374-1213-10m TEXAS AGRICULTURAL EXPERIMENT STATIONS BULLETIN NO. 162 DECEMBER. 191s DIVISION OE CHEMISTRY Composition and Digestibility of the (Ihloroform Extract of Hays and’ Fodders POSTOFFICE: College Station, Brazos Ccunty, Texas AUSTIN, TEXAS VON BOECKMANN-JONES 00., Pnmwna AGRICULTURAL AND MECHANICAL COLLEGE 0F TEXAS CHARLEs PURYEAR, President Pro Tern. TEXAS AGRICULTURAL EXPERIMENT STATION BOARD OF DIRECTORS FFWWU shah-m]; . B. CUSHING, President, Houston ...................... .. OHN I. GuIoN, Vice-President, Ballinger .............. .. . H. ASTIN, Bryan ................................................ .. . J. HART, San Antonio ..................................... 44 . L. BENNETT, Paris .......................................... .. . E. BATTLE, Marlin ......................................... .. .................................................... ..Term expires 1915 .......................................... ..Term expires 1919 .......................................... ..Term expires 1919 ................. ..Term expires 1919 ................. ..Term expires 1917 ................ .. Term expires 1917 . S. WILLIAMS, Paris ....................................................................................... ..Term expires 1917 . ALLEN KYLE, Houston ...... .. . . . . . . . . . . . . . . . . . . . . . . . . .. ALTON PETEET, Fort Worth ................................ .. ................. ..Term expires 1915 .............ili..illlllill.ll. ..................... ..Term expires 1915 GOVERNING BOARD, STATE SUBSTATIONS WILL H. IVIAYES, President, Brownwood .............. .. P. L. DOWNS, Vice-President, Temple ....................... .. CHARLEs ROGAN, Austin ............................................. .. .................................................... ..Term expires 1915 .................................................... ..Term expires 1915 ..................... ..Term expires 1919 ................. ..Term expires 1917 STATION STAFF ADMINISTRATION B. YOUNGBLOOD, M. S., Director A. B. CONNER, B. S., Assistant Director CHAs. A. FELKER, Chief Clerk A. S. WARE, Secretary DIVISION OF VETERINARY SCIENCE M. FRANcIs, D. V. S., Veterinarian in Charge _ _ H. SCHMIDT, D. V. M., Assistant Veter- inarian DIVISION OF CHEMISTRY G. S. FRAPs, Ph. D., Chemist in Charge J. B. RATHER, M. S., Assistant Chemist WILLIAM LEVIN, A. B., Assistant Chemist J. W. CHEWNING, B. S., Assistant Chemist DIVISION OF HORTICULTURE H. NEss, M. S., Horticulturist in Charge W. S. HOTCHKISS, Horticulturist DIVISION OF ANIMAL HUSBANDRY J. C. BURNS, B. S., Animal Husbandman in Charge , Animal Husbandman DIVISION OF ENTOMOLOGY WILMON NEwELL, M. S., Entomologist in Charge _ F. B. PADDOCK, B. S. E., Entomologist DIVISION OF AGRONOMY A. B. CONNER, B. S., Agronomist in Charge. A. H. LEIDIGH, B. S., Agronomist in Charge of Soil Improvement _ H. H. Jonson, B. S., Assistant Agronomist R. E. DICKSON, B. S., Assistant Agronomist DIVISION OF PLANT PATHOLOGY AND PHYSIOLOGY n,“ c-‘F. H. BLoncETr, Rh. D., Plant Pathologist and Physiologist in Charge *DIVISION OF FARM MANAGEMENTH" REx E. WILLARD, M. S., Farm Management Expert in Charge DIVISION OF FEED CONTROL W. L. BOYETI‘, State Feed Inspector J. H. RoGERs, Deputy Feed Inspector W. H. W001), Deputy Feed Inspector T. H. WoLTERs, Deputy Feed Inspector R. B. EHLINGER, Deputy Feed Inspector SUBSTATION N0. 1: Beeville, Bee County E. E. BINFORD, B. S., Superintendent SUBSTATION NO. 2: Troup, Smith County -W. S. HOTCHKISS, Superintendent R. W. Cox, B. S., Scientific Assistant SUBSTATION N0. 3: Angleton, Brazoria County N. E. WINTERs, B. S., Superintendent J. W. JAcKsoN, B. S., Scientific Assistant *SUBSTATION NO. 4: Beaumont, Jetferson County E. M. JoHNsToN, B. S., Superintendent SUBSTATION NO. 5: Temple, Bell County A. K. SHORT, B. S., Su erintendent W. Z. MILLER, B. S., cientific Assistant SUBSTATION NO. 6: Krum, Denton County T. W. BUELL, B. S., Superintendent SUBSTATION NO. 7: Spur, Dickens County I. S. YoRK, Superintendent _ E. W. HARRISON, B. S., Scientific Assistant SUBSTATION N0. 