1-Hexanol (YMDB01473)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Identification

YMDB ID

YMDB01473

Name

1-Hexanol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

1-Hexanol is an organic alcohol with a six carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. 1-Hexanol is an alcohol extracted from yeast and produced during fermentation of alcoholic beverages.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

1-Hexyl alcohol
1-Hydroxyhexane
Alcohol C-6
Alcohol(C6)
Amylcarbinol
BHL
C6 alcohol
Caproic alcohol
Caproyl alcohol
Cyclohexan-1-ol
Cyclohexanol
Epal 6
Exxal 6
HEX
Hexahydrophenol
Hexalin
Hexan-1-ol
Hexanol
Hexanol-(1)
Hexyl alcohol
n-C6H13OH
n-Hexan-1-ol
N-hexanol
N-hexenol
N-hexyl alcohol
Pentylcarbinol
1-Hexanol, aluminum salt
Fatty alcohol(C6)
Hexanol-CMPD
Hexyl alcohol (natural)
Hexyl alcohol, active
1-Hexanol

CAS number

111-27-3

Weight

Average: 102.1748
Monoisotopic: 102.10446507

InChI Key

ZSIAUFGUXNUGDI-UHFFFAOYSA-N

InChI

InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3

IUPAC Name

hexan-1-ol

Traditional IUPAC Name

hexanol

Chemical Formula

C₆H₁₄O

SMILES

CCCCCCO

Chemical Taxonomy

Description

belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:87393 )
Fatty alcohols (LMFA05000117 )
a small molecule (HEXANOL-CMPD )

Physical Properties

State

Liquid

Charge

Melting point

-44.6 °C

Experimental Properties

Property	Value	Reference
Water Solubility	5.9 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	2.03 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.22 g/L	ALOGPS
logP	2.03	ALOGPS
logP	1.69	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.34 m³·mol⁻¹	ChemAxon
Polarizability	13.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Alcoholic	FDB008072
Ethereal	FDB008072
Flower	FDB008072
Fruity	FDB008072
Fusel	FDB008072
Green	FDB008072
Oil	FDB008072
Resin	FDB008072
Sweet	FDB008072

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-029ae838da9e13a0e457	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-35926852ac4ed3ed0959	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-612a7e611628b904745f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-9000000000-48f5c5da7cd09948311e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-df7ed15b6c10248ee93a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-65cf94afbc05ce616b62	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-f121c161f3815adad6e6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-003fe1ca0e7fdfcbdd97	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-029ae838da9e13a0e457	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-35926852ac4ed3ed0959	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-612a7e611628b904745f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000i-9000000000-48f5c5da7cd09948311e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-df7ed15b6c10248ee93a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-65cf94afbc05ce616b62	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-f121c161f3815adad6e6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-003fe1ca0e7fdfcbdd97	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9000000000-118d12981b86ce381ebd	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9300000000-7090cf9145edfffd8de0	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-000i-9000000000-34d8cf6a0a5f99d7b239	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-000l-9000000000-93a8e902c6f20d518e6e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0006-9000000000-817448b00815a05c099f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0006-9000000000-bb995d565d8efee48a53	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0006-9000000000-9c2e3b526514227b5954	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0006-9000000000-ddd13faf0a10185ac38f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0006-9000000000-29d21c96ea231fc20c2f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0006-9000000000-cb2eaacaf54e58c3408b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0006-9000000000-af41c3ef4b594956cc94	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0006-9000000000-88cf8122694ad634e9ba	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0006-9000000000-05a459922ab22eb5a749	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0006-9000000000-4dfbfb07af734375bb20	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0006-9000000000-67f1d2fb3dcd71e1f02c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0006-9000000000-ac4cc1d63a02856aae86	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0006-9000000000-ad4885a4e0e7c3ce30d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0006-9000000000-46264fd40c3ba6acb30e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0006-9000000000-db820e796357d6b2dd1e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0006-9000000000-695b77a970e008201389	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0006-9000000000-8b4cec3d369d30b0fe83	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0006-9000000000-00882c5a71f3ac89f872	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0006-9000000000-df3f313f6cf901b9b25b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0006-9000000000-ea330b0bdd832ab426cf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0006-9000000000-42749ebd8ebeaa0ebb5c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-000f-9000000000-1ff1f3558a9db25d0067	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-000f-9000000000-6ac31d169cdb4a253db7	JSpectraViewer \| MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-26ed9611cc7f575d818b	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

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
Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
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:

Resource	Link
CHEBI ID	608596
HMDB ID	HMDB12971
Pubchem Compound ID	8103
Kegg ID	C00854
ChemSpider ID	7812
FOODB ID	FDB008072
Wikipedia	1-Hexanol
BioCyc ID	CPD-883

Enzymes

Protein Details

1. Alcohol O-acetyltransferase 1

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.

Protein Details

2. Alcohol O-acetyltransferase 2

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.

Structure for #<Compound:0xafdf6cb8>

Enzymes

Reactions

Reactions