4-Hydroxyphenylacetic acid

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4-Hydroxyphenylacetic acid
4-Hydroxyphenylacetic acid.svg
Names
Preferred IUPAC name
(4-Hydroxyphenyl)acetic acid
Other names
p-Hydroxyphenylacetic acid
Identifiers
3D model (JSmol)
1448766
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.321 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-851-3
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) Yes check.svgY
    Key: XQXPVVBIMDBYFF-UHFFFAOYSA-N Yes check.svgY
  • O=C(O)Cc1ccc(O)cc1
Properties
C8H8O3
Molar mass 152.149 g·mol−1
AppearanceBeige powder
Melting point 150 °C (302 °F; 423 K)
Hazards
Safety data sheet (SDS) MSDS at Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

4-Hydroxyphenylacetic acid is a chemical compound found in olive oil [1] and beer. [2]

Contents

Synthesis

4-Hydroxyphenylacetic acid is obtained by reducing 4-hydroxymandelic acid with elemental phosphorus and iodine. [3]

Uses

In industry, 4-hydroxyphenylacetic acid is an intermediate used to synthesize atenolol, [3] 3,4-dihydroxyphenylacetic acid, [4] and coclaurine.

Related Research Articles

<span class="mw-page-title-main">Olive oil</span> Liquid fat made from olives

Olive oil is a liquid fat obtained by pressing whole olives, the fruit of Olea europaea, a traditional tree crop of the Mediterranean Basin, and extracting the oil.

<span class="mw-page-title-main">Olive</span> Flowering plant in the family Oleaceae

The olive, botanical name Olea europaea, meaning 'European olive', is a species of small tree or shrub in the family Oleaceae, found traditionally in the Mediterranean Basin, with wild subspecies found further afield in Africa and western Asia. When in shrub form, it is known as Olea europaea'Montra', dwarf olive, or little olive. The species is cultivated in all the countries of the Mediterranean, as well as in Australia, New Zealand, North and South America and South Africa. It is the type species for its genus, Olea. The tree and its fruit give their name to the Oleaceae plant family, which also includes species such as lilac, jasmine, forsythia, and the true ash tree.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Salicylic acid</span> Chemical compound used in medicines and industry

Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or, white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.

<span class="mw-page-title-main">Tannin</span> Class of astringent, bitter plant polyphenolic chemical compounds

Tannins are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids.

<span class="mw-page-title-main">Wheat beer</span> Beer brewed in part with wheat

Wheat beer is a top-fermented beer which is brewed with a large proportion of wheat relative to the amount of malted barley. The two main varieties are German Weizenbier and Belgian witbier; other types include Lambic, Berliner Weisse, and Gose.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

The smoke point, also referred to as the burning point, is the temperature at which an oil or fat begins to produce a continuous bluish smoke that becomes clearly visible, dependent upon specific and defined conditions. Smoke point values can vary greatly, depending on factors such as the volume of oil utilized, the size of the container, the presence of air currents, the type and source of light as well as the quality of the oil and its acidity content, otherwise known as free fatty acid (FFA) content. The more FFA an oil contains, the quicker it will break down and start smoking. The lower the value of FFA, the higher the smoke point. However, the FFA content typically represents less than 1% of the total oil and consequently renders smoke point a poor indicator of the capacity of a fat or oil to withstand heat.

<span class="mw-page-title-main">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid derivative and a phenolic compound. 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, 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.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

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.

<span class="mw-page-title-main">4-Ethylguaiacol</span> Chemical compound

4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2. It can be produced in wine and beer by Brettanomyces. It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass.

<span class="mw-page-title-main">Hydroxytyrosol</span> Chemical compound

Hydroxytyrosol is an organic compound with the formula (HO)2C6H3CH2CH2OH. It is a phenylethanoid, i.e. a relative of phenethyl alcohol. Its derivatives are found in a variety of natural sources, notably olive oils and wines. Hydroxytyrosol is a colorless solid, although samples often turn beige during storage. It is a derivative, formally speaking, of catechol.

<span class="mw-page-title-main">Date honey</span> Syrup extracted from dates

Date honey, date syrup, date molasses, Debes, or rub is a thick dark brown, very sweet fruit syrup extracted from dates. It is widely used in Middle Eastern cuisine and Maghrebi cuisine.

<span class="mw-page-title-main">Olive leaf</span> Herbal medicinal product

Olive leaf is the leaf of the olive tree. Although olive oil is well known for its flavor and possible health benefits, the leaf and its extracts remain under preliminary research with unknown effects on human health.

<span class="mw-page-title-main">EDDHA</span> Chemical compound

EDDHA or ethylenediamine-N,N-bis(2-hydroxyphenylacetic acid) is a chelating agent. Like EDTA, it binds metal ions as a hexadentate ligand, using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water-soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related aminopolycarboxylic acid chelating agents feature tertiary amines and few have phenolate groups.

<span class="mw-page-title-main">Syringic acid</span> Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Picual</span> Olive cultivar

The Picual, also known as Marteña or Lopereña, is an olive cultivar from Spain. Picual olives are the most commonly grown olive today for olive oil production, with production centered in the Spanish province of Jaén. Picual trees are estimated to account for 25% of all olive oil production in the world. Naturally, this varietal is very high in oil content, at 20-27% by weight.

<span class="mw-page-title-main">4-Hydroxymandelic acid</span> Chemical compound

4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol. The compound typically occurs as a monohydrate.

References

  1. Papadopoulos, George; Boskou, Dimitrios (1991). "Antioxidant effect of natural phenols on olive oil". Journal of the American Oil Chemists' Society. 68 (9): 669. doi:10.1007/BF02662292. S2CID   85234954.
  2. Determination of free and bound phenolic acids in beer. M. Nardini and A. Ghiselli, Food Chemistry, January 2004, Volume 84, Issue 1, Pages 137–143, doi : 10.1016/S0308-8146(03)00257-7
  3. 1 2 Mattioda, Georges; Christidis, Yani (2000). Glyoxylic Acid. p. 2. doi:10.1002/14356007.a12_495. ISBN   978-3527306732.{{cite book}}: |journal= ignored (help)
  4. Sutton, Peter; Whittall, John (2012). Practical Methods for Biocatalysis and Biotransformations 2. Chichester, West Sussex: John Wiley & Sons, Ltd. pp. 150–153. ISBN   9781119991397.