8: Lubbock, Lubbock County V. L. CORY, B. S., Superintendent SUBSTATION NO. 9: Pecos, Reeves County H. C. STEWART, B. S., Superintendent J. M. THoMsoN, B. S., Scientific Assistant SUBSTATION NO. 10: Feeding and Breeding Substation, College Station, Brazos County C. S. SCHARFF, Acting Superintendent SUBSTATION NO. 11: Nacogdoches, Nacog- doches County G. T. McNEss, Superintendent CLERICAL ASSISTANTS STATION J. M. ScHAEnEL, Stenographer C. A. CAsE, Stenographer C. L. DURsT, Mailing Clerk FEED CONTROL DAISY LEE, Registration Clerk MATTIE THOMAS, Stenographer P. K. BROWNLEE, Shipping Clerk *In cooperation with Bureau of Plant Industry, United States Department of Agriculture. TABLE OF CONTENTS Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 5 Quantity of the Chloroform Extract . . . . . . . . . . . . . . . . . . . . . . . . . . .. 5 Constituents of the Chloroform Extract . . . . . . . . . . . . . . . . . . . . . .. 5 Quantitative Separation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 8 Digestibility of the Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..11 Method for Determination of Constituents in the Choloroform Extract of Hays and Fodders . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..13 Tables of Analyses and Calculations . . . . . . . . . . . . . . . . . . . . . . . . . . . . .15 Summary and Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20 BLANK PAGE IN ORIGINAL COMPOSITION AND DIGESTIBILITY OF THE CHLOROFORM EXTRACT OF HAYS AND FODDERS BY G. S. Faxrs, PH. D., Chemist. J. B. RATHER, M. S, Assistant Chemist. It was proposed to follow the examination of the ether extract of hays and foddcrs (published as Bulletin No. 150), with a study of the alcoholic extract, Preliminary studies showed, however, that on dilutio-n of the alcoholic extract with water, and extraction of it with ether, appreciable percentages of material were secured, which partly consisted of. unsaponifiable and saponifiable matter, together with chlorophyll. As previous studies (Bulletin 150) had shown that the feeding stuffs contain substances difficultly soluble in cold ether, but easily soluble in chloroform, some preliminary tests were made b-y extracting the material (previously extracted with ether) with chloro- form. As these tests showed appreciable quantities of chloroform- soluble substances, the investigation here reported was undertaken. QUANTITY OF THE CHLOROFORM EXTRACT. The quantity of ‘the chloroform extract is given in Table 1, for com- parison with the percentages of ether extract, secured by the extraction with ether which precedes the.chloroform extraction. The chloroform extract is, on an average, 0.80 per cent compared with 1.85 per cent for the ether extract, or 43 per cent. The comparative amounts are close with some of the hays, such as alfalfa, para. grass and Bermuda hay. CONSTITUENTS OF Tl-IE CHLOROFORM EXTRACT. The chloroform extract from the green hays and fodders Was highly colored, and clearly contained chlorophyll. The residue left after sa.ponification and extraction of the unsaponified material, was likewise highly colored. No attempt was made in the investigation of the ether extract to separate the coloring matter from the fatty acids. In the work on ‘the chloroform extract it was found that. if the alkali solution remaining after extraction of the unsaponified were made acid with acetic acid and extracted with petroleum ether, the coloring mat- ter remained in the aqueous solution, and the fatty acids secured were nearly colorless. On acidification of the aqueous solution with hydro- chloric acid and extraction withethyl ether, a third product was se- cured, which was highly colored when the source of the chloroform extract was green hays or’ fodders. This method is based upon state- ments in Beilstein III, page 657, according to which, alkachlorophyll may be purified by extracting the aqueous solution of the sodium salt, dissolved in water and acidified with acetic acid, with ether, and on TEXAS AG-RICIILTURAI, EXPERIMENT STATIONS. m? a2 ...................................................................................... ..%§< @@.% . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' - . - . ..