HSP Application note #33
offensive odor and Hansen Solubility Parameter (HSP)2010.4.19
HSPiP Team Senior Developer, Dr. Hiroshi Yamamoto
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.
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. |
I compiled offensive odor compounds.
The odor is very difficult to describe with word.
| offensive odor | CAS | |
| Ammonia | 7664-41-7 | ammoniacal |
| methyl mercaptan | 74-93-1 | decomposing cabbage garlic |
| Hydrogen Sulfide | 7783-06-4 | odor of rotten eggs |
| dimethyl sulfide | 75-18-3 | cabbage-like smell |
| dimethyl disulfide | 624-92-0 | sulfurous vegetable cabbage onion |
| trimethylamine | 75-50-3 | strong "fishy" odor |
| acetaldehyde | 75-07-0 | Pungent, fruity odor |
| propionaldehyde | 123-38-6 | pungent odor |
| butyraldehyde | 123-72-8 | pungent odor |
| isobutyraldehyde | 78-84-2 | pungent odor |
| pentanal | 110-62-3 | Diffusive, fermented, bready, fruity with berry nuances |
| 3-methylbutanal | 590-86-3 | ethereal aldehydic chocolate peach fatty |
| isobutanol | 78-83-1 | sweet musty odor |
| ethyl acetate | 141-78-6 | Etherial, fruity, sweet, grape and rum-like |
| 4-methyl-2-pentanone | 108-10-1 | Fruity, Ethereal, Spicy |
| toluene | 108-88-3 | sweet |
| styrene | 100-42-5 | sweet balsam floral plastic |
| xylene | ||
| propanoic acid | 79-09-4 | Pungent acidic and dairy-like |
| butyric acid | 107-92-6 | Sharp, dairy-like, cheesy, buttery with a fruity nuance |
| pentanoic acid | 109-52-4 | Acidic and sharp, cheese-like, sour milky, tobacco, with fruity nuances |
| 3-methylbutanoic acid | 503-74-2 | Cheese, dairy, acidic, sour, pungent, fruity, stinky, ripe fatty and fruity notes |
| Skatole | 83-34-1 | very strong animal fecal indole civet |
| Cadaverine | 462-94-2 | cadaverous |
| 1,4-Butanediamine | 110-60-1 | cadaverous |
These description is very difficult so I describe with Hansen Solubility parameter.
| Hcode | offensive odor | dD | dP | dH | Vol |
| 44 | Ammonia | 13.7 | 16.7 | 18.8 | 25 |
| 496 | methyl mercaptan | 16.6 | 7.7 | 8.6 | 54.2 |
| 424 | Hydrogen Sulfide | 17.9 | 6 | 10.2 | 35.9 |
| 301 | dimethyl sulfide | 16.1 | 6.4 | 7.4 | 73.7 |
| 294 | dimethyl disulfide | 17.6 | 7.8 | 6.5 | 89.1 |
| 665 | trimethylamine | 14.6 | 3.4 | 1.8 | 90.2 |
| 1 | acetaldehyde | 14.7 | 12.5 | 7.9 | 56.5 |
| 573 | propionaldehyde | 15.3 | 11.1 | 6.9 | 73.4 |
| 1060 | butyraldehyde | 15.6 | 10.1 | 6.2 | 90.5 |
| 5166 | isobutyraldehyde | 15.7 | 10.7 | 6.1 | 89.4 |
| 1061 | pentanal | 15.7 | 9.4 | 5.8 | 107 |
| 445 | 3-methylbutanal | 14.7 | 9.5 | 5 | 106 |
| 431 | isobutanol | 15.1 | 5.7 | 15.9 | 92.9 |
| 328 | ethyl acetate | 15.8 | 5.3 | 7.2 | 98.6 |
| 491 | 4-methyl-2-pentanone | 15.3 | 6.1 | 4.1 | 125.8 |
| 637 | toluene | 18 | 1.4 | 2 | 106.6 |
| 604 | styrene | 18.6 | 1 | 4.1 | 115.7 |
| xylene | 17.8 | 1 | 3.1 | 121.1 | |
| 576 | propanoic acid | 14.7 | 5.3 | 12.4 | 75 |
| 114 | butyric acid | 15.7 | 4.8 | 12 | 92.6 |
| 1023 | pentanoic acid | 15 | 4.1 | 10.3 | 109.5 |
| 1040 | 3-methylbutanoic acid | 16.4 | 4.1 | 10.7 | 110.3 |
| 832 | Skatole | 20 | 7.1 | 6.2 | 122.6 |
| 21275 | Cadaverine | 15.9 | 6.5 | 12.2 | 116.7 |
| 21257 | 1,4-Butanediamine | 15.8 | 7.4 | 11.5 | 100.9 |
Please compare description with HSP without structural information.
