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Wetting Tryptophan With Calcium Pantothenate

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Wetting Tryptophan With Calcium Pantothenate

Release Notes 2021-12-04 : I had mentioned on LinkedIn a few times that I thought pantothenate may be a
decent emulsifier based on its structure and observed effects when mixing food ingreients. It appears to help wetting
tryptophan and I finally did some more controlled at-home tests. This is not scientifically profound, you sometimes
see panothtenate labelled as an emulsifier, but it may not be well understood that vitamins have physical properties.
It solves an immediate problem - trying to get tryptophan to wet in Diet Coke or coffee or dog foods- and motivates
a larger inquiry. This is a draft and has not been peer reviewed or completely proof read but released
in some state where it seems worthwhile given time or other constraints. For information only, not
for use for any particular purpose see fuller disclaimers in the text. Caveat Emptor.
Wetting Tryptophan With Calcium Pantothenate
Mike Marchywka
306 Charles Cox , Canton GA 30115
(Dated: December 4, 2021)
All chemicals have physical or other properties that may be forgotten with some label such as
”vitamin.” In the case of hydrophobic nutrients, incidental mixtures with surfactants or emulsi-
fiers may change success or outcome of a formulation. Tryptophan is an excellent example of a
hydrophobic nutrient that may be manipulated by other components of a formulation. This work
explores pantothenate, without controls or comparators, as a vitamin that can enhance wetting of
tryptophan while motivating larger issues in nutrient behaviors both in vitro and in vivo.
1. INTRODUCTION
Hydrophobic nutrients can be difficult to integrate with formulations intended for consumption. Personal obser-
vations with tryptophan suggest it is difficult to even wet in common beverages like water, coffee, or Diet Coke at
reasonable concentrations ( 1/4 tsp/cup or so ). It was further observed ( unpublished observation ) that it would
segregate as a powder into the extra virgin olive oil (EVOO ) component of an EVOO:water mixture although no
attempt was made to determine dissolved concentrations. This behavior creates a concern about absorption in the
digestive tract but an emulsifier or wetting agent may avoid these problems.
OH
O
NH2
N
H
OH
OH
O
H
N OH
O
FIG. 1: Tryptophan (left) and pantothenate ( right) from NCBI Pubchem.
OH
O
OH
OH
HO
O
NH2
FIG. 2: Typical breakdown products of pantothenic acid : pantoic acid (left) and βalanine ( right) from NCBI Pubchem.
Exploration of the wetting and dissolution of tryptophan may help elucidate biologically important activities.
Tryptophan is well known to confer important properties to biological proteins due to its solvent preferences [7]
but less obvious attributes may not be fully appreciated. Tryptophan was observed to help yeast survive SDS
challenge [10] and there may be more interesting properties to be discovered with simple investigations. Solubility
data for proteinogenic amino acids is still a research topic. A recent work showing solubility in a water:ethanol mix
Electronic address: marchywka@hotmail.com; to cite or credit this work, see bibtex in Appendix E
Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
demonstrated tryptophan to have unusual behavior with a significant peak at about .3 ethanol molar fraction as
opposed to flat or decreasing curves for most others ( only tyrosine had similar behavior ) [5] ( or the related thesis
[4] ) .
While commonly considered as just a water soluble vitamin, calcium pantothenate is sometimes labelled as an
emulsifier [1]. The pantothenate contains one amide nitrogen, perhaps allowing it to be called an amide containing
surfactant [11] , and a neopentyl glycol from the pantoic acid component which may contribute some oil solubility.
Hydration of pantothenate has recently been explored with quantum mechanical simulations [6] although little work
on interactions with oils was found.
Both components are unstable and potentially able to react under relevant conditions. Tryptophan is subject to
photooxidation and pantothenate is well known to breakdown into pantoic acid and βalanine under pH extremes
[9] .
This work largely just illustrates that the combination appears to mix the water and EVOO phases but hopefully
motivates larger interest and consideration of the problems. An unstable emulsifier would not normally be a ”first
choice” but it may be suitable at point of use and unintentional usage may be an important confounding factor in
performance of related products.
