206 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table I. Proportions of free alcohols in Polychols, expressed as percentages of the amounts in the staxting material (Super Hartolan) Average "N" Lanosterol Cholesterol Long-chain alcohols Polychol • 12 95 50 30 Polychol 10 14 35 20 10 Polychol 20 23 15 5 5 Polychol 40 41 15 0 0 method (4). The results, expressed as percentages of the amount in the starting material, are shown in Table I. It is dear that the rate of reaction of ethylene oxide is fastest with the long chain alcohols and slowest with lanosterol. It follows that the derivatives of the long-chain alcohols are more extensively ethoxylated than those of lanosterol. Because the Polychols contain free alcohol, their N-values are misleading. Table I shows, approxi- mately, the average "N" for the total alcohol that has actually reacted, i.e., after allowance has been made for free alcohol. ' Fig. oe indicates that even the simplest of the Polychols is too complex a Figure 2. Chromatogram of polyethoxy derivatives of various alcohols. Substrate: Silicagel G Solvent: Cyclohexane/ethyl acetate (9 q-1) four elutions Key: H = Hartolan L=Product of the reaction between: Lanostenol (1 mole) and ethylene oxide (5 moles) P =Polychol I• O = Product of the reaction between: n-Octadecanol (1 mole) and ethylene oxide (5 moles) C=Product of the reaction between: Cholesterol (1 mole) and ethylene oxide (5 moles)

0 :M ! 1 2 3 M 4 5 6 M 7 8 9 Figure 3. Chromatograms of ethoxy cholesterols Substrate: Silicagel G Solvents: Left--Cyclohexane/ethyl acetate (3 +2) Right--Benzene/acetone/water (85 q- 40 q- 1) Loads: M, 100 gg others, 10 gg. Kev: M=Product of the reaction between: Cholesterol (1 mole) and ethylene oxide (5 moles) 0 = Cholesterol 5 = Penta-ethoxy cholesterol 1 =Mono-ethoxv cholesterol 6=Hexa-ethoxy cholesterol 2=Bi-ethoxy cholesterol 7----Hepta-ethoxy cholesterol 3=Tri-ethoxy cholesterol 8----Octa-ethoxy cholesterol .4=Tetra-ethoxy cholesterol 9•Nona-ethoxy cholesterol Facing page 206