Veratraldehyde
(Synonyms: 藜芦醛) 目录号 : GC39730Veratraldehyde (3,4-dimethoxybenzaldehyde, VD, VAD, VAld, Verapamil Related Compound E, Methylvanillin), a derivative of vanillin, is the chemical that is found and isolated from peppermint, ginger, bourbon vanilla, and fruits such as raspberry. Veratraldehyde is widely used as a flavorant and odorant because of its pleasant woody fragrance. Veratraldehyde also acts as a redox cycle agent.
Cas No.:120-14-9
Sample solution is provided at 25 µL, 10mM.
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Veratraldehyde (3,4-dimethoxybenzaldehyde, VD, VAD, VAld, Verapamil Related Compound E, Methylvanillin), a derivative of vanillin, is the chemical that is found and isolated from peppermint, ginger, bourbon vanilla, and fruits such as raspberry. Veratraldehyde is widely used as a flavorant and odorant because of its pleasant woody fragrance. Veratraldehyde also acts as a redox cycle agent.
[1] Hyun Wook Huh, et al. Molecules. 2020 Jun 17;25(12):2800.
Cas No. | 120-14-9 | SDF | |
别名 | 藜芦醛 | ||
Canonical SMILES | O=CC1=CC=C(OC)C(OC)=C1 | ||
分子式 | C9H10O3 | 分子量 | 166.17 |
溶解度 | DMSO : 100 mg/mL (601.79 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 6.0179 mL | 30.0897 mL | 60.1793 mL |
5 mM | 1.2036 mL | 6.0179 mL | 12.0359 mL |
10 mM | 0.6018 mL | 3.009 mL | 6.0179 mL |
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2.
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Bioanalytical Method Development and Validation of Veratraldehyde and Its Metabolite Veratric Acid in Rat Plasma: An Application for a Pharmacokinetic Study
Molecules 2020 Jun 17;25(12):2800.PMID:32560470DOI:10.3390/molecules25122800.
A simple, sensitive, and rapid UHPLC-MS/MS method was developed for the simultaneous determination of Veratraldehyde and its metabolite veratric acid in rat plasma. Cinnamaldehyde was used as an internal standard (IS) and the one-step protein precipitation method with 0.2% formic acid in acetonitrile (mobile phase B) was used for the sample extraction. Reversed C18 column (YMC-Triart C18 column, 50 mm × 2.0 mm, 1.9 µm) was used for chromatographic separation and was maintained at 30 °C. The total run time was 4.5 min and the electrospray ionization in positive mode was used with the transition m/z 167.07 → 139.00 for Veratraldehyde, m/z 183.07 → 139.00 for veratric acid, and m/z 133.00 → 55.00 for IS. The developed method exhibited good linearity (r2 ≥ 0.9977), and the lower limits of quantification ranged from 3 to 10 ng/mL for the two analytes. Intra-day precision and accuracy parameters met the criteria (within ±15%) during the validation. The bioanalytical method was applied for the determination of Veratraldehyde and veratric acid in rat plasma after oral and percutaneous administration of 300 and 600 mg/kg Veratraldehyde. Using the analytical methods established in this study, we can confirm the absorption and metabolism of Veratraldehyde in rats for various routes.
Photoenhanced degradation of Veratraldehyde upon the heterogeneous ozone reactions
Phys Chem Chem Phys 2010 Jul 21;12(27):7603-11.PMID:20502834DOI:10.1039/b922957d.
Light-induced heterogeneous reactions between gas-phase ozone and Veratraldehyde adsorbed on silica particles were performed. At an ozone mixing ratio of 250 ppb, the loss of Veratraldehyde largely increased from 1.81 x 10(-6) s(-1) in the dark to 2.54 x 10(-5) s(-1) upon exposure to simulated sunlight (lambda > 300 nm). The observed rates of degradation exhibited linear dependence with the ozone in the dark ozonolysis experiments which change in the non-linear Langmuir-Hinshelwood dependence in the experiments with simultaneous ozone and light exposure of the coated particles. When the coated silica particles were exposed only to simulated sunlight in absence of ozone the loss of Veratraldehyde was about three times higher i.e. 5.97 x 10(-6) s(-1) in comparison to the ozonolysis experiment under dark conditions at 250 ppb ozone mixing ratio, 1.81 x 10(-6) s(-1).These results clearly show that the most important loss of Veratraldehyde occurs under simultaneous ozone and light exposure of the coated silica particles. The main identified product in the heterogeneous reactions between gaseous ozone and adsorbed Veratraldehyde under dark conditions and in presence of light was veratric acid.Carbon yields of veratric acid were calculated and the obtained results indicated that at low ozone mixing ratio (250 ppb) the carbon yield obtained under dark conditions is 70% whereas the carbon yield obtained in the experiments with simultaneous ozone and light exposure of the coated particles is 40%. In both cases the carbon yield of veratric acid exponentially decayed leading to the plateau ( approximately 35% of carbon yield) at an ozone mixing ratio of 6 ppm. Two reaction products i.e. 3-hydroxy-4-methoxybenzoic acid and 4-hydroxy-3-methoxybenzoic acid were identified (confirmed with the standards) only in the experiments performed under simultaneous ozonolysis and light irradiation of the particles.