2. METHODS
2ml of well water ( high mineral content ) and old extra virgin olive oil were put into 10ml graduated cylinder.
Tryptophan [3] and calcium pantothenate [2] were added sequentially. No agitation was performed except light shaking
until after the pantothenate was added at which point the cylinder was vigorously shaken to mix the components and
allowed to settle. At various steps, the cylinder was illuminated with a white LED flashlight ( and varying amounts
of ambient light ) or a red laser pointer and photographed with a cell phone camera. The laser pointer illuminated
the sample at a right angle from the observation direction hopefully allowing for 90 degree scattering visualization.
Presumably micelles and undissolved matter can contribute to the observed scatter. The polarization and orientation
of the light source are unknown. Similarly, details of the imager and signal processing chain are not known but
potentially important as the areas of intense red laser illumination appear white only in the photos but appeared red
during visual observation.
Often ”limitations of study” are discussed in the discussion section but this is so limited as to deserve mention
early on. Note that for a reasonable study, negative and positive controls should have been included to compare
pantothenate to known emulsifiers and inert components. This work is just to demonstrate that pantothenate can
help wet tryptophan although chemical modifications can not be ruled out. Response curves, varying amounts of
pantothenate without tryptophan for example, could also be included .
3. RESULTS
The results are presented in chronological order as ingredients were added. An overview composite photograph with
all results is show in Fig. 3but each row is shown expanded in sequence later. Combinations of red laser pointer light
and white light from the flashlight at various angles are responsible for the different color distributions except that
the white color in areas of intense laser pointer red light was not observed by eye and likely reflects imager saturation
or overload. It is not known how the imaging system deals with overflow or color. In all cases illumination was from
the left or top with the laser pointer and right angle scattering is nominally observed .
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
FIG. 3: All the results : top row is original 50:50 water-oil, next row includes addition of tryptopham, third row includes
calcium pantothenate, finally the bottom is after settling over night.
Initially only water and oil were in the cylinder. The water was added first and never shaken. The first image on
the left illustrates laser pointer illumination from the top documenting baseline scattering from the EVOO and well
water below. Some scattering at interfaces is observed. The second or middle image shows the gold color of the oil
and clear water below ( illumination from the left ). The third image shows combined illumination for better context.
FIG. 4: Oil and water with differing illumination. The left or first is illuminated with a red laser pointe from the top. Note
the straight dim line of scattered light. The second one is just white light, mostly reflected, and the third combines white and
laser light.
After adding the tryptophan, again with only very mild agitation, 8 photographs were obtained, Fig. 5, in an
attempt to illustrate the tryptophan sinking to the bottom of the oil layer. The first and second of the four laser
pointer photos ( right ) shows illumination from the top and scattering at the interaces. The latter two show horizontal
illumination in the water layer( left) and oil layer ( right) with slightly more scatter.
FIG. 5: Addition of Trp did nothing except create white layer at bottom of oil . The added tryptophan quickly wetted on the
oil surface and sank. It is unknown how much dissolved into either phase.
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
After adding the calcium pantothenate and shaking to disrupt oil-water interface, , mixing was observed as shown
in Fig. 6. Note that no vigorous shaking or agitation was performed in prior steps as would occur in a well controlled
test but see comments in Methods and Introduction. The left photo with white light only demonstrates largely cloudy
mixture with only a small clear column at the bottom. The scatter is illustrated with the laser pointer showing some
visible scatter in the water but significantly more in the yellow cloudy layer. Turning off the white light does not help
much.
FIG. 6: Combining with calcium pantothenate and shaking created more scatter and mixing.
The apparent emulsion remained largely stable overnight as shown in Fig. 7although three layers were clearly
observed in white light. The bottom clear layer boundary retained a meniscus while a flat layer separates the two
yellow cloudy regions. With laser illumination from the left, intense scattering could be observed and leaving the
white light on provided better visual context. First, illumination was applied from the left illustrating beam spreading.
The fifth photo shows illumination from the top that appears to stop at the layer boundary. Illuminating the bottom
yellow layer from the left suggests no light gets to the top layer and any light that goes into the clear layer below is
apparently not scattering toward the camera.
