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HSP Application note #14

How to look at Flavor with Hansen Solubility Parameters(HSP)


HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto


How to look at Flavor

We found very good home page of fragrance of flower.
(Unfortunately this site is written in only Japanese.)
There is one table in that page. This table means which flower contains which chemicals. ◎: this chemical is most important for that fragrance. □ : main component of that fragrance.

Compounds A B C D E F G H I J K L
β-Phenylethyl alcohol
Benzyl acetate
Linalyl acetate
Benzyl alcohol
Methyl anthranilate
Methyl jasmonate
Jasmin lactone
Methyl benzoate
Benzyl Benzoate
Anis aldehide
Citronellyl acetate
Linalool oxide
Cinnamic alcohol
Benzyl salicylate

A: rose B: jasmine C: narcissus D: Ixora E: tuberose F: ilang-ilang G: orange-colored olive H: carnation I: Lavender J: Lilac K: majalis L: Common gardenia

At first, we calculate Hansen Solubility Parameter for the chemicals.

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.

Our basic concept is that we feel smell when some chemicals "Dissolve" to Olfactory Cell.
So, we believe Hansen Solubility Parameter will become very good descriptors to distinguish flavor of flower.

Compound Smiles HSPD HSPP HSPH
β-Phenylethyl alcohol OCCc1ccccc1 18.8 7.6 13.0
Geraniol CC(C)=CCC/C(C)=C/CO 16.3 4.1 11.3
Nerol C\C(C)=C\CCC(\C)=C\CO 16.3 4.1 11.3
Citronellol OCC[C@H](CC/C=C(/C)C)C 16.1 4.8 10.8
Linalool O[C@](/C=C)(C)CC/C=C(/C)C 16.0 4.0 9.9
Farnesol OCC=C(CCC=C(CC\C=C(/C)C)C)C 16.3 4.0 9.3
Rose_oxide O1C(\C=C(/C)C)CC(C)CC1 16.9 4.4 5.5
Damascenone O=C(\C1=C(\C=C/CC1(C)C)C)/C=C/C 17.4 4.9 5.3
Damascone O=C(/C=C/C)C1C(=C/CCC1(C)C)\C 17.1 5.7 5.8
Benzyl acetate CC(=O)OCc1ccccc1 18.2 7.3 6.4
Linalyl acetate C\C(C)=C\CCC(C)(C=C)OC(=O)C 15.7 3.7 5.4
Benzyl alcohol OCc1ccccc1 19.1 6.7 14.2
cis-Jasmone O=C1\C(=C(/CC1)C)C\C=C/CC 17.0 5.2 5.1
Indole C1(C=CC=C2)=C2NC=C1 19.8 8.1 9.2
Methyl anthranilate O=C(OC)c1ccccc1N 18.7 10.7 10.6
Methyl jasmonate O=C(OC)C[C@H]1[C@@H](C(=O)CC1)C\C=C/CC 17.1 4.9 7.3
Jasmin lactone O=C1OC(C/C=C/CC)CCC1 17.2 4.1 5.6
Methyl benzoate O=C(OC)c1ccccc1 18.5 7.9 6.4
Benzyl Benzoate O=C(OCc1ccccc1)c2ccccc2 19.4 5.2 4.5
Anis aldehide COc1ccc(C=O)cc1 19.2 13.3 9.1
Nerolidol O[C@](\C=C)(CC/C=C(/CC/C=C(\C)C)C)C 16.1 1.9 7.8
Eugenol Oc1ccc(cc1OC)CC=C 18.1 7.1 11.6
Citronellyl acetate O=C(OCCC(CC/C=C(\C)C)C)C 16.2 2.4 5.6
Ionone O=C(\C=C\C1C(=C/CCC1(C)C)\C)C 17.1 5.7 5.8
Decalactone O=C1O[C@H](CCCCCC)CC1 16.8 11.0 4.9
Linalool oxide OC1CCC(OC1(C)C)(\C=C)C 15.9 7.6 9.3
Hexenol CC\C=C/CCO 16.0 6.7 13.4
Cinnamic alcohol OCC=Cc1ccccc1 18.6 5.6 12.7
Benzyl salicylate O=C(OCc1ccccc1)c2ccccc2O 19.1 8.2 11.0
Camphor O=C1CC2CCC1(C)C2(C)C 17.3 10.0 4.9
Terpineol OC([C@@H]1C/C=C(/C)CC1)(C)C 17.5 4.7 9.8
Terpinene C\1=C(/C)C/C=C(/C(C)C)C/1 16.9 2.5 3.4
Pinene C\1=C(\C2CC(C/1)C2(C)C)C 17.4 3.0 3.2
Ocimene C=C\C(=C\C/C=C(\C)C)C 15.8 3.2 4.7
Benzaldehide O=Cc1ccccc1 19.3 11.1 6.0

We use HSPiP software to calculate HSP.

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 the Smiles structure, Y-MB calculate HSP of that molecule.

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.


Then we analyze this vectors with SOM (Self Organization Map) method.
Every chemicals are mapped at 40*40 matrix.
If the HSP vectors are near, then mapped very near position.

SOM: Self Organization Map Neural Network 

The 2D Map of "Smilar vector map to similar 2D position".

If we split dH to dHdo, dHac then HSP vector become 4 dimensions.
That is the very bad news for user. Because the Sphere and GUI can not expand to 4 dimensions.
So we start to develop SOM program to check vector similarity.

Pirika JAVA Demo Applet calculate SOM. SOMDemo is available here.


The most popular 5 flavor pattern become like this.
The pattern is so different.
Maybe our nose can distinguish these flavor. (We hope!)

Ixora, Narcissus, Jasmine patterns are similar.
Narcissus is very basic and Ixora and Jasmine are complicated composition.

Tuberose and ilang-ilang patterns are fairly similar.
And these flowers are not so familiar to us, maybe we can not distinguish.

Lavender and Common Gardenia have very strong flavor.
Basic pattern is similar.

Maialis, Rose, Jasmine are top 3 flavors in fragrance.
The patterns are very different.

Tuberose is something (Ixora+Rose+Jasmine)/3

So, every flower have their specific pattern.
If I can change the pattern to electric signal, I can make electric-Nose.

Such research is already done at CALTECH MSC.
They make sensors that change swelling rate to electric current.
So, if they use above 7 type HSP polymer sensor, that polymer swell effectively with covered chemicals. I searched corresponding polymer in HSPiP polymer database.

These technique is not only for flavor.
If you want to design Endocrine disruptors sensor, you can do same way.
Allergens, Offensive odor, VOC compounds, all the same.

But, for the flavor, I need take into account RER effect.
Relative Evaporation Rate(RER) is very different for each chemicals.
HSPiP have the function estimate RER, and I append 1000*RER on SOM.
Some large RER molecules disturb small RER neighbor.
So, choosing polymer will more complicate.

If you want to know how to draw molecules, please refer to Power Tools applications.

Other Flavor topics