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

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Synonym	Source
(2E)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(2e)3,7-Dimethyl-2,6-octadien-1-ol	HMDB
(2Z)-3,7-Dimethyl-2,6-octadien-1-ol	ChEBI
(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	ChEBI
(Z)-3,7-dimethyl-2,6-Octadien-1-ol	biospider
(Z)-3,7-Dimethyl-2,6-octadienol	PhytoBank

Showing 1 to 10 of 53 entries

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

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Property	Value	Reference
Boiling Point	Bp 225-226°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	3.47	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Experimental Water Solubility	0.531 mg/mL at 25 oC	MILLER,DJ & HAWTHORNE,SB (2000A)
Isoelectric point	Not Available
Mass Composition	C 77.87%; H 11.76%; O 10.37%	DFC
Melting Point	<-15 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti helicobacter	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 ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
estrogenic			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	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

Showing 1 to 10 of 10 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
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
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.
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.
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.