Yucca Angustifoua: A CHEMICAL STUDY # \ IB IT HELEN C. De S. ABBOTT, Fellow of the American Association for the Advancement of Science; Member of the Academy of Natural Sciences, Philadelphia; of the Berliner Chemische Gesellschaft, etc., etc. (Repi-inted from the Transactions of the American Philosophical Society.) PHILADELPHIA: McCalla & Stavely, Printers, 1886. A CHEMICAL STUDY » OF YUCCA ANGUSTIFOLIA. BY H. C. DE S ABBOTT. Read before the American Philosophical Society, December 18, 1885. ARTICLE III. A CHEMICAL STUDY OF YUCCA ANGUSTIFOLIA.* H. C. DE S. ABBOTT. Read before the American Philosophical Society, December 18, 1885. This plant is well known in the West as the “ soap-weed.” It grows very abun- dantly in most of the Western States and Territories. It has attracted the attention of botanists, and it is a plant of interest on account of the many uses to which it has been put in the countries where it is found. The results noted in this paper are based upon a first and introductory chemical analysis of the Yucca. Previously, little has been studied of its chemistry. It is briefly mentioned in the work of a French writer, Dr. Georges Pennetier ;f also, in a paper on the study of manganese found in the ash of plants in which M. Maumene states that the ash of the Yucca contains He does not name what spe- cies of Yucca was examined. The former writer gives the micro-chemical characters of the action of iodine and sulphuric acid, dilute chromic acid, and cuprammonia on the fibres of the Yucca angustifolia. The specimens of Yucca used in these analyses were of large growth and in good condition. The entire plant was examined, and a separate study made of the bark and wood of the root, and of the green leaf and the yellow basal part. The roots were air- dried, freed from adherent dust, reduced to a very fine powder, and passed through a 80 sieve. The leaves were less finely powdered. DragendorfFs scheme for plant analysis§ has been generally followed. Ten grams of the air-dried powder were used for the preliminary examination of soluble substances. For every gram of the powder, ten c.. c. of the solvents were em- ployed. An additional quantity of the powder was prepared for special purposes. Five grams of the air-dried powder were dried, in a hot-air oven, at a temperature * An abstract of this paper was read befere the Chemical Section of the American Association for the Advance- ment of Science, at Ann Arbor, Michigan, August 28, 1885. f Leqons sur les Matieres Premieres Organiques, Paris, 1881, p. 440. % M. E. J. Maumen6, Bui. de la SochSt6 Chimique de Paris. Tome xlii, p. 305. § Plant Analysis. Qualitative and Quantitative, by G, Dragendorff, Translated from the German by Henry Greenish, London,* 1884. A CHEMICAL STUDY OF YUCCA ANGUSTIFOLIA. 255 between 100° C. and 110° C. until the weight remained constant, for the estimation of moisture. This powder was incinerated in a covered porcelain crucible at a dull red heat until the carbon was entirely consumed. The per cent, of total ash was deter- mined from it. QUALITATIVE ASH ANALYSES. Calcium, magnesium, potassium, sodium, iron, manganese, chlorides, phosphates, and sulphates, were found in every part of the plant. I. MOISTURE II. TOTAL ASH Determination of on the powder. I. II. Color of Ash. ' (1.) The bark of the root 6.78 per cent. 11.67 8.11 37.00 17.38 per cent. 15.75 5.75 10.63 reddish “ gray gray white (2.) “ wood “ (3.) “ green leaf (4.) “ yellow base of leaf PETROLEUM SPIRIT EXTRACTS. Extract (1) Baric of Boot. The maceration was conducted in an apparatus similar to one described in Drag- endorff’s “ Plant Analysis.”* A light petroleum spirit was used which boiled between 25° C. and 45° C. The extract was filtered from the powder-residue. It was a clear pale yellow-colored liquid, and slightly acid in reaction. A drop of the extract on evaporating left a uniform spot on blue paper. The extract was evaporated at the ordinary temperature. The residue was a solid, and it had the odor and characteristic crystalline structure of fatty acids, suggesting the presence of a fixed oil. Its melt- ing point was taken. The substance melted at 60° C., and on cooling solidified amor- phous. To determine the total amount of solids extracted, a definite volume of the extract was evaporated, dried, and weighed. TOTAL SOLIDS. Petroleum spirit residue dried at 100° C 1.24 per cent of solids. “ “ “ 110° C 1.20 “ “ “ 0.04 “ “ loss. The residue was identified as a fixed oil. It was soluble in petroleum spirit, ether, benzole, chloroform, amyl alcohol, carbon di-sulphide, and cold aqueous alka- lies ; incompletely soluble in cold or boiling 86 per cent, alcohol, 95 per cent, alcohol, absolute alcohol, acetic ether, and ammonium hydrate. Ho change of color was * Page 99, Tollen’s apparatus. 