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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 20:02:11 UTC

Update Date

2023-02-21 17:24:36 UTC

HMDB ID

HMDB0035093

Secondary Accession Numbers

HMDB35093

Metabolite Identification

Common Name

D-Citronellol

Description

Citronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID:6991645 ). Citronellol occurs in many essential oils as either - or + enantiomers. -Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral¬†leathery¬†waxy¬†rose¬†citrus odor ( Ref:DOI). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID:2862274 ). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID:30453001 ) against human lung cancer (PMID:31280209 ), against induced rat breast cancer (PMID:31313341 ), has antifungal activity against Candida species (PMID:32150884 ) and has anti-hypertensive properties (PMID:26872991 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0035093
     RDKit          3D
D-Citronellol
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.9907    1.1869    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    0.3788    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2580   -0.2048   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680    0.1898    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.6054    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.2288   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895   -0.7019   -0.7972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8578   -1.8365    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.0330   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.8066   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    1.7939    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    2.1864    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.2605    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.6307    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.3183   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862    0.0206   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563    0.1514   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702    0.6271    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0540   -1.0154   -0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -1.4492    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    0.4738    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3819    1.1305   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -1.1230   -1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -1.4923    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -2.3174   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1002   -2.6353   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -0.6102   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870    0.7733   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3479    1.3656   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.1883    0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.8838    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
M  END

HMDB0035093
     RDKit          3D
D-Citronellol
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.9907    1.1869    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    0.3788    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2580   -0.2048   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680    0.1898    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.6054    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.2288   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895   -0.7019   -0.7972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8578   -1.8365    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.0330   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.8066   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    1.7939    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    2.1864    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.2605    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.6307    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.3183   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862    0.0206   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563    0.1514   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702    0.6271    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0540   -1.0154   -0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -1.4492    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    0.4738    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3819    1.1305   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -1.1230   -1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -1.4923    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -2.3174   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1002   -2.6353   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -0.6102   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870    0.7733   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3479    1.3656   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.1883    0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.8838    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
M  END

COMPND    HMDB0035093
HETATM    1  C1  UNL     1       3.991   1.187   0.774  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.935   0.379   0.105  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.258  -0.205  -1.237  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.768   0.190   0.678  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.683  -0.605   0.057  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.578   0.229  -0.164  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.589  -0.702  -0.797  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.858  -1.837   0.109  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.770   0.033  -1.308  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.555   0.807  -0.320  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.809   1.794   0.314  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.109   2.186   0.331  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.791   1.261   1.875  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.952   0.631   0.658  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.205  -1.318  -1.110  1.00  0.00           H  
HETATM   16  H5  UNL     1       4.286   0.021  -1.543  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.556   0.151  -1.993  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.570   0.627   1.649  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.054  -1.015  -0.907  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.401  -1.449   0.692  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.970   0.474   0.860  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.382   1.131  -0.753  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.061  -1.123  -1.705  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.715  -1.492   1.172  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.844  -2.317  -0.000  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.100  -2.635  -0.034  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.468  -0.610  -1.882  1.00  0.00           H  
HETATM   28  H17 UNL     1      -2.387   0.773  -2.073  1.00  0.00           H  
HETATM   29  H18 UNL     1      -4.348   1.366  -0.902  1.00  0.00           H  
HETATM   30  H19 UNL     1      -4.127   0.188   0.400  1.00  0.00           H  
HETATM   31  H20 UNL     1      -2.999   1.884   1.264  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9   23
CONECT    8   24   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   31
END

