Protocatechuic acid

3,4-dihydroxybenzoic acid

C7H6O4 (154.0266076)


Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. 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 . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

   

4-Hydroxybenzoic acid

4-hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid 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. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

Desaminotyrosine

3-(4-hydroxyphenyl)propanoic acid

C9H10O3 (166.062991)


Desaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases. Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID:15315398). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID:29168502). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID:29168502, 28393285, 19961416). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain. A normal constituent of human urine. A product of tyrosine metabolism; concentration in urine increases in patients with gastrointestinal diseases. (Dictionary of Organic Compounds) May also result from phenolic acid metabolism by colonic bacteria. (PMID 15315398) [HMDB]. Phloretic acid is found in many foods, some of which are arrowroot, olive, avocado, and peanut. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling.

   

Scytalone

3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone

C10H10O4 (194.057906)


   
   

2,4-Dihydroxy-3,6-dimethylbenzaldehyde

2,4-Dihydroxy-3,6-dimethylbenzaldehyde

C9H10O3 (166.062991)


   

4-hydroxybenzoate

4-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

p-Hydroxybenzoic acid

p-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

phloroglucinol

phloroglucinol

C6H6O3 (126.0316926)


A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents A benzenetriol with hydroxy groups at position 1, 3 and 5.

   

3,4-Dihydroxybenzoic acid

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)


   

(2r)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

(2r)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

C17H28O5 (312.1936638)


   

(3r)-3,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

(3r)-3,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.057906)


   

2,3-dihydroxypropyl 13-hydroxytetradeca-2,4,8-trienoate

2,3-dihydroxypropyl 13-hydroxytetradeca-2,4,8-trienoate

C17H28O5 (312.1936638)


   

8-hydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

8-hydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C11H12O3 (192.0786402)


   

(2s)-1,2,3,6-tetrahydroxyheptadeca-5,7,9-trien-4-one

(2s)-1,2,3,6-tetrahydroxyheptadeca-5,7,9-trien-4-one

C17H28O5 (312.1936638)


   

13-hydroxytetradeca-2,4,8-trienoic acid

13-hydroxytetradeca-2,4,8-trienoic acid

C14H22O3 (238.1568862)


   

(3r)-8-hydroxy-5-(hydroxymethyl)-3-methyl-3,4-dihydro-2-benzopyran-1-one

(3r)-8-hydroxy-5-(hydroxymethyl)-3-methyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0735552)


   

(3r,4r)-4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

(3r,4r)-4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0735552)


   

(3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

(3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

C11H10O5 (222.052821)


   

(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

C11H10O5 (222.052821)


   

7-hydroxy-3h-2-benzofuran-1-one

7-hydroxy-3h-2-benzofuran-1-one

C8H6O3 (150.03169259999999)


   

8-hydroxy-5-(hydroxymethyl)-3-methyl-3,4-dihydro-2-benzopyran-1-one

8-hydroxy-5-(hydroxymethyl)-3-methyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0735552)


   

4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0735552)


   

(3r,4s)-4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

(3r,4s)-4,8-dihydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0735552)


   

8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid

C11H10O5 (222.052821)


   

(2s)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

(2s)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

C17H28O5 (312.1936638)


   

(2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoic acid

(2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoic acid

C14H22O3 (238.1568862)


   

2-[(2s)-1,2,3-trihydroxypropyl]tetradeca-2,4,6-trienoic acid

2-[(2s)-1,2,3-trihydroxypropyl]tetradeca-2,4,6-trienoic acid

C17H28O5 (312.1936638)