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

Molecular Formula	C10H18O
Molecular Weight	154.2493
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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
Assessment of sensitization potential of monoterpenes using the rat popliteal lymph node assay.	2007 Aug	17383062
A low-cost repellent for malaria vectors in the Americas: results of two field trials in Guatemala and Peru.	2007 Aug 1	17678537
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.	2007 Jul-Aug	17913064
Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection.	2007 Mar 7	17266328
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
Structural determinants of odorant recognition by the human olfactory receptors OR1A1 and OR1A2.	2007 Sep	17601748
Essential oil composition of three accessions of Dracocephalum heterophyllum Benth. cultivated at Palampur, India.	2008	18629706
Oxidation of citronellal to citronellic acid by molecular oxygen using supported gold catalysts.	2008	18605213
Percutaneous permeation enhancement by terpenes: mechanistic view.	2008	18446512
Polar intermetallic compounds as catalysts for hydrogenation reactions: synthesis, structures, bonding, and catalytic properties of Ca(1-x)Sr(x)Ni4Sn2 (x=0.0, 0.5, 1.0) and catalytic properties of Ni3Sn and Ni3Sn2.	2008	18288652
Synthesis and catalysis of di- and tetranuclear metal sandwich-type silicotungstates [(gamma-SiW10O36)2M2(mu-OH)2]10- and [(gamma-SiW10O36)2M4(mu4-O)(mu-OH)6]8- (M = Zr or Hf).	2008 Apr 23	18370387
Phythochemical screening and anticonvulsant activity of Cymbopogon winterianus Jowitt (Poaceae) leaf essential oil in rodents.	2008 Aug	17976969
Anti-inflammation activity of fruit essential oil from Cinnamomum insularimontanum Hayata.	2008 Dec	18513962
Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.	2008 Dec 14	18955043
Feasibility of detection and quantification of gas-phase carbonyls in indoor environments using PFBHA derivatization and solid-phase microextraction (SPME).	2008 Jul	18688453
Citral derived amides as potent bacterial NorA efflux pump inhibitors.	2008 Jul 1	18524600
Essential Oil Composition and Antibacterial Studies of Vitex negundo Linn. Extracts.	2008 Jul-Aug	20046787
Herbal excipients in novel drug delivery systems.	2008 Jul-Aug	20046764
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.	2008 Jul-Aug	18810999
Chemical composition and in vitro antimicrobial activity of essential oil of Melissa officinalis L. from Romania.	2008 Jul-Sep	20201279
Expression of two old yellow enzyme homologues from Gluconobacter oxydans and identification of their citral hydrogenation abilities.	2008 Mar	18064575
Identification of molecular pathways affected by pterostilbene, a natural dimethylether analog of resveratrol.	2008 Mar 20	18366703
Host-seeking and blood-feeding behavior of Aedes albopictus (Diptera: Culicidae) exposed to vapors of geraniol, citral, citronellal, eugenol, or anisaldehyde.	2008 May	18533449
First asymmetric total syntheses of cernuane-type Lycopodium alkaloids, cernuine, and cermizine D.	2008 May 15	18429621
Synthesis of a dialuminum-substituted silicotungstate and the diastereoselective cyclization of citronellal derivatives.	2008 Nov 26	18975897
Melissa officinalis oil affects infectivity of enveloped herpesviruses.	2008 Sep	18693101
The promoting effect of a dicyanamide based ionic liquid in the selective hydrogenation of citral.	2008 Sep 14	18758625
A tin-tungsten mixed oxide as an efficient heterogeneous catalyst for C-C bond-forming reactions.	2009	19288486
Zr-zeolite beta: a new heterogeneous catalyst system for the highly selective cascade transformation of citral to (+/-)-menthol.	2009	19132702
Reactivity in the confined spaces of zeolites: the interplay between spectroscopy and theory to develop structure-activity relationships for catalysis.	2009 Apr 28	19421502
Laboratory evaluation of products to reduce settling of sweetpotato whitefly adults.	2009 Aug	19736760
Characterization and antioxidant activity of essential oils from fresh and decaying leaves of Eucalyptus tereticornis.	2009 Aug 12	19722579
Cultured skin microbiota attracts malaria mosquitoes.	2009 Dec 17	20017925
Chemistry of secondary polyphenols produced during processing of tea and selected foods.	2009 Dec 28	20161999
Cyclisation of citronellal over heterogeneous inorganic fluorides--highly chemo- and diastereoselective catalysts for (+/-)-isopulegol.	2009 Jan 28	19137185
Coupling reactions of catechins with natural aldehydes and allyl alcohols and radical scavenging activities of the triglyceride-soluble products.	2009 Jul 22	19537756
Chemical compositions and antioxidant/antimicrobial activities of various samples prepared from Schinus terebinthifolius leaves cultivated in Egypt.	2009 Jun 24	19462981
Effects of olfactory training in patients with olfactory loss.	2009 Mar	19235739
Larvicidal and oviposition-altering activity of monoterpenoids, trans-anithole and rosemary oil to the yellow fever mosquito Aedes aegypti (Diptera: Culicidae).	2009 Mar	19086001
Catalytic conjugate additions of geminal bis(sulfone)s: expanding the chemistry of sulfones as simple alkyl anion equivalents.	2009 Nov 9	19780123
In vitro larvicidal activity of geraniol and citronellal against Contracaecum sp (Nematoda: Anisakidae).	2009 Oct	19787148
Citral and carvone chemotypes from the essential oils of Colombian Lippia alba (Mill.) N.E. Brown: composition, cytotoxicity and antifungal activity.	2009 Sep	19876560
Semiochemical-mediated oviposition avoidance by female house flies, Musca domestica, on animal feces colonized with harmful fungi.	2010 Feb	20148358
Synthesis, structural characterization and antiproliferative and toxic bio-activities of copper(II) and nickel(II) citronellal N4-ethylmorpholine thiosemicarbazonates.	2010 Feb	19962763
Repellent activity of essential oils: a review.	2010 Jan	19729299
Essential oil of Lindera neesiana fruit: chemical analysis and its potential use in topical applications.	2010 Jan	19586610
Chemical composition of Eucalyptus spp. essential oils and their insecticidal effects on Lutzomyia longipalpis.	2010 Jan 20	19896276
Solution to spectroscopy challenge 14. Citronellal.	2010 Mar	20099061
High loading fragrance encapsulation based on a polymer-blend: preparation and release behavior.	2010 May 31	20170720

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:02:19 GMT 2023` Edited by `admin` on `Fri Dec 15 17:02:19 GMT 2023`
Record UNII	QB99VZZ7GZ
Record Status	`Validated (UNII)`
Record Version

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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