Hansen Solubility Parameter (HSP) and natural herbs

HSP Application note #15

2010.2.5

HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto

Chinese Page Translated by Dong xin-yan, Zhejiang University, Hangzhou,China

Last week, I ate Oyster and got sick.
So, I checked Chinese (Natural herbs) medicines in the Net. But there is no such medicine.
Anyway, I made database and calculated HSP of those molecules.

Hansen Solubility Parameters (HSP)

Hansen Solubility Parameters(HSP) were developed by Charles M. Hansen as a way of predicting if one material will dissolve in another and form a solution. They are based on the idea that "like dissolves like" where one molecule is defined as being 'like' another if it bonds to itself in a similar way.
Specifically, each molecule is given three Hansen parameters, each generally measured in MPa0.5:
dD:The energy from dispersion bonds between molecules
dP:The energy from dipolar intermolecular force between molecules
dH:The energy from hydrogen bonds between molecules.
These three parameters can be treated as Vector for a point in three dimensions also known as the Hansen space. The nearer two molecules HSP Vector are in this three dimensional space, the more likely they are to dissolve into each other.

What can perhaps be surprising is that one can assign HSP to so many different things. Gases like carbon dioxide, solids like carbon-60, sugar, and biological materials like human skin, depot fat, DNA, and even some proteins all have HSP. The list can be continued with drugs, polymers, plasticizers, and in fact any organic material and even many inorganic materials like salts. The only requirement for an experimental confirmation is that the material must behave differently in a sufficient number of test solvents upon contact.

Pirika JAVA Demo Applet calculate HSP. HSPLight is available here.
Please refer to e-Book of HSPiP if you want know more about HSP.
About the Power Tools that handle HSP more effectively.

(from here nothing to do with oyster)
At that time, I was very interested in matatabi-lactone.
As you know, Cat love this fruit and when Cat smell this molecule, cat become as if it drunk alcohol.
(Flehmen reaction)
I researched further.
(Matatabi = Silvervine)


1:matatabi-lactone	Matatabi Fruit (from Wikipedia)

I checked other molecules which show Flehmen Reaction for cat.
Kiwifruit tree is the same kind tree of Matatabi, so it is natural for cat love this smell.
One is lactone and one is amine, but structure is similar, I think.


2:Actinidine CAS# 524-03-8	Kiwifruit (from WikiPedia)

Catnip leaf contains Nepetalactone. This tree name come from "Cat Chew", so it is natural for cat love this tree. And Matatabi-Lactone and Nepetalactone is so similar.


3:cis,cis-Nepetalactone CAS# 490-10-8	Catnip (from WikiPedia)

And I searched cat owner blog with key word "cat love smell".
Then I got, cigarette with menthol, chewing gum, cold compress medicine.
It would be menthol.


4:menthol CAS# 1490-04-6	Mint (from Wikipedia)

Someone said cat love smell of soap especially violet flavor.
The violet flavor is alpha-lonone.


5:alpha-lonone CAS# 127-41-3	Violet (from wikipedia)

And I calculated Hansen Solubility Parameter(HSP) of these molecules.
I used HSPiP ver.3, and got the results.

HSPiP(Hansen Solubility Parameters in Practice)

The first edition of HSPiP that appeared in November, 2008, greatly enhanced the usefulness of the Hansen solubility parameters (HSP).

The HSP values of over 1200++ chemicals and 500 polymers are provided in convenient electronic format and have been revised and updated using the latest data sources in the second edition (March, 2009).

A third edition of the HSPiP appeared in March, 2010. There are now 10,000 compounds in the HSP file which also includes data on density, melting point, boiling point, critical parameters, Antoine constants and much more. The user is able to carry out many different sorts of optimisations of solubility, evaporation, diffusion, adhesion, create their own datasets (automatically if required) and explore the huge range of applications for HSP in coatings, paints, nanoparticles, cosmetics, pharma, organic photovoltaics and much more.

The 3rd Edition v3.1 was released on 12 December 2010. Current users can upgrade free (now v3.1.09) by downloading the latest .msi installer from http://hansen-solubility.com

The 4th Edition v4.0.x was released on 2 Jan. 2013. The Current users can upgrade with free charge.

2013.1.28 The Visual How to manual of HSPiP. You can understand what HSPiP can do.
Please check the Functional Group List whether your targets are available with HSPiP.
How to purchase HSPiP
2013..1.2 The HSPiP ver. 4 include Power Tools for HSPiP power user.

If you have Smiles structure and HSPiP software, Y-MB function will calculate HSP immediately.

