COMPOSITIONS COMPRISING ORGANO-SILANOL COMPOUNDS, AND APPLICATIONS

Abstract

A composition comprising stabilised organo-silanol compounds, said composition comprising two different organo-silanols and an organo-silanol(s) stabilising/complexing agent.

Claims

1. A hydroglycolic composition comprising: a) a first organo-silanol of the following general formula (I):
X—Si(OH).sub.3  (I) wherein X is a linear or branched C.sub.1-C.sub.4 alkyl group, optionally substituted with at least one hydroxyl group; b) a second organo-silanol of the following general formula (III):
X—Si(OH).sub.2O—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (III) wherein: the X is a linear or branched C.sub.1-C.sub.4 alkyl group, optionally substituted with at least one hydroxyl group; R.sub.1 is —H or —CH.sub.3; R.sub.2 is —H, —OH, or —CH.sub.3; R.sub.3 is —CH.sub.3, —CH.sub.2—CH.sub.3, —CH.sub.2OH, —CH(CH.sub.3)OH, —CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2— CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—OH, or —C(CH.sub.3)(CH.sub.3)—OH; c) an organo-silanol(s) stabilising/complexing agent, suitable for allowing the formation of a molecular complex with at least one organo-silanol via the establishment of at least one weak chemical bond, with said at least one organo-silanol; and d) at least one glycolic solvent.

2. The composition of claim 1, wherein the molar ratio between said first organo-silanol and said second organo-silanol is between 100/1 and 100/20.

3. The composition of claim 1, said composition being a hydroglycolic solution.

4. The composition of any one of claims 1-3, wherein said at least one glycolic solvent is of formula (II):
HO—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (II) wherein: R.sub.1 is —H or —CH.sub.3; R.sub.2 is —H, —OH, or —CH.sub.3; and R.sub.3 is —CH.sub.3, —CH.sub.2—CH.sub.3, —CH.sub.2OH, —CH(CH.sub.3)OH, —CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—OH, or —C(CH.sub.3)(CH.sub.3)—OH.

5. The composition of claim 4, wherein: i) the water/glycol solvent mass ratio is between 98/2 and 20/80, and/or ii) the pH of said composition is between about 4 and about 6.

6. The composition of claim 1, wherein said organo-silanol(s) stabilising agent is selected from adenosine, glycyrrhizic acid and/or its salts, glycyrrhizin and/or its salts, lactobionic acid and/or its salts, alginic acid and/or its salts, hyaluronic acid and/or its salts, lactose, trehalose, 6-deoxy-L-mannopyranose and/or its salts, theophylline acetic acid, ascorbic acid, lactic acid, salicylic acid and/or its salts, pyrrolidone carboxylic acid and/or its salts, arginine, serine, lysine and/or their salts, methionine and/or its salts, acetyl methionine, threonine, hydroxyproline, N-acetyl tyrosine, aspartic acid, glutamic acid and/or their salts, oleic alcohol, panthenol, caffeine, pectin, acefylline, chondroitin sulfate and/or their salts, hydrolysed pearl, a protein hydrolysate of animal or plant origin, for example a collagen hydrolysate of marine origin such as a collagen hydrolysate from fish skin(s), and mixtures thereof.

7. The composition of claim 1, wherein said second organo-silanol is of formula (III):
X—Si(OH).sub.2—O—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (III) wherein: X is methyl group; R.sub.1 is hydrogen atom; R.sub.2 is hydrogen atom; and R.sub.3 is —CH.sub.2—OH.

