Re: butyrate (was Invasive Breast Cancer)

[Guest guest]

Oh Heidi,

Isn't " butyric acid " a fatty acid in butter? And wouldn't " butyrate " just

be butyric acid missing an H+ proton? So it seems to make *more* sense it's in

butter than anywhere else, and seems to be a derivative of fat???

Chris

[Guest guest]

In a message dated 7/23/03 10:46:54 PM Eastern Daylight Time,

s.fisher22@... writes:

> ---->butyric acid was named after butter because it was first isolated from

> butter. unfortunately though, butyric acid that's *eaten* generally (or

> always) gets digested before it reaches the large bowel, so is not useful

> for " feeding " colonocytes.

but could that be what makes the butyrate when it sours? do the bacteria in

milk digest butyric acid to butyrate outside the body?

chris

[Guest guest]

>>>>Isn't " butyric acid " a fatty acid in butter? And wouldn't " butyrate "

just

be butyric acid missing an H+ proton? So it seems to make *more* sense it's

in

butter than anywhere else, and seems to be a derivative of fat???

---->butyric acid was named after butter because it was first isolated from

butter. unfortunately though, butyric acid that's *eaten* generally (or

always) gets digested before it reaches the large bowel, so is not useful

for " feeding " colonocytes.

Suze Fisher

Lapdog Design, Inc.

Web Design & Development

http://members.bellatlantic.net/~vze3shjg/

mailto:s.fisher22@...

[Guest guest]

>Oh Heidi,

>

>Isn't " butyric acid " a fatty acid in butter? And wouldn't " butyrate " just

>be butyric acid missing an H+ proton? So it seems to make *more* sense it's in

>butter than anywhere else, and seems to be a derivative of fat???

>

>Chris

Well, maybe it is missing an H+ ion because the H+ got oxidized, and oxidized

fats are what they call " rancid " . I.e. they smell different. I don't know -- the

studies

talk about butyrate, and they mostly concentrate on grains and fermentation

processes. Maybe the cows get it by fermenting grasses. If it is true that

gut cells NEED it though, it must be pretty common.

-- Heidi

[Guest guest]

In a message dated 7/24/03 4:03:19 AM Eastern Daylight Time,

heidis@... writes:

> Well, maybe it is missing an H+ ion because the H+ got oxidized, and

> oxidized

> fats are what they call " rancid " . I.e. they smell different. I don't know --

> the studies

> talk about butyrate, and they mostly concentrate on grains and fermentation

> processes. Maybe the cows get it by fermenting grasses. If it is true that

> gut cells NEED it though, it must be pretty common.

No, it can't be, because " oxidation " is a loss of electrons, creating an

overall increased positive charge, which would be just the opposite. H+ ions

are

often involved in redox (oxidation-reduction) reactions though, if they take

place in an acidic medium, because they combine with oxygens from the " reduced "

(opposite of oxidized) species to make water.

The H+ donation I would think would have to come from an isolated fatty acid

and not a triglyceride, since I don't think fats act as acids, but " fatty

acids " obviously do. I also don't think it would be desaturation because C-H

bonds generally don't donate H+ ions.

Anyone know more about this?

Chris

[Guest guest]

> ---->butyric acid was named after butter because it was first isolated

from

> butter. unfortunately though, butyric acid that's *eaten* generally (or

> always) gets digested before it reaches the large bowel, so is not useful

> for " feeding " colonocytes.

>>but could that be what makes the butyrate when it sours? do the bacteria

in

milk digest butyric acid to butyrate outside the body?

------>i have no idea.

Suze Fisher

Lapdog Design, Inc.

Web Design & Development

http://members.bellatlantic.net/~vze3shjg/

mailto:s.fisher22@...

[Guest guest]

In a message dated 7/24/03 2:40:32 PM Eastern Daylight Time,

heidis@... writes:

> Oxydation involves the reaction of oxygen + an ion, in my understanding. So

> if you add an O- ion to 2 H+, then you get H2O. So if O2 got added

> to Butyric acid, you get butyrate. Whether that is butter going " rancid "

> or not I have no idea?

>

Oxidation has nothing to do with oxygen, believe it or not. Oxygen just

happens to be a common oxidizing agent. The process got named waaaaaaaay back

in

the day when the observed processes of oxidation were primarily metals

combining with oxygen. When metals would turn from oxides back into their

elemental

form it was called " reduction " because the metal was " reduced " from its more

complex oxide form to its simpler elemental form.

But then it was discovered that there were a plethora of reactions that occur

with the very same dynamic, many many which do not involve oxygen at all. So

the name " oxidation " stuck, but when the process was understood in greater

detail the definition changed.

