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Author Topic: Methyl anthranilate (Grape Ester)  (Read 8437 times)

Offline ynotbrusum

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Re: Methyl anthranilate (Grape Ester)
« Reply #30 on: April 12, 2016, 07:52:32 pm »
I judged a recent Vienna and Marzen category with another judge and in two beers we both noticed the grape issue and I suspected Munich malt as the culprit.
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Offline Saccharomyces

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Re: Methyl anthranilate (Grape Ester)
« Reply #31 on: April 13, 2016, 10:11:47 pm »
As I explained to Martin yesterday, the conversion of heptanal to ethyl heptonoate requires multiple reactions.   The first reaction involves the conversion of the alkyl aldehyde heptanal to the higher alcohol heptanol (CH3(CH2)5CH2OH or C7H16O).  The conversion of heptanal to heptanol results in the production of the carboxylic acids heptanoic acid and 2-hydroxyheptanoic acid. Anyone who has read "Have You Seen Ester?" knows that a carboxylic acid is an acid whose formula ends in COOH, which is also known as a carboxyl group.



As one can clearly see, the formulas for heptanoic acid and 2-hydroxyheptanoic acid both end in COOH.


Ethyl heptanoate is the condensation reaction between ethanol and heptanoic acid.

C2H6O + CH3(CH2)5COOH → C9H18O2 + H2O

The above reaction reads one molecule of ethanol plus one molecule of heptanoic acid yields one molecule of ethyl heptanoate plus one molecule of water.

I have the links to the publications that I provided to Martin if anyone is interested.

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Offline hopfenundmalz

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Re: Methyl anthranilate (Grape Ester)
« Reply #32 on: April 13, 2016, 10:53:20 pm »
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
As I explained to Martin yesterday, the conversion of heptanal to ethyl heptonoate requires multiple reactions.   The first reaction involves the conversion of the alkyl aldehyde heptanal to the higher alcohol heptanol (CH3(CH2)5CH2OH or C7H16O).  The conversion of heptanal to heptanol results in the production of the carboxylic acids heptanoic acid and 2-hydroxyheptanoic acid. Anyone who has read "Have You Seen Ester?" knows that a carboxylic acid is an acid whose formula ends in COOH, which is also known as a carboxyl group.



As one can clearly see, the formulas for heptanoic acid and 2-hydroxyheptanoic acid both end in COOH.


Ethyl heptanoate is the condensation reaction between ethanol and heptanoic acid.

C2H6O + CH3(CH2)5COOH → C9H18O2 + H2O

The above reaction reads one molecule of ethanol plus one molecule of heptanoic acid yields one molecule of ethyl heptanoate plus one molecule of water.

I have the links to the publications that I provided to Martin if anyone is interested.

Good to have some advanced knowledge laid on us!
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Offline narcout

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Re: Methyl anthranilate (Grape Ester)
« Reply #33 on: April 13, 2016, 10:58:38 pm »
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
I have the links to the publications that I provided to Martin if anyone is interested.

Cool. Please post.
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Offline klickitat jim

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Re: Methyl anthranilate (Grape Ester)
« Reply #34 on: April 14, 2016, 12:30:18 am »
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
As I explained to Martin yesterday, the conversion of heptanal to ethyl heptonoate requires multiple reactions.   The first reaction involves the conversion of the alkyl aldehyde heptanal to the higher alcohol heptanol (CH3(CH2)5CH2OH or C7H16O).  The conversion of heptanal to heptanol results in the production of the carboxylic acids heptanoic acid and 2-hydroxyheptanoic acid. Anyone who has read "Have You Seen Ester?" knows that a carboxylic acid is an acid whose formula ends in COOH, which is also known as a carboxyl group.



As one can clearly see, the formulas for heptanoic acid and 2-hydroxyheptanoic acid both end in COOH.


Ethyl heptanoate is the condensation reaction between ethanol and heptanoic acid.

C2H6O + CH3(CH2)5COOH → C9H18O2 + H2O

The above reaction reads one molecule of ethanol plus one molecule of heptanoic acid yields one molecule of ethyl heptanoate plus one molecule of water.

I have the links to the publications that I provided to Martin if anyone is interested.
Howdy sir!
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Offline jeffy

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Re: Methyl anthranilate (Grape Ester)
« Reply #35 on: April 14, 2016, 05:28:19 am »
Quote from: klickitat jim on April 14, 2016, 12:30:18 am
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
As I explained to Martin yesterday, the conversion of heptanal to ethyl heptonoate requires multiple reactions.   The first reaction involves the conversion of the alkyl aldehyde heptanal to the higher alcohol heptanol (CH3(CH2)5CH2OH or C7H16O).  The conversion of heptanal to heptanol results in the production of the carboxylic acids heptanoic acid and 2-hydroxyheptanoic acid. Anyone who has read "Have You Seen Ester?" knows that a carboxylic acid is an acid whose formula ends in COOH, which is also known as a carboxyl group.