8. A pharmaceutical composition comprising the composition of claim 1, and a pharmaceutically acceptable excipient.

9-10. (canceled)

11. A process for preparing an organosilanol of formula (III),
X—Si(OH).sub.2O—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (III) wherein: X is a linear or branched C.sub.1-C.sub.4 alkyl group optionally substituted with at least one hydroxyl group; R.sub.1 is —H or —CH.sub.3; R.sub.2 is —H, —OH, or —CH.sub.3; R.sub.3 is —CH.sub.3, —CH.sub.2—CH.sub.3, —CH.sub.2OH, —CH(CH.sub.3)OH, —CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2— CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—OH, or —C(CH.sub.3)(CH.sub.3)—OH; comprising a) obtaining an organo-silanol of the following general formula (I):
X—Si(OH).sub.3  (I) wherein X is a linear or branched C.sub.1-C.sub.4 alkyl group; b) contacting said organo-silanol of formula (I) with at least one glycolic solvent of formula (II):
HO—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (II) wherein: R.sub.1 is —H or —CH.sub.3; R.sub.2 is —H, —OH, or —CH.sub.3; R.sub.3 is —CH.sub.3, —CH.sub.2—CH.sub.3, —CH.sub.2OH, —CH(CH.sub.3)OH, —CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—OH, or —C(CH.sub.3)(CH.sub.3)—OH; for a sufficient period of time to obtain, via a mono-alkoxylation reaction, the organo-silanol of formula (III).

12. A method of increasing the stability of a composition, wherein the composition comprises: an organo-silanol of the following general formula (I):
X—Si(OH).sub.3  (I) wherein the radical X is a linear or branched C.sub.1-C.sub.4 alkyl group, and an organo-silanol(s) stabilising agent as defined in claim 1 or 6, suitable for allowing the formation of a molecular complex with at least one organo-silanol via the establishment of at least one weak chemical bond with said at least one organo-silanol; the method comprising, contacting the composition with an organo-silanol of formula (III):
X—Si(OH).sub.2O—CH(R.sub.1)—CH(R.sub.2)(R.sub.3)  (III) wherein: X is a linear or branched C.sub.1-C.sub.4 alkyl group optionally substituted with at least one hydroxyl group; R.sub.1 is —H or —CH.sub.3; R.sub.2 is —H, —OH, or —CH.sub.3; R.sub.3 is —CH.sub.3, —CH.sub.2—CH.sub.3, —CH.sub.2OH, —CH(CH.sub.3)OH, —CH.sub.2—CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2— CH.sub.2—CH.sub.3, —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—OH, or —C(CH.sub.3)(CH.sub.3)—OH.

13. The method of claim 12, wherein, in the organo-silanol of formula (III): X is methyl; R.sub.1 is hydrogen; R.sub.2 is hydrogen; and R.sub.3 is —CH.sub.2—OH.

14-15. (canceled)

16. A cosmetic or dermocosmetic composition comprising the composition of claim 1, and a cosmetically or dermocosmetically acceptable excipient.

17. The cosmetic or dermocosmetic composition of claim 16 for topical cutaneous administration.

18. A method of reducing the size and/or visibility of noticeable skin pores associated with age, comprising contacting the skin with the cosmetic or dermocosmetic composition of claim 17.

19. The hydroglycolic composition of claim 1, wherein X in each instance is methyl.

20. The process of claim 11, wherein X in each instance is methyl.

21. The method of claim 12, wherein X in each instance is methyl.

22. The composition of claim 2, wherein the molar ratio between said first organo-silanol and said second organo-silanol is between 100/10 and 100/15.

23. The composition of claim 5, wherein the water/glycol solvent mass ratio is between 80/20 and 50/50.

24. The composition of claim 6, wherein said organo-silanol(s) stabilising agent is alginic acid and/or its salts, or hyaluronic acid and/or its salts.

Description

DETAILED DESCRIPTION

[0098] The following detailed description is intended to set out the invention in a sufficiently clear and complete manner, notably using examples, but should in no way be considered as limiting the scope of protection to the particular embodiments and examples presented hereafter.

