4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde

Names
IUPAC name 4-Hydroxybenzaldehyde
Other names p-Hydroxybenzaldehyde
Identifiers
CAS Number	123-08-0
ChEBI	CHEBI:17597
ChEMBL	ChEMBL14193
ChemSpider	123
DrugBank	DB03560
Jmol interactive 3D	Image
KEGG	C00633
PubChem	126
UNII	O1738X3Y38
InChI InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H Key: RGHHSNMVTDWUBI-UHFFFAOYSA-N InChI=1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H Key: RGHHSNMVTDWUBI-UHFFFAOYAN
SMILES O=Cc1ccc(O)cc1
Properties
Chemical formula	C7H6O2
Molar mass	122.12 g·mol^−1
Appearance	yellow to tan powder
Density	1.226 ± 0.06 g/cm^3
Melting point	112 to 116 °C (234 to 241 °F; 385 to 389 K)
Boiling point	310 to 311 °C (590 to 592 °F; 583 to 584 K)
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-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchids Gastrodia elata^[1] and Galeola faberi.^[2] It is also found in vanilla.

Chemistry

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced.

Metabolism

p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).^[3]

See also

• Salicylaldehyde (2-hydroxybenzaldehyde)
• 3-Hydroxybenzaldehyde

References

1. 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.
2. 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.
3. 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.