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4-Hydroxybenzoic acid

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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 .

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47-680: It is found in plants of the genus Vitex such as V. agnus-castus or V. negundo , and in Hypericum perforatum (St John's wort). It is also found in Spongiochloris spongiosa , a freshwater green alga. The compound is also found in Ganoderma lucidum , a medicinal mushroom with the longest record of use. Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4-hydroxybenzoate. 4-Hydroxybenzoic acid can be found naturally in coconut . It

94-559: A chloridometer , which detects silver ions once all chloride in the assay has precipitated via this reaction. Chlorided silver electrodes are commonly used in ex vivo electrophysiology . Chlorine can assume oxidation states of −1, +1, +3, +5, or +7. Several neutral chlorine oxides are also known. In nature, chloride is found primarily in seawater, which has a chloride ion concentration of 19400 mg/liter. Smaller quantities, though at higher concentrations, occur in certain inland seas and in subterranean brine wells , such as

141-415: A laboratory . A major application involving chloride is desalination , which involves the energy intensive removal of chloride salts to give potable water . In the petroleum industry , the chlorides are a closely monitored constituent of the mud system . An increase of the chlorides in the mud system may be an indication of drilling into a high-pressure saltwater formation. Its increase can also indicate

188-686: A biological control agent by planting them around vineyards to trap the H. obsoletus . V. agnus-castus was found not only to be an appropriate food source for the adult vectors, but also a reservoir of Candidatus phytoplasma solani (bacterial Phytoplasma species), the causal agent of the black wood disease in grapevines. The pathogen-caused leaf spot disease can almost defoliate V. agnus castus . Furthermore, root rot can occur when soils are kept too moist. Flavonoids ( vitexin , casticin ), iridoid glycoside ( agnuside , aucubin), p-hydroxybenzoic acid , alkaloids , essential oils , fatty oils, diterpenoids and steroids have been identified in

235-588: A fruit yield loss. This plant can also be reproduced vegetatively . One possibility is to use 5–8-centimetre (2–3 in) pieces of the ripening wood with buds in July or August and another is to cut the ripe wood in November and then let it root in a coldframe. Also in vitro reproduction with spike of the shoots or node explants is possible. The flowering and ripening processes do not happen simultaneously, enabling harvesting of both fresh fruits and seeds over

282-403: A hormone-sensitive condition, such as breast cancer , are advised not to use chasteberry. Use of Vitex is discouraged for pregnant or breastfeeding women, and for children. Chloride The term chloride refers to a compound or molecule that contains either a chlorine anion ( Cl ), which is a negatively charged chlorine atom, or a non-charged chlorine atom covalently bonded to

329-559: A linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents. 4-Hydroxybenzoic acid is produced commercially from potassium phenoxide and carbon dioxide in the Kolbe-Schmitt reaction . It can also be produced in the laboratory by heating potassium salicylate with potassium carbonate to 240 °C, followed by treating with acid. 4-Hydroxybenzoic acid has about one tenth

376-434: A local breakdown of the protective oxide form in alkaline concrete, so that a subsequent localized corrosion attack takes place. Increased concentrations of chloride can cause a number of ecological effects in both aquatic and terrestrial environments. It may contribute to the acidification of streams, mobilize radioactive soil metals by ion exchange, affect the mortality and reproduction of aquatic plants and animals, promote

423-410: A long span of time. The fruits tend to fall from the plant as they ripen, getting lost in the soil. Thus, it has no optimal fixed harvest time. Consequently, to avoid yield loss, unripe fruits need to be harvested. This early harvesting has no effect on quality. Overall, harvesting the fruits by hand likely is the most convenient solution. Thysanoptera, also known as thrips , can cause great damage to

470-415: A mammalian cell). Characteristic concentrations of chloride in model organisms are: in both E. coli and budding yeast are 10–200  mM (dependent on medium), in mammalian cells 5–100 mM and in blood plasma 100 mM. Chloride is also needed for the production of hydrochloric acid in the stomach. The concentration of chloride in the blood is called serum chloride , and this concentration

517-462: A polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate . This enzyme participates in ubiquinone biosynthesis. The enzyme 4-hydroxybenzoate geranyltransferase utilizes geranyl diphosphate and 4-hydroxybenzoate to produce 3-geranyl-4-hydroxybenzoate and diphosphate. Biosynthetically, alkannin is produced in plants from the intermediates 4-hydroxybenzoic acid and geranyl pyrophosphate . This enzyme