EXAMPLES

[0099] Test 1: Process for Preparing an Organic Silicon in Hydroglycolic Solution According to the Invention (Namely the Above-Mentioned “Ternary Complex Represented by the Scheme ° SW—AS—OS(11l)”) Involving the Substances Methylsilanetriol and (3-Hydroxypropoxy)-(Methyl)Silanediol as Well as Adenosine as a Stabilising/Complexing Agent

[0100] First, 8.55 g of adenosine (32 mmoles) is suspended in approximately 320 g of water. Then, 6.92 g of a commercial solution of sodium methylsiliconate (equivalent to 32 mmoles of methylsilanetriol), previously diluted in approx. 40 ml of water, are added to the previous suspension. The resulting pH is adjusted to 4.95 using a few drops of 1N HCl. 500 g of 1,3-propanediol are then introduced with stirring at room temperature. The mass of solution is finally adjusted to 1 kg by adding water. The resulting complex solution (in a water/1,3-propanediol 50/50 weight ratio) is finally adjusted to a pH of 5 using a few drops of 1N HCl. A clear, colourless and odourless solution is obtained.

[0101] Test 2: Skin Penetration Profile for Organic Silicon in Hydroglycolic Solution

[0102] Principle: the skin epidermis is composed of four layers from the most superficial one (“stratum corneum”) to the deepest one (“basal layer”). For a structurally defined organic entity, it is thus possible to determine its octanol/buffer partition coefficient (“Log P”), enabling: [0103] the determination of the skin permeability constant (“Kp”) from the so-called “Potts & Guy” model equation (according to the article “Predicting skin permeability”) (Potts R. 0. & Guy R. H., Pharm. Res., 1992, vol. 9, pp. 663-669); [0104] and thus making it possible to express for the targeted entity its ability to cross the epidermal skin barrier (Arct J. et al., SOFW J., 2003, vol. 129, pp. 2-9).

[0105] In the case of the present invention, a theoretical determination of Log P was carried out using the “Chemdraw®” prediction software marketed by the company “Cambridge soft”, for the two following cases: [0106] case 1: methylsilanetriol associated and stabilised, in exclusively aqueous solution, by a stabilising/complexing agent (weak bonds) [0107] case 2: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (3-hydroxypropoxy)-(methyl)silanediol, and a stabilising/complexing agent.

[0108] The results are collated in table 1 below:

TABLE-US-00001 TABLE 1 Organic silicon Log P Kp (cm .Math. h.sup.−1) .Math. 10.sup.−5 Case 1 −1.30 5.8 Case 2 (according to the invention) −0.71 6.7

[0109] Considering that the flux (i.e. the quantity of solute which passes into skin per unit area) is proportional to “Kp” and that the higher the “Kp” the more the product penetrates, the results above evidence a higher permeability constant for the composition according to the invention. It is therefore predicted that such a composition (“ternary complex”) has a greater ability to cross the epidermal skin barrier and therefore a greater bioavailability than, for example, a methylsilanetriol belonging to the state of the art and stabilised by weak bonds (hydrogen bonds).

[0110] Test 3: Discovering the Stability Over Time of an Organic Silicon in Hydroglycolic Solution

[0111] Principle: the stability of methylsilanetriol complexes with various metallic elements of the periodic table, in an acidic medium, is known and has been studied (Vevere I. et al., Latvijas Kïmijas Zurnâls, 1996, vol. 1, pp. 70-73, and references cited). The aim is to observe the appearance of insoluble species in aqueous solution, which, under an incident and reflected light beam, are visually expressed by a blue opalescence of the solution.

[0112] The same stability study as the one from the state of the art was therefore conducted, for the two following cases: [0113] case 1: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak bonds (hydrogen bonds) with ascorbic acid [0114] case 2: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol, as well as the same stabilising/complexing agent from case 1

[0115] The results are collated in table 2 below:

TABLE-US-00002 TABLE 2 Maximum stability Organic silicon pH T (days) Case 1 4.0-5.0 110 Case 2 (according to the invention) 5.0-6.0 551

[0116] The results underline a much higher stability of an organic silicon in hydroglycolic solution according to the invention than of the same organic silicon but without a glycolic compound in solution.

[0117] Test 4: Discovering the Cytostimulant Effect of an Organic Silicon in Hydroglycolic Solution on Reconstructed Epidermis of Human Origin

[0118] The culturing of the RHE consisted in placing them in an “MCDB 153” growth medium (supplier: SkinEthic®) containing 5 mg/mL of insulin, 1.5 mM of CaCl.sub.2 and 25 mg/mL of gentamycin, for 24 hours at 37° C. and 5% CO.sub.2.