Similar HSP compounds have similar odor, I think.
(But some offensive odors are use for perfume as to concentration)
Hansen SphereTo 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). |
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. Pirika JAVA Demo Applet getting Smiles. Draw2Smiles is available here. |
Y-MB Properties EstimationY-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. |
We Japanese feel Japanese (Matsutake) mushroom smell very good (though, I do not think so), but other country people think that odor is "Soldier's Socks wore long time"
Matsutake mushroom flavor composition is
10808 Cinnamic acid 621-82-9
17121 1-Octen-3-ol 3391-86-4
18811 trans-2-Octen-1-ol 18409-17-1
9091 methyl cinnamate 103-26-4
These HSP are,
Cinnamic acid 18.8 5.7 9.6 131.5
1-Octen-3-ol 15.7 4.4 11.4 154.5
trans-2-Octen-1-ol 16.1 4.5 9.7 150.8
methyl cinnamate 19.1 3.2 4.6 148.5
HSP [16, 4.5, 10] compounds are, 114, 1023, 1040, 21275, 21257 above list.
Daily, Sour, Sharp, Cheese, Cadaverous odor.
So, it is natural they feel, "Soldier's Socks wore long time"
The Durian fruit smell so bad.
568 propyl mercaptan 107-03-9
19118 ethyl methyl trisulfide 31499-71-5
324 ethyl mercaptan 75-08-1
262 diethyl disulfide 110-81-6
928 ethylbutyrate 105-54-4
16990 Ethyl-2-Methyl Butyrate 7452-79-1
929 Ethyl Capronate 123-66-0
propyl mercaptan 16.1 5.8 5.7 90.5
ethyl methyl trisulfide 18.5 7.1 5.5 122.5
ethyl mercaptan 15.7 6.5 7.1 74.3
diethyl disulfide 17 6.7 5.7 123.7
HSP [17, 6.5, 5.7] are very bad smell like 391,294 above list.
Recently, Japanese cosmetic company Shiseido determined "Aging odor" as (E)-2-nonen-1-al Hcode 17819 CAS 2463-53-8.
As aging, 2-nonen-1-al production increase, they said.
This compound's HSP is [16.2, 6.5, 5].
Pentatomoidea (insect) release bad smell and that is trans-2-hexenal Hcode 8360、 CAS 6728-26-3.
HSP is [16, 9.3, 6.3].
So, these odor is very similar.
If you want to wash out these smell, what kind of soap is best?
The original compounds are palmitoleic acid 373-49-9 Vaccenic acid 693-72-1
and oxidation of these compounds produce 2-nonen-1-al.
| [16.2, 3.5, 5.4] | [16.3, 3, 5.2] |
So, if you design soap glyceride HSP [16.3, 3, 5], it will dissolve very well.
Please use HSPiP to design soap.
If you want to make fiber that contains odor eater, how about use Phthalocyanine?
We can not calculate metal salt of Phthalocyanine, so calculate just pure Phthalocyanine with HSPiP. The result become [21.7, 14.5, 0].
This compound have symmetry so dP value might be more small.
If you have experimental solubility values, please let me know.
And search HSPiP polymer DB to find best match with Phthalocyanine.
No. 403 PMMA [19.3, 16.7, 4.7]
No. 382 NBR [19.8, 17.8, 3.2]
are good choice for fiber.
Retention time for HPLC
HPLC analysis of PAHs
HPLC analysis of medicine of Epilepsia
HPLC analysis of Anti-oxidant.
HPLC analysis of Sulfa Drugs.
HPLC analysis of Plasticizer
