Diabetes Talking

Question:

a question about octanoic acid— i was reading about long-chain fatty acid oxidation and came across a reference to a medium-chain fatty acid, octanoic acid. it was able to reverse the effects of CPT inhibitors. what is a source of this fatty acid and what is its structure? i am seeking out substances which raise CPT II levels in the mitochondria. a friend’s son has two unusual metabolic problems described briefly below. this fatty acid may suggest pharmaceutical interventions in his case. here is a reposting from several months ago on his case: the son of a man i know was diagnosed with insulin-dependent diabetes shortly after a bout with meningitis. he had experienced extreme fatigue prior to the meningitis. a few years ago a muscle biopsy showed low levels of carnitine palmitoyl transferase. the lab reports i have read on his case do not distinguish between CPT I and CPT II. ( the medical tests now specify low levels of CPT II ). in fact the research i have read is most inconsistent in nomenclature. this lack of consistency in naming reflects a difference in the intellectual models employed by researchers on how fats are metabolised at the mitochondrial interface. his liver levels of CPT have not been assayed. CPT is part of the process the body uses to derive energy from fats. it is considered by diabetes and lipid researchers to be a rate limiting enzyme. some researchers hypothesise that substances which act to lower CPT will also lead to lower blood glucose levels in type II diabetics. here is a child whose blood glucose levels remain high even when his CPT levels are about one-fifth the normal expected value. his case thus departs from randle’s conjectures on how lipid levels and blood glucose levels interact. so far his symptoms of extreme fatigue and delayed sleep cycle have not been brought under control. the administration of levo carnitine orally for a year showed no positive effect on symptoms or CPT levels in the muscle. his diabetes is not ketosis prone. does anyone out there know of any other type I diabetes with this muscle disorder? or does anyone know of any research articles on diabetics with sleep or muscle disorders? i prefer peer review literature with footnotes and sections on methods employed. i am familiar with dr. j. denis mcgarry’s research on lipid disorders in diabetes. i read science as well as diabetes care and the new publication diabetes reviews. melynda reid   who wears hats but does not type caps   snail: p o box 378 greensboro, florida 32330

Response:

a question about octanoic acid— i was reading about long-chain fatty acid oxidation and came across a reference to a medium-chain fatty acid, octanoic acid. it was able to reverse the effects of CPT inhibitors. what is a source of this fatty acid and what is its structure?

.. Don’t know about CPT inhibitors, but to my knowledge octanoic acid is:   CH3-CH2-CH2-CH2-CH2-CH2-CH2-COOH ie 8 carbons.  It is also known as caprylic acid. I also don’t know about the source of it, but with a name like caprylic acid I’d put my money on goat’s milk. Peter A. Stockwell

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=Don’t know about CPT inhibitors, but to my knowledge octanoic acid is: = =  CH3-CH2-CH2-CH2-CH2-CH2-CH2-COOH It’s been a long time since I took a chemistry course.  Could this compound also be described as something like Methyl-ethyl-ethyl-ethyl-ethyl-ethyl-ethyl-alcohol? Again, it’s been over two decades since the last time I took a chemistry course, and the question is entirely off the wall.

Response:

=Don’t know about CPT inhibitors, but to my knowledge octanoic acid is: = =  CH3-CH2-CH2-CH2-CH2-CH2-CH2-COOH It’s been a long time since I took a chemistry course.  Could this compound also be described as something like Methyl-ethyl-ethyl-ethyl-ethyl-ethyl-ethyl-alcohol?

No.  To begin with the COOH makes this a carboxylic acid, not an alcohol. Also the nomenclature of alcoholS would hardly be consistent with your string of ethyls. e.g. Methyl alcohol       CH3-OH Ethyl alcohol        CH3-CH2-OH Propionyl alcohol    CH3-CH2-CH2-OH Butyl alcohol        CH3-CH2-CH2-CH2-OH Pentanyl alcohol     CH3-CH2-CH2-CH2-CH2-OH Hexanyl alcohol      CH3-CH2-CH2-CH2-CH2-CH2-OH etc. Each has its corresponding carboxylic acid, potentially formed by oxidation to give the series Formic Acid          H-COOH Acetic Acid          CH3-COOH Propionic Acid       CH3-CH2-COOH Butyric Acid         CH3-CH2-CH2-COOH       (smells like vomit) Pentanioc Acid       CH3-CH2-CH2-CH2-COOH etc. The series continues down to very long chain lengths (C20-ish) to produce the long chain fatty acids (e.g. stearic acid) which are components of fats.  The biochemistry of synthesis and breakdown of fatty acids favours the even lengths, (C-16, C-18).  Also, one or more of the C-C bonds can be oxidized to double bonds (-HC=CH-), so that the C18 fatty acid stearic acid becomes progressively oleic acid (1 double bond), linoleic acid and linolenic acid.  The presence of double bonds lowers the melting point and additionally correlates with a reduction in LDL lipids, an increase in HDL lipids and, I think, a reduction in serum cholesterol, all of which changes reduce the risk of heart trouble. Again, it’s been over two decades since the last time I took a chemistry course, and the question is entirely off the wall.

Peter A. Stockwell

Response:

a question about octanoic acid— i was reading about long-chain fatty acid oxidation and came across a reference to a medium-chain fatty acid, octanoic acid. it was able to reverse the effects of CPT inhibitors. what is a source of this fatty acid and what is its structure?

Octanoic acid synonyms: hexylacetic acid, octoic acid, octic acid, caprilic acid. Properties: colorless oily liquid, slightly unpleasant odor. Specific gravity 0.910.  Melting point 17 deg. C.  Boiling point 236 deg. C. Refractive index 1.4285.  Very slightly soluble in water, soluble in alcohol and ether. Derivation: By saponification and subsequent distillation of coconut oil. Uses: dyes, drugs, perfumes, flavors, antiseptics, fungicides, ore separations, plasticizer.

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