[0119] The cell proliferation is observed by the immunostaining technique (Gerdes et al., Int. J. Cancer (1983), vol. 31, pp. 13-20) by using the cell proliferation marker “Ki67”, for the three following configurations (after twice-daily deposition of 100 μl on the RHE): [0120] case 1: PBS buffer solution (control) [0121] case 2: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak (hydrogen) bonds with alginic acid [0122] case 3: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol as well as the same stabilising/complexing agent from case 2

[0123] The results obtained are collated in table 3 below:

TABLE-US-00003 TABLE 3 % cells expressing Ki67/ Concentration total number of cells Organic silicon (%) (% compared to the control) Case 1 (control) — — Case 2 5 +35 ± 0.5 Case 3 (according to the 5 +58 ± 1   invention)

[0124] The results underline a potentiated cytostimulation for the organic silicon in hydroglycolic solution according to the invention, superior to that of the same organic silicon but devoid of a glycolic compound in solution.

[0125] Test 5: Determining and Discovering the Ability of an Organic Silicon in Hydroglycolic Solution According to the Invention to Limit the Endogenous Synthesis of an Intracellular Signalling Agent, Nitric Oxide (NO)

[0126] As a preamble, it is stated that nitric oxide is a free radical species involved in skin ageing mechanisms (Ahsanuddin S. et al., AIMS Molecular Sciences, 2016, vol. 3, pp. 187-195). Then experimentally, the test was performed on murine macrophages of cell line “RAW 264.7”. These macrophages were cultured in a complete culture medium “DMEM” (with 4.5 g/l of glucose and 10% foetal calf serum (FCS)), then kept in an atmosphere of 37° C. and 5% CO.sub.2. On D-1, the macrophages were seeded in 24-well plates at 65789 cells/cm.sup.−2. At DO+2 hours, the macrophages were then stressed by the application of lipopolysaccharides (LPS), inducing the production of nitric oxide (LPS at 10 ng/ml), and then incubated at 37° C. and 5% CO.sub.2 for a further 22 hours still in the presence of the treatments. On D+1, the culture supernatants were harvested for nitric oxide/nitrites quantification (Griess Reagent Kit for nitrite quantitation, Invitrogen, reference G7921) and statistical analysis in triplicate or quadriplicate (depending on the complex), at 540 nm absorbance, for the five following configurations: [0127] case 1: control with LPS stress (abbreviation “LPS-stress”) [0128] case 2: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak (hydrogen) bonds with hydroxyproline [0129] case 3: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol as well as the same stabilising/complexing agent from case 2 [0130] case 4: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak (hydrogen) bonds with 6-deoxy-L-mannopyranose [0131] case 5: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol as well as the same stabilising/complexing agent from case 4.

[0132] Similarly to the above-mentioned tests 2 and 4, the present test allows a comparison, for a same concentration, of an in vitro biological behaviour between an associated and stabilised methylsilanetriol complex in exclusively aqueous solution, and the same associated and stabilised methylsilanetriol complex but in hydroglycolic solution.

[0133] The results are collated in table 4 below, notably expressed as % inhibition of nitric oxide secretion compared to the untreated control.

TABLE-US-00004 TABLE 4 Secreted quantity % inhibition of NO of NO Compound (% LPS) secretion Case 1 - Control (“LPS-stress”) 100 N/A Case 2 - “LPS-stress” + organic silicon 75 −25% at 0.5% conc. Case 3 - “LPS-stress” + organic silicon 55 −45% at 0.5% conc. Case 4 - “LPS-stress” + organic silicon 74 −26% at 0.25% conc. Case 5 - “LPS-stress” + organic silicon 62 −38% at 0.25% conc.

[0134] The results underline an inhibition of nitric oxide production induced by LPS stress potentiated for organic silicon in hydroglycolic solution according to the invention, greater than that of the same organic silicon but without a glycolic compound in solution.

