPH-dependent alcohol dehydrogenase: relevance in aldehyde reduction." Biochem J 361:163-172.11742541
  • Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID46645
HMDB IDHMDB06006
Pubchem Compound ID6560
Kegg IDC14710
ChemSpider ID6312
FOODB IDFDB030942
WikipediaIsobutanol
BioCyc IDISOBUTANOL

Enzymes

General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH3
Uniprot ID:
P07246
Molecular weight:
40369.19922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
Oxidizes long-chain alcohols and, in the presence of glutathione, is able to oxidize formaldehyde. Is responsible for yeast resistance to formaldehyde
Gene Name:
SFA1
Uniprot ID:
P32771
Molecular weight:
41041.69922
Reactions
S-(hydroxymethyl)glutathione + NAD(P)(+) → S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of primary unbranched alcohols to their corresponding aldehydes. Also also shows activity toward secondary alcohols
Gene Name:
ADH1
Uniprot ID:
P00330
Molecular weight:
36849.0
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Reduces acetaldehyde to ethanol during glucose fermentation. Specific for ethanol. Shows drastically reduced activity towards primary alcohols from 4 carbon atoms upward. Isomers of aliphatic alcohol, as well as secondary alcohols and glycerol are not used at all
Gene Name:
ADH4
Uniprot ID:
P10127
Molecular weight:
41141.69922
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
An alcohol + NAD(+) = an aldehyde or ketone + NADH
Gene Name:
ADH5
Uniprot ID:
P38113
Molecular weight:
37647.89844
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in zinc ion binding
Specific function:
This isozyme preferentially catalyzes the conversion of ethanol to acetaldehyde. Acts on a variety of primary unbranched aliphatic alcohols
Gene Name:
ADH2
Uniprot ID:
P00331
Molecular weight:
36731.60156
Reactions
An alcohol + NAD(+) → an aldehyde or ketone + NADH.
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Catalyzes the esterification of isoamyl alcohol and various other alcohols by acetyl-CoA
Gene Name:
ATF1
Uniprot ID:
P40353
Molecular weight:
61035.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
General function:
Involved in alcohol O-acetyltransferase activity
Specific function:
Acetyl-CoA + an alcohol = CoA + an acetyl ester
Gene Name:
ATF2
Uniprot ID:
P53296
Molecular weight:
61897.5
Reactions
Acetyl-CoA + an alcohol → CoA + an acetyl ester.
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH7
Uniprot ID:
P25377
Molecular weight:
39348.19922
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
General function:
Involved in enzyme regulator activity
Specific function:
Required for calcium regulation. May regulate calcium accumulation by a non-vacuole organelle. Also regulates the activity of CSH1 and SUR1 during mannosyl phosphorylinositol ceramide synthesis
Gene Name:
CSG2
Uniprot ID:
P35206
Molecular weight:
45441.60156
Reactions
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
General function:
Involved in hydrolase activity
Specific function:
Plays a crucial role in the hydrolysis of isoamyl acetate in sake mash
Gene Name:
IAH1
Uniprot ID:
P41734
Molecular weight:
27346.0
Reactions