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564-403: Is 2200 mg/kg in mice (oral). 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo , and stimulates the growth of human breast cancer cell lines. It is a common metabolite of paraben esters , such as methylparaben . The compound is a relatively weak estrogen, but can produce uterotrophy with sufficient doses to an equivalent extent relative to estradiol , which

611-466: Is a weak base as indicated by the negative value of the p K a of hydrochloric acid. Chloride can be protonated by strong acids , such as sulfuric acid: Ionic chloride salts react with other salts to exchange anions. The presence of halide ions like chloride can be detected using silver nitrate . A solution containing chloride ions will produce a white silver chloride precipitate: The concentration of chloride in an assay can be determined using

658-568: Is a major consumer of the world's energy budget. This process converts concentrated sodium chloride solutions into chlorine and sodium hydroxide, which are used to make many other materials and chemicals. The process involves two parallel reactions: An example is table salt, which is sodium chloride with the chemical formula NaCl. In water , it dissociates into Na and Cl ions. Salts such as calcium chloride , magnesium chloride , potassium chloride have varied uses ranging from medical treatments to cement formation. Calcium chloride (CaCl 2 )

705-654: Is a plant native of the Mediterranean region . It is one of the few temperate-zone species of Vitex , which is on the whole a genus of tropical and subtropical flowering plants . Vitex is a cross-pollinating plant, but its self-pollination has been recorded. Theophrastus mentioned the shrub several times, as agnos (ἄγνος) in Enquiry into Plants . It has been long believed to be an anaphrodisiac – leading to its name as "chaste tree" – but its effectiveness for such action remains unproven. The shrub

752-415: Is a plant pathogen that commonly inhabits fertile soil. It is known to metabolize aromatic compounds of low molecular weight, such as p -hydroxybenzoic acid. The enzyme 4-hydroxybenzoate 4- O -beta- D -glucosyltransferase transforms UDP-glucose and 4-hydroxybenzoate into UDP and 4-(beta- D -glucosyloxy)benzoate . It can be found in the pollen of Pinus densiflora . The Hammett equation describes

799-530: Is a salt that is marketed in pellet form for removing dampness from rooms. Calcium chloride is also used for maintaining unpaved roads and for fortifying roadbases for new construction. In addition, calcium chloride is widely used as a de-icer , since it is effective in lowering the melting point when applied to ice. Examples of covalently-bonded chlorides are phosphorus trichloride , phosphorus pentachloride , and thionyl chloride , all three of which are reactive chlorinating reagents that have been used in

846-425: Is also a neutral chlorine atom covalently bonded by a single bond to the rest of the molecule. For example, methyl chloride CH 3 Cl is an organic compound with a covalent C−Cl bond in which the chlorine is not an anion. Other examples of covalent chlorides are carbon tetrachloride CCl 4 , sulfuryl chloride SO 2 Cl 2 and monochloramine NH 2 Cl . A chloride ion (diameter 167  pm )

893-400: Is also found in evaporite minerals such as chlorapatite and sodalite . Chloride has a major physiological significance, which includes regulation of osmotic pressure , electrolyte balance and acid-base homeostasis. Chloride is present in all body fluids , and is the most abundant extracellular anion which accounts for around one third of extracellular fluid 's tonicity . Chloride

940-486: Is an essential electrolyte , playing a key role in maintaining cell homeostasis and transmitting action potentials in neurons. It can flow through chloride channels (including the GABA A receptor) and is transported by KCC2 and NKCC2 transporters. Chloride is usually (though not always) at a higher extracellular concentration, causing it to have a negative reversal potential (around −61 mV at 37 °C in

987-473: Is bonded by the protic end of the water molecules. Chloride can be oxidized but not reduced. The first oxidation, as employed in the chlor-alkali process, is conversion to chlorine gas. Chlorine can be further oxidized to other oxides and oxyanions including hypochlorite (ClO , the active ingredient in chlorine bleach ), chlorine dioxide (ClO 2 ), chlorate ( ClO 3 ), and perchlorate ( ClO 4 ). In terms of its acid–base properties, chloride