Smiles(Simplified Molecular Input Line Entry Syntax)

SMILES is a string obtained by printing the symbol nodes encountered in a depth-first tree traversal of a chemical graph.
"Organic subset" of B, C, N, O, P, S, F, Cl, Br, and I, brackets can be omitted.
Branches are described with parentheses, as in CCC(=O)O for propionic acid
Double and triple bonds are represented by the symbols '=' and '#'
Ring closure labels are used to indicate connectivity between non-adjacent atoms in the SMILES

Pirika JAVA Demo Applet getting Smiles. Draw2Smiles is available here.
Now we have Power Tool "Draw 2 Smiles", GUI HTML5 software on HSPiP ver. 4.

Y-MB Properties Estimation

Y-MB break Smiles into correspponding Functional Groups and Estimate various Properties. These estimation schemes are come from Pirika technologies.

Pirika JAVA Demo Applet calculate Properties. PirikaLight is available here.
Now we have Power Tool "Y-Predict", GUI HTML5 software on HSPiP ver. 4.

name	dD	dP	dH	Volume
matatabi-lactone	17.6	7.5	5.6	166.7
Actinidine	18.5	4.5	3.1	152.2
Nepetalactone	17.7	7.4	5.6	161.8
menthol	16.7	4.3	9	175.8
alpha-lonone	16.7	4.7	4.8	208.7
Ave.	17.44	5.68	5.62	173.04

It is natural matatabi-lactone and nepetalactone has almost same HSP, because structure is almost same. And the other molecules are also very similar, I think. For the beginner, "Smilar HSP"or "not Similar" is very hard to determin.

2011.4.25

<p>Please Use HTML5 Browser</p>

Drag=Rotate, Drag+Shift=Larger/Smaller, Drag+Alt or Command(Window key)=Translate.

If you are using HTML5 enable browser such as Chrome, Safari or FireFox (IE9 is out of support), you will see the Canvas. If you pick solvent, solvent name will appear.

The solvent(Blue small sphers) are most widely selected popular slvents. Please check the position of your molecules in this space.

HSP theory is very simple.
Similar HSP vectors materials solve similar HSP materials.
"Like seeks like"

Hansen Sphere

To determine if the parameters of two molecules (usually a solvent and a polymer) are within range a value called interaction radius (R0) is given to the substance being dissolved. This value determines the radius of the sphere in Hansen space and its center is the three Hansen parameters.

From version 3.1.X, Double Spheres function is available.

Pirika provide JAVA 3D Demo Applet to browse the Sphere(s).
The HTML5 Sphere Viewer examples are available here.
Now we have Power Tool "Sphere Viewer", GUI HTML5 software on HSPiP ver. 4.

So if cat's Jacobson's Organ HSP is average of 5 molecules above [17.4, 5.7, 5.6], then this organ will solve these molecules very well.

Cat nose

In HSPiP ver.3, there is function of search similar HSP molecules, and has 10000 molecules database. So I searched matatabi-lactone like HSP and volume molecules.
I got 41 molecules.
I show several fragrance molecules.
(Actually, prof. Abbott compiled a lot of fragrance compounds in DB and almost all candidates are fragrance compounds)

NO	name	CAS#	dD	dP	dH	Volume
1	Pulegone	89-82-7	17.3	6.5	5.1	162.5
2	Cis-Jasmone	488-10-8	17.2	6	4.8	173.9
3	verbenone	80-57-9	17.7	7.1	4	153.9
4	mint lactone	13341-72-5	17.9	7.3	5.7	159.5
5	2-isobutyl-3-methyl pyrazine	13925-06-9	17.3	6.2	5.4	163.3
6	wine lactone	57743-63-2	17.7	7.5	5.6	161.9
7	dehydromenthofurolactone	80417-97-6	17.9	7.1	5.8	154.7
8	allyl benzoate	583-04-0	17.9	7.7	4.5	154
9	alpha-isopropyl phenyl acetaldehyde	2439-44-3	17.9	6.8	4.7	168.3

I think, all these lactone compounds are very similar structure with matatabi-lactone, so it will have Flehmen reaction for cat. With this result, if your cat close to you when you drink wine a lot, that does not mean your cat love you. Wine lactone(6) density in your breath may be very high.

These molecules are used as flavor for soap, food, cosmetics.
I really want know the result of cat's reaction for these flavor.
If you test these, please let me know.

This matatabi-lactone is also used as avoidance compounds for cockroach and mosquito.
If some fragrances which are very safe for human, avoid insects, it is very interesting.
We hope HSPiP works in that field.

But in fact, I want to know the fragrance of avoiding my programming BUGS!
(I am very sorry for delaying release of ver.3 with my bugs and health problem.)

I should back to work!