3-Hydroxybenzaldehyde

3-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde.

3-Hydroxybenzaldehyde

Names
IUPAC name 3-Hydroxybenzaldehyde
Other names m-Hydroxybenzaldehyde; m-Formylphenol; 3-Formylphenol
Identifiers
CAS Number	100-83-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16207
ChEMBL	ChEMBL243816
ChemSpider	21105795
ECHA InfoCard	100.002.630
KEGG	C03067
PubChem CID	101
UNII	8Z2819J40E
CompTox Dashboard (EPA)	DTXSID7059220
InChI InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H Key: IAVREABSGIHHMO-UHFFFAOYSA-N 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	light-tan crystals
Melting point	100 to 103 °C (212 to 217 °F; 373 to 376 K)
Boiling point	191 °C (376 °F; 464 K) (50 mmHg)
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

Function

3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.[1]

Chemistry

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.[2][3]

Metabolism

3-hydroxybenzyl-alcohol dehydrogenase is an enzyme that uses 3-hydroxybenzyl alcohol and NADP⁺ to produce 3-hydroxybenzaldehyde, NADPH and H⁺.

Uses

3-Hydroxybenzaldehyde is used in the synthesis of monastrol.

See also

• Salicylaldehyde (2-hydroxybenzaldehyde)
• 4-Hydroxybenzaldehyde

References

1. 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. doi:10.1371/journal.pone.0149394. PMC 4803227. PMID 27002821.
2. m-HYDROXYBENZALDEHYDE, Organic Syntheses, Coll. Vol. 3, p.453 (1955); Vol. 25, p.55 (1945)
3. m-METHOXYBENZALDEHYDE Archived 2012-10-04 at the Wayback Machine, Organic Syntheses, Coll. Vol. 3, p.564 (1955); Vol. 29, p.63 (1949)