256 A CHEMICAL STUDY OF observed on treating the fixed oil with concentrated sulphuric acid, nor on the addi- tion of syrupy phosphoric acid, though it was partially soluble in these acids. Phos- phoric acid colored it yellow; it was colored yellowish by concentrated hydrochloric acid and nitric acid of 1.22 specific gravity. A mixture of concentrated, sulphuric acid and nitric acid of 1.22 specific gravity changed the color of the fixed oil to a red- dish-brown ; it was colored pale green by sulphuric acid of 1.634 sp. gr. and of 1.53 sp. gr. Calcium di-sulphide gave a bright green color reaction with the fixed oil, but did not form an emulsion with it; aqueous solutions of gold and platinum chlorides were reduced by it. The fixed oil was saponified with difficulty by alcoholic soda; but readily by boiling aqueous soda; a white fragile soap was separated and filtered from the liquid. The soap was decomposed by hydrochloric acid and the fatty acids separated. The filtrate from the soap was examined for glycerin. By the method* used, an oily liquid was obtained, it was heated with anhydrous borax on platinum foil, and gave the usual green-colored flame test for glycerin. The alcoholic solution of the petroleum spirit residue was fractionally precipitated with an alcoholic solution of magnesium acetate, and traces of an amorphous residue were recovered.f The petroleum spirit residue was digested with water containing sulphuric acid, and examined for alkaloids which are sometimes brought down with fixed oils. The usual reagents failed to detect traces of alkaloids. Extract (2), Wood of the Hoot. The maceration was carried out under the same conditions as in extract (1). The extract was a clear, colorless solution, neutral in reaction. A drop of the liquid left no uniform spot on blue paper. The extract was evaporated at the ordinary temperature. The residue was light yellow-colored, of a semi-solid consistency and melted at 36°fcC. A definite volume of the extract was evaporated, dried, and weighed. TOTAL SOLIDS. Petroleum spirit residue dried at 100° C 0.55 per cent of solids. “ “ “ 110° C 0.35 “ 0.20 “ “ loss. The residue was identified as a fixed oil; associated with volatile fatty acids. The latter were indicated by the 0.2 per cent of loss, and the disagreeable odor of the residue which was dissipated on heating at 110° C. The petroleum spirit residue from the extract was evaporated at the ordinary tem- perature, dissolved with difficulty in cold 95 per cent, alcohol, and in boiling weaker * “Plant Analysis.” G. Draggendorff, p. 12. fLoc. cit., page 16. 257 YUCCA A^CUSTIFOLIA. alcohol; absolute alcohol hardened and discolored it. Concentrated sulphuric acid, nitric acid, and hydrochloric acid, did not appreciably act on the residue. It was not saponified, but slowly dissolved by boiling aqueous and alcoholic soda. The alco- holic solution of the petroleum spirit residue was submitted to a fractional precipi- tation with an alcoholic solution of magnesium acetate. The first precipitation obtained was purified by boiling alcohol; it was an opaque scaly crystalline solid which melted at 85° C. The second precipitation yielded traces of a white amorphous substance. The third precipitation resulted from adding strong ammonia water to the magnesium acetate solution, and the purified residue melted at 60° C. Negative tests for alkaloids followed an examination of the aqueous treatment of the petroleum spirit residue. Extract (3), Qreen Part of the Leaf. The method of extraction was the same as that used in the previous extractions. The extract was clear, pale green in color, and