Names | |
---|---|
Preferred IUPAC name 3,4-Dihydroxybenzaldehyde | |
Other names Protocatechualdehyde Rancinamycin IV 3,4-Dihydroxybenzyl aldehyde | |
Identifiers | |
3D model (JSmol) | |
774381 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.004.889 |
EC Number |
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123001 | |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C7H6O3 | |
Molar mass | 138.12 g/mol |
Related compounds | |
Related compounds | 2,4-Dihydroxybenzaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Protocatechuic aldehyde is a phenolic aldehyde, a compound released from cork stoppers into wine. [1]
This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens , a type of Chili pepper. [2] It is also found in the mushroom Phellinus linteus . [3]
Protocatechuic aldehyde regulates G protein-coupled estrogen receptor-1 (GPER-1) and exhibits protective effects in endothelial dysfunction and atherosclerosis. [4]
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.
Selective estrogen receptor modulators (SERMs), also known as estrogen receptor agonist/antagonists (ERAAs), are a class of drugs that act on the estrogen receptor (ER). A characteristic that distinguishes these substances from pure ER agonists and antagonists is that their action is different in various tissues, thereby granting the possibility to selectively inhibit or stimulate estrogen-like action in various tissues.
An angiogenesis inhibitor is a substance that inhibits the growth of new blood vessels (angiogenesis). Some angiogenesis inhibitors are endogenous and a normal part of the body's control and others are obtained exogenously through pharmaceutical drugs or diet.
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.
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 in rat has been described in literature, and is part of the WikiPathways machine readable pathway collection.
Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.
Placental growth factor(PlGF) is a protein that in humans is encoded by the PGF gene.
Nuclear receptor coactivator 6 is a protein that in humans is encoded by the NCOA6 gene.
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.
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 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.
Phellinus is a genus of fungi in the family Hymenochaetaceae. Many species cause white rot. Fruit bodies, which are found growing on wood, are resupinate, sessile, and perennial. The flesh is tough and woody or cork-like, and brown in color. Clamp connections are absent, and the skeletal hyphae are yellowish-brown.
Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in the Asian "barbed skullcap" Scutellaria barbata and the north American plant S. lateriflora both of which have been used in traditional medicine. The compound is found only in trace amounts in the "Chinese skullcap" Scutellaria baicalensis, another plant used in traditional Chinese medicine.
Phenolic aldehydes are derivatives of phenol. Phenolic aldehydes can be found in wines and cognacs.
Hispidin is a natural substance. It can also be synthesized.
4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP) is a metabolite of the plastic Bisphenol A (BPA). MBP has potent estrogenic activity in vitro and in vivo, up to thousandfold stronger than BPA. It may also play a role in neuronal cell apoptosis and may increase risk for several forms of cancer.
Inoscavins are chemical compounds isolated from Phellinus linteus.
Inoscavin A is an antioxidant isolated from the mushroom Inonotus xeranticus.
5α-Dihydrolevonorgestrel (5α-DHLNG) is an active metabolite of the progestin levonorgestrel which is formed by 5α-reductase. It has about one-third of the affinity of levonorgestrel for the progesterone receptor. In contrast to levonorgestrel, the compound has both progestogenic and antiprogestogenic activity, and hence has a selective progesterone receptor modulator-like profile of activity. This is analogous to the case of norethisterone and 5α-dihydronorethisterone. In addition to the progesterone receptor, 5α-DHLNG interacts with the androgen receptor. It has similar affinity for the androgen receptor relative to levonorgestrel, and has androgenic effects similarly to levonorgestrel and testosterone. 5α-DHLNG is further transformed into 3α,5α- and 3β,5α-THLNG, which bind weakly to the estrogen receptor and have weak estrogenic activity. These metabolites are considered to be responsible for the weak estrogenic activity of high doses of levonorgestrel.