Nerol (YMDB01760)

Identification

YMDB ID

YMDB01760

Name

Nerol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Geraniol, also known as (Z)-geraniol or neryl alcohol, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geraniol is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on Geraniol.

Structure

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

Synonyms

(2E)3,7-dimethyl-2,6-Octadien-1-ol
(2Z)-3,7-Dimethyl-2,6-octadien-1-ol
(2Z)3,7-dimethyl-2,6-Octadien-1-ol
(cis)3,7-dimethyl-2,6-Octadien-1-ol
(E)3,7-dimethyl-2,6-Octadien-1-ol
(E)3,7-Dimethyl-Octadien-1-ol
(Z)-3,7-dimethyl-2,6-octadien-1-ol
(z)-geraniol
(Z)3,7-dimethyl-2,6-Octadien-1-ol
2-cis-3,7-Dimethyl-2,6-octadien-1-ol
2-trans-3,7-Dimethyl-2,6-octadien-1-ol
2-trans-3,7-dimethyl-2,6-octadiene-1-ol
2, 6-Octadien-1-ol, 3,7-dimethyl-,(Z)-
2,6-Dimethyl-2,6-octadien-8-ol
2,6-dimethyl-trans-2,6-octadien-8-ol
2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-
2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-
2E-geraniol
3,7-dimethyl-2,6-Octadien-1-ol
3,7-Dimethyl-Octane-1-ol tetrahydro derivative
3,7-Dimethyl-trans-2, 6-octadien-1-ol
3,7-dimethylocta-2,6-dien-1-ol
Beta-geraniol
cis-3,7-Dimethyl-2,6-octadien-1-ol
Cis-geraniol
Geraniol (natural)
Geraniol alcohol
Geranyl alcohol
Guaniol
Lemonol
Nerol
Nerol (cis-geraniol)
Nerol (natural)
Nerolidyl diphosphate
Neryl alcohol
NPP
trans-3,7-dimethyl-2,6-octadien-1-ol
Trans-geraniol
Vernol
(Z)-3,7-Dimethylocta-2,6-dien-1-ol
Geraniol, (e)-isomer
Geraniol, (Z)-isomer
Geraniol, 1-(14)C-labeled, (e)-isomer
Geraniol, 2-(14)C-labeled, (e)-isomer
Geraniol, titanium (4+) salt
Geraniol
(Z)-3,7-Dimethyl-2,6-octadienol
(Z)-3,7-Dimethyloct-2,6-diene-1-ol
(Z)-Nerol
3,7-Dimethyl-cis-2,6-octadien-1-ol
cis-1-Hydroxy-3,7-dimethyl-2,6-octadiene
beta-Nerol
β-Nerol

CAS number

106-25-2

Weight

Average: 154.2493
Monoisotopic: 154.135765198

InChI Key

GLZPCOQZEFWAFX-YFHOEESVSA-N

InChI

InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-

IUPAC Name

(2Z)-3,7-dimethylocta-2,6-dien-1-ol

Traditional IUPAC Name

nerol

Chemical Formula

C₁₀H₁₈O

SMILES

CC(C)=CCC\C(C)=C/CO

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3,7-dimethylocta-2,6-dien-1-ol (CHEBI:29452 )
Acyclic monoterpenoids (C09871 )
Linear monoterpenes (C09871 )
Acyclic monoterpenoids (LMPR0102010010 )

Physical Properties

State

Liquid

Charge

Melting point

<-15 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.531 mg/mL at 25 oC [MILLER,DJ & HAWTHORNE,SB (2000A)]	PhysProp
LogP	3.47 [GRIFFIN,S ET AL. (1999)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.37 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	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	51.18 m³·mol⁻¹	ChemAxon
Polarizability	19.29 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

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bitter	FDB014945
Citrus	FDB014945
Magnolia	FDB014945
Natural	FDB014945
Neroli	FDB014945
Sweet	FDB014945

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)	splash10-014l-9000000000-8132ea67e057a3dd9c80	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-a5bdece739d0cb5bf629	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-015c-9200000000-eea073073c86ea4d9a38	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-0625da1bcd5a7d1938a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-41e0055b618413366b81	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-8132ea67e057a3dd9c80	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9100000000-a5bdece739d0cb5bf629	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-015c-9200000000-eea073073c86ea4d9a38	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-0625da1bcd5a7d1938a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-41e0055b618413366b81	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-014l-9000000000-2ab93357dd27a7c07eb7	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014u-9300000000-c85bc4c928fbf7d824e8	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-030c-9520000000-69b7fbbb25764f7b612e	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001r-9600000000-69c0de28e07b8b530c9a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9100000000-0ee3622152359826448f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-003r-9000000000-d5bb693fadd752735f31	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-014l-9000000000-8132ea67e057a3dd9c80	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-014l-9100000000-a5bdece739d0cb5bf629	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-015c-9200000000-eea073073c86ea4d9a38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive	splash10-0006-9000000000-0625da1bcd5a7d1938a6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-014l-9000000000-7b5a5cfbbe0b42fdd23e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-0900000000-73a127efb4137eb42580	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-3d437630e5bec67a7e07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-8900000000-0e505c85cec6344cab5c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-c7400df359a9559bd594	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-113756054eed13d33ee4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0900000000-dea43b41c5b791cef9d2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9800000000-c028a2bd655026094251	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-9100000000-6e205fbbb6213cf2eb8c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-a55b9b951ba285782da9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-29f4b3188008e31f7b9f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d3a143bdeacdf3ef0e94	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-f29389e574ed8f84a683	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-1a426588f258e723527c	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	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	29452
HMDB ID	HMDB05812
Pubchem Compound ID	3327
Kegg ID	C06111
ChemSpider ID	558917
FOODB ID	FDB014945
Wikipedia ID	Nerol
BioCyc ID	Not Available

Structure for #<Compound:0xacacfee8>