non-fluorescent. It was colored by a small quantity of chlorophyll, which the petroleum spirit dissolved. The liquid was acid in reaction. A drop of it left a permanent stain on blue paper when evaporating. The extract was evaporated at the ordinary temperature, and the residue was a dark greenish-yellow semi-fluid substance. The solidifying point was taken. It was found to be about 15° C. A definite volume of the petroleum spirit extract was evaporated, dried, and weighed. TOTAI. SOIjIDS. Petroleum spirit residue dried at 100° C 2.20 per cent of solids. “ “ “ 110° C 2.01 0.19 “ “ loss. The petroleum spirit residue was identified as a fixed oil with a small amount of chlorophyll that had been brought into solution by it. It was soluble in cold 83 per cent, alcohol, 95 per cent, alcohol, absolute alcohol, amyl alcohol, ether, acetic ether, chloroform, benzole, carbon di-sulphide and glycerin. It was also soluble in oil of turpentine, almond oil, ammonium hydrate, mercuric chloride, and slowly soluble in acetic acid. Concentrated nitric acid, and hydrochloric acid slowly dissolved the fixed oil, the former colored it dark green, and on stirring the mixture the color was changed to a brown. Concentrated sulphuric acid dissolved and changed it to a very dark-brown color; on adding concentrated nitric acid, the liquid was changed to a reddish-brown color. The following reactions were noted: The fixed oil changed to a hard greenish- yellow substance on heating it with anhydrous borax on platinum foil. When rubbed 258 A CHEMICAL STUDY OF on a crucible lid with powdered rosaniline, it was colored red, showing the presence of free fatty acids. It did not emulsify with calcium di-sulphide nor with syrupy anti- mony chloride, but it was colored dark-green by the latter. It was imperfectly dis- solved by phosphoric acid, and slowly soluble in equal parts of cane sugar and concen- trated hydrochloric acid; more rapidly soluble in equal parts of cane sugar and nitric acid. An aqueous solution of picric acid made alkaline by sodium carbonate colored the fixed oil a light reddish-brown color, cane sugar added to the solution facilitated dissolving it. It was instantly dissolved by equal parts of picric acid and acid ammo- nium phosphate, and on warming with stannous chloride, leaving a turbid yellow- colored liquid. It was insoluble in aqueous barium hydrate; soluble in alcoholic am- monia with no coloration, and in sulphurous acid. It was colored brown when mixed with sulphuric acid of 1.634 specific gravity, and incompletely dissolved-; it was also colored brown by ferric chloride. On adding to the fixed oil sulphuric acid of 1.4T5 specific gravity, and a small quantity of zinc, hydrogen was generated, and the solubil- ity of the oil in the acid liquid was accompanied by a rosy tint given to the solution. Extract (4), Yellow Part of the Leaf. This extract was obtained by a similar process as that used for the other petro- leum spirit extracts. The extract was a pale yellow-colored liquid. The reaction was slightly acid. A uniform spot was left on blue paper as the drop evaporated. The petroleum spirit was evaporated at the ordinary temperature, and a yellow-colored residue recovered, of a semi-solid consistency and crystalline in structure. It solidi- fied at 12° C. From a definite volume of the petroleum spirit extract, the amount of total solids was determined. TOTAL SOLIDS. Petroleum, spirit residue dried at 100°tC 1.1 per cent of solids. “ “ “ 110° C 1.1 0.00 “ “ loss. The residue was identified as a fixed oil. It was soluble in warm absolute alcohol, incompletely soluble in weaker alcohol; soluble in cold acetic ether, chloroform, ben- zole, amyl alcohol, ether, carbon di-sulphide, and glycerin. It was saponified with aqueous soda and a white soap separated. No reaction was observed with picric acid and ammonium phosphate, nor with nitric acid of 1.32 specific gravity and 1.18 spe- cific gravity. The fixed oil was soluble in potassio-mercuric iodide solution; and colored dark-brown by alcoholic ammonia. A mixture of ferric chloride solution and powdered rosaniline gave a fine violet-colored reaction with the fixed oil. An examination of the aqueous treatment of the petroleum spirit residues (3) and YUCCA ANGUSTIFOLIA. 