Boron-containing capsaicinoids
RSC Adv 2021 Jul 23;11(39):24282-24291.PMID:35479014DOI:10.1039/d1ra04943g.
This study reports on the preparation of eight new boron-containing capsaicinoids bearing long aliphatic chains, as an expansion of our previous studies to include tertiary amide derivatives into our substrate scope. Our boron-moiety, a pinacolboronate ester (Bpin) fragment, has been incorporated in two locations: as an aryl substituent of the capsaicinoid produced by the reductive amination of Veratraldehyde, or at the terminal end of an aliphatic substituent using an iridium catalyzed hydroboration reaction. We report that most compounds in our series show moderate antimicrobial and cytotoxic activity, surpassing activities noted in our previous study.
Anisaldehyde and Veratraldehyde Acting as Redox Cycling Agents for H(2)O(2) Production by Pleurotus eryngii
Appl Environ Microbiol 1994 Aug;60(8):2811-7.PMID:16349349DOI:10.1128/aem.60.8.2811-2817.1994.
The existence of a redox cycle leading to the production of hydrogen peroxide (H(2)O(2)) in the white rot fungus Pleurotus eryngii has been confirmed by incubations of 10-day-old mycelium with veratryl (3,4-dimethoxybenzyl) and anisyl (4-methoxybenzyl) compounds (alcohols, aldehydes, and acids). Veratraldehyde and anisaldehyde were reduced by aryl-alcohol dehydrogenase to their corresponding alcohols, which were oxidized by aryl-alcohol oxidase, producing H(2)O(2). Veratric and anisic acids were incorporated into the cycle after their reduction, which was catalyzed by aryl-aldehyde dehydrogenase. With the use of different initial concentrations of either veratryl alcohol, Veratraldehyde, or veratric acid (0.5 to 4.0 mM), around 94% of Veratraldehyde and 3% of veratryl alcohol (compared with initial concentrations) and trace amounts of veratric acid were found when equilibrium between reductive and oxidative activities had been reached, regardless of the initial compound used. At concentrations higher than 1 mM, veratric acid was not transformed, and at 1.0 mM, it produced a negative effect on the activities of aryl-alcohol oxidase and both dehydrogenases. H(2)O(2) levels were proportional to the initial concentrations of veratryl compounds (around 0.5%), and an equilibrium between aryl-alcohol oxidase and an unknown H(2)O(2)-reducing system kept these levels steady. On the other hand, the concomitant production of the three above-mentioned enzymes during the active growth phase of the fungus was demonstrated. Finally, the possibility that anisaldehyde is the metabolite produced by P. eryngii for the maintenance of this redox cycle is discussed.
Manipulating Interfacial Stability Via Absorption-Competition Mechanism for Long-Lifespan Zn Anode
Nanomicro Lett 2021 Dec 13;14(1):31.PMID:34902080DOI:10.1007/s40820-021-00777-2.
The stability of Zn anode in various Zn-based energy storage devices is the key problem to be solved. Herein, aromatic aldehyde additives are selected to modulate the interface reactions between the Zn anode and electrolyte. Through comprehensively considering electrochemical measurements, DFT calculations and FEA simulations, novel mechanisms of one kind of aromatic aldehyde, Veratraldehyde in inhibiting Zn dendrite/by-products can be obtained. This additive prefers to absorb on the Zn surface than H2O molecules and Zn2+, while competes with hydrogen evolution reaction and Zn plating/stripping process via redox reactions, thus preventing the decomposition of active H2O near the interface and uncontrollable Zn dendrite growth via a synactic absorption-competition mechanism. As a result, Zn-Zn symmetric cells with the Veratraldehyde additive realize an excellent cycling life of 3200 h under 1 mA cm-2/1 mAh cm-2 and over 800 h even under 5 mA cm-2/5 mAh cm-2. Moreover, Zn-Ti and Zn-MnO2 cells with the Veratraldehyde additive both obtain elevated performance than that with pure ZnSO4 electrolyte. Finally, two more aromatic aldehyde additives are chosen to prove their universality in stabilizing Zn anodes.