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β cyclocitral

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β-cyclocitral is a chemical compound used in laboratory settings. It is a colorless liquid with a characteristic odor. β-cyclocitral is commonly used as a reagent or standard in various analytical procedures, but a more detailed description cannot be provided while maintaining an unbiased and factual approach.

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Lab products found in correlation

β ionone, by Merck Group (6 mentions) Benzaldehyde, by Merck Group (4 mentions) Furfural, by Merck Group (3 mentions) Ethyl decanoate, by Merck Group (3 mentions) Limonene, by Merck Group (3 mentions) Safranal, by Merck Group (2 mentions) Phenylethyl alcohol, by Merck Group (2 mentions) Linalool, by Merck Group (2 mentions) Decanal, by Merck Group (2 mentions) Dihydroactinidiolide, by Merck Group (2 mentions) Nonanal, by Merck Group (2 mentions) Phenylacetaldehyde, by Merck Group (2 mentions) 2 phenylethanol, by Merck Group (2 mentions) Ethyl hexanoate, by Merck Group (2 mentions) Ethyl nonanoate, by Merck Group (2 mentions) Ethyl octanoate, by Merck Group (2 mentions) Diethyl succinate, by Merck Group (2 mentions) Ethyl isovalerate, by Merck Group (2 mentions) Isoamyl acetate, by Merck Group (2 mentions) 2 nonanone, by Merck Group (2 mentions)

15 protocols using β cyclocitral

1

Odor Compound Analysis Protocol

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The standard of four odor compounds DMDS, DMTS, β-cyclocitral and β-ionone (100 mg/L, methanol) were purchased from Sigma-Aldrich (Milwaukee, WI, USA), and the standard solutions were diluted with MilliQ-water. Other reagents were of analytical grade and used without further purification.
Solid phase micro-extraction (SPME) coated with stableflex DVB/CAR/PDMS fibers(50/30 μm) was purchased from Sigma-Aldrich (Milwaukee, WI, USA).
Huang H., Xu X., Liu X., Han R., Liu J, & Wang G. (2018). Distributions of four taste and odor compounds in the sediment and overlying water at different ecology environment in Taihu Lake. Scientific Reports, 8, 6179.
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2

Reduction of β–cyclocitral to Compound 3b

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An oven-dried 25 mL, two-necked, round-bottomed flask was sealed under argon and charged with sodium borohydride (735 mg, 19.5 mmol), ethanol (2.5 mL) and propane-2-ol (2.5 mL). The mixture was cooled to 0 °C. Then β–cyclocitral (Sigma-Aldrich, purity 94.9%) (2 g, 13 mmol) in propan-2-ol (3.5 mL) was added dropwise to the stirred reaction mixture. The mixture was allowed to warm to ambient temperature by removing the ice bath while stirring was maintained for 1 h. The reaction mixture then was poured into water (10 mL) and subsequently saturated with sodium chloride and extracted with ether (3×5 mL). The organic extracts were combined, washed with water (10 mL), brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc/petroleum ether 20:80) afforded 1.7 g (85%) of compound 3b as colorless waxy solid 37 . 1H NMR (400 MHz, CDCl3) δ 4.1 (s, 2H), 1.95(t, 2H, J = 6.4 Hz), 1.72(s, 3H), 1.61-1.53(m, 2H), 1.45-1.39(m, 2H), 1.01(m, 6H). 13C NMR (100 MHz, CDCl3) δ 137.7, 133.7, 58.9, 39.4, 34.1, 32.8, 28.6, 19.7, 19.4. 1H NMR and 13C values matched those previously reported 38 .
Kiser P.D., Zhang J., Badiee M., Li Q., Shi W., Sui X., Golczak M., Tochtrop G.P, & Palczewski K. (2015). Catalytic mechanism of a retinoid isomerase essential for vertebrate vision. Nature chemical biology, 11(6), 409-415.
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3

