3-Hydroxybenzaldehyde

3-Hydroxybenzaldehyde
Names

Preferred IUPAC name 3-Hydroxybenzaldehyde
Other names m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol^[1]
Identifiers
CAS Number	100-83-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16207^Y
ChEMBL	ChEMBL243816^Y
ChemSpider	21105795^Y
ECHA InfoCard	100.002.630
KEGG	C03067^Y
PubChem CID	101
UNII	8Z2819J40E^N
CompTox Dashboard (EPA)	DTXSID7059220
InChI InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H^Y Key: IAVREABSGIHHMO-UHFFFAOYSA-N^Y InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H Key: IAVREABSGIHHMO-UHFFFAOYAC
SMILES O=Cc1cc(O)ccc1
Properties
Chemical formula	C₇H₆O₂
Molar mass	122.123 g·mol⁻¹
Appearance	colorless solid
Density	1.1179 g/cm³ (130 °C)^[1]
Melting point	106 °C (223 °F; 379 K)^[1]
Boiling point	240 °C (464 °F; 513 K)^[1]
Acidity (pK_a)	8.98 (25 °C)^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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.

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Preparation

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.^[3]^[4]

3-hydroxybenzyl-alcohol dehydrogenase is an NADP-dependent enzyme that produces 3-hydroxybenzaldehyde from 3-hydroxybenzyl alcohol.^[5]

Biomedical properties

3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.^[6] 3-Hydroxybenzaldehyde is used in the synthesis of monastrol.^[7]^[8]

References

^ ^a ^b ^c ^d Haynes, p. 3.304
^ Haynes, p. 5.92
^ Woodward, R. B. (1945). "m-Hydroxybenzaldehyde". Organic Syntheses. 25: 55. doi:10.15227/orgsyn.025.0055.
^ Icke, Roland N.; Redemann, C. Ernst; Wisegarver, Burnett B.; Alles, Gordon A. (1949). "m-Methoxybenzaldehyde". Organic Syntheses. 29: 63. doi:10.15227/orgsyn.029.0063.
^ Forrester, P. I.; Gaucher, G. M. (1972). "M-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae". Biochemistry. 11 (6): 1108–1114. doi:10.1021/bi00756a026. PMID 4335290.
^ Kong, Byung Soo; Im, Soo Jung; Lee, Yang Jong; Cho, Yoon Hee; Do, Yu Ri; Byun, Jung Woo; Ku, Cheol Ryong; Lee, Eun Jig (22 March 2016). "Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation". PLOS ONE. 11 (3): e0149394. Bibcode:2016PLoSO..1149394K. doi:10.1371/journal.pone.0149394. PMC 4803227. PMID 27002821.
^ Dallinger, Doris; Kappe, C Oliver (2007). "Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis". Nature Protocols. 2 (2): 317–321. doi:10.1038/nprot.2006.436. PMID 17406591. S2CID 35508377.
^ Dondoni, Alessandro; Massi, Alessandro; Sabbatini, Simona (2002). "Improved synthesis and preparative scale resolution of racemic monastrol". Tetrahedron Letters. 43 (34): 5913–5916. doi:10.1016/S0040-4039(02)01269-8.

Cited sources

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

This page was last edited on 13 August 2023, at 11:09

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