Citral

Manufactured by Merck Group

Sourced in United States, Germany, Italy, United Kingdom, Macao, Sao Tome and Principe, India, Spain, Hungary, China

Citral is a colorless, oily liquid that is commonly used as a flavoring and fragrance ingredient. It is a naturally occurring compound found in various plant oils, such as lemongrass and citrus fruits. Citral is a key component in the production of various chemicals and is widely used in the food, cosmetic, and pharmaceutical industries.

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Lab products found in correlation

Linalool, by Merck Group (24 mentions) Geraniol, by Merck Group (23 mentions) Eugenol, by Merck Group (14 mentions) Limonene, by Merck Group (12 mentions) Carvacrol, by Merck Group (10 mentions) Geranyl acetate, by Merck Group (9 mentions) Citronellol, by Merck Group (8 mentions) Myrcene, by Merck Group (8 mentions) Thymol, by Merck Group (7 mentions) Citronellal, by Merck Group (7 mentions) α terpineol, by Merck Group (7 mentions) Cinnamaldehyde, by Merck Group (6 mentions) Camphor, by Merck Group (6 mentions) Nerol, by Merck Group (6 mentions) Dimethyl sulfoxide (dmso), by Merck Group (6 mentions) γ terpinene, by Merck Group (5 mentions) α pinene, by Merck Group (5 mentions) Chitosan, by Merck Group (4 mentions) Isoamyl acetate, by Merck Group (4 mentions) Eucalyptol, by Merck Group (4 mentions)

Close spelling variants of this product

Citral 1 (6 citations) Citral 2 (6 citations) Citral (CIT) (2 citations) 3,7-Dimethyl-2,6-octadienal (citral, (2 citations) Citral in vehicle (2 citations) Citral analytical standard (2 citations)

103 protocols using citral

Evaluating Preterm Birth Interventions in Rats

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The animals were divided into 6 groups (n = 6–8): (1) intact pregnant rats on day 22 of pregnancy (normal term labor, n = 16); (2) pregnant rats, orally treated with olive oil, as a vehicle control, on days 18–22 once daily; (3) pregnant rats, orally treated with citral (240 mg/kg [3 (link)], administered by oral gavage; in olive oil vehicle; Sigma-Aldrich, Budapest, Hungary) on days 18–22 once daily; (4) pregnant rats treated with LPS (50 μg/animal, intraperitoneally; Sigma Aldrich, Hungary) on day 18 of pregnancy to induce preterm birth on day 20 [16 (link)]; and (5) pregnant rats treated with LPS on day 18 and citral on days 18–22 once daily. The administration protocol is outlined in Table 1. The rats were closely observed for any signs of preterm delivery (e.g., decreased movement, nest-building behavior or vaginal bleeding). The beginning of labor was defined by the delivery of the first pup.

Seres-Bokor A., Kemény K.K., Taherigorji H., Schaffer A., Kothencz A., Gáspár R, & Ducza E. (2021). The Effect of Citral on Aquaporin 5 and Trpv4 Expressions and Uterine Contraction in Rat—An Alternative Mechanism. Life, 11(9), 897.

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Chitosan-based 5-Fluorouracil Delivery

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Citral (95%), low molecular weight chitosan (217 kDa, DD (deacetylation degree): 85%), 5-fluorouracil, lysozyme from chicken white egg and phosphate buffer solution have been purchased from Aldrich (Germany) and used as received.

Ailincai D., Tartau Mititelu L, & Marin L. (2018). Drug delivery systems based on biocompatible imino-chitosan hydrogels for local anticancer therapy. Drug Delivery, 25(1), 1080-1090.

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Citronellal Isolation from Citronella Oil

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Essential oil of citronella (C. nardus (L.) Rendle) was commercial product, produced in southern Brazil (Pólo Oleoquímico de Três Passos-RS). (R)-Citronellal was isolated from the essential oil by column chromatography using silicagel as a stationary phase and a solution of hexane/ethyl acetate (99:1) as the eluent. Citral (a 1:1 mixture of neral and geranial) and the other reagents were purchased from Aldrich (St. Louis, MO, USA).

Ferraz M.C., Mano R.A., Oliveira D.H., Maia D.S., Silva W.P., Savegnago L., Lenardão E.J, & Jacob R.G. (2017). Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal. Medicines, 4(2), 39.

