Showing Compound Dihydrocitronellol (FDB014093)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:04 UTC

Update date

2019-11-26 03:09:30 UTC

Primary ID

FDB014093

Secondary Accession Numbers

FDB014088

Chemical Information

FooDB Name

Dihydrocitronellol

Description

Dihydrocitronellol, also known as 3,7-dimethyloctan-1-ol or tetrahydrogeraniol, is a member of the class of compounds known as fatty alcohols. Fatty alcohols are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, dihydrocitronellol is considered to be a fatty alcohol lipid molecule. Dihydrocitronellol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocitronellol is an aldehydic, bitter, and citrus tasting compound found in lemon, which makes dihydrocitronellol a potential biomarker for the consumption of this food product.

CAS Number

106-21-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Dihydrocitronellol	MeSH
Tetrahydrogeraniol	MeSH
3,7-Dimethyl-1-octanol	MeSH
3,7-Dimethyloctan-1-ol, titanium salt	MeSH
2,6-Dimethyl-8-octanol	HMDB
3,7-Dimethyl-(.+/-.)-1-octanol	HMDB
3,7-Dimethyl-(R)-1-octanol	HMDB
3,7-Dimethyl-(S)-1-octanol	HMDB
3,7-Dimethyloctan-1-ol	HMDB, MeSH
dihydro-Citronellol	HMDB
Dimethyl octanol	HMDB
Dimethyl-1-octanol	HMDB
Dimethyloctan-2-ol	HMDB
Dimethyloctanol	HMDB
Geraniol tetrahydride	HMDB
Pelargol	HMDB
perhydro-Geraniol	HMDB
S-3,7-Dimethyl-1-octanol	HMDB
tetrahydro-Geraniol	HMDB
FEMA 2391	db_source
Perhydrogeraniol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	3.96	ALOGPS
logP	3.16	ChemAxon
logS	-3.2	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	6	ChemAxon
Refractivity	49.64 m³·mol⁻¹	ChemAxon
Polarizability	20.97 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

C10H22O

IUPAC name

3,7-dimethyloctan-1-ol

InChI Identifier

InChI=1S/C10H22O/c1-9(2)5-4-6-10(3)7-8-11/h9-11H,4-8H2,1-3H3

InChI Key

PRNCMAKCNVRZFX-UHFFFAOYSA-N

Isomeric SMILES

CC(C)CCCC(C)CCO

Average Molecular Weight

158.2811

Monoisotopic Molecular Weight

158.167065326

Classification

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

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 - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 75.88%; H 14.01%; O 10.11%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
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
GC-MS	(R)-Dihydrocitronellol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-cf4e5b3123dc8268afe3	Spectrum
GC-MS	(R)-Dihydrocitronellol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-cf4e5b3123dc8268afe3	Spectrum
Predicted GC-MS	(R)-Dihydrocitronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-022l-9400000000-a82ed7d0f4f4755f36c6	Spectrum
Predicted GC-MS	(R)-Dihydrocitronellol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4m-9610000000-0ca6035f57f928ad187d	Spectrum
Predicted GC-MS	(R)-Dihydrocitronellol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-1900000000-ae95dfe4e9ba656e1b1c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-7900000000-aacea2d911c47e71282b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-cb894cdd71ed845de559	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-b86498e83f376ec918ae	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0900000000-e9cdc4c9eb7a745aabab	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvr-9800000000-b3654cce129ff74febe7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-45f48cadb8b4ef8a602f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0900000000-680af2fd94b1c3853325	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9500000000-e6f488f230acbc414ba1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05g0-9200000000-5272d0d7a828c5c7fed4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-fd135c154c0dd705ca4b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f6d0d8356a7878a8e5b1	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JNT29-L:JNT29-L

EAFUS ID

1015

Dr. Duke ID

TETRAHYDROGERANIOL

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1000591

SuperScent ID

Not Available

Wikipedia ID

Not Available

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
soapy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
aldehydic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leathery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	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.
green	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