4-Hydroxyphenylacetic acid

Last updated
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
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).
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Infobox references

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.

An alternative use is in the synthesis of Efaproxiral [131179-95-8].

Related Research Articles

Olive oil Liquid fat made from olives

Olive oil is a liquid fat obtained from olives, a traditional tree crop of the Mediterranean Basin, produced by pressing whole olives and extracting the oil. It is commonly used in cooking: for frying foods or as a salad dressing. It can be found in some cosmetics, pharmaceuticals, soaps, and fuels for traditional oil lamps. It also has additional uses in some religions. The olive is one of three core food plants in Mediterranean cuisine; the other two are wheat and grapes. Olive trees have been grown around the Mediterranean since the 8th millennium BC.

Olive Species of 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. 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. Olea europaea is the type species for the genus Olea.

Phenol Chemical compound

Phenol (also called carbolic acid) 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 (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.

Salicylic acid Chemical compound used in medicines and industry

Salicylic acid is an organic compound with the formula HOC6H4CO2H. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). 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. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Alkylation Transfer of an alkyl group from one molecule to another

Alkylation is the transfer of an alkyl group from one molecule to another. 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.

Ferulic acid Chemical compound

Ferulic acid is a hydroxycinnamic acid, 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.

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.

4-Ethylphenol (4-EP) is an organic compound with the formula C2H5C6H4OH. It is one of three isomeric ethylphenols. A white solid, it occurs as an impurity in xylenols and as such is used in the production of some commercial phenolic resins. It is also a precursor to 4-vinylphenol.

4-Ethylguaiacol 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.

Hydroxytyrosol Chemical compound

Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. In nature, hydroxytyrosol is mainly found in olives, olive leaves, and olive oil in the form of its elenolic acid ester, oleuropein. It is a constituent of red and white wines.

Tyrosol Chemical compound

Tyrosol is a phenylethanoid, a derivative of phenethyl alcohol. It is a natural phenolic antioxidant present in a variety of natural sources. The principal source in the human diet is olive oil. It is also one of the main natural phenols in argan oil. In olive oil, tyrosol forms esters with fatty acids.

Oleuropein Chemical compound

Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves, and argan oil. The term oleuropein is derived from the botanical name of the olive tree, Olea europaea.

Olive leaf

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.

EDDHA 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.

Syringic acid Chemical compound

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

Naturally occurring phenols Group of chemical compounds

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. 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.

Wine chemistry

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4.

Picual 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.

4-Hydroxymandelic acid 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. Ullmann's Encyclopedia of Industrial Chemistry. p. 2. doi:10.1002/14356007.a12_495. ISBN   978-3527306732.
  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.