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Synthesis and Characterization of Antimicrobial Nanocomposites

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All chemicals used for the study were of analytical grade; hexadecyltrimethylammonium bromide (CTAB, ≥98%), tetraethyl orthosilicate (TEOS, ≥98%), cyclohexane (99.5%), thymol (≥99.5%), carvacrol (99%), eugenol (≥98%), citral (≥96%), cinnamon oil (ceylon type), sodium hydroxide (NaOH, ≥99%), ammonium nitrate (NH₄NO₃, ≥98%), sodium phosphate monobasic (NaH₂PO₄, 98–102%), sodium phosphate dibasic (Na₂HPO₄, ≥99%) and halloysite nanotubes (HNT) were purchased from Sigma-Aldrich (Merck KGaA, Darmstadt, Germany). Absolute ethanol was obtained from Antibac (Kiilto Oy, Tampere, Finland).

Gulin-Sarfraz T., Kalantzopoulos G.N., Haugen J.E., Axelsson L., Raanaas Kolstad H, & Sarfraz J. (2022). Controlled Release of Volatile Antimicrobial Compounds from Mesoporous Silica Nanocarriers for Active Food Packaging Applications. International Journal of Molecular Sciences, 23(13), 7032.

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Citral Inhibits Breast Cancer Spheroid Formation

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In ultra-low attachment plates, primary spheroid cultures derived from MDA-MB-231 cell line were treated with different concentrations (2.5, 5 and 10 μg/mL) of citral (Sigma-Aldrich, USA). The spheroid formation was measured after 7 days of treatment using a Nikon Eclipse microscope (Nikon, Japan). Then, single cells from untreated and treated primary spheroid cultures were obtained by incubation in a 0.25% trypsin-EDTA solution (Gibco. USA), for about 5–10 min at 37 °C. Subsequently, the cells were plated in ultra-low attachment plates at a density of 100 to 500 cells/mL for the generation of subsequent passages. The second passage was grown in the absence of treatment. The spheroids were observed after 7 days using a Nikon Eclipse microscope (Nikon, Japan).

Nigjeh S.E., Yeap S.K., Nordin N., Kamalideghan B., Ky H, & Rosli R. (2018). Citral induced apoptosis in MDA-MB-231 spheroid cells. BMC Complementary and Alternative Medicine, 18, 56.

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Metabolism of Bioactive Compounds Assay

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Phenacetin, dextromethorphan, chlorzoxazole, and testosterone were obtained from Aladdin Biochemical Technology Co. Ltd (Shanghai, People’s Republic of China). Citral (>99% pure) was purchased from Sigma-Aldrich Co. LLC. (St. Louis, MO, USA). The liver microsomal incubation system was purchased from Puleite Biomedical Technology Co. Ltd (Wuhan, People’s Republic of China). All molecular biology reagents were purchased from Bio-Rad Laboratories Inc. (Hercules, CA, USA), all analytical kits were purchased from Jiancheng Biology Engineering Institute (Nanjing, People’s Republic of China), and all other chemicals and reagents were of analytical grade and obtained commercially. ProcartaPlex mouse multifactor kits were purchased from eBioscience (Thermo Fisher Scientific Inc., Waltham, MA, USA).

Tang H., Long N., Lin L., Liu Y., Li J., Sun F., Guo L., Zhang F, & Dai M. (2018). Effect of MRSA on CYP450: dynamic changes of cytokines, oxidative stress, and drug-metabolizing enzymes in mice infected with MRSA. Infection and Drug Resistance, 11, 229-238.

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Diverse Chemical Reagents for Cellular Assays

Cited 1 time

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Chemicals purchased from Cayman Chemical (Ann Arbor, MI) include 5-azacytidine, Bay 11-7085, camptothecin, D-ribofuranosylbenzimidazole, H-8 HCl, kenpaullone, 3,4-Methylenedioxy-β-nitrostyrene (MNS), niclosamide, PD 98059, and topotecan hydrochloride. Citral, DMSO, LY-294002, retinol, and SU 4312 were purchased from Sigma-Aldrich (St. Louis, MO). CD437, ER50891, HX531, and SR11237 were purchased from Torcris (Minneapolis, MN). AM580 was purchased from Enzo Life Sciences (Farmingdale, NY). Chemicals were prepared as stock solution aliquots in DMSO and stored in the vapor phase of liquid nitrogen. Chemicals were protected from extended exposure to light when being prepared and used in assays. The LOPAC was purchased from Sigma-Aldrich and stored following the protocols at the National Center for Advancing Translational Sciences (NCATS) ^{22 (link)}. The Cignal lentiviral reagent, which had a lentivirus concentration of 1.7 × 10⁷ transducing units (TU)/ml, was obtained from SABiosciences (Qiagen, Frederick, MD). The MTT cell viability assay kit was obtained from ATCC (Manassas, VA) and used following the manufacturer's instructions.

