What flavor chemist isn’t a little bored with vanilla flavors? Who has not seen the same old cast of characters over and over again? Vanillin, ethyl vanillin, maltol, ethyl maltol, veratraldehyde, heliotropine, acetoin, maybe some lactones. Sigh.
As a bottle-fed baby, my first exposure to vanilla was from birth, so it is my longest relationship with any flavor. Is it any wonder that vanilla is my favorite flavor profile? Doesn’t the aroma of a great vanilla extract or oleoresin just make your eyeballs roll into the back of your head with its sumptuousness? Then why is it, that we so often stop at the threshold of greatness and settle for the same old, same old? Can’t we be more creative and show vanilla some love? Why yes, people! Yes, we can.
4-Hydroxybenzaldehyde is found in several different foodstuffs such as apple brandy, beer, coffee, brandy, sake, sherry, tea, vinegar, whiskey and wine.Adobe Stock
I’m often combing databases and research papers to find the aroma compounds which occur naturally in different foods. My background is in research and development. Data and facts are comfortable to me. My goal is always to create a flavor that mimics Mother Nature as closely as I can. I have prided myself on being a flavorist who has embraced this huge variety of aroma chemicals and understanding what that nuance will bring to the flavor overall. So, I comb those lists of materials to gain insight into that particular profile and look specifically at things that make me say “huh!” and allow myself to be jettisoned out of ordinary one-dimensional flavors.
So, let’s just start with vanillin. The preferred IUPAC name is 4-hydroxy-3-methoxybenzaldehyde. Keep that in the back of your mind while reading this because some of these babies are closely related structurally. Vanillin is present in Bourbon vanilla extract at about 8,000 ppm to 23,000 ppm. So, the materials we will chat about here are just accent notes with a giant bow to the queen of spices.
1. 4-Hydroxy-3-methoxybenzyl alcohol
One such compound is 4-hydroxy-3-methoxybenzyl alcohol or vanillin alcohol or vanillyl alcohol (FEMA# 3737, CAS# 498-00-0). It shows up at about 100 ppm in Bourbon vanilla extract. This compound is a dry powder and when diluted presents as a sweet, almost heliotropine-like impact and has somewhat of an anisic lift to it. It also carries a bit of a smokey phenolic note. It has a creamy mouthfeel and has a slight balsamic quality when tasted. It is found in a few other foods but at less than 1 ppm levels. I’d put a checkmark next to this one folks.
2. 4-Hydroxy-3-methoxybenzoic acid
4-hydroxy-3-methoxybenzoic acid (FEMA# 3988, CAS# 121-34-6) is also known as vanillic acid. Bourbon vanilla extract contains between about 1,000 ppm and 2,000 ppm of this material which is certainly the highest level found in foods. But you can also find this in whiskey, rice bran and date. FEMA is not nearly as gracious as their use levels hover around 5 ppm to 25 ppm in finished items. I find this material to be not only vanillic but also rounded, brown and somewhat resinous. Also, very deserving of a check mark.
3. 4-Hydroxybenzaldehyde
Another interesting player is 4-hydroxybenzaldehyde or 4-formylphenol. (FEMA# 3984, CAS# 123-08-0). This compound is found in several different foodstuffs such as apple brandy, beer, coffee, brandy, sake, sherry, tea, vinegar, whiskey and wine. It’s in vanilla extract at a pretty good slug running between 1,000 ppm and 2,000 ppm. The initial odor is slightly plastic and has a mild yeasty note. Not something I would ordinarily love based on those descriptors. When tasted, it is a bit astringent and has a slightly brown alcoholic note and has some heliotropine character as well.
I think 4-vinyl phenol would work especially well aiming for Indonesian or Mexican profiles.Adobe Stock
4. 4-Vinyl phenol
4-vinyl phenol (FEMA# 3739, CAS# 2628-17-3) achieves a similar aroma impact as the 4-hydroxybenzaldehyde. That typical, band-aid impression with slightly earthy, dirty notes. This item shows up at about 20 ppm to 100 ppm in the bourbon extract but also makes an appearance in peanut, popcorn and some wines. When tasted, this is phenolic but also contains some Tahitensis-like character and some smokey earthy notes. I also think this would work especially well aiming for Indonesian or Mexican profiles. I think this is important for grounding, but I think I would start somewhere close to a 5 ppm usage rate.
5. 2-Methoxy-4-vinylphenol
Perhaps another phenol we might think of is 2-methoxy-4-vinylphenol also known as 4-vinyl guaiacol. (FEMA# 2675, CAS# 7786-61-0). The odor is sweet, smokey, phenolic, warm, powdery, vanillic, clove, cinnamic and brown. At 2 ppm, it is mild, slightly vanillic, spicy and warming. It’s present in Bourbon vanilla at about 1,200 ppm but also shows up in coffee, curry, corn, sage and wine.
6. Vanilla Oleoresin
Vanilla oleoresin contains many fatty acids. These fatty acids bestow a somewhat yellow or glossy appearance to the oleoresin. (I’m sure you are visualizing that right now.) So, which fatty acids are we talking about? Palmitic acid at about 35 ppm to 40 ppm; linoleic acid in the 60 ppm to 100 ppm range; stearic 10 ppm to 15 ppm and oleic at 13 ppm to 23 ppm. But depending on the solvent system that you are considering for your flavor, these might not work for you. In times when solubility is at issue, I consider the ethyl and methyl esters of these acids as an answer. Methyl myristate (FEMA# 2722, CAS# 122-10-2) is present in the extract at 40 ppm. If you are fortunate enough to have access to methyl linoleate (48%) (FEMA# 3411)/methyl linoleate (52%) check that one out. I can’t find a vendor for this.
7. p-Anisyl acetate
Oddly, p-anisyl acetate (FEMA# 2098, CAS# 104-21-2) is present in Bourbon vanilla (which I would not have expected) at 200 ppm but push that number up to 4,500 for Tahitensis profiles (where I certainly would have expected it). Vanilla is the only food item that this material occurs in.
2-Methoxy-4-vinylphenol is present in Bourbon vanilla at about 1,200 ppm but also shows up in coffee, curry, corn, sage, and wine.Adobe Stock
8. Methyl cinnamate
Another interesting compound is methyl cinnamate (FEMA# 2698, CAS# 103-26-4). Depending on the isomer you could have between about 150 ppm to almost 600 ppm. I think most people typically think strawberry when considering this compound.
9. 5-Methyl furfural
I will leave you with another option that made me say “huh!” Maybe you know this one. It’s a commonly used flavor ingredient. 5-methyl furfural (FEMA# 2702, CAS# 620-02-0) is found at a bit over 100 ppm in Bourbon vanilla.
Now there are no excuses to produce a ho-hum vanilla flavor. Permanently leave your safe vanilla creation place in a brave and confident way. Sally forth my friends!
A Quick Thanks
I would like to express gratitude for the numerous samples donated to me for this article from Millipore Sigma. They have been my friends and supporters since the very beginning of my flavor career!
Aroma compounds donated by Millipore Sigma for evaluation (not all of these were presented in this article):
- W398403 4-Hydroxybenzaldehyde
- W373923 4-Vinylphenol solution (10% in PG)
- W394505 p-Anisic acid
- W373702 Vanillyl alcohol
- W398802 Vanillic acid
- W398705 4-Hydroxybenzyl alcohol
- W370906 Methyl nicotinate
- W310808 Vanillin acetate
- W381512 Vanillyl ethyl ether
- W481015 Ethyl homovanillate
- W343900 Myrtenol