259 (4), for alkaloids, gave negative results. A portion of the original powder, from each of the four parts of the plant, was mixed with an aqueous solution of caustic soda, and the distillate examined for volatile alkaloids with negative results. SUMMARY i. Petroleum Spirit Extracts. Solids extracted. Character of residue Reaction with litmus. Melting point. Solidifying point. 1. The bark of the root..... 2. “ wood “ 3. “ green leaf 4. “ yellow base of leaf.. 1.24 per cent. 0.55 2.20 “ 1.10 fixed oil t i < < / «« « 1 1. chlorophyll / fixed oil slightly acid neutral acid faintly acid 60° C. 36° C. f semi-fluid at 1 ordinary V (temperature j f solid at ordinary \ temperature 15° C. 12° C. The solids extracted by petroleum spirit from the four parts of the plant are iden- tified as fixed oils*; associated with a volatile principle (0.2 per cent) in extract (2), and with traces of chlorophyll in extract (3). Fixed oil (1) was crystalline in structure. It was soluble in ether, chloroform, benzole, carbon di-sulphide, and amyl alcohol; incompletely soluble in cold or boiling alcohol, acetic ether, and ammonium hydrate. It was colored pale green by sulphuric acid of 1.634 specific gravity, and changed to a bright-green color by calcium di- sulphide, but formed no emulsion with it. Phosphoric acid colored it yellow. The fixed oil was saponified, and a white soap separated. This was decomposed, and the fatty acids recovered. Glycerin was separated from the soap filtrate. Fixed oil (2) was dissolved with difficulty in boiling 95 per cent, alcohol, and hardened and discolored by absolute alcohol. It was not saponified. Crystalline solids were separated by precipitating the alcoholic solution with magnesium acetate. They melted at 85° C., and at 60° C., respectively. Fixed oil (3) was soluble in alcohol, ether, chloroform, benzole, carbon di-sul- phide, oil of turpentine, almond oil, glycerin, and slowly soluble in acetic ether. The presence of free fatty acids was demonstrated. The fixed oil was colored dark-green by syrupy antimony chloride; on adding to it sulphuric acid of 1.475 specific gravity, and a small quantity of zinc, hydrogen was generated, and the solubility of the oil in the acid liquid was accompanied by a rosy tint given to the solution. Fixed oil (4) was crystalline in structure. It was soluble in warm absolute alcohol, in cold acetic ether, chloroform, benzole, amyl alcohol, ether, carbon di-sul- phide, and glycerin. It was saponified, and a white soap separated. The fixed oil was colored dark-brown by alcoholic ammonia, and a mixture of ferric chloride solu- tion and powdered rosaniline gave a violet-colored reaction with it. * Fixed Oils. Science, Sept. 11, 1885. A. P. s.—VOL. XVI. 2a. 260 A CHEMICAL STUDY OF These fixed oils differed in their physical characters and chemical reactions. This difference may be due to the presence of free fatty acids and glycerides in vary- ing proportions in the four parts of the plant. It is of interest to note that in the sub- terranean part of the Yucca, the oil extracted from the bark was solid at the ordinary temperature; from the wood it was of a less solid consistency; while the yellow base of the leaf contained an oil quite soft, and in the green leaf the oil was almost fluid. Extract (2) contained an oil of low melting point. It melted at 36° C. An alcoholic solution was fractionally precipitated with magnesium acetate, and three members of the fatty acid series were isolated. The quantities obtained were small, and it was impossible to do more than to take the melting point of two of the purified crystalline residues. They melted at 85° C., and at (50° C. respectively. It is a well- known fact that a mixture of fat acids in certain proportions has a lower melting point than those of its constituents. Alkaloids and volatile-alkaloids were not detected in the 'petroleum spirit extracts. ETHER EXTRACTS. Extract (1), Baric of the Boot. The residual powder from the petroleum spirit extraction was dried until thoroughly freed from petroleum spirit. It was then macerated with Squibbs’ stronger ether in the apparatus already described. The ethereal extract was filtered from the powder. It was a clear crimson-colored liquid, tinted by some red coloring matter dissolved; and acid in reaction. The extract was slowly evaporated at the ordinary temperature; white needle-shaped crystals were seen as the liquid concentrated. The ethereal residue was of a resinous character. It was ruby-colored, transparent, and of a softer consistency than ordinary resin. Microscopically, the residue was identified as a resin by its color reaction with Hanstein’s aniline violet solution.