FIG. 7: Little change was observed over night although the oil contents settled into two layers. Possible contributors to scatter
are micelles and suspended solids.
4. DISCUSSION
The calcium pantothenate and tryptophan combination apparently emulsifies the water-oil mixture inline with
expectations after observing the panothenate facilitate trytophan wetting . This was not intended to compare to
other possible wetting agents or emulsifiers although many simple control tests and extensions suggest themselves.
Cleaner liquids such as DI water and a less complicated oil phase would help as would agitation at more steps. Positive
and negative controls instead of the pantothenate would create more of an indication of panotothenate’s uniqueness
in this role. Many other putative emulsifiers exist.
Pantothenate is known to be unstable and various techniques have been investigated to improve this [8]. There can
be no assurance that chemical or photochemical reactions did not occur with the impure liquids of old olive oil and
well water. Breakdown products are typically pantoic acid and βalanine. Both products are soluble in water and in
varying other solvents.
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
5. CONCLUSIONS
Calcium pantothenate allows water to wet trytophan and to form a water and oil emulsion. It is not known how
the tryptophan is distributed but it does not seem to be segregated to a pure oil phase. This observation may relate
to the immediate problem of getting tryptophan to wet in diet coke or coffee and this simple system may be useful
for understanding more obscure behaviors of tryptophan in biological systems.
6. SUPPLEMENTAL INFORMATION
6.1. Computer Code
1. keep/trpetc/trppan/IMG˙20211129˙201946.jpg : data image
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22. keep/trpetc/overnight/IMG˙20211130˙050835.jpg : data image
23. keep/trpetc/IMG˙20211129˙063700.jpg : data image
making the composite images,
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
cat convert_images
cat origs.tex | while read
do
x=‘echo "$REPLY" | awk ’{print "convert "$1" -crop 2000x600+"$3"+"$4" -rotate 90 "$2".jpg"}’‘
echo $x
$x
done
#convert keep/trpetc/overnight/IMG_20211130_050559.jpg -crop 1000x600+0+600 -rotate 90 final_vis.jpg
convert +append cropped15.jpg cropped16.jpg cropped23.jpg orgingals.jpg
convert +append cropped2.jpg cropped1.jpg cropped5.jpg cropped4.jpg cropped6.jpg combined.jpg
#convert +append cropped8.jpg cropped10.jpg cropped12.jpg cropped14.jpg cropped7.jpg cropped9.jpg cropped13
.jpg cropped11.jpg trponly.jpg
convert +append cropped8.jpg cropped10.jpg cropped12.jpg cropped14.jpg cropped7.jpg cropped13.jpg cropped11
.jpg cropped9.jpg trponly.jpg
convert +append cropped17.jpg cropped19.jpg cropped20.jpg cropped21.jpg cropped18.jpg cropped22.jpg onight.
jpg
convert -append orgingals.jpg trponly.jpg combined.jpg onight.jpg composite.jpg
7. BIBLIOGRAPHY
[1] Calcium d-pantothenate supplier distributor- cas -. 12 2021. URL: https://www.parchem.com/
chemical-supplier-distributor/Calcium-D-Pantothenate-020414.aspx.
[2] Calcium pantothenate — vitamin b5 supplement — pantothenic acid bulksupplements.com. 12 2021. URL: https:
//www.bulksupplements.com/products/vitamin-b5-calcium-pantothenate-pantothenic-acid-powder.
[3] L tryptophan powder — tryptophan supplement — amino acid supplements bulksupplements.com. 12
2021. URL: https://www.bulksupplements.com/products/l-tryptophan-powder?gclid=CjwKCAiAwKyNBhBfEiwA_
mrUMgZivpzz9zF0k41-GBiqwxwDlqP7Ak6MSvriGJei7ASlF_yoGXBYpxoC2fUQAvD_BwE.
[4] Nathan A. Bowden. Modelling the solubility of the 20 proteinogenic amino acids with experimentally derived saturation
data, 05 2021. URL: http://dx.doi.org/10.18174/446739,doi:10.18174/446739.