HMDB0035093
     RDKit          3D
D-Citronellol
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.9907    1.1869    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    0.3788    0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2580   -0.2048   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680    0.1898    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -0.6054    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5775    0.2288   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895   -0.7019   -0.7972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8578   -1.8365    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697    0.0330   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.8066   -0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    1.7939    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093    2.1864    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.2605    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.6307    0.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.3183   -1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862    0.0206   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5563    0.1514   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702    0.6271    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0540   -1.0154   -0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -1.4492    0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    0.4738    0.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3819    1.1305   -0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0607   -1.1230   -1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -1.4923    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441   -2.3174   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1002   -2.6353   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -0.6102   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870    0.7733   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3479    1.3656   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.1883    0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991    1.8838    1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-(+)-Citronellol	Kegg
(+)-beta-Citronellol	HMDB
(+)-R-Citronellol	HMDB
(3R)-3,7-Dimethyloct-6-en-1-ol	HMDB
(R)-(+)-beta -Citronellol	HMDB
(R)-(+)-beta-Citronellol	HMDB
(R)-3,7-Dimethyl-6-octen-1-ol	HMDB
(R)-3,7-Dimethyloct-6-en-1-ol	HMDB
3,7-Dimethyl-(3R)-6-octen-1-ol	HMDB
3,7-Dimethyl-(R)-6-octen-1-ol	HMDB
Citronellol, (+-)-isomer	MeSH, HMDB
Citronellol	MeSH, HMDB
Citronellol, (R)-isomer	MeSH, HMDB
Citronellol, (S)-isomer	MeSH, HMDB
Citronellol, titanium (+4) salt	MeSH, HMDB
b-Citronellol	Generator, HMDB
Β-citronellol	Generator, HMDB
(+)-(R)-Citronellol	HMDB
(+)-Citronellol	HMDB
(+)-β-Citronellol	HMDB
(3R)-(+)-beta-Citronellol	HMDB
(3R)-(+)-β-Citronellol	HMDB
(3R)-3,7-Dimethyl-6-octen-1-ol	HMDB
(R)-(+)-3,7-Dimethyl-6-octen-1-ol	HMDB
(R)-(+)-β-Citronellol	HMDB
(R)-Citronellol	HMDB
(R)-beta-Citronellol	HMDB
(R)-β-Citronellol	HMDB
D-Citronellol	HMDB
d-Citronellol	HMDB

Chemical Formula

C₁₀H₂₀O

Average Molecular Weight

156.2652

Monoisotopic Molecular Weight

156.151415262

IUPAC Name

(3R)-3,7-dimethyloct-6-en-1-ol

Traditional Name

β-citronellol

CAS Registry Number

1117-61-9

SMILES

C[C@@H](CCO)CCC=C(C)C

InChI Identifier

InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m1/s1

InChI Key

QMVPMAAFGQKVCJ-SNVBAGLBSA-N

Chemical Taxonomy

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

citronellol (CHEBI:10360 )
Acyclic monoterpenoids (C09849 )
Linear monoterpenes (C09849 )
Acyclic monoterpenoids (LMPR0102010008 )

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 21970810)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035093)

Source

Endogenous

Endogenous (HMDB: HMDB0035093)

Plant

Plant (HMDB: HMDB0035093)

Animal

Animal (HMDB: HMDB0035093)

Exogenous

Food

Food (HMDB: HMDB0035093)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035093)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035093)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035093)

Lipid metabolism pathway (HMDB: HMDB0035093)

Cellular process

Cell signaling (HMDB: HMDB0035093)

Biochemical process

Lipid transport (HMDB: HMDB0035093)

Role

Biological role

Energy source (HMDB: HMDB0035093)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035093)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	221.00 to 224.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	105.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.239 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	20.08 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.767	31661259
DarkChem	[M-H]-	136.804	31661259
DeepCCS	[M+H]+	141.623	30932474
DeepCCS	[M-H]-	138.979	30932474
DeepCCS	[M-2H]-	174.772	30932474
DeepCCS	[M+Na]+	149.758	30932474
AllCCS	[M+H]+	138.9	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	142.6	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	141.5	32859911
AllCCS	[M+Na-2H]-	143.7	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Citronellol	C[C@@H](CCO)CCC=C(C)C	1728.6	Standard polar	33892256
D-Citronellol	C[C@@H](CCO)CCC=C(C)C	1197.7	Standard non polar	33892256
D-Citronellol	C[C@@H](CCO)CCC=C(C)C	1207.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Citronellol,1TMS,isomer #1	CC(C)=CCC[C@@H](C)CCO[Si](C)(C)C	1307.2	Semi standard non polar	33892256
D-Citronellol,1TBDMS,isomer #1	CC(C)=CCC[C@@H](C)CCO[Si](C)(C)C(C)(C)C	1521.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-9400000000-ba08b011d6d2fa548e82	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Citronellol GC-MS (1 TMS) - 70eV, Positive	splash10-0ir0-9620000000-5dec8fa14f289a16a8b8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Citronellol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-015c-9000000000-dfb40ffb3fb172759b4f	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 10V, Positive-QTOF	splash10-052r-1900000000-9f559c6b6bae07c69978	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 20V, Positive-QTOF	splash10-052r-8900000000-f8c3d1ff7e6f87d6e43d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 40V, Positive-QTOF	splash10-066u-9100000000-8ae7fa4f01b76f1eed16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 10V, Negative-QTOF	splash10-0a4i-0900000000-82f8313ff8eb7c68242b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 20V, Negative-QTOF	splash10-056r-0900000000-de94d5335c77bdb5afcf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 40V, Negative-QTOF	splash10-0a6u-9800000000-b04acf4b20ad46274796	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 10V, Negative-QTOF	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 20V, Negative-QTOF	splash10-0ab9-0900000000-4432dcd3f704b4a61b30	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 40V, Negative-QTOF	splash10-014i-9400000000-fe45ce059cb434ed5e0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 10V, Positive-QTOF	splash10-05o0-9200000000-e66f9e249b523e6771bb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 20V, Positive-QTOF	splash10-053r-9000000000-6e0012cc1ab177db56c0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Citronellol 40V, Positive-QTOF	splash10-0006-9000000000-97567d47518fef28ec28	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	0-17960.919 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	0-717668.852 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details