* The ethereal residue was treated with petroleum spirit to remove any traces of fat that may have been extracted with it. It was heated in a small tube, at 50° C. it experienced a slight change, and melted at 70° C. For a determination of the total solids, a defi- nite volume of the ethereal extract was evaporated, dried, and weighed. TOTAL SOLIDS. Ethereal residue dried at 100° C 3.16 per cent of solids. “ “ “ 110° C 3.16 “ “ “ 0.00 “ “ loss. The resin was incompletely soluble in 95 per cent, alcohol, absolute alcohol, and * Botanical Micro-Cliemistry. Poulsen-Trclease. Boston, 1884, p. 59. 261 YUCCA ANGUSTIFOLIA. amyl alcohol; readily soluble in ether; not appreciably soluble in chloroform, benzole, and carbon di-sulphide. It was dissolved by sulphuric acid to a colorless solution, which, on warming, turned to a yellow color, and gradually darkened to a dull brown color, fading to a pale yellow. An attempt was made to separate the white needle-shaped crystals mentioned above. The ethereal residue was agitated with acetic ether. The liquid was filtered from the insoluble matter and evaporated. Traces of a resinous substance were sepa- rated. The insoluble matter was treated with boiling ether, filtered hot, and the fil- trate concentrated. On cooling, the white needle-shaped crystals reappeared. They were insoluble in water and in acetic ether. A separate portion of the ethereal extract was evaporated, and treated with warm distilled water. The aqueous extract was made up to a definite volume, and a known quantity evaporated, dried, and weighed. The amount of total solids was almost in- appreciable by weight. The aqueous extract was not colored by iron salts, and it did not form a precipitate with alum and gelatine solution, lead acetate, potassio-mercuric iodide, nor gold chloride solutions; showing absence of tannin, gallic acid, and alka- loids. The ethereal extract was directly tested for these compounds, and with nega- tive results. A portion of the aqueous extract was evaporated to dryness, and treated with potassa solution, and the residue dissolved with no coloration. Another por- tion of the aqueous extract was agitated with acetic-ether, and the liquids were sepa- rated ; on evaporating the acetic ether solution, traces of a residue were obtained which sulphuric acid acted upon. A resinous substance separated from the green- ish-colored acid liquid, the former was partially disintegrated by cold water. The specific gravity of the resin was 1.091. Extract (2), the Wood of the Root. The residual powder from the petroleum spirit extraction was macerated in stronger ether. The ethereal extract was of a reddish-yellow color; slightly acid in reaction. It was slowly evaporated at the ordinary temperature, and as the liquid con- centrated, white needle-shaped crystals appeared, and presented the same physical structure as the crystals found in the ether extract (1). The ethereal residue was identified as a resin. It was a transparent, ruby-colored substance, and acid in reaction. It was heated to 50° C., at that temperature its color deepened, and at 70° C. it melted. The specific gravity of the resin was 1.091. A definite volume of the ether extract was evaporated, dried, and weighed to determine the amount of total solids. 