4-Hydroxybenzaldehyde

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4-Hydroxybenzaldehyde
4-hydroxybenzaldehyde.svg
4-Hydroxybenzadehyde sample.jpg
Names
Preferred IUPAC name
4-Hydroxybenzaldehyde
Other names
p-Hydroxybenzaldehyde, 4-formylphenol [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.182 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H Yes check.svgY
    Key: RGHHSNMVTDWUBI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
    Key: RGHHSNMVTDWUBI-UHFFFAOYAN
  • O=Cc1ccc(O)cc1
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearanceyellow to tan powder
Density 1.129 g/cm3 (130 °C) [1]
Melting point 116 °C (241 °F; 389 K) [1]
Boiling point 310 to 311 °C (590 to 592 °F; 583 to 584 K)
12.9 g/L [2]
Acidity (pKa)7.61 (25 °C) [3]
-78.0·10−6 cm3/mol
1.57051 (130 °C) [1]
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-Hydroxybenzaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). [4] [5] Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

Contents

Synthesis, reactions, uses

4-Hydroxybenzaldehyde is prepared by reaction of phenol with chloroform, which gives isomeric hydroxybenzal chlorides. Hydrolysis of the C-Cl bonds gives the aldehyde. [5]

4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, a precursor to penicillins. In the Dakin oxidation, 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form hydroquinone.

Metabolism and occurrence

p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots ( Daucus carota ). [6]

4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata , [7] Galeola faberi , [8] and the Vanilla orchids.

See also

Related Research Articles

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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.

<i>Daucus carota</i> Species of flowering plant

Daucus carota, whose common names include wild carrot, European wild carrot, bird's nest, bishop's lace, and Queen Anne's lace, is a flowering plant in the family Apiaceae. It is native to temperate regions of the Old World and was naturalized in the New World.

<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.

Salicylic aldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily liquid has a bitter almond odor at higher concentration. Salicylaldehyde is a precursor to coumarin and a variety of chelating agents.

<span class="mw-page-title-main">Phenanthrenoid</span>

Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.

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

Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.

<span class="mw-page-title-main">Carrot seed oil</span> Essential oil extract of carrot seed

Carrot seed oil is the essential oil extract of the seed from the carrot plant Daucus carota. The oil has a woody, earthy sweet smell and is yellow or amber-coloured to pale orange-brown in appearance. The pharmacologically active constituents of carrot seed extract are three flavones: luteolin, luteolin 3'-O-beta-D-glucopyranoside, and luteolin 4'-O-beta-D-glucopyranoside. Rather than the extract the distilled (ethereal) oil is used in perfumery and food aromatization. The main constituent of this oil is carotol.

<i>Gastrodia elata</i> Species of plant

Gastrodia elata is a saprophytic perennial herb in the family Orchidaceae. It is found in Nepal, Bhutan, India, Japan, Korea, Siberia, Taiwan, and China.

In enzymology, a 4-hydroxybenzaldehyde dehydrogenase (EC 1.2.1.64) is an enzyme that catalyzes the chemical reaction

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

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.

<span class="mw-page-title-main">3-Hydroxybenzaldehyde</span> Chemical compound

3-Hydroxybenzaldehyde is an organic compound with the formula HOC6H4CHO. It is a colorless solid although most samples appear tan. Two other isomers of hydroxybenzaldehyde exist.

<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">Gastrodin</span> Chemical compound

Gastrodin is a chemical compound which is the glucoside of gastrodigenin. It has been isolated from the orchid Gastrodia elata and from the rhizome of Galeola faberi. It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.

2,4-Bis(4-hydroxybenzyl)phenol is a phenolic compound produced by the saprophytic orchid Gastrodia elata and by the myco-heterotroph orchid Galeola faberi.

Galeola faberi is an orchid species in the genus Galeola found in central and southern China, as well as in Nepal, the eastern Himalayas, Vietnam and Sumatra.

Gastrol is a phenolic compound produced by the saprophytic orchid Gastrodia elata.

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

Gastrodigenin is a phenolic compound found in the rhizome of Gastrodia elata.

4-<i>O</i>-Methylhonokiol Chemical compound

4-O-Methylhonokiol is a neolignan, a type of phenolic compound. It is found in the bark of Magnolia grandiflora and in M. virginiana flowers.

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

Salicyl alcohol (saligenin) is an organic compound with the formula C6HOH(CH2OH. It is a white solid that is used as a precursor in organic synthesis.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

References

  1. 1 2 3 4 Haynes, p. 3.304
  2. ↑ Haynes, p. 5.154
  3. ↑ Haynes, p. 5.92
  4. ↑ Merck Index, 11th Edition, 8295
  5. 1 2 Maliverney, Christian; Mulhauser, Michel (2000). "Hydroxybenzaldehydes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0825041813011209.a01. ISBN   978-0-471-48494-3.
  6. ↑ Sircar, D.; Mitra, A. (2008). "Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota". Journal of Plant Physiology. 165 (4): 407–414. doi:10.1016/j.jplph.2007.05.005. PMID   17658659.
  7. ↑ Ha, J. H.; Lee, D. U.; Lee, J. T.; Kim, J. S.; Yong, C. S.; Kim, J. A.; Ha, J. S.; Huh, K. (2000). "4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain". Journal of Ethnopharmacology. 73 (1–2): 329–333. doi:10.1016/S0378-8741(00)00313-5. PMID   11025174.
  8. ↑ Li, Y. M.; Zhou, Z. L.; Hong, Y. F. (1993). "(title in Chinese)" [Studies on the phenolic derivatives from Galeola faberi Rolfe]. Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 28 (10): 766–771. PMID   8009989.

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