The Peter Attia Drive - Qualy #120 - What is the difference between ketone salts and esters？

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00:00:40.540 Maybe explain for people what the difference is between a salt and an ester. So we'll leave

00:00:45.060 acetoacetate out of that for a moment. But if you talk about beta-hydroxybutyrate...

00:00:49.380 But you can have acetoacetate salt too, so I can mention that.

00:00:52.400 I didn't know that. I thought it was only a diester. So we'll definitely want to hear about that. So

00:00:56.080 on the BHB front, people are sort of inundated with ketone salts, ketone esters, and then a whole

00:01:02.020 bunch of complete weird stuff like raspberry ketones and stuff. But let's just leave the

00:01:06.440 nonsense off the table. Yeah. But if you just talk about comparing a ketone, a BHB ester to a BHB salt,

00:01:12.100 what's the chemical difference?

00:01:13.380 Yeah. So a salt is just an ionic bond, right, between the ketone molecule, beta-hydroxybutyrate,

00:01:19.840 a monovalent or a divalent cation, or an alkaline amino acid like arginine, citrulline, histidine,

00:01:27.540 lysine. So you can literally ionically bond beta-hydroxybutyrate to a number of different

00:01:33.040 things. The easiest thing to do is to bond it with sodium, potassium, calcium, and magnesium.

00:01:39.960 Now, calcium and magnesium have two positive charges.

00:01:43.080 You could put two BHBs on them.

00:01:44.980 Yeah. That's the advantage, sort of an advantage. A disadvantage, I guess, with magnesium BHB,

00:01:51.240 which is actually is very bioavailable magnesium. I measured my magnesium after taking it. It went

00:01:57.280 up quite, quite high. Disadvantage is that your GI tolerability to something like magnesium beta-hydroxybutyrate

00:02:04.240 may be only somewhere between one to three grams, you know, three grams max per dose.

00:02:11.240 Wow. Which is not that much.

00:02:12.720 One gram, three times a day, at least for me, has no issues. I could probably tolerate two or

00:02:19.760 three grams per day. So it's nice. I mean, it's something that's contributing, but ideally what

00:02:24.420 you want to do with a ketone salt is, because salt has a stigma, I call them ketone electrolyte

00:02:29.620 formulations, is to spread the beta-hydroxybutyrate out across monovalent and divalent cations. And

00:02:37.140 they're the four that have the most utility. And then an ester, of course, is a covalent bond,

00:02:42.940 not an ionic bond, right?

00:02:44.140 Yeah. So you can take one, three butane diol and you could create a monoester with

00:02:51.180 beta-hydroxybutyrate, right? And just add it, do a trans esterification reaction and combine that

00:02:57.460 beta-hydroxybutyrate to one, three butane diol or acetoacetate. You can combine with one, three butane,

00:03:03.800 or you could take glycerol. So with glycerol, you can come up with a triester of glycerol,

00:03:09.740 which we have.

00:03:10.380 Basically, you're creating a triglyceride that is, instead of three fatty acids, you put three

00:03:14.620 BHBs. 0.99

00:03:15.320 It's a pretty cool molecule, yeah. So we have some experience using that.

00:03:19.840 I told a story many, many years ago, probably four or five years ago on Tim Ferriss' podcast about how

00:03:24.900 I drank this jet fuel and almost thought I was going to go blind. Of course, what I may or may

00:03:30.820 not have omitted from that story was that you gave it to me. And so the ketones today taste a heck

00:03:36.860 of a lot better than that earlier gen stuff. And even when I told you that I just took the 50 ml

00:03:42.000 vial you sent and chugged it in one sitting, even you were sort of horrified. You're like,

00:03:46.760 wait, wait, wait. You didn't read the note I wrote you explaining how to dilute it and mix it.

00:03:51.320 I thought we had talked about it.

00:03:52.440 We had assuredly talked about it.

00:03:54.820 I know you're very enthusiastic about getting started.

00:03:57.460 Yeah, yeah. I couldn't resist.

00:03:59.240 I was too.

00:03:59.980 That stuff's unbearably bad.

00:04:02.200 Yeah.

00:04:02.380 So what, I mean, whereas the ketone salts actually don't taste bad. They're obviously

00:04:06.560 strong, but they're awesome.

00:04:08.460 Yeah. Yeah. So why does the ester, is there an obvious reason from an olfactory slash taste

00:04:14.080 perspective why they are so staggeringly horrible? Yeah. Or at least they were. And I mean, I'm told

00:04:20.260 they're better today.

00:04:21.320 Yeah. I would say the ketogenic potency is inversely proportional to taste. So it just seems like,

00:04:29.320 you know, the more, the more potent these compounds get, even the, the triester beta

00:04:34.400 hydroxybutyrate, uh, you know, is pretty nasty stuff.

00:04:38.280 Meaning that glycerol, triglycerol, that.

00:04:40.600 Yeah. It's a great molecule. I mean, it has like lots of, you know, tremendous utility.

00:04:45.720 Well, making a ketone ester with one, three butane diol is really cool because the one,

00:04:50.260 three butane diol itself gets more substrate broken down. Yeah. So that goes into another question,

00:04:55.320 the whole enantiomer. So if you use the R beta hydroxybutyrate with the R one, three butane

00:05:00.700 diol, then you can really get ketone levels up pretty high. And that would be sort of the Delta

00:05:05.940 G or the human, you know, ketone ester that's out there.

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The Peter Attia Drive - February 28, 2020

Qualy #120 - What is the difference between ketone salts and esters？

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