Safranal Synthesis Standards Calibration

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High purity gases carbon dioxide 99.998% (Messer France SAS, Saint -Georges-d’Espéranche, France) and hydrogen 99.999% (Messer France SAS, Saint -Georges-d’Espéranche, France) were used as working reference gas. Helium flow at 99.999% was used as carrier gas. One microliter of paraffin 1-decane (Sigma Aldrich Corp, St Louis, MO, USA) was injected to install a coating in the pyrolysis alumina tube prior to the start of the analysis process.
International standards IAEA CH7 (polyethylene foil: δ13C (‰) −32.15, δ2H (‰) −100.3) and IAEA NBS 22 (oil: δ13C (‰) −29.79, δ2H (‰) −120) supplied by IAEA (International Agency of Atomic Energy) permit the calibration of Safranal synthesis standards.
Safranal was purchased from Sigma Aldrich Corp (St Louis, MO, USA). Unfortunately, Sigma Aldrich was the only supplier of synthesis Safranal origin found on commercial market. For this reason, three Safranal batches were bought at different times, with high levels of purity (98.4%), and were stored at 4 °C., and β-cyclocitral was purchased from Sigma Aldrich (Ref 16976. Purity ≥ 97%); crocin (trans-crocetin-4-GG) was purchased from Phytolab (Ref 80391, purity 99.04%); kaempferol-3-O-glucoside was purchased from Extrasynthese (Ref 1243 S batch purity 99%); trans-crocetin was purchased from Toronto Research (Ref C794950, purity 95%).
Moras B., Pouchieu C., Gaudout D., Rey S., Anchisi A., Saupin X, & Jame P. (2022). Authentication of Iranian Saffron (Crocus sativus) Using Stable Isotopes δ13C and δ2H and Metabolites Quantification. Molecules, 27(20), 6801.
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4

Differentiation of ARPE-19 Cells for Physiological Studies

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The human retinal pigmented epithelium cell line ARPE-19 (BCRC number 60383) was obtained from the Food Industry Research and Development Institute (FIRDI, Hsinchu, Taiwan). These cells were maintained in a 1:1 mixture of DMEM/F-12, supplemented with 10% fetal bovine serum (FBS, GIBCO) and 1% penicillin/streptomycin (PS, Gibco) in a humidified 5% CO2 incubator at 37°C. To differentiate ARPE-19 cells to a more native and physiologically relevant state, once confluent, the media was switched to a specialized DMEM media that contained high glucose (4.5 g/l) supplemented with 1% heat-inactivated FBS, 1 mM sodium pyruvate (Hyclone),2 mM L-glutamine (Hyclone), and 10 mM nicotinamide (Sigma) for 2 months. In all cases, media exchange was performed three times a week. Before treatment, ARPE-19 cells were seeded into 96-well plates or 6 cm Petri dishes at a density of 5 × 104 cells/mL and incubated overnight. After overnight culture, the culture medium was replaced with a serum-free medium and treated with different concentrations (25, 50, 100, and 200 μg/ml) of Scoparia dulcis L. extract (SDE) for 24 h. Following this, the cells were treated with 50 mM D-glucose (Sigma) for an additional 48 h. β-cyclocitral (Sigma), 1-methyl-2-pyrrolidinone (Sigma), procaine (Sigma), cyclohexylamine (Sigma), and N1- acetylspermine (Sigma) are used as the standard for HPLC–MS analysis.
Lin H.D., Lee Y.C., Chiang C.Y., Lin Y.J., Shih C.Y., Tsai R.K., Lin P.Y., Lin S.Z., Ho T.J, & Huang C.Y. (2023). Protective effects of Scoparia dulcis L. extract on high glucose-induced injury in human retinal pigment epithelial cells. Frontiers in Nutrition, 10, 1085248.
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5

