4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde
Names
	Preferred IUPAC name 4-Hydroxybenzaldehyde
	Other names p-Hydroxybenzaldehyde, 4-formylphenol[1]
Identifiers
CAS Number	123-08-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17597 ;
ChEMBL	ChEMBL14193 ;
ChemSpider	123 ;
DrugBank	DB03560 ;
ECHA InfoCard	100.004.182
KEGG	C00633 ;
PubChem CID	126;
UNII	O1738X3Y38 ;
CompTox Dashboard (EPA)	DTXSID8059552 ;
	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	122.123 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)
Solubility in water	12.9 g/L[2]
Acidity (pKa)	7.61 (25 °C)[3]
Magnetic susceptibility (χ)	-78.0·10−6 cm3/mol
Refractive index (nD)	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). verify (what is ?) Infobox references

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchids Gastrodia elata,[4] Galeola faberi,[5] and the Vanilla orchids.

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.

Derivatives

Claisen-Schmidt condensation with acetone can have afforded raspberry ketone in an 80% overall yield.
Vanillin

Metabolism

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

References

Haynes, p. 3.304
Haynes, p. 5.154
Haynes, p. 5.92
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.
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.
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.

Cited sources

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

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[crc-1] Haynes, p. 3.304

[2] Haynes, p. 5.154

[3] Haynes, p. 5.92

[4] 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.

[5] 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.

[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.