Author Topic: Methyl anthranilate (Grape Ester)  (Read 4954 times)

Offline blair.streit

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Re: Methyl anthranilate (Grape Ester)
« Reply #15 on: April 11, 2016, 03:14:00 PM »
I've experienced significant cherry esters with beers heavy on Munich and CaraMunch. Cutting back on the CaraMunich has reduced this for me but I don't pretend that I fully understand what happened and would like to experiment more.

I'm wondering if there's something similar in the Pils/CaraPils family that lends grape rather than cherry esters.

I realize I'm way out in speculation-land here, but it strikes me that the kilning temperature and process could lend certain precursors in the wort that then produce elevated levels of these esters during fermentation.

Offline narcout

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Re: Methyl anthranilate (Grape Ester)
« Reply #16 on: April 11, 2016, 04:14:01 PM »
Isnt this the grape-lollipop ester that S Cerv. talks about in some British strains?

Per the last blog post, that is ethyl heptanoate.
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Offline morticaixavier

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Re: Methyl anthranilate (Grape Ester)
« Reply #17 on: April 11, 2016, 07:13:23 PM »
I get grape and candy from pils malt. particularly german pils malt. not noticed a relation to DMS though.
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Offline mabrungard

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Re: Methyl anthranilate (Grape Ester)
« Reply #18 on: April 12, 2016, 12:37:56 PM »
Per the last blog post, that is ethyl heptanoate.

I've just been alerted that methyl anthranilate is more typically found in wine and ethyl heptanoate is more typically the source of the grape ester in beer. So, let's consider my concern is with ethyl heptanoate!
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Offline blair.streit

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Re: Methyl anthranilate (Grape Ester)
« Reply #19 on: April 12, 2016, 12:47:04 PM »
Per the last blog post, that is ethyl heptanoate.

I've just been alerted that methyl anthranilate is more typically found in wine and ethyl heptanoate is more typically the source of the grape ester in beer. So, let's consider my concern is with ethyl heptanoate!
This suggests it's a fatty acid ester and that it will dissipate with time. Still no hint at the source, but this is fun so I'll keep digging:

http://www.ymdb.ca/compounds/YMDB01474

Offline blair.streit

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Re: Methyl anthranilate (Grape Ester)
« Reply #20 on: April 12, 2016, 01:20:44 PM »
Saccharomyces' blog on Experimental Brewing seems to suggest that it's more common among certain yeasts:

http://www.experimentalbrew.com/blogs/saccharomyces/have-you-seen-ester

Ethyl heptanoate is my all-time favorite ale ester. It smells like one of those grape lollipops that were often given to children by bank tellers and medical office receptionists when I was young. Ales fermented with the Young’s Ram Brewery strain usually contain high levels of this ester when young, which is why I refer to ethyl heptanoate as the British lollipop ester.

Martin, I assume this is a new flavor for you (and you didn't mention trying out anything unique in this brew). Maybe someone can ping Saccharomyces and get him to weigh in on potential sources?

Offline Hooper

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Re: Methyl anthranilate (Grape Ester)
« Reply #21 on: April 12, 2016, 04:04:20 PM »
Not kidding...I just dumped 2 cans of frozen white grape juice at 0 in the kettle in my latest Soma Saison...I guess I won't be too upset if get a touch of grape flavor...1st time I've tried this so I have no idea what I will get...
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Offline beersk

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Re: Methyl anthranilate (Grape Ester)
« Reply #22 on: April 12, 2016, 04:22:52 PM »
Saccharomyces' blog on Experimental Brewing seems to suggest that it's more common among certain yeasts:

http://www.experimentalbrew.com/blogs/saccharomyces/have-you-seen-ester

Ethyl heptanoate is my all-time favorite ale ester. It smells like one of those grape lollipops that were often given to children by bank tellers and medical office receptionists when I was young. Ales fermented with the Young’s Ram Brewery strain usually contain high levels of this ester when young, which is why I refer to ethyl heptanoate as the British lollipop ester.

Martin, I assume this is a new flavor for you (and you didn't mention trying out anything unique in this brew). Maybe someone can ping Saccharomyces and get him to weigh in on potential sources?
Interesting. Wonder where it comes into play in terms of something like a pilsner or helles.

