Names | |||
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Preferred IUPAC name 4-Hydroxy-3-methoxybenzoic acid | |||
Other names 4-Hydroxy-m-anisic acid, Vanillate | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.004.061 | ||
KEGG | |||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
C8H8O4 | |||
Molar mass | 168.148 g·mol−1 | ||
Appearance | White to light yellow powder or crystals | ||
Melting point | 210 to 213 °C (410 to 415 °F; 483 to 486 K) | ||
Hazards | |||
NFPA 704 (fire diamond) | |||
Related compounds | |||
Related compounds | Vanillin, vanillyl alcohol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. [2] [3]
The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis , [4] an herb indigenous to China, which is used in traditional Chinese medicine.
Açaí oil, obtained from the fruit of the açaí palm ( Euterpe oleracea ), is rich in vanillic acid (1616±94 mg/kg). [5] It is one of the main natural phenols in argan oil.[ citation needed ] It is also found in wine and vinegar. [6]
Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions. [7]
Vanillic acid can be obtained from the oxidation of vanillin by various oxidizing agents. With Pd/C, NaBH4, and KOH as the oxidizing agent, the conversion was reported to occur in ~89% yield. [8]
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.
Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.
The açaí palm, Euterpe oleracea, is a species of palm tree (Arecaceae) cultivated for its fruit, hearts of palm, leaves, and trunk wood. Global demand for the fruit has expanded rapidly in the 21st century, and the tree is cultivated for that purpose primarily.
Ferulic acid is a hydroxycinnamic acid; it is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical or polyphenol, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.
4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.
Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.
Euterpe is a genus of palm trees, containing eight species that are native to Central America and the Yucatan, the West Indies, and South America, from Belize and the Windward Islands southward to Brazil, Peru and Argentina. These palms grow mainly in swamps and floodplains.
Açaí oil is obtained from the fruit of Euterpe oleracea, which grows in the Amazon rainforest. The oil is rich in phenolic compounds similar in profile to the pulp itself, such as vanillic acid, syringic acid, p-hydroxybenzoic acid, protocatechuic acid and ferulic acid as well as (+)-catechin and numerous procyanidin oligomers.
Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.
Euterpe precatoria is a tall, slender-stemmed, pinnate-leaved palm native to Central and South America and Trinidad and Tobago. E. precatoria is used commercially to produce fruits, although Euterpe oleracea is more commonly cultivated due to its larger fruits.
In enzymology, a vanillin synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a trans-feruloyl—CoA synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a trans-feruloyl-CoA hydratase (EC 4.2.1.101) is an enzyme that catalyzes the chemical reaction
Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.
Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.
Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function. Two important naturally occurring types of phenolic acids are hydroxybenzoic acids and hydroxycinnamic acids, which are derived from non-phenolic molecules of benzoic and cinnamic acid, respectively.
The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.