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1034-514: Is commonly recommended in Germany, V. agnus-castus should be avoided during pregnancy due to the possibility of complications. In ancient Greece, the chaste tree played a significant role in the female agricultural festival of Thesmophoria , dedicated to honoring the goddesses Demeter and Persephone in Greek cities. In Archaic Sparta , in the 8th–6th centuries BCE, it was incorporated into

1081-399: Is filtered by the glomerulus , is reabsorbed by both proximal and distal tubules (majorly by proximal tubule) by both active and passive transport. The presence of chlorides, such as in seawater, significantly worsens the conditions for pitting corrosion of most metals (including stainless steels, aluminum and high-alloyed materials). Chloride-induced corrosion of steel in concrete lead to

1128-468: Is generally prepared by the rearrangement of p -hydroxyphenylbenzoate. Alternatively, p -hydroxybenzoic acid can be converted to p -acetoxybenzoyl chloride . This acid chloride reacts with phenol to give, after deacetylation, 4,4′-dihydroxybenzophenone. Examples of drugs made from PHBA include nifuroxazide , orthocaine , ormeloxifene and proxymetacaine . 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. The LD 50

1175-422: Is hardy to −23 °C (−9 °F) USDA Zone 6. In colder zones, the plant tends to die back to the ground, but as it flowers on new wood, flowering is not affected on vigorous growth in the following season. This plant is a brackish water dweller, indicating that it tolerates salt. Cold and wet weather results in dieback and losses. The plant grows well on loamy, neutral to alkaline soil. In cultivation in

1222-2252: Is involved in shikonin biosynthesis. It can be found in Lithospermum erythrorhizon . The enzyme 3-hydroxybenzoate—CoA ligase uses ATP, 3-hydroxybenzoate and CoA to produce AMP, diphosphate and 3-hydroxybenzoyl-CoA . The enzyme works equally well with 4-hydroxybenzoate. It can be found in Thauera aromatica . The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H and O 2 into hydroquinone , NAD(P), H 2 O and CO 2 . This enzyme participates in 2,4-dichlorobenzoate degradation. It can be found in Candida parapsilosis . The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H and O 2 into protocatechuate , NADP and H 2 O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation. It can be found in Pseudomonas putida and Pseudomonas fluorescens . The enzyme 4-hydroxybenzoate 3-monooxygenase (NAD(P)H) utilizes 4-hydroxybenzoate, NADH, NADPH, H and O 2 to produce 3,4-dihydroxybenzoate ( protocatechuic acid ), NAD, NADP and H 2 O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation. It can be found in Corynebacterium cyclohexanicum and in Pseudomonas sp . The enzyme 4-hydroxybenzoate decarboxylase uses 4-hydroxybenzoate to produce phenol and CO 2 . This enzyme participates in benzoate degradation via coenzyme A (CoA) ligation. It can be found in Klebsiella aerogenes ( Aerobacter aerogenes ). The enzyme 4-hydroxybenzoate—CoA ligase transforms ATP, 4-hydroxybenzoate and CoA to produce AMP, diphosphate and 4-hydroxybenzoyl-CoA . This enzyme participates in benzoate degradation via CoA ligation. It can be found in Rhodopseudomonas palustris . Coniochaeta hoffmannii

1269-454: Is much larger than a chlorine atom (diameter 99 pm). The chlorine atom's hold on the valence shell is weaker because the chloride anion has one more electron than it does. The ion is colorless and diamagnetic. In aqueous solution, it is highly soluble in most cases; however, for some chloride salts, such as silver chloride , lead(II) chloride , and mercury(I) chloride , they are only slightly soluble in water. In aqueous solution, chloride

1316-549: 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 Macrotyloma uniflorum (horse gram), carob and in Phyllanthus acidus (Otaheite gooseberry). Açaí oil , obtained from the fruit of the açaí palm ( Euterpe oleracea ), is rich in p -hydroxybenzoic acid ( 892 ± 52 mg/kg ). It is also found in cloudy olive oil and in

1363-411: Is regulated by the kidneys . A chloride ion is a structural component of some proteins; for example, it is present in the amylase enzyme. For these roles, chloride is one of the essential dietary mineral (listed by its element name chlorine ). Serum chloride levels are mainly regulated by the kidneys through a variety of transporters that are present along the nephron . Most of the chloride, which