As one can clearly see, the formulas for heptanoic acid and 2-hydroxyheptanoic acid both end in COOH.


Ethyl heptanoate is the condensation reaction between ethanol and heptanoic acid.

C2H6O + CH3(CH2)5COOH → C9H18O2 + H2O

The above reaction reads one molecule of ethanol plus one molecule of heptanoic acid yields one molecule of ethyl heptanoate plus one molecule of water.

I have the links to the publications that I provided to Martin if anyone is interested.
Howdy sir!
We missed you.
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Offline HoosierBrew

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Re: Methyl anthranilate (Grape Ester)
« Reply #36 on: April 14, 2016, 06:06:49 am »
Welcome back!
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Jon H.

Offline beersk

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Re: Methyl anthranilate (Grape Ester)
« Reply #37 on: April 14, 2016, 07:18:28 am »
That's some crazy science-y sh*t! Welcome back!
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Jesse

Offline AmandaK

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Re: Methyl anthranilate (Grape Ester)
« Reply #38 on: April 14, 2016, 08:24:19 am »
Quote from: jeffy on April 12, 2016, 06:55:30 pm
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.

Totally agree. Thanks guys!
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Offline Saccharomyces

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Re: Methyl anthranilate (Grape Ester)
« Reply #39 on: April 16, 2016, 07:57:39 am »
Quote from: narcout on April 13, 2016, 10:58:38 pm
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
I have the links to the publications that I provided to Martin if anyone is interested.

Cool. Please post.


Bioconversion of heptanal to heptanol by Saccharomyces cerevisiae, http://onlinelibrary.wiley.com/doi/10.1002/yea.1750/pdf


Characterization of volatile aroma compounds in different brewing barley cultivars,
https://www.researchgate.net/publication/273755180_Characterization_of_volatile_aroma_compounds_in_different_brewing_barley_cultivars
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Offline 69franx

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Re: Methyl anthranilate (Grape Ester)
« Reply #40 on: April 16, 2016, 08:46:32 am »
All great info. Thanks saccharomyces
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RPIScotty

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Re: Methyl anthranilate (Grape Ester)
« Reply #41 on: April 16, 2016, 08:59:57 am »
Quote from: Saccharomyces on April 13, 2016, 10:11:47 pm
As I explained to Martin yesterday, the conversion of heptanal to ethyl heptonoate requires multiple reactions.   The first reaction involves the conversion of the alkyl aldehyde heptanal to the higher alcohol heptanol (CH3(CH2)5CH2OH or C7H16O).  The conversion of heptanal to heptanol results in the production of the carboxylic acids heptanoic acid and 2-hydroxyheptanoic acid. Anyone who has read "Have You Seen Ester?" knows that a carboxylic acid is an acid whose formula ends in COOH, which is also known as a carboxyl group.



As one can clearly see, the formulas for heptanoic acid and 2-hydroxyheptanoic acid both end in COOH.


Ethyl heptanoate is the condensation reaction between ethanol and heptanoic acid.

C2H6O + CH3(CH2)5COOH → C9H18O2 + H2O

The above reaction reads one molecule of ethanol plus one molecule of heptanoic acid yields one molecule of ethyl heptanoate plus one molecule of water.

I have the links to the publications that I provided to Martin if anyone is interested.

Glad to have you back.
« Last Edit: April 16, 2016, 09:01:52 am by RPIScotty »
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Offline ynotbrusum

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Re: Methyl anthranilate (Grape Ester)
« Reply #42 on: April 18, 2016, 04:15:48 pm »
It's so nice when knowledgeable people share information relating to a topic here.  Thanks, Mark!
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Offline brewinhard

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Re: Methyl anthranilate (Grape Ester)
« Reply #43 on: April 18, 2016, 04:40:50 pm »
Quote from: ynotbrusum on April 18, 2016, 04:15:48 pm
It's so nice when knowledgeable people share information relating to a topic here.  Thanks, Mark!

And when it is freely offered without any smug replies.  Welcome back Mark!
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Offline bucketbiochemist

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Re: Methyl anthranilate (Grape Ester)
« Reply #44 on: May 10, 2016, 10:06:24 pm »
I've had a "grape" flavor noted at the AHA comp. for Kolsch made with WLP029.  Do people think this is the same flavor?  Is WLP029 (or other Kolsch strains) known for this compound?

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