Geraniol (YMDB01700)

Identification

YMDB ID

YMDB01700

Name

Geraniol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

beta-Geraniol, also known as (2E)-geraniol or (e)-nerol, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, beta-geraniol is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on beta-Geraniol.

Structure

MOL SDF PDB SMILES InChI

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
(2E)-3,7-Dimethyl-2,6-octadien-1-ol
(2E)-Geraniol
(e)-3,7-Dimethyl-2,6-octadien-1-ol
(e)-Geraniol
(e)-Nerol
3,7-Dimethyl-trans-2,6-octadien-1-ol
t-Geraniol
b-Geraniol
Β-geraniol
(2E)-3,7-Dimethylocta-2,6-dien-1-ol
3,7-Dimethyl-(2E)-2,6-octadien-1-ol
3,7-Dimethyl-(e)-2,6-octadien-1-ol
FEMA 2507
Geraniol
trans-2,6-Dimethyl-2,6-octadien-8-ol
trans-3,7-Dimethy- octa-2,6-dien-1-ol
Geraniol, (Z)-isomer
Geraniol, 1-(14)C-labeled, (e)-isomer
Geraniol, 2-(14)C-labeled, (e)-isomer
Geraniol, titanium (4+) salt
Geraniol, (e)-isomer
(E)-3,7-Dimethyl-2,6-octadienol
trans-1-Hydroxy-3,7-dimethyl-2,6-octadiene

CAS number

106-25-2

Weight

Average: 154.2493
Monoisotopic: 154.135765198

InChI Key

GLZPCOQZEFWAFX-JXMROGBWSA-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

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

Traditional IUPAC Name

geraniol

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

primary alcohol (CHEBI:17447 )
monoterpenoid (CHEBI:17447 )
3,7-dimethylocta-2,6-dien-1-ol (CHEBI:17447 )
Acyclic monoterpenoids (C01500 )
Linear monoterpenes (C01500 )
Acyclic monoterpenoids (LMPR0102010016 )

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	19.67 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
Citrus	FDB013792
Floral	FDB013792
Fruity	FDB013792
Geranium	FDB013792
Rose	FDB013792
Sweet	FDB013792
Waxy	FDB013792

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 - GC-MS (1 TMS)	splash10-002f-9800000000-16b748da465c428492a4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-25934c23f4bc9ba87142	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9000000000-a4d79e7813b94cf0d54b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3a5359aae818f9966cbd	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9200000000-4a8a23071f388f446451	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-f24e92e3c3efdc35a606	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-d8e4f64753ef594f6d40	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-2bce8c0905dd12aa5dac	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-002f-9800000000-16b748da465c428492a4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-4900000000-7e43c8601ed65028cae5	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-1900000000-710389d2548f45d60502	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-001r-9500000000-d864036a8f8b4cdb20ae	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-001r-9400000000-e3661fd0b608943d6b6c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-001i-9200000000-d748b4cd92b7c69ffee3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-001i-9100000000-b6abc8d3af3aa99879b4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-001i-9000000000-710e0ba546f9b86b8e40	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-001i-9000000000-4cc179896d0516270659	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-001i-9000000000-7f3a48636d9da2cda821	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-001i-9000000000-4b196d3d8e84ecd0e9f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-003r-9000000000-718f1d4e975f4b2446d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-003u-9000000000-2e43acc8a377504a4329	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-005c-9000000000-fe7ffaf2c7e121c33b7c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-005c-9000000000-467c307d1f0822b86ea0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-005c-9000000000-5939202301ea6107df2c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-002f-9000000000-0e13687577d30f6265cc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0f96-9000000000-e478c8b2587c1134117d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-5f3fc91bdf843e40a266	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-ab16b7d86a06d659d4f3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-3900000000-4dd10bbea41237cba535	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
MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-f59382e51acd0b540204	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Gramatica, P., Manitto, P., Ranzi, B. M., Delbianco, A., & Francavilla, M. (1982) Stereospecific reduction of geraniol to (R)-(+)-citronellol by Saccharomyces cerevisiae. Experientia, 38, 775–776

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17447
HMDB ID	HMDB0035155
Pubchem Compound ID	637566
Kegg ID	C01500
ChemSpider ID	24603745
FOODB ID	FDB013792
Wikipedia ID	Geraniol
BioCyc ID	Not Available

Structure for #<Compound:0xb0e06964>