Showing Compound Nerol (FDB014945)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:33 UTC

Update date

2020-09-17 15:30:02 UTC

Primary ID

FDB014945

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Nerol

Description

Nerol or (Z)-3,7-dimethyl-2,6-octadien-1-ol or cis-Geranial is formally classified as an alkylalcohol although it is biochemically a monoterpenoid synthesized from isoprene units. It is soluble in water and very soluble in alcohol. Nerol is a naturally occurring organic compound found in the essential oils of many plants and was originally found in neroli oil, from which its name was derived. The largest natural source is palmarosa oil and it is the primary constituent of rose oil, palmarosa oil, and citronella oil (Java type) with in small quantities found in geranium, lemon, and many other essential oils. Different foods contain nerol with the highest concentration found in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. Nerol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. Nerol has a sweet, citrus and floral flavor with a sweet rose-like odor. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. This alcohol is widely and frequently used in perfumery as it has a freshness to a rose base (PMID: 18640199). It is detected in small quantities in orange peel and together with other oils, was found to have antimicrobial properties (PMID: 27535797).

CAS Number

106-25-2

Structure

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

Synonyms

Synonym	Source
(2Z)-3,7-Dimethyl-2,6-octadien-1-ol	ChEBI
(Z)-3,7-Dimethyl-2,6-octadien-1-ol	ChEBI
(Z)-3,7-Dimethylocta-2,6-dien-1-ol	ChEBI
(Z)-Geraniol	ChEBI
2-cis-3,7-Dimethyl-2,6-octadien-1-ol	ChEBI
cis-3,7-Dimethyl-2,6-octadien-1-ol	ChEBI
cis-Geraniol	ChEBI
Neryl alcohol	ChEBI
Geraniol, (e)-isomer	MeSH
Geraniol, (Z)-isomer	MeSH
Geraniol, 1-(14)C-labeled, (e)-isomer	MeSH
Geraniol, 2-(14)C-labeled, (e)-isomer	MeSH
Geraniol, titanium (4+) salt	MeSH
(2E)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(2Z)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(cis)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(e)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(e)3,7-Dimethyl-octadien-1-ol	HMDB
(Z)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
2,6-Dimethyl-trans-2,6-octadien-8-ol	HMDB
2-trans-3,7-Dimethyl-2,6-octadien-1-ol	HMDB
2-trans-3,7-Dimethyl-2,6-octadiene-1-ol	HMDB
2E-Geraniol	HMDB
3,7-Dimethyl-2,6-octadien-1-ol	HMDB
3,7-Dimethyl-octane-1-ol tetrahydro derivative	HMDB
3,7-Dimethyl-trans-2, 6-octadien-1-ol	HMDB
3,7-Dimethylocta-2,6-dien-1-ol	HMDB
beta-Geraniol	HMDB
Geraniol (natural)	HMDB
Geraniol alcohol	HMDB
Geranyl alcohol	HMDB
Guaniol	HMDB
Lemonol	HMDB
Nerol	HMDB
Nerol (natural)	HMDB
Nerolidyl diphosphate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-ol	HMDB
trans-Geraniol	HMDB
Vernol	HMDB
Geraniol	MeSH
(Z)-3,7-Dimethyl-2,6-octadienol	PhytoBank
(Z)-3,7-Dimethyloct-2,6-diene-1-ol	PhytoBank
(Z)-Nerol	PhytoBank
3,7-Dimethyl-cis-2,6-octadien-1-ol	PhytoBank
cis-1-Hydroxy-3,7-dimethyl-2,6-octadiene	PhytoBank
beta-Nerol	PhytoBank
β-Nerol	PhytoBank
(2e)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(Z)-3,7-dimethyl-2,6-Octadien-1-ol	biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (2Z)-	biospider
2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-	biospider
FEMA 2770	db_source
Nerolidyl diate	HMDB

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	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

(2Z)-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-YFHOEESVSA-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

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

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

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 225-226°	DFC
Experimental Water Solubility	0.531 mg/mL at 25 oC	MILLER,DJ & HAWTHORNE,SB (2000A)
Experimental logP	3.47	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	n20D 1.4744	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-8132ea67e057a3dd9c80	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-a5bdece739d0cb5bf629	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-015c-9200000000-eea073073c86ea4d9a38	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-0625da1bcd5a7d1938a6	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-41e0055b618413366b81	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-8132ea67e057a3dd9c80	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9100000000-a5bdece739d0cb5bf629	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-015c-9200000000-eea073073c86ea4d9a38	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-0625da1bcd5a7d1938a6	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-41e0055b618413366b81	Spectrum
GC-MS	Nerol, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-2ab93357dd27a7c07eb7	Spectrum
Predicted GC-MS	Nerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014u-9300000000-c85bc4c928fbf7d824e8	Spectrum
Predicted GC-MS	Nerol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-030c-9520000000-69b7fbbb25764f7b612e	Spectrum
Predicted GC-MS	Nerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001r-9600000000-69c0de28e07b8b530c9a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9100000000-0ee3622152359826448f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-003r-9000000000-d5bb693fadd752735f31	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-014l-9000000000-8132ea67e057a3dd9c80	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-014l-9100000000-a5bdece739d0cb5bf629	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-015c-9200000000-eea073073c86ea4d9a38	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive	splash10-0006-9000000000-0625da1bcd5a7d1938a6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-014l-9000000000-7b5a5cfbbe0b42fdd23e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, negative	splash10-0a4i-0900000000-73a127efb4137eb42580	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-3d437630e5bec67a7e07	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-8900000000-0e505c85cec6344cab5c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-c7400df359a9559bd594	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-113756054eed13d33ee4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0900000000-dea43b41c5b791cef9d2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9800000000-c028a2bd655026094251	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-9100000000-6e205fbbb6213cf2eb8c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-a55b9b951ba285782da9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-29f4b3188008e31f7b9f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-d3a143bdeacdf3ef0e94	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-f29389e574ed8f84a683	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-1a426588f258e723527c	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

29452

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05812

CRC / DFC (Dictionary of Food Compounds) ID

JVC33-F:JXL41-N

EAFUS ID

2649

Dr. Duke ID

NEROL

BIGG ID

Not Available

KNApSAcK ID

C00000855

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

106-25-2

GoodScent ID

rw1008951

SuperScent ID

Not Available

Wikipedia ID

Nerol

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
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti helicobacter	33282	An agent that targets and eradicates Helicobacter pylori bacteria, reducing inflammation and preventing ulcers. Therapeutically, it's used to treat gastrointestinal disorders, such as peptic ulcers and gastritis, and to prevent gastric cancer.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti ulcer	49201	An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.	DUKE
Estrogenic		An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.	DUKE
Name	48318	flavor	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE
Trichomonicide		An agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	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.
natural	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
neroli	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.
magnolia	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755