cis-3-hexen-1-ol (YMDB01420)

Identification

YMDB ID

YMDB01420

Name

cis-3-hexen-1-ol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes. cis-3-Hexen-1-ol is an alcohol and its esters are also important flavor and fragrance raw materials. The related aldehyde cis-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated trans-2-hexenal. [Wikipedia]

Structure

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

Synonyms

(3Z)-3-Hexen-1-ol
(Z)-Hex-3-en-1-ol
(Z)-Hex-3-ene-1-ol
(Z)-hex-3-enol
3-(Z)-Hexen-1-ol
3-(Z)-Hexenol
3-Hexen-1-ol
3-Hexen-1-ol, (Z)-
3-Hexen-1-ol, cis-
3-Hexenol
3-Hexenol, cis-
c-3-Hexen-1-ol
cis-3-1-Hexenol
cis-3-Hexene-1-ol
cis-3-Hexenol
cis-hex-3-en-1ol
cis-Hex-3-enol
hex-3( Z)-en-1-ol
Hex-3(Z)-enol
HEXEN-30L-1
Leaf alcohol
Z-3-Hexenol
(3Z)-Hex-3-en-1-ol
(Z)-3-Hexen-1-ol
Blatteralkohol
cis-3-Hexen-1-ol
(Z)-3-Hexeno1
3-Hexen-1-ol, (Z)-isomer
(3Z)-Hexenol
(Z)-3-Hexenol
1-Hydroxy-3-hexene
3Z-Hexen-1-ol
beta-gamma-Hexenol
cis-1-Hydroxy-3-hexene
cis-3-Hexenyl alcohol
β-γ-Hexenol
Folic alcohol
Green leaf alcohol
cis-Hex-3-en-1-ol

CAS number

928-96-1

Weight

Average: 100.1589
Monoisotopic: 100.088815006

InChI Key

UFLHIIWVXFIJGU-ARJAWSKDSA-N

InChI

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3-

IUPAC Name

(3Z)-hex-3-en-1-ol

Traditional IUPAC Name

cis-3-hexenol

Chemical Formula

C₆H₁₂O

SMILES

CC\C=C/CCO

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:28857 )
Fatty alcohols (LMFA05000059 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	16.2 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.33	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Acidic)	16.79	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	3	ChemAxon
Refractivity	32.45 m³·mol⁻¹	ChemAxon
Polarizability	12.28 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
Green	FDB008091
Leafy	FDB008091

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)	splash10-00l6-9000000000-54ee041e574aedb72ec1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-3930494d4cdcbeff30de	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00l6-9000000000-54ee041e574aedb72ec1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-3930494d4cdcbeff30de	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pvl-9000000000-98dcc9fd68f2a94b0486	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-338134b6dd87472ddcd6	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-9600000000-3331cb74588b75ccc6b0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9200000000-d2497aba2144909b82de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-a37fe1e4c1e79fc8f47c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-04ee26e1d76a08ecd25b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-f9a77a1598d22451fda4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l7-9000000000-581b5f1f1575ce7ca0d9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0apl-9000000000-642389f113888c5ed259	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9772027f35e4f4098572	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9000000000-6d54f605cc9d67d182a8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-658fe53778817eb82301	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-9000000000-e4909a87b286f17e5bc5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbc-9000000000-199292b1321498e28904	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-014l-9000000000-5622c90de0e7476ece50	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	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

References

References:

Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	28857
HMDB ID	HMDB0030003
Pubchem Compound ID	10993
Kegg ID	C08492
ChemSpider ID	21105914
FOODB ID	FDB008091
Wikipedia	cis-3-hexen-1-ol
BioCyc ID	Not Available

Structure for #<Compound:0xaf6f601c>