[5] Nathan A. Bowden, Johan P.M. Sanders, and Marieke E. Bruins. Solubility of the proteinogenic -amino acids in water,
ethanol, and ethanolwater mixtures. Journal of Chemical & Engineering Data, 63(3):488–497, 2018. PMID: 29545650. URL:
https://doi.org/10.1021/acs.jced.7b00486,arXiv:https://doi.org/10.1021/acs.jced.7b00486,doi:10.1021/acs.
jced.7b00486.
[6] Davide Corinti, Barbara Chiavarino, Debora Scuderi, Caterina Fraschetti, Antonello Filippi, Simonetta Fornarini, and
Maria Elisa Crestoni. Molecular properties of bare and microhydrated vitamin b5calcium complexes. International Journal
of Molecular Sciences, 22(2), 2021. URL: https://www.mdpi.com/1422-0067/22/2/692,doi:10.3390/ijms22020692.
[7] Armando J. de Jesus and Toby W. Allen. The role of tryptophan side chains in membrane protein anchoring and hy-
drophobic mismatch. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1828, 2 2013. URL: http://dx.doi.org/
10.1016/j.bbamem.2012.09.009,doi:10.1016/j.bbamem.2012.09.009.
[8] Xuan Liang, Qi Zhang, Zaiyong Zhang, Qiaoce Ding, and Xuefeng Mei. Improving stability of vitamin b5 through double
salt formation. Crystal Growth & Design, 21(9):4997–5005, 2021. URL: https://doi.org/10.1021/acs.cgd.1c00437,
arXiv:https://doi.org/10.1021/acs.cgd.1c00437,doi:10.1021/acs.cgd.1c00437.
[9] Alisa Schnellbaecher, Dennis Binder, Stephanie Bellmaine, and Aline Zimmer. Vitamins in cell culture media: Stability
and stabilization strategies. Biotechnology and Bioengineering, 116(6):1537–1555, 2019. URL: https://onlinelibrary.
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https://doi.org/10.1002/bit.26942.
[10] Lea Schroeder and Amy E. Ikui. Tryptophan confers resistance to sds-associated cell membrane stress in saccharomyces
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[11] Bao Cai Xu, Gui Ju Zhang, Yun Xia Li, and Lu Cui. Preparation and properties of amide surfactants. Advanced
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10.4028/www.scientific.net/amr.550-553.99.
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
Acknowledgments
1. Pubmed eutils facilities and the basic research it provides.
2. Free software including Linux, R, LaTex etc.
3. Thanks everyone who contributed incidental support.
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
Appendix A: Statement of Conflicts
No specific funding was used in this effort and there are no relationships with others that could create a conflict of
interest. I would like to develop these ideas further and have obvious bias towards making them appear successful.
Barbara Cade, the dog owner, has worked in the pet food industry but this does not likely create a conflict. We have
no interest in the makers of any of the products named in this work.
Appendix B: About the Authors and Facility
This work was performed at a dog rescue run by Barbara Cade and housed in rural Georgia. The author of this
report ,Mike Marchywka, has a background in electrical engineering and has done extensive research using free online
literature sources. I hope to find additional people interested in critically examining the results and verify that they
can be reproduced effectively to treat other dogs.
Appendix C: Symbols, Abbreviations and Colloquialisms
TERM definition and meaning
EVOO Extra Virgin Olive Oil
SDS Sodium Dodecyl Sulfate
Appendix D: General caveats and disclaimer
This document was created in the hope it will be interesting to someone including me by providing information
about some topic that may include personal experience or a literature review or description of a speculative theory
or idea. There is no assurance that the content of this work will be useful for any paricular purpose.
All statements in this document were true to the best of my knowledge at the time they were made and every attempt
is made to assure they are not misleading or confusing. However, information provided by others and observations
that can be manipulated by unknown causes ( ”gaslighting” ) may be misleading. Any use of this information should
be preceded by validation including replication where feasible. Errors may enter into the final work at every step from
conception and research to final editing.