Quantitative Analysis of β-Cyclocitral

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A 100 mg quantity of fresh tissue was extracted with 1 ml of methanol. The suspension was mixed by vortexing for 5 min and centrifuged for 20 min at 20, 000 × g and 4°C. The supernatant was centrifuged as above for 10 min, and 200 μl of the new supernatant were taken for the analysis using an Agilent 1260 Infinity high-performance liquid chromatography (HPLC) system coupled to an API 5000 tandem mass spectrometer. β-cyclocitral was separated on an Zorbax Eclipse XDB-C18 column (50 × 4.6 mm, 1.8 μm) Chromatographic separation was performed by using a gradient of formic acid 0.05% in water, (solvent A) and acetonitrile (solvent B). The flow rate was set at 0.5 ml min–1. The initial mobile phase consisted of 95/5% (v/v) solvent A/solvent B. Then, solvent A was decreased to 50% in 2 min and held for 3 min. After solvent A was decreased to 0% in 9 min and held for 11 min, it was raised again to 95%. β-cyclocitral was monitored by following the precursor ion → product ion reaction: m/z 153.191 → 109.0. Quantification was done using an external standard curve made with an authentic standard of β-cyclocitral (Sigma-Aldrich).
Perreca E., Rohwer J., González-Cabanelas D., Loreto F., Schmidt A., Gershenzon J, & Wright L.P. (2020). Effect of Drought on the Methylerythritol 4-Phosphate (MEP) Pathway in the Isoprene Emitting Conifer Picea glauca. Frontiers in Plant Science, 11, 546295.
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6

Reduction of β–cyclocitral to Compound 3b

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An oven-dried 25 mL, two-necked, round-bottomed flask was sealed under argon and charged with sodium borohydride (735 mg, 19.5 mmol), ethanol (2.5 mL) and propane-2-ol (2.5 mL). The mixture was cooled to 0 °C. Then β–cyclocitral (Sigma-Aldrich, purity 94.9%) (2 g, 13 mmol) in propan-2-ol (3.5 mL) was added dropwise to the stirred reaction mixture. The mixture was allowed to warm to ambient temperature by removing the ice bath while stirring was maintained for 1 h. The reaction mixture then was poured into water (10 mL) and subsequently saturated with sodium chloride and extracted with ether (3×5 mL). The organic extracts were combined, washed with water (10 mL), brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc/petroleum ether 20:80) afforded 1.7 g (85%) of compound 3b as colorless waxy solid 37 . 1H NMR (400 MHz, CDCl3) δ 4.1 (s, 2H), 1.95(t, 2H, J = 6.4 Hz), 1.72(s, 3H), 1.61-1.53(m, 2H), 1.45-1.39(m, 2H), 1.01(m, 6H). 13C NMR (100 MHz, CDCl3) δ 137.7, 133.7, 58.9, 39.4, 34.1, 32.8, 28.6, 19.7, 19.4. 1H NMR and 13C values matched those previously reported 38 .
Kiser P.D., Zhang J., Badiee M., Li Q., Shi W., Sui X., Golczak M., Tochtrop G.P, & Palczewski K. (2015). Catalytic mechanism of a retinoid isomerase essential for vertebrate vision. Nature chemical biology, 11(6), 409-415.
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7

Alkane Standard Solutions for GC-MS

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Alkane standard solutions from C8 to C20 (40 mg/L each in hexane) and C21 to C40 (40 mg/L each in toluene) were purchased from Sigma-Aldrich. A standard solution from C5 to C10 was prepared using pure substances in a ratio resulting in narrow and symmetric peak shapes as described by Weingart, et al.35 (link).
Pure VOCs were selected according to the SPME/GC-MS results, such as Benzenethanol, β-caryophyllene, trans-2-pentenal, 2-ethylfuran and β-cyclocitral (Sigma-Aldrich); cadinene (a mixture of ɣ-cadinene and δ-cadinene; (BOC Sciences); β-selinene and ledol (Xiamen Freede Industry). Pure VOCs were used in functional assays and for identity confirmation with HS-SPME/GC-MS analysis (Supplementary Fig. S2)
Lazazzara V., Bueschl C., Parich A., Pertot I., Schuhmacher R, & Perazzolli M. (2018). Downy mildew symptoms on grapevines can be reduced by volatile organic compounds of resistant genotypes. Scientific Reports, 8, 1618.
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8

