AFCDB: Geraniol (FDB013792)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:54 UTC

Update date

2020-09-17 15:31:23 UTC

Primary ID

FDB013792

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Geraniol

Description

beta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403)

CAS Number

106-24-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H18O

IUPAC name

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

InChI Identifier

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

InChI Key

GLZPCOQZEFWAFX-JXMROGBWSA-N

Isomeric SMILES

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

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	<-15 oC
Boiling Point	Bp 230°	DFC
Experimental Water Solubility	0.1 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Experimental logP	3.56	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 195 (e 19000) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	n30D 1.4777	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-f59382e51acd0b540204	2014-09-20	View Spectrum
GC-MS	Geraniol, 1 TMS, GC-MS Spectrum	splash10-002f-9800000000-16b748da465c428492a4	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-25934c23f4bc9ba87142	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014i-9000000000-a4d79e7813b94cf0d54b	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-3a5359aae818f9966cbd	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-00kf-9200000000-4a8a23071f388f446451	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-f24e92e3c3efdc35a606	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-d8e4f64753ef594f6d40	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-2bce8c0905dd12aa5dac	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-002f-9800000000-16b748da465c428492a4	Spectrum
GC-MS	Geraniol, non-derivatized, GC-MS Spectrum	splash10-0006-4900000000-7e43c8601ed65028cae5	Spectrum
Predicted GC-MS	Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014u-9300000000-c85bc4c928fbf7d824e8	Spectrum
Predicted GC-MS	Geraniol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-030c-9520000000-69b7fbbb25764f7b612e	Spectrum
Predicted GC-MS	Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Geraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-1900000000-710389d2548f45d60502	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-001r-9500000000-d864036a8f8b4cdb20ae	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-001r-9400000000-e3661fd0b608943d6b6c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-001i-9200000000-d748b4cd92b7c69ffee3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-001i-9100000000-b6abc8d3af3aa99879b4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-001i-9000000000-710e0ba546f9b86b8e40	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-001i-9000000000-4cc179896d0516270659	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-001i-9000000000-7f3a48636d9da2cda821	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-001i-9000000000-4b196d3d8e84ecd0e9f3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-003r-9000000000-718f1d4e975f4b2446d1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-003u-9000000000-2e43acc8a377504a4329	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-005c-9000000000-fe7ffaf2c7e121c33b7c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-005c-9000000000-467c307d1f0822b86ea0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-005c-9000000000-5939202301ea6107df2c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-002f-9000000000-0e13687577d30f6265cc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0f96-9000000000-e478c8b2587c1134117d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-5f3fc91bdf843e40a266	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-ab16b7d86a06d659d4f3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000i-3900000000-4dd10bbea41237cba535	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-3d437630e5bec67a7e07	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-8900000000-0e505c85cec6344cab5c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-c7400df359a9559bd594	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-113756054eed13d33ee4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0900000000-dea43b41c5b791cef9d2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9800000000-c028a2bd655026094251	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17447

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35155

CRC / DFC (Dictionary of Food Compounds) ID

JVC33-F:JHG09-C

EAFUS ID

1460

Dr. Duke ID

GERANIOL

BIGG ID

Not Available

KNApSAcK ID

C00000845

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

106-24-1

GoodScent ID

rw1006991

SuperScent ID

Not Available

Wikipedia ID

Geraniol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti helmintic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
ascaricide	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
embryotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
emetic			DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
Insectiphile	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
mycobactericide			DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
trichomonicide			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
rose	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
geranium	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Geraniol (FDB013792)

Structure for FDB013792 (Geraniol)