2-Hydroxy-4-methoxybenzaldehyde
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2-Hydroxy-4-methoxybenzaldehyde
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. See also * Vanillin * 2-Hydroxy-5-methoxybenzaldehyde * Isovanillin * ortho-Vanillin ''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 ... References Hydroxybenzaldehydes {{phenol-stub ...
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Vanillin
Vanillin is an organic compound with the molecular formula . 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. Vanillin and ethylvanillin are used by the food industry; ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (−O−CH2CH3) instead of a methoxy group (−O−CH3). Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available na ...
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Vanillin
Vanillin is an organic compound with the molecular formula . 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. Vanillin and ethylvanillin are used by the food industry; ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (−O−CH2CH3) instead of a methoxy group (−O−CH3). Natural vanilla extract is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available na ...
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2-Hydroxy-5-methoxybenzaldehyde
2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin. Synthesis and reactions The chemical is produced by the Reimer-Tiemann reaction on 4-methoxyphenol with a 79% yield. It reacts with malononitrile to form 2-imino-6-methoxy-2H-1-benzopyran-3-carbonitrile. It can be reduced by sodium borohydride in ethanol to form 2-hydroxy-5-methoxybenzyl alcohol. See also * Vanillin * Isovanillin * ortho-Vanillin ''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 ... * 2-Hydroxy-4-methoxybenzaldehyde References Phenol ethers Hydroxybenzaldehydes {{aromatic-stub ...
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Isovanillin
Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. 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. Isovanillin can be used as a precursor in the chemical total synthesis of morphine. The proposed metabolism of isovanillin (and vanillin) in rat has been described in literature, and is part of the WikiPathways machine readable pathway collection. See also * Vanillin * 2-Hydroxy-5-methoxybenzaldehyde * ortho-Vanillin ''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 ... * 2-Hydroxy-4-methoxybenzaldehyde References Hydroxybenzaldehydes Flavors Perfume ingredients Phenol ...
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Ortho-Vanillin
''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. ''ortho''-Vanillin is a fibrous, light-yellow, crystalline solid. Present in a variety of food products, it is not specifically sought after, and is therefore a less-commonly produced and encountered food additive. History ''ortho''-Vanillin was first isolated, in 1876, by renowned German chemist Ferdinand Tiemann. By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins. By ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''bonds'' between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-for ...
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Urolithin M7
Urolithins are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins. They are produced in the gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as pomegranate. During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity ''in vivo''. Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites. Urolithins are found in plasma mostly as glucuronides at low concentrations. Urolithins production is dependent on the gut microbiome enterotype. Individuals producing urolithins show a much higher abundance of the '' Clostridium leptum'' group of Firmicutes phylum than '' Bacteroides'' or '' Prevotella''. Known molecules * Urolithin A (3,8-Dihydroxyurolithin) * Urolithin A glucuronide * Urolithin B (3-Hydroxyurolithin) * urolithin B glucur ...
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Urolithin
Urolithins are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins. They are produced in the gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as pomegranate. During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity ''in vivo''. Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites. Urolithins are found in plasma mostly as glucuronides at low concentrations. Urolithins production is dependent on the gut microbiome enterotype. Individuals producing urolithins show a much higher abundance of the ''Clostridium leptum'' group of Firmicutes phylum than ''Bacteroides'' or ''Prevotella''. Known molecules * Urolithin A (3,8-Dihydroxyurolithin) * Urolithin A glucuronide * Urolithin B (3-Hydroxyurolithin) * urolithin B glucuronide * U ...
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Inverse Electron-demand Diels–Alder Reaction
The inverse electron demand Diels–Alder reaction, or DAINV or IEDDA is an organic chemical reaction, in which two new chemical bonds and a six-membered ring are formed. It is related to the Diels–Alder reaction, but unlike the Diels–Alder (or DA) reaction, the DAINV is a cycloaddition between an electron-rich dienophile and an electron-poor diene. During a DAINV reaction, three pi-bonds are broken, and two sigma bonds and one new pi-bond are formed. A prototypical DAINV reaction is shown on the right. DAINV reactions often involve heteroatoms, and can be used to form heterocyclic compounds. This makes the DAINV reaction particularly useful in natural product syntheses, where the target compounds often contain heterocycles. Recently, the DAINV reaction has been used to synthesize a drug transport system which targets prostate cancer. History The Diels–Alder reaction was first reported in 1928 by Otto Diels and Kurt Alder; they were awarded the Nobel Prize in chemistr ...
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