Volatility-Induced Treatment of Agar-Grown Cells

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For treatments, advantage was taken of the volatility of β-cyclocitral (Sigma-Aldrich), which was placed on a paper wick within the middle of a sealed Petri dish to treat agar-grown cells, in an identical approach used for acrolein treatments [13 (link)]. Β-cyclocitral was diluted in 100% p.a. methanol and 1 μL containing 0–0.3 μL of diluted β-cyclocitral (mock = 1 μL pure methanol) was placed on a paper wick in an Eppendorf lid in the centre of a 11 cm Petri dish, which was immediately sealed with Parafilm and left under very LL (2 μmol photons m−2 s−1). After 2–4 h, as indicated, cells within 2 cm of the middle of the plate were gently scraped from the agar with a spatula and immediately frozen in liquid nitrogen prior to biochemical analyses. Β-cyclocitral concentrations in parts per million (ppm) were calculated on a volume basis, considering a 30 cm3 air space in a 11 cm Petri dish, a β-cyclocitral density of 0.943 g mL−1, 95% purity, and the particle-related gas concentration of 0.0241 m³/mol, so that 0.12 μL of β-cyclocitral corresponded to 600 ppm inside the Petri dish.
Roach T., Baur T, & Kranner I. (2022). β-Cyclocitral Does Not Contribute to Singlet Oxygen-Signalling in Algae, but May Down-Regulate Chlorophyll Synthesis. Plants, 11(16), 2155.
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9

Volatile Compounds in Duck Leg Meat

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Duck leg meat that was purchased from a local market (Xiamen, China) was stored at −20 °C in a refrigerator. Instant Oolong tea powder containing 25.07% (label provision) of tea polyphenols was purchased from Fujian Da Ming Co., Ltd. (Zhangzhou, China). A standard series of C8-C20 alkanes for retention index (RI) determination and the internal standard 2,4,6-trimethylpyridine (≥98%) and ethyl decanoate (≥98%) were purchased from Sigma-Aldrich Co., Ltd. (St. Louis, USA). The standards, including 1-pentanol (≥98%), (Z)-3-hexen-1-ol (≥90%), benzaldehyde (≥97%), furfural (≥95%), (E)-2-hexenal (≥98%), benzeneacetaldehyde (≥98%), (E)-linalool oxide (≥96%), linalool (≥95%), phenylethyl alcohol (≥90%), 1-octen-3-ol (98%), (E)-2-nonenal (≥95%), (E,E)-2,4-heptadienal (≥98%), (E)-2-nonenal (≥98%), safranal (≥90%), decanal ≥(95%), β-cyclocitral (≥95%), 2,4-decadienal (≥90%), (E,E)-2,4-decadienal (≥95%), (E)-dodecanal (≥95%), alpha-terpineol (≥96%), hexanal (≥95%), β-ionone (≥97%), nonanal (≥96%), limonene (≥97%), dihydroactinidiolide (≥95%) and diisobutyl phthalate (≥98%) were purchased from Sigma-Aldrich (St Louis, USA). Anhydrous sodium chloride was purchased from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China).
Liu X., Cai N., Cai Z., Li L., Ni H, & Chen F. (2024). The effect of instant tea on the aroma of duck meat. Food Chemistry: X, 22, 101401.
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10

Analytical Characterization of Aromatic Compounds

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The following chemicals and reagents were used for the analyses: benzyl alcohol, benzaldehyde, β-cyclocitral, dihydroactinidiolide, eugenol, geraniol, trans-2-hexenol, trans-2-hexenal, cis-3-hexenol, cis-3-hexenal, β-ionone, jasmine lactone, linalool, methyl salicylate (MeSA), MeJA, 2-phenylethanol, phenylacetaldehyde, and phenylacetonitrile (Sigma–Aldrich, Germany).
Shi J., Xie D., Qi D., Peng Q., Chen Z., Schreiner M., Lin Z, & Baldermann S. (2019). Methyl Jasmonate-Induced Changes of Flavor Profiles During the Processing of Green, Oolong, and Black Tea. Frontiers in Plant Science, 10, 781.
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