Chemistry: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
KEGG
UNII
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearance yellow 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).
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4-Hydroxybenzaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C
6
H
4
OH(CHO)
.[4][5] Along with 3-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

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

References

  1. Jump up to: 1.0 1.1 1.2 1.3 Haynes, p. 3.304
  2. Haynes, p. 5.154
  3. Haynes, p. 5.92
  4. Merck Index, 11th Edition, 8295
  5. Jump up to: 5.0 5.1 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)" (in zh). Yao Xue Xue Bao = Acta Pharmaceutica Sinica 28 (10): 766–771. PMID 8009989. 

Cited sources