[0135] Test 6: Determining and Discovering the Ability of an Organic Silicon in Hydroglycolic Solution According to the Invention to Limit the Production of a Lipid Mediator, Prostaglandin E.sub.2 (PG E2)

[0136] As a preamble, it is stated that prostaglandin E.sub.2 (PGE2) is a marker in particular designated for studying the effects of ageing on type I collagen production (Shim J. H, Int. J. Mol. Sc., 2019, vol. 20, 5555, pp. 1-12). Then experimentally, the test was performed under the same conditions as test 5 above, i.e. the same macrophage line and the same culturing, except for the following step: on D+1, the culture supernatants were harvested in order to perform quantification of secreted PGE2 (Prostaglandin E.sub.2 Parameter Assay Kit, reference KGE004B, R&D System) and a statistical analysis in triplicate, at 450 nm absorbance, the three tested configurations being: [0137] case 1: control with stress (LPS-stress) [0138] case 2: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak (hydrogen) bonds with hyaluronic acid (<700 kDa) [0139] case 3: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (i.e. the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol as well as the same stabilising/complexing agent from case 2 [0140] case 4: methylsilanetriol complex associated and stabilised, in exclusively aqueous solution, by weak (hydrogen) bonds with 6-deoxy-L-mannopyranose [0141] case 5: organic silicon in hydroglycolic solution (water/glycol: 50/50) according to the invention (i.e. the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol and (3-hydroxypropoxy)-(methyl)silanediol as well as the same stabilising/complexing agent from case 4.

[0142] Similarly to the above-mentioned tests 2 to 5, the present test allows a comparison, for the same concentration, of an in vitro biological behaviour between an associated and stabilised methylsilanetriol complex in exclusively aqueous solution and the same associated and stabilised methylsilanetriol complex but in hydroglycolic solution.

[0143] The results are collated in table 5 below, notably expressed as % inhibition of PGE2 secretion compared to the untreated control.

TABLE-US-00005 TABLE 5 Secreted quantity % inhibition of PGE.sub.2 of PGE.sub.2 Compound (% LPS) secretion Case 1 - Control (“LPS-stress”) 100 N/A Case 2 - “LPS-stress” + organic silicon 108 N/A at 0.25% conc. Case 3 - “LPS-stress” + organic silicon 74 −26% at 0.25% conc. Case 2 - “LPS-stress” + organic silicon 105 N/A at 0.5% conc. Case 3 - “LPS-stress” + organic silicon 66 −34% at 0.5% conc. Case 2 - “LPS-stress” + organic silicon 99  −1% at 1% conc. Case 3 - “LPS-stress” + organic silicon 63 −27% at 1% conc. Case 4 - “LPS-stress” + organic silicon 99  −1% at 0.25% conc. Case 5 - “LPS-stress” + organic silicon 78 −22% at 0.25% conc.

[0144] The results underline an inhibition of the PGE2 production induced by LPS stress, potentiated for organic silicon in hydroglycolic solution according to the invention, dose-dependent and superior to that of the same organic silicon but without a glycolic compound in solution.

[0145] Test 7: Process for Preparing an Organic Silicon in Hydroglycolic Solution According to the Invention (Namely the Above-Mentioned “Ternary Complex Represented by the Scheme ° SW—AS—OS(III)”) Involving Various Organo-Silanols of General Formula (I), Various Organo-Silanols of General Formula (III), Various Glycolic Solvents of General Formula (II), Various Water/Glycolic Solvent Weight Ratios, and Finally Various Stabilising/Complexing Agents

[0146] Experimentally, the preparation processes for each of the illustrative examples below were carried out according to the chronology and operating conditions described in test 1 above. They led, in each of the 10 generated examples set out in table 6 below, to a clear, colourless and odourless solution, which was then analysed in .sup.29Si NMR spectroscopy using a “Brucker Avance 500” spectrometer under the following conditions: [0147] analysis temperature: room temperature (300° K) [0148] relaxation time: 30 seconds [0149] number of scans: 6000 [0150] analysis time: 50 hours [0151] external reference: D.sub.2O (deuterated solvent) [0152] NMR tube internal diameter: 10 mm [0153] core: .sup.29Si; frequency: 99.36 MHz; Pulse program: Zgig