Associated Disorders and Diseases

Disease References

Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Citronellol

METLIN ID

Not Available

PubChem Compound

101977

PDB ID

Not Available

ChEBI ID

10360

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056991

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Taylor WG, Schreck CE: Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol. J Pharm Sci. 1985 May;74(5):534-9. doi: 10.1002/jps.2600740508. [PubMed:2862274 ]
Santos PL, Matos JPSCF, Picot L, Almeida JRGS, Quintans JSS, Quintans-Junior LJ: Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food Chem Toxicol. 2019 Jan;123:459-469. doi: 10.1016/j.fct.2018.11.030. Epub 2018 Nov 16. [PubMed:30453001 ]
Yu WN, Lai YJ, Ma JW, Ho CT, Hung SW, Chen YH, Chen CT, Kao JY, Way TD: Citronellol Induces Necroptosis of Human Lung Cancer Cells via TNF-alpha Pathway and Reactive Oxygen Species Accumulation. In Vivo. 2019 Jul-Aug;33(4):1193-1201. doi: 10.21873/invivo.11590. [PubMed:31280209 ]
Rajendran J, Pachaiappan P, Subramaniyan S: Dose-dependent chemopreventive effects of citronellol in DMBA-induced breast cancer among rats. Drug Dev Res. 2019 Sep;80(6):867-876. doi: 10.1002/ddr.21570. Epub 2019 Jul 16. [PubMed:31313341 ]
Silva D, Diniz-Neto H, Cordeiro L, Silva-Neta M, Silva S, Andrade-Junior F, Leite M, Nobrega J, Morais M, Souza J, Rosa L, Melo T, Souza H, Sousa A, Rodrigues G, Oliveira-Filho A, Lima E: (R)-(+)-beta-Citronellol and (S)-(-)-beta-Citronellol in Combination with Amphotericin B against Candida Spp. Int J Mol Sci. 2020 Mar 5;21(5). pii: ijms21051785. doi: 10.3390/ijms21051785. [PubMed:32150884 ]
Ribeiro-Filho HV, de Souza Silva CM, de Siqueira RJ, Lahlou S, dos Santos AA, Magalhaes PJ: Biphasic cardiovascular and respiratory effects induced by beta-citronellol. Eur J Pharmacol. 2016 Mar 15;775:96-105. doi: 10.1016/j.ejphar.2016.02.025. Epub 2016 Feb 9. [PubMed:26872991 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for D-Citronellol (HMDB0035093)

MOL for HMDB0035093 (D-Citronellol)

3D MOL for HMDB0035093 (D-Citronellol)

3D SDF for HMDB0035093 (D-Citronellol)

3D-SDF for HMDB0035093 (D-Citronellol)

PDB for HMDB0035093 (D-Citronellol)

3D PDB for HMDB0035093 (D-Citronellol)

SMILES for HMDB0035093 (D-Citronellol)

INCHI for HMDB0035093 (D-Citronellol)

Structure for HMDB0035093 (D-Citronellol)

3D Structure for HMDB0035093 (D-Citronellol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra