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Citronellal

Alias: NSC 46106 NSC-46106 NSC46106
Cat No.:V12014 Purity: ≥98%
Citronellal (rhodinal or 3,7-dimethyloct-6-en-1-al), a naturally occuring monoterpenoid, is reported to be the major component the essential oils in various aromatic species of plants.
Citronellal
Citronellal Chemical Structure CAS No.: 106-23-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
Other Sizes
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Citronellal (rhodinal or 3,7-dimethyloct-6-en-1-al), a naturally occuring monoterpenoid, is reported to be the major component the essential oils in various aromatic species of plants. It is found in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent. It has depressant, hypnotic, and antinociceptive properties. Citronellal attenuates mechanical nociception, mediated in part by the NO-cGMP-ATP-sensitive K channel pathway.

Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Metabolism / Metabolites
A bacterium capable of utilizing citronellal or citral as the sole source of carbon and energy has been isolated from soil by the enrichment culture technique. It metabolizes citronellal to citronellic acid (65%), citronellol (0.6%), dihydrocitronellol (0.6%), menthol (0.75%), and 3,7-dimethyl-1,7-octane diol (1.7%). The metabolites of citral were geranic acid (62%), 6-methyl-5-heptanoic acid (0.5%), 3-methyl-2-butenoic acid (1%), and 1-hydroxy-3, 7-dimethyl-6-octen-2-one (0.75%).
The cytochrome p450-catalyzed formation of olefinic products from a series of xenobiotic aldehydes has been demonstrated. Citronellal, a beta-branched aldehyde, was found to undergo the oxidative deformylation reaction to yield 2,6-dimethyl-1,5-heptadiene but only with p450 2B4.
Feeding 50 g citronellal to rabbits followed by isolation of 13 g of a cysralline glucoronide, which proved to be p-menthane-3,8-diol-D-glucoronide. The citronellal appeared to have been /nonenzymatically/ cyclized and the glucoronide obtained was identical with that obtaind on feeding p-menthane-3,8-diol (menthoglycol).
Citronellal was transformed by Solanum aviculare suspension cultures to menthane-3,8-diols. cis-Menthane-3,8-diol dominated over the trans-isomer (39% and 15%, respectively). Absolute configurations of menthane-3,8-diols were assigned by critical analysis of 1H and 19F NMR spectra of prepared esters with 2-methoxy-2-phenyl-3,3,3-trifluoropropanoic acid. Citronellol and isopulegol were other products of the transformation (23% and 17%, respectively). The reaction course was identical for both citronellal enantiomers.
For more Metabolism/Metabolites (Complete) data for CITRONELLAL (6 total), please visit the HSDB record page.
Toxicity/Toxicokinetics
Toxicity Summary
IDENTIFICATION AND USE: Citronellal is a colorless to slightly yellow liquid with an intense lemon odor. It is used as a flavoring agent and insect repellant. It has been tested as a medication. HUMAN EXPOSURE AND TOXICITY: A maximization test was carried out on 25 volunteers. The material was tested at a concentration of 4% in petrolatum and produced no sensitization reactions. Three cases of eczematous contact-type hypersensitivity to oils of citronella have been recorded. In two instances detailed patch-test studies were made with the ingredients of oil of citronella and some related substances. The essential allergen in oil of citronella was reported to be citronellal. ANIMAL STUDIES: Citronellal applied full strength to intact or abraded rabbit skin for 24 hr under occlusion was moderately irritating. Citronellal injected into white leghorn embryos caused dose-dependent teratogenesis. Morphological malformation occurred mainly in the craniofacial area. Citronellal produced antinociceptive effects in mice and was a strong skin sensitizer in guinea pigs. Mutagenicity was evaluated by the Salmonella/microsome assay (TA97a, TA98, TA100 and TA102 tester strains), without and with metabolic activation. Citronellal was not mutagenic in this test. ECOTOXICITY STUDIES: Citronellal inhibited embryonic development of yellow fever mosquito A aegypti eggs deposited on water. Citronellal causes a severe phytotoxicity on weeds.
Interactions
Citronellal is a monoterpene present in the oil of many species, including Cymbopogon winterianus Jowitt (Poaceae). The present study investigated the effect of citronellal on inflammatory nociception induced by different stimuli and examined the involvement of the NO-cGMP-ATP-sensitive K+ channel pathway. This study used male Swiss mice (n=6 per group) that were treated intraperitoneally with citronellal(25, 50 or 100 mg/kg) 0.5 hr after the subplantar injection of 20 uL of carrageenan (CG; 30 ug/paw), tumor necrosis factor-alpha (TNF-a; 100 pg/paw), prostaglandin E2 (PGE2; 100 ng/paw) or dopamine (DA; 30 ug/paw). The mechanical nociception was evaluated at 0.5, 1, 2 and 3 hr after the injection of the agents, using a digital analgesimeter (von Frey). The effects of citronellal were also evaluated in the presence of L-NAME (30 mg/kg) or glibenclamide (5 mg/kg). At all times, citronellal in all doses inhibited the development of mechanical nociception induced by CG (p<0.001 and p<0.01) and TNF-a (p<0.001, p<0.01, and p<0.05). The citronellal was able to increase the pain threshold in the DA test (p<0.001, p<0.01, and p<0.05) and in the PGE2 test at all times (p<0.001 and p<0.05). L-NAME and glibenclamide reversed the antinociceptive effects of the citronellal at higher doses in the PGE2 test. These data suggest that citronellal attenuated mechanical nociception, mediated in part by the NO-cGMP-ATP-sensitive K+ channel pathway.
Complementary and alternative medicines can be applied concomitantly with conventional medicines; however, little drug information is available on these interactions. Previously, we reported on the inhibitory effects of an extract and monoterpenoids (e.g., (R)-(+)-citronellal) contained in citrus herbs on P-glycoprotein (P-gp) using P-gp-overexpressed LLC-PK1 cells. The objective of the present study was to investigate the effects of (R)-(+)-citronellal on P-gp-mediated transport in the intestinal absorption process in vitro and in vivo. Transcellular transport of [(3)H]digoxin across Caco-2 cell monolayers was measured in the presence or absence of (R)-(+)-citronellal. (R)-(+)-citronellal reduced the basolateral-to-apical transport and efflux ratio for [(3)H]digoxin significantly. Serum concentration-time profiles and pharmacokinetic parameters of digoxin after intravenous and oral administration were analyzed in rats pretreated with oral (R)-(+)-citronellal. The bioavailability of digoxin after oral administration decreased significantly to 75.8% of that after intravenous administration at the same dose. (R)-(+)-citronellal increased the bioavailability of oral digoxin to 99.9% but had no effects on total body clearance, volume of distribution, or elimination rate. These findings suggest that (R)-(+)-citronellal can increase the bioavailability of oral digoxin based on the blockade of P-gp-mediated efflux of digoxin from intestinal epithelia to the lumen in the absorption process.
Non-Human Toxicity Values
LD50 Rabbit dermal >2.5 g/kg
LD50 Rats oral > 5 g/kg
References