TABLE-US-00006 TABLE 6 Composition according to the invention [ternary, stabilised complex] Silylated Glycolic solvent OS(I) -- AS -- OS(III) reagent of formula (II) OS(I) OS(III) Stabilising HO—CH(R.sub.1)—CH(R.sub.2)(R.sub.3) X—Si(OH).sub.3 X—Si(OH).sub.2—O—CH(R1)—CH(R.sub.2)(R.sub.3) agent H.sub.2O/glycol [δ in ppm] [δ in ppm] Δδ [AS] weight ratio Lot Lot (ppm) sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.51 methylsiliconate R.sub.2 = H δ = −37.33 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −37.84 ppm hyaluronic acid 50/50 E17384 E17384 sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.59 methylsiliconate R.sub.2 = CH.sub.3 δ = −37.46 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = CH.sub.3 R.sub.3 = —CH.sub.2OH δ = −38.05 ppm hyaluronic acid 50/50 E17390 E17390 sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.25 methylsiliconate R.sub.2 = H δ = −37.85 ppm R.sub.1 = H R.sub.3 = —CH(CH.sub.3)OH R.sub.2 = H R.sub.3 = —CH(CH.sub.3)OH δ = −38.10 ppm hyaluronic acid 50/50 E17385 E17385 sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.51 methylsiliconate R.sub.2 = H δ = −37.34 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −37.85 ppm alginic acid 50/50 E17386 E17386 sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.52 methylsiliconate R.sub.2 = H δ = −37.33 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −37.85 ppm 6-deoxy-L- 50/50 E17387 E17387 mannopyranose sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.30 methylsiliconate R.sub.2 = OH δ = −37.26 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = OH R.sub.3 = —CH.sub.2OH δ = −37.56 ppm 6-deoxy-L- 30/70 E17483 E17483 mannopyranose sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.28 methylsiliconate R.sub.2 = OH δ = −37.00 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = OH R.sub.3 = —CH.sub.2OH δ = −37.28 ppm theophylline 50/50 E17482 E17482 acetic acid sodium R.sub.1 = H X = —CH.sub.3 X = —CH.sub.3 0.51 methylsiliconate R.sub.2 = H δ = −37.33 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −37.84 ppm hydroxyproline 50/50 E17388 E17388 butyltrichloro- R.sub.1 = H X = —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.3 X = —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.3 0.90 silane R.sub.2 = H δ = −38.24 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −39.14 ppm lactic acid 50/50 E38480 E38480 hydroxymethyl- R.sub.1 = H X = —CH.sub.2OH X = —CH.sub.2OH 1.15 triethoxysilane R.sub.2 = H δ = −47.93 ppm R.sub.1 = H R.sub.3 = —CH.sub.2OH R.sub.2 = H R.sub.3 = —CH.sub.2OH δ = −49.08 ppm caffeine 50/50 E38478 E38478

[0154] Finally, by way of final illustrations, we mention below five examples of formulations of compositions according to the invention containing an organic silicon in hydroglycolic solution which is the object of the aforementioned invention, together with a description used for the preparation of each formulated organic silicon.

[0155] Formula A (Cream)

[0156] Organic silicon in hydroglycolic solution (water/1,3-propanediol; 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (3-hydroxypropoxy)-(methyl)silanediol and adenosine as a stabilising/complexing agent, said organic silicon in

TABLE-US-00007 hydroglycolic solution being prepared according to test 1 5% described above Hydrogenated polyisobutene 7% Isobutyl myristate 3% Cetyl palmitate 7% Ethylene glycol monostearate 5% Sorbitan laurate 2% Polysorbate 20 2% Carbomer (copolymer of acrylate/acrylamide & mineral oil) 0.3%   Phenoxyethanol 0.5%   Water qsp 100%

[0157] Formula B (Gel)

