Molested fats, Op. 139

Trans fats, part IV

Proceed with caution, this is an exploratory post.  Replacing CakesCookiesPiesPastriesBreadCerealsBiscuitsPizzaMuffins with [insert any whole food item here] is just a good idea.  And more reasons to eat dark chocolate.

In Inflammatory, trans, or linoleate? the idea was explored that it might not be the theorized textbook pro-inflammatory end products of omega-6 fats that give them a bad rap, but rather the foods that contain them – ie, “cakes, cookies, pies, and pastries” (Kris-Etherton et al., 2012 NHANES), or “bread, cereals, cakes, biscuits, pies, pizza, and muffins” (Meyer et al., 2003 from down under).

dark chocolate

Further, what starts out as an omega-6 fat can easily become peroxidized or isomerized into an oxidized or trans fat, respectively, via industrial molestation or just plain old cooking (eg, Romero et al., 1998, Marmesat et al., 2012, & Minami et al., 2012) – even just a few minutes in the microwave (Herzallah et al., 2005)!  I don’t know exactly what all of these end products are for sure, but they might look something like this:ox linoleate

Thus, the culprit may not be native Dc9,c1218:2n6 linoleate.

Optional background reading – the trans fats series:
Part I (3/2011) epidemiology, microwave popcorn, etc.
Part II (4/2011) all calories are not created equal, especially in cats – kitty biology is rather fascinating, eg.,  this).
Part III (7/2011African green monkeys, and trans fats vs. carbs in postmenopausal women.

Part I.  The players, cis & trans, point-counterpoint.

Of the 18-carbon varietals:
Olive oil’s famous omega-9 fat oleate (Dc918:1n9). Cis, and largely health neutral.  The trans version is elaidate (Dt918:1n9), which comes from the processing and/or partial hydrogenation of vegetable oils.  This is likely what linoleate was prior to industrial molestation or microwaving.  Viper.

Vaccenic acid (Dt1118:1n7) is the major 18-carbon trans fat in dairy.  It is a natural precursor to the magical CLA (Dc9,t1118:2n7 aka rumenic acid), which is also found in meat & dairy.  Both are trans fats, and both seem OK, although one study showed ruminant trans fats was associated with sudden death (Laake et al., 2012)…  although this study also showed lower stroke risk in those who ate the most partially hydrogenated vegetable oil :/

Of the shorter albeit no less interesting 16-carbon varietals:
Palmitoleate (Dc916:1n7), it’s like a 16-carbon version of oleate found in dairy, macadamia nut oil & sea buckthorn oils, and rose to fame from a sketchily designed study in mice lacking two fatty acid binding proteins (ie, A- & K-FABP) (Cao et al., 2009).  There is yet to be a verdict, but human studies have shown it to be associated it with increased CHD, heart failure, and IR (Djousse et al., 2012Djousse et al., 2012Bergman et al., 2013; Kurotani et al., 2013) (thanks to George Henderson for pointing me in this direction).

Palmitelaidate (Dt916:1n7), the trans version of palmitoleate – it’s the most abundant 16-carbon trans fat in dairy.  Bulls turn it into CLA (Kadegowda et al., 2013), and it’s been associated with less diabetes (Mozaffarian et al., 2013 & Mozaffarian et al., 2010).

The worst trans fat seems to be elaidate viper, the trans version of oleate and/or 18-carbon version of palmitelaidate.  Vaccenate & palmitelaidate get a temporary pass [for now], probably due to their relative absence from CakesCookiesPiesPastriesBreadCerealsBiscuitsPizzaMuffins.

Part II.  It’s not unfixable.

12 weeks of reducing intake of the artist formerly known as linoleate from 6.7% to 2.3% markedly decreased plasma OXLAMs (Oxidized Linoleic Acid Metabolites) (Ramsden et al., 2012):OXLAMs

Group 1 achieved this by replacing “linoleate [wink wink*]” with saturated fat whereas group 2 with saturated fat & a smidge of EPA & DHA – compliance confirmed via biomarkers +1.  Coconut oilCocoa butter.  Notably, the n6/n3 ratio didn’t matter, only total amount of n6 (shoutout to Jamie Scott  & Walter Willett for stressing the importance of that point).

*I say “wink wink” because we think it was native linoleate that they were reducing, but who knows which derogatory linoleate metabolite it actually was.

Peroxidized metabolites of linoleate reduce the anti-inflammatory nature of HDL in mice (Imaizumi et al., 2010).  It might not be the linoleate per se.

just sayin’

Replacing CakesCookiesPiesPastriesBreadCerealsBiscuitsPizzaMuffins with [insert any whole food item here] is just a good idea.



calories proper



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  • George Henderson

    Always good to read one your posts Bill.
    Of course the “good” trans fats are all solidly reliable markers for dietary saturated fat, esp palmitic/palmitoleic but also stearic acids. Wonder if that confounds much…
    Peter at Hyperlipid had a series on palmitic/palmitoleic recently.

    Probably best read from the bottom up, or from this one.
    this FADH2/NADH effect of long-chain SFAs mitigates the complex 1 inhibition that you see in most metabolic disease – including DM2 – and may be the key to the protective effect in the MESA TPA studies.

    • Hi George, Thanks. Good point, it’d be difficult to dissect the contribution of individual fatty acids when they are just one part of entire dietary patterns. I read a lot of Peter’s stuff but it usually takes a few re-reads for it to sink in – brilliant guy, really (especially the whole “Protons” series).

  • George Henderson

    Although the 3:6 ratio may not matter as much as total n6, interventions that elevate n3 give much quicker benefits than interventions that restrict n6… So the +n3 is the quick fix, the -n6 the long term solution (of course the HTML couldn’t handle greater than/lesser than signs).

    • That’s interesting, I hadn’t heard it before but I can see how it could work – let me know what you think: adipose half life is on the order of years, so reducing dietary n6 would take a while to deplete stores, whereas ingesting n3 puts them instantly into your bloodstream (?).

  • Colour me sceptical, but…
    “milk heated at 63 ± 1.0°C for 30 min and milk microwaved for 5 min”
    1) Who eats milk that’s been heated for 30 mins? I don’t eat rice pud.
    2) How much milk was microwaved for 5 mins? Half a cup = boiled to death. 1 pint = warm.

  • “Roasted” almonds…

    Acrylamide formation in almonds (Prunus dulcis): influences of roasting time and temperature, precursors, varietal selection, and storage.

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  • “Lowering dietary linoleic acid reduces bioactive oxidized linoleic acid metabolites in humans.”