262 A CHEMICAL STUDY OF TOTAL SOLIDS. Ethereal residue dried at 100° C 1.70 per cent, of solids “ “ “ 110° C 1.45 “ “ “ 0.25 “ “ loss. The resin was examined by Hirschsohn’s scheme* with a view to classify it with known resins. It was imperfectly soluble in 95 per cent, alcohol and chloroform ; soluble in ether. The alcoholic solution gave a turbidity with lead acetate, not cleared upon boiling, and with ferric chloride formed a clear mixture. Concentrated sulphuric acid dissolved the resin, leaving a dark yellow-brown liquid which faded to a dull yel- low color. The sulphuric acid solution when mixed with alcohol, changed to a pale gray color. On addition of water to the acid solution, there was no coloration nor separation of the resin. Alcohol containing hydrochloric acid gave no color reaction with the resin. Bromine solution added to the chloroform-resin extract, and iodine solution to the ether-petroleum-resin extract, gave no reactions. Sodium carbonate at the ordinary temperature had no elfect on the resin, but on boiling the liquid was colored yellow. By the above examination, this resin was thrown out of the numerous classes of described resins. It is proposed to name it yuccal.t Yuccal was soluble in boiling-absolute alcohol and acetic ether; incompletely soluble in benzole, carbon di-sulphide, alcoholic ammonia, and cold acetic ether. The red color of the resin was removed by cold acetic ether, a transparent substance remaining, soluble in hot acetic ether.J Yuccal was dissolved by potassio-mercuric iodide. It reduced aqueous solutions of gold and platinum chlorides. A blood-red color reaction was obtained by warming a small quantity of the resin on a crucible lid with a crystal of ammonium molybdate and a few drops of nitric acid. On adding to the resin mixture a few drops of strong sulphuric acid, and again warming, it was dis- solved. Warm dilute nitric acid dissolved the resin, colorless ; cold nitric acid gave a brownish-green color reaction.§ Yuccal was heated on platinum foil, and as it decom- *E. Hirsclisolin. Watts Chem. Diet. Yol. viii, Pt. ii, p. 1743. f I suggest that in future all resins be distinguished by the terminal syllable al, for uniformity of resin nomencla- ture. Yuccal ; Science, September 11, 1885, p. 210. $ I have examined the action of acetic ether as a solvent for resins. Cold acetic ether dissolved ordinary resin, turpentine, styrax, tolu-balsam, mastic, elemi, Canada-balsam, Peru-balsam, copaiba-balsam, Yenice-turpentine, and incompletely spruce gum, and yuccal. In hot acetic ether spruce-gum and yuccal were soluble. The following resins were insoluble in hot or cold acetic ether, guiacum, sandarac, shellac, benzoin, olibanum, ammoniac, myrrh, galba- num, and asafoetida. § A reddish-yellow decomposition product resulted from the action of nitric acid on many resins which fol- lowed generally quite soon after adding the acid to a small quantity of the resin (0.1 gram of the resin and 5 c. c. of nitric acid 1.4 sp. gr.). But the reaction which took place varied according to the conditions, i. e., strength of acid used, 263 YUCCA ANGUSTIFOLIA. posed the fumes that were given off were pleasant and aromatic. Tests failed to show the presence of benzoic or cinnamic acids. The ethereal residue was treated with warm water, and on cooling, the liquid was agitated with acetic ether, which was separated, and when evaporated yielded a small quantity of resinous substance. The ethereal residue insoluble in water was treated with boiling ether, and as the liquid concentrated, the white needle-shaped crystals were seen floating in it, but on further concentration they could not be seen, and a yellow greasy-looking mass settled in the bottom of the beaker. On driving off the ether, a transparent and ruby-colored resinous substance remained. The aqueous extract obtained in the way described above gave no coloration with iron salts, and no precipitate with gelatine and alum solution, potassio-mercuric iodide, or gold chloride solutions. Fehling’s solution was not reduced by boiling, though the aqueous ex- tract was boiled with acid, then rendered alkaline before adding the copper test. The preceding tests gave negative results for gallic acid, tannin, alkaloids, and glucosides. A portion of the aqueous extract was acidified and agitated successively with differ- ent solvents, for glucosides, bitter principles, and alkaloids which may be removed from solution by this means. The acid liquid was then rendered alkaline with am- monia, and agitated successively with the same order of solvents that were used with the acidified liquid. Yo solids were separated by these