Chen Y., Sakamuru S., Huang R., Reese D.H, & Xia M. (2016). Identification of compounds that modulate retinol signaling using a cell-based qHTS assay. Toxicology in vitro : an international journal published in association with BIBRA, 32, 287-296.

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Chemical Compound Sourcing for Research

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Fructose (99%) and tannic acid (95%) were purchased from J.T. Baker (Avantor; Radnor, PA, USA). Tartaric acid (99.7%) was provided by Chem-Lab (Eernegem, West-Vlaanderen, Belgium), and caffeine (99.2%) by ACEF (Piacenza, Italy). 2-Phenylethanol (≥99%), citral (95%), linalool (97%), 1-octen-3-one (96%), cis-3-hexen-1-ol (≥98%), ethyl butyrate (≥99%), damascenone (1.1–1.4 wt.%), benzaldehyde (≥99.5%), isoamyl acetate (≥95%), gamma-dodecalactone (≥97%), sotolone (≥97%), 4-ethylguaiacol (≥98%), 4-ethylphenol (99%), eucalyptol (99%), furaneol (≥98%), ethyl caproate (≥99%), eugenol (≥98%), citronellol (95%), phenylacetaldehyde (≥95%), furfuryl acetate (≥98%), 2,4,6-trichloroanisole (99%), 2-methyl-1-propanol (99.5%), methanethiol (≥98%) were all provided by Sigma-Aldrich (St. Louis, MO, USA). Ethanol (food grade, 70%) was supplied by ITW Reagents (Milano, Italy). Tanin VR colour, Tanin VR grape, Tanin plus, Tanin galalcool were all purchased from Laffort (Bordeaux, France).

Pittari E., Moio L., Arapitsas P., Curioni A., Gerbi V., Parpinello G.P., Ugliano M, & Piombino P. (2020). Exploring Olfactory–Oral Cross-Modal Interactions through Sensory and Chemical Characteristics of Italian Red Wines. Foods, 9(11), 1530.

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Citral and Fluconazole Preparation

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Citral (95% of purity) and fluconazole (98% of purity) were purchased from Sigma-Aldrich (MO). Stock solutions were prepared in dimethyl sulfoxide (DMSO, Sigma-Aldrich). The Citral was prepared on the day of use, while fluconazole was stored for up to one month at – 70°C.

Miranda-Cadena K., Marcos-Arias C., Perez-Rodriguez A., Cabello-Beitia I., Mateo E., Sevillano E., Madariaga L., Quindós G, & Eraso E. (2022). In vitro and in vivo anti-Candida activity of citral in combination with fluconazole. Journal of Oral Microbiology, 14(1), 2045813.

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Quantifying Antioxidant Potential of Terpenes

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The terpenes (−)-isopulegol (≥99%), menthol (≥99%), p-cymene (≥99%), eucalyptol (≥99%), (R)-(+)-pulegone (97%), γ-terpinene (97%), α-terpinene (≥95%), linalool (≥97%), (S)-(+)-carvone (≥96%), citronellal (≥95%), (−)-terpinene-4-ol (≥95%), citral (≥95%), menthone (≥90%), farnesene (mixtures of isomers, ≥90%), α-phellandrene (≥90%), β-myrcene (≥90%), and TPTZ (2,4,6-Tri(2-pyridyl)-s-triazine)) were obtained from Sigma-Aldrich (St. Louis, MO, USA). Acetic acid (ACS), FeCl₃ × 6H₂O, FeSO₄ × 7H₂O, phosphoric acid (ACS), hydrochloric acid (ACS), chloroform (ACS), ethyl acetate (ACS), 2-butanone (ACS), and methanol (analytic purity grade) were obtained from Polish Reagents (Gliwice, Poland). The standards trolox ((±)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid, 97%) and gallic acid (>98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA).

, & Wojtunik-Kulesza K.A. (2020). Approach to Optimization of FRAP Methodology for Studies Based on Selected Monoterpenes. Molecules, 25(22), 5267.

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