Names | |
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Preferred IUPAC name 3-Hydroxy-4-methoxybenzaldehyde [1] | |
Other names 5-Formylguaiacol 3-Hydroxy-p-anisaldehyde | |
Identifiers | |
3D model (JSmol) | |
1073021 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.009.724 |
EC Number |
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MeSH | Isovanillin |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C8H8O3 | |
Molar mass | 152.149 g·mol−1 |
Appearance | Translucent crystals |
Melting point | 113 to 116 °C (235 to 241 °F; 386 to 389 K) |
Boiling point | 179 °C (354 °F; 452 K) at 15 mmHg |
log P | 1.25 |
Acidity (pKa) | 9.248 |
Related compounds | |
Related compounds | Anisaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. [2] It is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which could make it a candidate drug for use in alcohol aversion therapy. [3] Isovanillin can be used as a precursor in the chemical total synthesis of morphine. [4] [5] The proposed metabolism of isovanillin (and vanillin) in rat has been described in literature, [6] and is part of the WikiPathways [7] machine readable pathway collection.
Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.
Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:
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The article concerns the total synthesis of galanthamine, a drug used for the treatment of mild to moderate Alzheimer's disease.
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The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was discovered by Tohru Fukuyama et al. in 1998.
Tohru Fukuyama is a Japanese organic chemist and Professor of Chemistry at University of Tokyo in Japan. He discovered the Fukuyama coupling in 1998.
ortho-Vanillin (2-hydroxy-3-methoxybenzaldehyde) is an organic solid present in the extracts and essential oils of many plants. Its functional groups include aldehyde, ether and phenol. ortho-Vanillin, a compound of the formula C8H8O3, is distinctly different from its more prevalent isomer, meta-vanillin. The "ortho-" prefix refers to the position of the compound’s hydroxyl moiety, which is found in the para-position in vanillin.
The Fukuyama reduction is an organic reaction and an organic reduction in which a thioester is reduced to an aldehyde by a silyl hydride in presence of a catalytic amount of palladium. This reaction was invented in 1990 by Tohru Fukuyama. In the original scope of the reaction the silyl hydride was triethylsilane and the catalyst palladium on carbon:
Merrilactone A is one of the four sesquiterpenes that were newly discovered from the fruit of Illicium merrillianum in 2000. Members of the genus Illicium include Chinese star anise, widely used as a spice for flavouring food and beverages, and also poisonous plants such as Japanese star anise. Chemical studies of Illicium have developed rapidly over the last 20 years, and merrilactone A has been shown to have neurotrophic activity in fetal rat cortical neuron cultures. This has led researchers to believe that Merrilactone A may hold therapeutic potential in the treatment of neuro-degenerative diseases such as Alzheimer's disease and Parkinson's disease.
The Saegusa–Ito oxidation is a chemical reaction used in organic chemistry. It was discovered in 1978 by Takeo Saegusa and Yoshihiko Ito as a method to introduce α-β unsaturation in carbonyl compounds. The reaction as originally reported involved formation of a silyl enol ether followed by treatment with palladium(II) acetate and benzoquinone to yield the corresponding enone. The original publication noted its utility for regeneration of unsaturation following 1,4-addition with nucleophiles such as organocuprates.
Synthesis of morphine-like alkaloids in chemistry describes the total synthesis of the natural morphinan class of alkaloids that includes codeine, morphine, oripavine, and thebaine and the closely related semisynthetic analogs methorphan, buprenorphine, hydromorphone, hydrocodone, isocodeine, naltrexone, nalbuphine, oxymorphone, oxycodone, and naloxone.
Altemicidin is monoterpene alkaloid first identified in isolates from marine actinomycetes in 1989. It may also be produced synthetically. Altemicidin displays both acaricidal and antitumor activity.
2-Hydroxy-4-methoxybenzaldehyde is a chemical compound and an isomer of vanillin. Urolithin M7, one of the urolithins, has also been synthesized from 2-hydroxy-4-methoxybenzaldehyde using the inverse electron-demand Diels–Alder reaction.
2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin.
MoOPH, also known as oxodiperoxymolybdenum(pyridine)-(hexamethylphosphoric triamide), is a reagent used in organic synthesis. It contains a molybdenum(VI) center with multiple oxygen ligands, coordinated with pyridine and HMPA ligands. It is an electrophilic source of oxygen that reacts with enolates and related structures, and thus can be used for alpha-hydroxylation of carbonyl-containing compounds. Other reagents used for alpha-hydroxylation via enol or enolate structures include Davis oxaziridine, oxygen, and various peroxyacids. This reagent was first utilized by Edwin Vedejs as an efficient alpha-hydroxylating agent in 1974 and an effective preparative procedure was later published in 1978.
(2-Hydroxyethyl) dimethylsulfoxonium chloride is an organic salt found in sea chervils and sea sponges that causes the Dogger Bank itch.