[0158] Organic silicon in hydroglycolic solution (water/1,3-propanediol; 80/20) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (3-hydroxypropoxy)-(methyl)silanediol and N-acetyl-tyrosine as a stabilising/complexing agent, said organic silicon in hydroglycolic solution being prepared according to the preparation process described in test 1 above, but using successively 7.1 g of N-acetyl-tyrosine (32 mmoles) in 690 g of H.sub.2O, 6.92 g of a commercial solution of sodium methylsiliconate (equivalent to 32 mmoles of methylsilanetriol) diluted in 40 g of water, 200 g of 1,3-propanediol and then

TABLE-US-00008 mass-adjustment by addition of H.sub.2O to 1 kg   6% Carbomer (copolymer of acrylate/acrylamide & mineral oil) 1.5% Sodium benzoate 0.2% Sorbic acid   1% Soda 0.13%  Phenoxyethanol 0.9% Water qsp 100%

[0159] Formula C (Lotion)

[0160] Organic silicon in hydroglycolic solution (water/1,3-butanediol; 50/50) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (2-methyl-3-hydroxypropoxy)-(methyl)silanediol and trehalose as a stabilising/complexing agent, said organic silicon in hydroglycolic solution being prepared according to the preparation process described in test 1 above, but using successively 50 g of trehalose (146 mmoles) in 690 g of H.sub.2O, 6.92 g of a commercial solution of sodium methylsiliconate (equivalent to 32 mmoles of methylsilanetriol) diluted in 40 g of water, 500 g of 1,3-butanediol and then

TABLE-US-00009 mass-adjusted by addition of H.sub.2O to 1 kg   3% Chlorphenesin 0.2% Phenonip (parabens - butyl, ethyl, isobutyl, methyl, propyl 0.6% parahydroxybenzoate and phenoxyethanol) Xanthan gum 0.3% Triethanolamine 0.03%  Water qsp 100%

[0161] Formula D (Emulsion)

[0162] Organic silicon in hydroglycolic solution (water/1,2,3-propanetriol; 30/70) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (2,3-dihydroxypropoxy)-(methyl)silanediol and L-arginine HCl as a stabilising/complexing agent, said organic silicon in hydroglycolic solution being prepared according to the preparation process described in test 1 above, but using successively 6.7 g of L-arginine HCl (32 mmoles), 6.92 g of a commercial solution of sodium methylsiliconate (equivalent to 32 mmoles of methylsilanetriol) diluted in 40 g of water, 700 g of 1,2,3-propanetriol and then

TABLE-US-00010 mass-adjustment by addition of H.sub.2O to 1 kg 8% Hydrogenated polydecene 8% Capric/caprylic triglycerides 2% Ethoxydiglycol oleate 8% Glyceryl stearate 2% Dimethicone 1% Polyethylene glycol-100 stearate and glyceryl stearate 5% Propyl paraben 0.3%   Stearyl alcohol 1% EDTA (Ethylenediaminetetraacetic acid disodium dihydrate 0.2%   salt) Xanthan gum 0.4%   Wheat germ oil 1% Macadamia seed oil 1% Polyethylene glycol-8 & tocopherol & ascorbyl palmitate & 0.07%   ascorbic acid & citric acid Triethanolamine 0.35%   Water qsp 100%

[0163] Formula E (Food Supplement)

[0164] Organic silicon in hydroglycolic solution (water/1,2,3-propanetriol; 80/20) according to the invention (namely the above-mentioned “ternary complex represented by the scheme ° SW—AS—OS(11l)”) involving the substances methylsilanetriol, (2,3-dihydroxypropoxy)-(methyl)silanediol and alginic acid as a stabilising/complexing agent, said organic silicon in hydroglycolic solution being prepared according to the preparation process described in test 1 above, but using successively 3.9 g of alginic acid (18 mmoles), 6.92 g of a commercial solution of sodium methylsiliconate (equivalent to 32 mmoles of methysilanetriol) diluted in 40 g of water, 200 g of 1,2,3-propanetriol and then

TABLE-US-00011 mass-adjustment by addition of H.sub.2O up to 1 kg   14% Potassium sorbate 0.05% Sodium benzoate  0.1% Flavourings 0.03% Water qsp 100%