methods. The ethereal residue insoluble in water was treated with alcohol; and yielded traces of a resinous sub- stance. The residue insoluble in water and alcohol was not dissolved by ether, acids or alkalies. Yuccal or the ethereal residue soluble in ether and alcohol was saponified, and the soap boiled with lead acetate. The yellow masses were collected on a filter and treated with boiling ether, and the filtrate was slowly evaporated. The residue was a granular solid. This substance was imperfectly purified by repeated boiling with ether, and a solid of crystalline structure obtained. It gave an acid reaction with litmus, and a red color with concentrated sulphuric acid. The acid dissolved a substance enclosing the crystals, leaving the structure of the latter uninjured and colored. Strong nitric acid dissolved the crystals with no coloration. They were soluble in absolute alcohol, amyl alcohol, benzole, chloroform, glycerin, and a solution of alcoholic soda; soluble in potassium iodide, potassium chromate, mercurous nitrate, cobalt nitrate, potassium ferro-and-ferri-cyanide solutions; insoluble in ammonia and aqueous alkalies. the application of heat to the resin acid mixture, or the addition of solvents to the mixture. The more concentrated the acid the more rapid was the reaction. The application of heat also hastened the change, especially if a more dilute acid was used in the mixture. Some solvents acted like heat by increasing the energy of the reactions. Alcohol and ether were active solvents, and the reaction was attended by the escape of nitrous fumes from the combination of alco- hol or ether and nitric acid. Chloroform and benzole were indifferent. Amyl alcohol acted feebly. 264 A CHEMICAL STUDY OF Yuccal was treated with spirit of different strengths, as a means of separating resin acids if any were present. It was treated with 85 per cent, spirit; an opaque brown substance was left undissolved, which was soluble in absolute alcohol; insolu- ble in ether, and colored brown by concentrated sulphuric acid. The color was not discharged by alcohol or ether. The 85 per cent, spirit solution was evaporated, and the residue treated with 50 per cent, spirit and a small quantity of a brown residue was insoluble. The 50 per cent, spirit solution on evaporating left a non-crystalline, transparent, reddish-colored solid; acid to litmus. It was colored cherry-red by con- centrated sulphuric acid, and slowly dissolved to a yellowish-red liquid. Extract (3), the Green Part of the Leaf. The residual powder from the petroleum spirit maceration was thoroughly dried, and again placed in the percolator. It was treated with Squibbs’ stronger ether. The extract was a deep-green colored liquid and fluorescent. The reaction was slightly acid. Alcohol, benzole, and petroleum spirit added to the ethereal extract did not cause a precipitation. An amorphous and green-colored residue was obtained on evaporating the extract. The amount of total solids was estimated from a definite volume of the extract, which was evaporated, dried, and weighed. TOTAL SOLIDS. Ethereal residue dried at 100° C 1.25 per cent of solids. “ “ “ 110° C 1.14 “ “ “ 0.11 “ “ loss. The ethereal residue was brought into a state of fine division and treated with water. The amount of total solids soluble in ether and water was 0.34 per cent. The aqueous extract was neutral in reaction. It was faintly colored and slightly bitter to the taste. It was not colored by iron salts nor precipitated with alum and gelatine solution, showing absence of gallic acid or tannin. Copper solutions were not reduced, indicating absence of glucosides, though the precaution was observed of boiling the aqueous extract with acid and rendering alkaline before adding the copper solution. The aqueous extract was agitated with acetic ether and a distinctly crystalline resi- due separated. Under the microscope these crystals were white, needle-shaped and arranged in bundles. They did not respond to tests for gallic acid. Potash solution formed a yellow mixture with the crystals. The color was discharged by a drop of hydrochloric acid. Chloroform did not dissolve any substance from the ethereal residue. The ethereal residue was treated with acidulated water and tested negatively for alkaloids. The ethereal residue insoluble in water was treated with alcohol. The amount of YUCCA ANGUSTIFOLIA. 