CITRONELLAL

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H18O
Molecular Weight	154.2493
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CCC=C(C)C)CC=O

InChI

InChIKey=NEHNMFOYXAPHSD-UHFFFAOYSA-N

InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26907246 | https://www.ncbi.nlm.nih.gov/pubmed/26447139 | https://www.ncbi.nlm.nih.gov/pubmed/27598633 | https://www.ncbi.nlm.nih.gov/pubmed/22350215

Citronellal is one of the main constituents of the essential oil from lemongrass (Cymbopogon). Citronellal is a major isolate from Cymbopogon plants, lemon-scented gum, and lemon-scented tea tree. Citronellal is a well-known plant-derived mosquito repellent. In addition, citronellal is very effective repellent against Sitophilus zeamais. Citronellal showed anticandidal activity against C. albicans and non-albicans species of Candida. Citronellal is effective as an analgesic compound in various rodent pain models, with its action probably mediated by the inhibition of peripheral mediators as well as central inhibitory mechanisms that could be related to its strong antioxidant effect observed in vitro.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Taste receptor type 2 member 43 1 Target ID: P59537 Gene ID: 259289.0 Gene Symbol: TAS2R43 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27569025	Negative Allosteric Modulator 42	84.0 µM [IC50]
Taste receptor type 2 member 46 1 Target ID: P59540 Gene ID: 259292.0 Gene Symbol: TAS2R46 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27569025	Negative Allosteric Modulator 42
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26447139	Agonist 2678
Olfactory receptor 1A2 1 Target ID: Q9Y585 Gene ID: 26189.0 Gene Symbol: OR1A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25513961	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22350215 https://www.ncbi.nlm.nih.gov/pubmed/27387403 https://www.ncbi.nlm.nih.gov/pubmed/20645719	Primary		Preclinical	Unknown Approved Use Unknown
Hepatocarcinoma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25513961	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of vetiver oil and seven insect-active essential oils against the Formosan subterranean termite.	2001 Aug	11521400
Local anaesthetic activity of monoterpenes and phenylpropanes of essential oils.	2001 Aug	11509984
Acute, sublethal, antifeedant, and synergistic effects of monoterpenoid essential oil compounds on the tobacco cutworm, Spodoptera litura (Lep., Noctuidae).	2001 Feb	11262018
Susceptibility of the bruchid Callosobruchus maculatus (Coleoptera: Bruchidae) and its parasitoid Dinarmus basalis (Hymenoptera: Pteromalidae) to three essential oils.	2002 Feb	11942754
Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry.	2003 May 23	12862384
Repellency of essential oils of some Kenyan plants against Anopheles gambiae.	2004 Oct	15474566
Inhibition of P-glycoprotein-mediated transport by extracts of and monoterpenoids contained in Zanthoxyli fructus.	2005 Dec 1	15890377
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.	2005 Jul	16000717
A highly selective, organocatalytic route to chiral dihydro-1,2-oxazines.	2005 Sep 15	16146384
Chemical composition and phytotoxicity of volatile essential oil from intact and fallen leaves of Eucalyptus citriodora.	2006 Jul-Aug	16989303
Repellence of the red bud borer Resseliella oculiperda from grafted apple trees by impregnation of rubber budding strips with essential oils.	2007 May	17421054
Differences in (-)citronellal binding to various odorant receptors.	2007 Oct 5	17681278
Phythochemical screening and anticonvulsant activity of Cymbopogon winterianus Jowitt (Poaceae) leaf essential oil in rodents.	2008 Aug	17976969
The promoting effect of a dicyanamide based ionic liquid in the selective hydrogenation of citral.	2008 Sep 14	18758625
Cultured skin microbiota attracts malaria mosquitoes.	2009 Dec 17	20017925
Cyclisation of citronellal over heterogeneous inorganic fluorides--highly chemo- and diastereoselective catalysts for (+/-)-isopulegol.	2009 Jan 28	19137185
Larvicidal and oviposition-altering activity of monoterpenoids, trans-anithole and rosemary oil to the yellow fever mosquito Aedes aegypti (Diptera: Culicidae).	2009 Mar	19086001
Citral and carvone chemotypes from the essential oils of Colombian Lippia alba (Mill.) N.E. Brown: composition, cytotoxicity and antifungal activity.	2009 Sep	19876560
Synthesis, structural characterization and antiproliferative and toxic bio-activities of copper(II) and nickel(II) citronellal N4-ethylmorpholine thiosemicarbazonates.	2010 Feb	19962763
Chemical composition of Eucalyptus spp. essential oils and their insecticidal effects on Lutzomyia longipalpis.	2010 Jan 20	19896276

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: 25, 50 and 100 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Data from the broth microdilution assay revealed that citronellal showed an antifungal activity against C. albicans at an MIC of 1mg/ml. These results were confirmed by the data obtained from the spot assay. Similar drug susceptibility assays were performed on C. krusei, C. glabrata, C. parapsilosis, and C. tropicalis. The MIC determined by broth microdilution assay was 1.2mg/ml, which was further confirmed with a spot assay.

Name

Type

Language

CITRONELLAL

Official Name

English

CITRONELLAL [MI]

Common Name

English

CITRONELLAL [INCI]

Common Name

English

CITRONELLAL [FCC]

Common Name

English

RHODINAL

Systematic Name

English

POLY((1,3A,4,6,7,7A-HEXAHYDRO-1,3-DIOXO-3H-FURO(3,4-C)PYRAN-4,6-DIYL)(TETRAHYDRO-2,5-DIOXO-3,4-FURANDIYL)METHYLENE)

Common Name

English

3,7-DIMETHYLOCT-6-EN-1-AL

Systematic Name

English

CITRONELLAL [FHFI]

Common Name

English

6-OCTENAL, 3,7-DIMETHYL-

Systematic Name

English

(±)-CITRONELLAL

Systematic Name

English

NSC-46106

Code

English

FEMA NO. 2307

Code

English

CITRONELLAL [HSDB]

Common Name

English

3,7-DIMETHYL-6-OCTENAL

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

CITRONELLAL