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2,6-Dimethoxyphenol

By: John Wright
Posted: November 30, 2011, from the December 2011 issue of P&F magazine.

Phenolic notes are widespread throughout nature but are often peculiarly difficult to recreate realistically in flavors. The problem with most phenolic raw materials is that they are either too leathery or they are overly harsh and too close a resemblance to phenol itself. In nature, phenolic complexes exhibit a much more attractive, deeper and softer character.

2,6-Dimethoxyphenol (FEMA# 3137, CAS# 91-10-1; F-1) is probably the single phenol that is most responsible for this attractive character in nature. None of the alternative dimethoxyphenol configurations are as interesting. 3,4-Dimethoxyphenol (CAS# 2033-89-8) is more burnt in character but is quite useful in smoke and coffee flavors; 2,3-dimethoxyphenol (CAS# 5150-42-5) is quite soft and can be helpful in vanilla flavors; and 3,5-dimethoxyphenol (CAS# 500-99-2) is relatively harsh, but all are much less useful than 2,6-dimethoxyphenol.

4-Methyl-2,6-dimethoxyphenol (FEMA# 3704, CAS# 6638-05- 7), 4-ethyl-2,6-dimethoxyphenol (FEMA# 3671, CAS# 14059-92- 8), 4-propyl-2,6-dimethoxyphenol (FEMA# 3729, CAS# 6766-82-1), 4-allyl-2,6-dimethoxyphenol (FEMA# 3655, CAS# 6627-88-9) and 4-propenyl- 2,6-dimethoxyphenol (FEMA# 3728, CAS# 6635-22-9) all have positive and realistic characters similar to 2,6-dimethoxyphenol and can work well, especially in smoke flavors. Unfortunately, they are all much less cost-effective in use.

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