Offline blair.streit

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Re: Methyl anthranilate (Grape Ester)
« Reply #23 on: April 12, 2016, 04:30:13 PM »
Interesting. Wonder where it comes into play in terms of something like a pilsner or helles.
I know. Martin was talking about a Helles so likely a lager yeast. Sacc's post mentions a specific ale yeast.

However, looking at this MBAA paper on esters in wheat beers, it indicates that it is more prevalent in lager yeast:

http://www.mbaa.com/districts/MidSouth/Events/Documents/2010-03-13Wheat_Beer_Yeast__Fermentation2.pdf

Sorry, still not any closer to an answer on what conditions might cause increased production....

Offline mabrungard

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Re: Methyl anthranilate (Grape Ester)
« Reply #24 on: April 12, 2016, 08:06:43 PM »
A smart birdy landed on my shoulder this morning and whispered some sage information to me.

It turns out that malt contains a precursor to this ester. Its an alkyl aldehyde called heptanal. There are journal articles that show that the heptanal content of barley is dependent upon the cultivar. I would also have to assume that it's concentration might change during malting and kilning. I see that the Kovats retention index for that compound is fairly low, so it is likely to be driven off to some degree during kilning. Paler malts are therefore more likely to contain this precursor.

Heptanal is converted to ethyl heptanoate through the metabolic action of yeast. Ale yeasts are most prone to this metabolic action. Interestingly, this Helles I'm referring to was fermented with US-05 at 52F. So it is possible that this is the source of that ester in my beer.

Thanks, Mark!
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Offline klickitat jim

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Re: Methyl anthranilate (Grape Ester)
« Reply #25 on: April 12, 2016, 08:57:00 PM »
Isnt this the grape-lollipop ester that S Cerv. talks about in some British strains?
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Offline beersk

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Re: Methyl anthranilate (Grape Ester)
« Reply #26 on: April 12, 2016, 09:34:18 PM »
A smart birdy landed on my shoulder this morning and whispered some sage information to me.

It turns out that malt contains a precursor to this ester. Its an alkyl aldehyde called heptanal. There are journal articles that show that the heptanal content of barley is dependent upon the cultivar. I would also have to assume that it's concentration might change during malting and kilning. I see that the Kovats retention index for that compound is fairly low, so it is likely to be driven off to some degree during kilning. Paler malts are therefore more likely to contain this precursor.

Heptanal is converted to ethyl heptanoate through the metabolic action of yeast. Ale yeasts are most prone to this metabolic action. Interestingly, this Helles I'm referring to was fermented with US-05 at 52F. So it is possible that this is the source of that ester in my beer.

Thanks, Mark!
Wow, US-05 at 52F? Dang. And that ain't no helles! ;)

Thanks for posting that info, Martin.

Offline HoosierBrew

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Re: Methyl anthranilate (Grape Ester)
« Reply #27 on: April 12, 2016, 09:39:16 PM »
Thanks for the info, Martin. I felt since the correlation seemed strong with pils malt, that malt had to play some part. Good to know.
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Offline erockrph

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Re: Methyl anthranilate (Grape Ester)
« Reply #28 on: April 12, 2016, 11:05:45 PM »
A smart birdy landed on my shoulder this morning and whispered some sage information to me.

It turns out that malt contains a precursor to this ester. Its an alkyl aldehyde called heptanal. There are journal articles that show that the heptanal content of barley is dependent upon the cultivar. I would also have to assume that it's concentration might change during malting and kilning. I see that the Kovats retention index for that compound is fairly low, so it is likely to be driven off to some degree during kilning. Paler malts are therefore more likely to contain this precursor.

Heptanal is converted to ethyl heptanoate through the metabolic action of yeast. Ale yeasts are most prone to this metabolic action. Interestingly, this Helles I'm referring to was fermented with US-05 at 52F. So it is possible that this is the source of that ester in my beer.

Thanks, Mark!
Wow, US-05 at 52F? Dang. And that ain't no helles! ;)

Thanks for posting that info, Martin.
Call it a lollipop blonde? ;)

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Offline jeffy

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Re: Methyl anthranilate (Grape Ester)
« Reply #29 on: April 13, 2016, 12:55:30 AM »
This has been fun and educational to read.  I have experienced that flavor described as grape before, but had never associated it with actual grape flavor in my pallet.  I kind of think of the flavor as an under-fermented Pilsner malt flavor - kind of sour, but not really.  Nice to put a name and origin on it.
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