1410-803: Is the ester of aucubin and p -hydroxybenzoic acid. 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. Benzoate 4-monooxygenase is an enzyme that utilizes benzoate , NADPH, H and O 2 to produce 4-hydroxybenzoate, NADP and H 2 O. This enzyme can be found in Aspergillus niger . 4-Hydroxybenzoate also arises from tyrosine. The enzyme 4-methoxybenzoate monooxygenase (O-demethylating) transforms 4-methoxybenzoate , an electron acceptor AH 2 and O 2 into 4-hydroxybenzoate, formaldehyde,

1457-445: Is the major sesquiterpene compound found in the fruits of V. agnus-castus . Some slight differences occur between fruits from white-flowering plants compared to violet-flowering ones. The oil of fruits of former has a higher amount of monoterpene constituents. The leaves mainly contain 1,8-cineole , trans-beta-farnesene , alpha-pinene , trans-beta-caryophyllene , and terpinen-4-ol . The oil, particularly from white-flowering plants,

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1504-671: Is under preliminary research for its potential antibacterial effects. The chaste tree, a local shrub known since the Lower Paleolithic for various applications including as a spice, was also historically valued for its medicinal properties, including uses as anaphrodisiac and abortifacient, with further properties suggested by modern studies. The shrub has been used by several ancient Mediterranean cultures. Vitex has been used in traditional medicine for reproductive health issues in women, but only limited high-quality clinical evidence supports its effectiveness. Although it

1551-470: Is unusual for a weakly estrogenic compound and indicates that it may be a full agonist of the estrogen receptor with relatively low binding affinity for the receptor. It is about 0.2% to 1% as potent as an estrogen as estradiol. 4-Hydroxybenzoic acid at Phenol-Explorer .eu Vitex agnus-castus Vitex agnus-castus (also called vitex , chaste tree / chastetree , chasteberry , Abraham's balm , lilac chastetree , or monk's pepper )

1598-667: The Great Salt Lake in Utah and the Dead Sea in Israel. Most chloride salts are soluble in water, thus, chloride-containing minerals are usually only found in abundance in dry climates or deep underground. Some chloride-containing minerals include halite (sodium chloride NaCl ), sylvite (potassium chloride KCl ), bischofite (MgCl 2 ∙6H 2 O), carnallite (KCl∙MgCl 2 ∙6H 2 O), and kainite (KCl∙MgSO 4 ∙3H 2 O). It

1645-843: The 6th–3rd centuries BCE. In a Philistine temple at Gath , an excavation uncovered around 100 chaste tree fruits, a find unparalleled in both quantity and context compared to other locations in Israel . This suggests their deliberate use in religious practices, possibly in celebration of a goddess related to Hera. Notably, the chaste tree is linked to the binding of Hera, where it featured in rituals celebrating her mythology at Samos . Adverse effects from Vitex can include nausea , headache, gastrointestinal discomfort , menstrual discomfort , fatigue, and skin disorders. People taking dopamine -related medications or Parkinson's disease medications should avoid using chasteberry. Women on birth-control pills, hormone-replacement therapy , or having

1692-537: The UK, the form V. agnus-castus f. latifolia has gained the Royal Horticultural Society 's Award of Garden Merit . The fruits from one single tree can be harvested for more than 15 years. This indicates that the tree cannot be integrated in a usual crop rotation system. It is suggested to sow dissimilar plants such as monocots as its subsequent crop so that it might be easier to control

1739-524: The acidity of benzoic acid , having an acid dissociation constant K a = 3.3 × 10 M at 19 °C. Its acid dissociation follows this equation: Vectran is a manufactured fiber, spun from a liquid crystal polymer . Chemically it is an aromatic polyester produced by the polycondensation of 4-hydroxybenzoic acid and 6-hydroxynaphthalene-2-carboxylic acid . The fiber has been shown to exhibit strong radiation shielding used by Bigelow Aerospace and produced by StemRad . 4,4′-Dihydroxybenzophenone

1786-451: The chemical analysis of V. agnus-castus . They occur in the fruits and in the leaves. Essential oils have been found in the fruits and in the leaves. The oil of leaves, unripe, and ripe fruits differ in compounds; 50 compounds were identified in the oil of unripe fruits, 51 compounds in the oil of ripe fruits, and 46 compounds in the oil of the leaves. 1,8-Cineole and sabinene are the main monoterpene components and beta-caryophyllene

