Showing Compound Citronellol (FDB014490)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:18 UTC

Update date

2019-11-26 03:10:10 UTC

Primary ID

FDB014490

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Citronellol

Description

Occurs in many essential oils, usually as a partial racemate. obtained mainly from geranium oil or synthetically. Flavour for use in citrus compositions Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer. (-)-Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums.

CAS Number

106-22-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2,3-Dihydrogeraniol	ChEBI
2,6-Dimethyl-2-octen-8-ol	ChEBI
3,7-Dimethyl-6-octen-1-ol	ChEBI
beta-Citronellol	ChEBI
Cephrol	ChEBI
Elenol	ChEBI
b-Citronellol	Generator
Β-citronellol	Generator
Citronellol, (S)-isomer	MeSH
Citronellol, (R)-isomer	MeSH
Citronellol, (+-)-isomer	MeSH
Citronellol, titanium (+4) salt	MeSH
(±)-3,7-Dimethyl-6-octen-1-ol	manual
(±)-beta-Citronellol	manual
(±)-Citronellol	manual
3,7-Dimethyloct-6-en-1-ol	biospider
6-Octen-1-ol, 3,7-dimethyl-	biospider
Citronellol	db_source
Dihydrogeraniol	manual
DL-Citronellol	manual
Rhodinol	manual
Yacarol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	3.48	ALOGPS
logP	2.75	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	-1.9	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	5	ChemAxon
Refractivity	50.49 m³·mol⁻¹	ChemAxon
Polarizability	20.05 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

C10H20O

IUPAC name

3,7-dimethyloct-6-en-1-ol

InChI Identifier

InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3

InChI Key

QMVPMAAFGQKVCJ-UHFFFAOYSA-N

Isomeric SMILES

CC(CCO)CCC=C(C)C

Average Molecular Weight

156.269

Monoisotopic Molecular Weight

156.151415264

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

monoterpenoid (CHEBI:50462 )
citronellol (CPD-7980 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 76.86%; H 12.90%; O 10.24%	DFC
Melting Point	< 25 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	3.91	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	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Citronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-02go-9400000000-68f35447a1addaa3c7e9	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-1900000000-9f559c6b6bae07c69978	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-8900000000-f8c3d1ff7e6f87d6e43d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066u-9100000000-8ae7fa4f01b76f1eed16	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-82f8313ff8eb7c68242b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0900000000-de94d5335c77bdb5afcf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-9800000000-b04acf4b20ad46274796	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

8842

Pubchem Substance ID

Not Available

ChEBI ID

50462

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JRJ33-M:JRJ33-M

EAFUS ID

695

Dr. Duke ID

CITRONELLOL|BETA-CITRONELLOL

BIGG ID

Not Available

KNApSAcK ID

C00000844

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

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 bacterial	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 staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti streptococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
candidicide			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
irritant			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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
geranium	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leather	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.
rose bud	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.