Vanillyl alcohol

Last updated
Vanillyl alcohol
Vanillylalkohol.svg
Names
Preferred IUPAC name
4-(Hydroxymethyl)-2-methoxyphenol
Other names
3-Methoxy-4-hydroxybenzyl alcohol
4-Hydroxy-3-methoxybenzenemethanol
4-Hydroxy-3-methoxybenzyl alcohol
Vanillic alcohol
Vanillin alcohol
Identifiers
ChEBI
ChemSpider
ECHA InfoCard 100.007.140 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
Properties
C8H10O3
Molar mass 154.165 g·mol−1
AppearanceCrystalline white to off-white powder
Melting point 113 °C (235 °F; 386 K) [1]
Boiling point 293 °C (559 °F; 566 K) [1]
Acidity (pKa)9.75 [1]
Related compounds
Related phenols
 vanillic acid, vanillin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vanillyl alcohol is derived from vanillin. [2] It is used to flavor food [1] and scent fragrances, and is described to have a mild, sweet, balsamic vanilla-like scent. Recent studies have shown that vanillyl alcohol has some neuro-protective effects by suppressing the oxidative stress and anti-apoptotic activity in toxin-induced dopaminergic MN9D cells. This could make it a potential candidate for the treatment of neurodegenerative diseases like Parkinson's disease. [3]

Contents

Chemistry

Vanillyl alcohol can be produced by reducing vanillin with sodium borohydride under basic conditions, then quenching using a strong acid such as hydrochloric acid.

See also

References

  1. 1 2 3 4 "Vanillyl alcohol(498-00-0) MSDS Melting Point Boiling Point Density Storage Transport".
  2. ↑ "Microsoft PowerPoint - Borohydride Reduction of Vanillin.ppt". 2005. Retrieved January 10, 2013.
  3. ↑ "Vanillyl alcohol Ten Chongqing Chemdad Co. ，Ltd". chemdad.com. Retrieved 2025-10-18.
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