1833-527: The cult of the local agriculture goddess, Artemis Orthia . The first century physician Dioscorides documented various synonyms for the lilac chaste tree. In the second century CE, Pausanias mentioned that the wooden image of Asclepius in Sparta was crafted from the chaste tree. Additionally, there is botanical and textual evidence supporting the significance of the chaste tree at the Heraion of Samos during

1880-418: The edible mushroom Russula virescens (green-cracking russula). p -Hydroxybenzoic acid glucoside can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces ( Picea abies ). Violdelphin is an anthocyanin, a type of plant pigments, found in blue flowers and incorporating two p -hydroxybenzoic acid residues, one rutinoside and two glucosides associated with a delphinidin . Agnuside

1927-474: The growth and the generative development of V. agnus-castus . The insect feeds on chaste tree by sucking up the fruit contents or puncturing them. Also, chaste tree is the only known host (especially in Israel) for Hyalesthes obsoletus . This cicada is the vector for black wood disease of grapevines. H. obsoletus prefers V. agnus-castus as a host to the grapevine. In this case, chaste trees can be used as

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1974-473: The invasion of saltwater organisms into previously freshwater environments, and interfere with the natural mixing of lakes. Sodium chloride has also been shown to change the composition of microbial species at relatively low concentrations. It can also hinder the denitrification process, a microbial process essential to nitrate removal and the conservation of water quality, and inhibit the nitrification and respiration of organic matter. The chlor-alkali industry

2021-433: The monk's pepper plant, the dicot . Because the fruits of monk's pepper tend to fall constantly and uncontrollably, the plant likely can germinate from seed. The overall best yield per hectare reportedly can be achieved if the plant spacing is around 70 cm (28 in). Pruning back the branches in autumn has a positive influence on fruit yield while repruning in spring can induce an increase of vegetative shoots, thus

2068-1198: The reduction product A and H 2 O. This enzyme participates in 2,4-dichlorobenzoate degradation in Pseudomonas putida . The enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde , NAD and H 2 O to produce 4-hydroxybenzoate, NADH and H. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina . It is also found in carrots ( Daucus carota ). The enzyme that 2,4'-dihydroxyacetophenone dioxygenase transforms 2,4'-dihydroxyacetophenone and O 2 into 4-hydroxybenzoate and formate . This enzyme participates in bisphenol A degradation. It can be found in Alcaligenes species. The enzyme 4-chlorobenzoate dehalogenase uses 4-chlorobenzoate and H 2 O to produce 4-hydroxybenzoate and chloride . It can be found in Pseudomonas species. The enzyme 4-hydroxybenzoyl-CoA thioesterase utilizes 4-hydroxybenzoyl-CoA and H 2 O to produce 4-hydroxybenzoate and CoA. This enzyme participates in 2,4-dichlorobenzoate degradation. It can be found in Pseudomonas species. The enzyme 4-hydroxybenzoate polyprenyltransferase uses

2115-621: The rest of the molecule by a single bond ( −Cl ). Many inorganic chlorides are salts . Many organic compounds are chlorides. The pronunciation of the word "chloride" is / ˈ k l ɔːr aɪ d / . Chloride salts such as sodium chloride are often soluble in water. It is an essential electrolyte located in all body fluids responsible for maintaining acid/base balance, transmitting nerve impulses and regulating liquid flow in and out of cells. Other examples of ionic chlorides are sodium chloride NaCl, calcium chloride CaCl 2 and ammonium chloride [NH 4 ]Cl . The chloride

2162-517: The virginal goddess Hestia / Vesta . The most common names are "chaste tree", "vitex", and "monk's pepper". Vitex agnus-castus is widely cultivated in warm, temperate, and subtropical regions for its delicately textured, aromatic foliage and butterfly -attracting midsummer spikes of lavender flowers opening in late summer in cooler climates. It grows to a height of 1–5 m (3–16 ft). It requires full sun, though tolerates partial shade, along with well-draining soil. Under ideal conditions, it

2209-626: Was utilized for religious rituals in ancient Greece and among the Philistines in modern-day Israel . Vitex , its name in Pliny the Elder , is derived from the Latin vieo , meaning to weave or to tie up, a reference to the use of V. agnus-castus in basketry. Its macaronic specific name agnus-castus repeats " chaste " in both Greek and Latin; the small tree was considered to be sacred to

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