[1]. Melo MS, et al. Antinociceptive effect of citronellal in mice. Pharm Biol. 2010 Apr;48(4):411-6.

[2]. de\nSantana MT, et al. Citronellal, a monoterpene present in Java\ncitronella oil, attenuates mechanical nociception response in mice.\nPharm Biol. 2013 Sep;51(9):1144-9.

[3]. Chemical composition and antibacterial activity of essential oils from Citrus aurantifolia leaves and fruit peel against oral pathogenic bacteria. An Acad Bras Cienc. 2018 Apr-Jun;90(2):1285-1292.

Additional Infomation
Citronellal is a monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma. It has a role as a metabolite and an antifungal agent. It is a monoterpenoid and an aldehyde.
Citronellal has been reported in Micromeria biflora, Curcuma kwangsiensis, and other organisms with data available.
See also: Java citronella oil (part of); Citronella Oil (annotation moved to).
Therapeutic Uses
EXPL THER The anti-inflammatory and redox protective effects of the citronellal (CT) were evaluated using in vivo and in vitro tests. Intraperitoneal (i.p.) administration of CT (50, 100, and 200 mg/kg) inhibited (p < 0.05) the carrageenan-induced leukocyte migration to the peritoneal cavity. Additionally, the carrageenan- and arachidonic acid-induced rat hind paw edema was significantly inhibited (p < 0.05) by i.p. administration of 100 and 200 mg/kg of the compound. When the redox activity was evaluated, CT (200 mg/kg) significantly reduced hepatic lipoperoxidation (p < 0.001), as well as oxidation of plasmatic (p < 0.05) and hepatic (p < 0.01) proteins. The results of the present study support the hypothesis that CT possesses anti-inflammatory and redox protective activities. It is suggested that its effects are associated with the inhibition of the enzymes in the arachidonic acid pathway, which prevent cell migration by inhibiting leukotriene production, edema formation and the increase of reactive oxygen species in tissues. Therefore, CT is of potential benefit to manage inflammatory disorders and correlated damages caused by oxidant agents.
EXPL THER Anti-Candida potential of six terpenoids were evaluated in this study against various isolates of Candida albicans (n=39) and non-C. albicans (n=9) that are differentially susceptible to fluconazole. All the six terpenoids tested, showed excellent activity and were equally effective against isolates of Candida sps., tested in this study. Linalool and citral were the most effective ones, inhibiting all the isolates at ?0.064% (v/v). Five among the six terpenoids tested were fungicidal. Time dependent kill curve assay showed that MFCs of linalool and eugenol were highly toxic to C. albicans, killing 99.9% inoculum within seven min of exposure, while that of citronellal, linalyl acetate and citral required 15min, 1h and 2h, respectively. FIC index values (Linalool - 0.140, benzyl benzoate - 0.156, eugenol - 0.265, citral - 0.281 and 0.312 for linalyl acetate and citronellal) and isobologram obtained by checker board assay showed that all the six terpenoids tested exhibit excellent synergistic activity with fluconazole against a fluconazole resistant strain of C. albicans. Terpenoids tested arrested C. albicans cells at different phases of the cell cycle i.e. linalool and LA at G1, citral and citronellal at S phase and benzyl benzoate at G2-M phase and induced apoptosis. Linalool, citral, citronellal and benzyl benzoate caused more than 50% inhibition of germ tube induction at 0.008%, while eugenol and LA required 0.032 and 0.016% (v/v) concentrations, respectively. MICs of all the terpenoids for the C. albicans growth were non toxic to HeLa cells. Terpenoids tested exhibited excellent activity against C. albicans yeast and hyphal form growth at the concentrations that are non toxic to HeLa cells. Terpenoids tested in this study may find use in antifungal chemotherapy, not only as antifungal agents but also as synergistic agents along with conventional drugs like fluconazole.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H18O
Molecular Weight
154.25
Exact Mass
154.135
CAS #
106-23-0
PubChem CID
7794
Appearance
Colorless to light yellow liquid
Density
0.8±0.1 g/cm3
Boiling Point
208.4±9.0 °C at 760 mmHg
Melting Point
147 °C
Flash Point
75.6±0.0 °C
Vapour Pressure
0.2±0.4 mmHg at 25°C
Index of Refraction
1.437
LogP
3.48
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
5
Heavy Atom Count
11
Complexity
132
Defined Atom Stereocenter Count
0
SMILES
CC(=CCCC(C)CC=O)C
InChi Key
NEHNMFOYXAPHSD-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
Chemical Name
6-Octenal, 3,7-dimethyl-
Synonyms
NSC 46106 NSC-46106 NSC46106
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~648.30 mM)
Ethanol : ~100 mg/mL (~648.30 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.4830 mL 32.4149 mL 64.8298 mL
5 mM 1.2966 mL 6.4830 mL 12.9660 mL
10 mM 0.6483 mL 3.2415 mL 6.4830 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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