265 substances insoluble in water, and soluble in ether and alcohol was 0.15 per cent. The alcoholic solution was evaporated, and the residue was crystalline in structure. Concentrated sulphuric acid imperfectly dissolved it, and gave a reddish-yellow color reaction; acetic ether discolored the solution. The alcoholic residue was insoluble in acetic ether, cold and boiling aqueous alkalies; soluble in chloroform. It saponified with alcoholic soda. The amount of the ethereal residue insoluble in water and alcohol was 0.65 per cent. It not soluble in alcoholic or aqueous soda. This would indicate a resin anhy- dride. Concentrated sulphuric acid gave no color reaction with it; and a mixture of sulphuric acid and cane sugar dissolved the residue. The ethereal residue on treating with cold ether was not entirely soluble in it. It was soluble in chloroform, benzole, and carbon di sulphide ; incompletely soluble in cold alcohol, and insoluble in amyl alcohol. The ethereal residue was treated with 95 per cent, alcohol, in which it was slightly soluble. A turbidity formed in the alcoholic so- lution on adding lead acetate, ferric chloride, ammonium hydrate, and sulphuric acid; it did not clear up on warming. Hydrochloric acid made a muddy mixture with the alcoholic solution. The ethereal residue was not entirely soluble in acetic ether; the latter separated coloring matter from it. The ethereal residue, insoluble in acetic ether and freed from coloring matter (chlorophyll), was a resinous substance. It melted at 80° C. The resin was boiled with absolute alcohol, and on throwing the alcoholic so- lution into cold water it was precipitated as a white cloud. It was not saponified. Extract (4), Yellow Base of Leaf. The residual powder from the petroleum spirit maceration was dried and extracted with stronger ether. The ether extract was a turbid yellow liquid; slightly acid in reac- tion. On evaporating the ethereal extract at the ordinary temperature a reddish-yellow granular solid remained. It melted at 79° C. For the determination of total solids extracted, a definite volume of the extract was evaporated, dried, and weighed. I. TOTAL SOLIDS. Ethereal residue dried at 100° 1-7 Per cent of solids. “ “ “ 110° 1.7 “ “ '* 0.0 “ “ loss. The ethereal residue was treated successively with distilled water, alcohol, and ether. ii. Substances souble in ether and water 0-8 Per cent* “ “ “ alcohol 0*4 “ insoluble in water and “ 0.5 Total solids, 1-7 266 A CHEMICAL STUDY OF The aqueous extract gave a neutral reaction with litmus. Negative results fol- lowed examination for tannin, gallic acid, glucosides, alkaloids, and any compounds containing nitrogen. The ethereal residue (the residue insoluble in water) was an opaque reddish-yellow colored substance, and was identified as a resin. It melted at 79° C. It was insoluble in ether, benzole, chloroform, and acetic ether; incompletely soluble in cold absolute alcohol, amyl-alcohol, carbon di-sulphide, and oil of turpentine. It was soluble in aqueous and alcoholic soda. On boiling with them, it was saponified. Concentrated sulphuric acid dissolved the resin and colored it a yellowish-brown. Chloroform formed a turbid mixture with the acid solution. The action of strong nitric acid on the resin was slow. The resin was incompletely soluble in 95 per cent, alcohol. Lead acetate gave a cloudiness with the alcoholic solution which increased on boiling. Ferric chloride thickened the alcoholic solution, and on boiling it gave a yellow precipitate which was insoluble in acids, alkalies, absolute alcohol, and acetic ether. The chloro- form extract gave no coloration with bromine solution. SUMMARY II. Ethereal Extracts. Solids ex- tracted. Character of residue. Reaction with litmus. Melting Point. Specific gravity Substances soluble in ether and water. Substances soluble in alcohol and water. Substances soluble only in ether. 1. The bark of the root 2. “ wood “ 3. • “ green leaf. 4. “ yellow base of leaf... 3.16 p. ct. 1.70 “ 1.25 “ 1.70 “ resin { chlorophyll } resin acid slightly “ iC <(