Documents labelled ”NOTES” or ”not public” contain substantial informal or speculative content that may be
terse and poorly edited or even sarcastic or profane. Documents labelled as ”public” have generally been edited to be
more coherent but probably have not been reviewed or proof read.
Generally non-public documents are labelled as such to avoid confusion and embarassment and should be read with
that understanding.
Appendix E: Citing this as a tech report or white paper
Note: This is mostly manually entered and not assured to be error free.
This is tech report MJM-2021-014.
Version Date Comments
0.01 2021-11-30 Create from empty.tex template
- December 4, 2021 version 0.80 MJM-2021-014
0.8 2021-12-04 Draft Note form, time constraint
1.0 20xx-xx-xx First revision for distribution
Released versions,
build script needs to include empty releases.tex
Version Date URL
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Mike J Marchywka , MJM-2021-014 December 4, 2021 v. 0.80 PUBLIC NOTES
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run-date =”December 4, 2021” ,
title =”Wetting Tryptophan With Calcium Pantothenate ” ,
author =”Mike J Marchywka ” ,
type =”techreport” ,
name =”marchywka-MJM-2021-014-0.80 ” ,
number =”MJM-2021-014” ,
version =”0.80 ” ,
institution =”not institutionalized, independent ” ,
address =” 306 Charles Cox , Canton GA 30115” ,
date =”December 4, 2021” ,
startdate =”2021-11-30” ,
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author1email =”marchywka@hotmail.com” ,
contact =”marchywka@hotmail.com” ,
author1id =”orcid.org/0000-0001-9237-455X” ,
pages =” 10” ,
filename =”trppath”
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Nowadays, chemically defined cell culture media (CCM) have replaced serum‐ and hydrolysate‐based media that rely on complex ingredients, such as yeast extracts or peptones. Benefits include a significantly lower lot‐to‐lot variability, more efficient manufacturing by reduction to essential components, and the ability to exclude components that may negatively influence growth, viability, or productivity. Even though current chemically defined CCMs provide an excellent basis for various mammalian biotechnological processes, vitamin instabilities are known to be a key factor contributing to the variabilities still present in liquid CCM as well as to short storage times. In this review, the chemical degradation pathways and products for the most relevant vitamins for CCM will be discussed, with a focus on the effects of light, oxygen, heat, and other CCM compounds. Different approaches to stabilize vitamins in solution, such as replacement with analogs, encapsulation, or the addition of stabilizing compounds will also be reviewed. While these vitamins and vitamin stabilization approaches are presented here as particular for CCM, the application of these concepts can also be considered relevant for pharmaceutical, medical, and food supplement purposes. More precise knowledge regarding vitamin instabilities will contribute to stabilize future formulations and thus decrease residual lot‐to‐lot variability.
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Wetting Tryptophan With Calcium Pantothenate " , author ="Mike J Marchywka " , type ="techreport
  • Bao Cai Xu
  • Gui Ju Zhang
  • Yun Xia Li
  • Lu Cui
Bao Cai Xu, Gui Ju Zhang, Yun Xia Li, and Lu Cui. Preparation and properties of amide surfactants. Advanced Materials Research, 550-553, 7 2012. URL: http://dx.doi.org/10.4028/www.scientific.net/amr.550-553.99, doi: 10.4028/www.scientific.net/amr.550-553.99. @techreport{marchywka-MJM-2021-014-0.80, filename ="trppath", run-date ="December 4, 2021", title ="Wetting Tryptophan With Calcium Pantothenate ", author ="Mike J Marchywka ", type ="techreport", name ="marchywka-MJM-2021-014-0.80 ", number ="MJM-2021-014", version ="0.80 ", institution ="not institutionalized, independent ", address =" 306 Charles Cox, Canton GA 30115", date ="December 4, 2021", startdate ="2021-11-30", day ="4", month ="12", year ="2021", author1email ="marchywka@hotmail.com", contact ="marchywka@hotmail.com", author1id ="orcid.org/0000-0001-9237-455X", pages =" 10", filename ="trppath" } Supporting files. Note that some dates,sizes, and md5's will change as this is rebuilt. This really needs to include the data analysis code but right now it is auto generated picking up things from prior build in many cases