So oxidation means to lose an electron and nothing more, and reduction means

to gain an electron and nothing more, which may or may not involve oxygen (it

often does). And a short name for these reduction-oxidation reactions is

" redox reaction. "

I always thought oxidation involved oxygen necessarily too, but I've been

spending 16 hours a week in chemistry class for the last two months and I now

stand corrected ;-)

On the other hand, an acid is an H+-donator and a base is an H+-acceptor. The

conjugate base of an acid, i.e. the acid without the H+, is usually named

after the acid with the " -ate " ending, which would make butyric acid butyrate

plus an H+ ion, and it would have to lose the H+ ion to become butyrate.

It's my understanding that it would be far more likely for an H+ to join a

hydroxide (OH-) to beocme water than an O- (actually have to be O with a -2

charge) to meet two H+ ions.

> I should study my chemistry again. Seems like fats were considered

> " acidic " because they have a free H+ hanging out, and some molecules

> have a free OH hanging out, so they can react, but they aren't actually

> ionized in solution.

Nope, I don't think so as triglycerides, but don't know about individual

fatty acids. If the H+ can't ionize in solution though, it isn't an extra H+,

so

don't see how it would be called an acid if the H+ could come off.

Chris

[Guest guest]

>No, it can't be, because " oxidation " is a loss of electrons, creating an

>overall increased positive charge, which would be just the opposite. H+ ions

are

>often involved in redox (oxidation-reduction) reactions though, if they take

>place in an acidic medium, because they combine with oxygens from the " reduced "

>(opposite of oxidized) species to make water.

Oxydation involves the reaction of oxygen + an ion, in my understanding. So

if you add an O- ion to 2 H+, then you get H2O. So if O2 got added

to Butyric acid, you get butyrate. Whether that is butter going " rancid "

or not I have no idea?

>The H+ donation I would think would have to come from an isolated fatty acid

>and not a triglyceride, since I don't think fats act as acids, but " fatty

>acids " obviously do. I also don't think it would be desaturation because C-H

>bonds generally don't donate H+ ions.

I should study my chemistry again. Seems like fats were considered

" acidic " because they have a free H+ hanging out, and some molecules

have a free OH hanging out, so they can react, but they aren't actually

ionized in solution.

-- Heidi

[Guest guest]

>> I should study my chemistry again. Seems like fats were considered

>> " acidic " because they have a free H+ hanging out, and some molecules

>> have a free OH hanging out, so they can react, but they aren't actually

>> ionized in solution.

>

>Nope, I don't think so as triglycerides, but don't know about individual

>fatty acids. If the H+ can't ionize in solution though, it isn't an extra H+,

so

>don't see how it would be called an acid if the H+ could come off.

I didn't mean " free " as in ionizing, just that the end of the molecule

is positive. Like I said, it's been a long time since I studied chemistry!

BTW it is interesting that another name for butyric acid in German

is " Buttersaeure " (soured butter?).

Butanic Acid; Butanoic Acid; Propylformic Acid; Butyrate;

Buttersaeure (German); Ethylacetic Acid; Kyselina Maselna (Czech);

1-Propanecarboxylic Acid;

DERIVATION

Oxidation of n-Butyraldehyde

butyric acid [bju?'tirik]

noun a carboxylic acid existing in two isomeric forms, one of which produces the

smell in rancid butter. Its esters are used in flavouring. Formula: C3(CH2)2COOH

[ETYMOLOGY: C19 butyric, from Latin butyrum butter]

butyrate ['bju?ti?reit]

noun any salt or ester of butyric acid, containing the monovalent group C3H7COO-

or ion C3H7COO--

So the butyrate lost it's H+, which is what you were saying ... ???

-- Heidi

-- Heidi

[Guest guest]

In a message dated 7/25/03 3:08:54 AM Eastern Daylight Time,

heidis@... writes:

> So the butyrate lost it's H+, which is what you were saying ... ???

That's correct. All carboxylic acids will ionize. None of them will *fully*

ionize, though. So *most* of the butyric acids will retain their H+ if

dissolved in water (but maybe not with a very strong base?), but that's true of

most other acids too.

The question is what happens during the fermenting that causes it to lose

it's H+?

How funny that they say it causes the smell in *rancid* butter... and it's

used for... *drumroll*... FLAVORING!!!

Hahaha!

Chris

[Guest guest]

>How funny that they say it causes the smell in *rancid* butter... and it's

>used for... *drumroll*... FLAVORING!!!

>

>Hahaha!

>

>Chris

Actually that kind of makes sense ... a lot of yecchy smells (like musk gland

odor!) make good perfume!

-- Heidi