~% E w? HHHHHHmxmmmxmmmunmmmHHmHHHUQHYYHHHHHHHHHHHHm .......................... Qmgwrmwwww M 3H N? .......................................§...................HHHHHUHHinwiéwswqomvEEEE 2 U» fi S o Acmmmwv Bmbw ofifl N. 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By means of this procedure, xvhich is described in detail below, the chloroform extract was separated into three constituents: A. Unsaponifiable material, B. Colorless saponified material. C. Colored saponified material. Quantities of five hundred grams each of the hays, fodders or excre- ments were separated into these three constituents, and they were then subjected to further study. Unsaponified Material.—'l‘he acetyl compounds of the unsaponified -material from three products were prepared and recrystallized twice from alcohol. The mother liquors were combined and evaporated. The a.cetyl numbers of the products are as follows: ‘ PROPERTIES OF CRYSTALLIZED ACETYL PRODUCTS. Saponification Melting Number. Point. 4240 Excrement, Johnson grass hay . . . . . . . . .. 112.0 69-70° 4261 Excrement, peanut hay . . . . . . . . . . . . . . . . . 124.0 71-73° 4665 Excrement, rice straw . . . . . . . . . . . . . . . . .. 115.0 72-‘73° The acetyl numbers of the crystals are near to that of myricyl alco- hol, which is 116.4. This corresponds to the crystals separated from the ether extract of burr clover. The saponification numbers of the acetyl compounds in the.mother liquors also correspond to some extent with the saponification numbers of the mother liquors from the acetyl compounds from the ether "ex- tract (Bulletin No. 150). The former were extracted from the excre- ments, the latter from the feeds. SAPQNlFyICATlON NUMBER OF ACETYL COMPOUNDS OF MOTHER LIQUORS. " Chloroform extract. Ether extract. l 424.0 Johnson grass hay . . . . . . . . . . . . .. 176.9 163.1 4261 Peanut hay ., . . . . . . . . . . . . . . . . . .. 196.7 168.7 4665 Rice straw . . . . . . . . . . . . . . . . . . . .. 203.8 ' 190.0 It appears probable that the unsaponified material of the chloroform extract consists of wax alcohols or is derived from waxes, which were not completely extracted during the previous extraction with ether. Fatty Ac~ids.—The fatty acids, which were nearly colorless, had the fOllOXR-‘lllg neutralization numbers. The corresponding values for the ether extract are also given. Chloroform extract. Ether extract. 3279 Excrement, alfalfa . . . . . . . . . . . . .. 87.1 165 4240 Excrement, Johnson grass. . . . . . . . 127.8 140 4261 Excrement, peanut hay . . . . . . . . .. 171.2 205 4665 Excrement, rice straw . . . . . . . . . . .. 160.5 169 The error may be several units, on account of the small quantity of 8 TEXAS Ae-RIoULTURAL EXPERIMENT STATIONS. "est: material used. The saponified material from the ether extract con-J tained chlorophyll, and was green in color, which interfered with the titration. There are considerable differences between the fatty acids of the ether extract and of the chloroform extract; yet we must allow for the pres- ence of the chlorophyll in the ether extract and for the fact that the fats and oils are easily soluble in ether, which would account for a part of the differences, It is quite probable that the fatty acids are in the form of waxes not easily soluble in ether; it is also possible that a por- tion comes from the decomposition of other substances soluble in chlo- roform. Colored Saponified Ezvtract.—The colored saponified extract was pre- pared by a method which could separate chlorophyll from the fatty. acids. From rice straw, it was yellow in color. The following are some estimations of nitrogen in these products; 0.7 gm. substance was used: i 3279 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..Per cent nitrogen 1.42 3700 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Per cent nitrogen 0.72 3877 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..Per cent nitrogen 0.26 3223 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..Per cent nitrogen 0.58 4240 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..Per cent nitrogen 0.56 4261 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Per cent nitrogen 0.64 4665 . . . . . . . . . . . . . . . . . . . . . . . . . .' . . . . . . . .Per cent nitrogen 0.38 Average . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 0.65 The chlorophyll present in this saponified extract would pro-bably be present as phyllotaoin, containing 1.2.0 per cent nitrogen. If We as- sume that all the nitrogen is present in this compound, the colored saponified extract would contain, on an average, 5.41 per cent; the maximum amount present would be 11.53 per cent. The bulk of the product must, therefore, consist of other substances than chlorophyll. This conclusion is also in accord with a number of other determinations of nitrogen made directly on the total chloroform extract. QUANTITATIVE SEPARATION. The method for the quantitative separation of the constituents of the chlorophyll extract is described in deta.il below. The results of the separation of the constituents of ‘the hays and fodders are given in Table 2. Table 3 shows the percentage composition of the extracts, based upon the total chloroform extract as 100. A comparison of the. percentage composition of the ether extract and of the chloroform extract, from the hays and fodders, shows great dif- ferences. Unsaponifiable. Total saponifiable. Loss. Ether extract . . . . . . . . . . . . . . . . .. 58 36 6 Chloroform extract . . . . . . . . . . . . .. 25 55 20 The chloroform extract contains much less unsaponifiable matter and, when both colorless and colored saponified are taken together to be the CHLOROFORM EXTRACT OF HAYS AND FODDERS. 530* - ¢ - - . - - - - - - - - - - - - - - - - - - - - . - . - - - . - - . ¢ . . ~ - Q - §ono -- ¢ u . - ~ - . - . - . - . - ¢ . - - - - - . - . - - - . ¢ . - ~ - ~ | ~ - - - - - ¢ - - . - ¢ - - - ¢ - - . - . - . - . . ~ . - - - - - - - - - - nuOlunoruhmn w bud £6 .070 2.0 w» 0 . . . . . . . . . . . . . . . . . . . . >2 559cm m mad 0m.0 2.0 2.0 Nwd .. IN . . . . . . . . . . . . . . . . . . . . . .. 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If, l1owever, we consider that tl1e colorless saponifiable matter of tl1e chloroform ex- tract corresponds to t_l1e saponifiable matter of tl1e ether extract, we- havc 36 per cent of the ether extract to compare with 20 per cent in the chloroform extract. This assumption is justified, to a. certain ex-v tent, for we know that the ether extract contains fats and oils (if present) and that the chloroform extract will contain non-fats, The chief differences between the ether extract and the chloroform extract would then consist in much larger quantities of colored saponified matter (not liberated by acetic acid and dissolved by petroleum ether) and a n1ucl1 higher percentage of loss. The higher percentage of loss may be in part due to the loss inherent in Working on such small quan- tities; it may also be due to the solution of substances in water, not: subsequently extracted by the ether. The conclusion is, that while chloroform dissolves some waxes or wax: alcohols not dissolved by the previous extraction with ether, it also» dissolves materials not soluble easily in ether; which are neither waxes, wax alcohols nor fatty acids, and which contain only a comparatively- small percentage of chlorophyll, but are somewhat related to chlorophyll in their behavior towards acetic acid and solvents. ‘ vi ll _E DIGEsTIBILITY or THE PRODUCTS. The digestibility of the chloroform extract and its products is worked out in the tables given at the end of this Bulletin. Table 4 shows the average digestibility of the chloroform extract of the various hays and fodders. A comparison of the average percentage of digestibility of the ether extract and the chloroform extract is made below: COEFFICIENTS OF DIGESTITIBILTTS.’ OF (‘ONSTITUENTS OF EXTRACTS. Chloroform extract. Ether extract. Total . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 45.7 41.9 Unsaponifiable . . . . . . . . . . . . . . . . . . . . . . .. 21.4 29.1 Saponifiable (total) . . . . . . . . . . . . . . . . . . . . . 66.4 Saponifiable (colorless) . . . . . . . . . . . . . . . .. 45.4 Saponifiable (colored) . . . . . . . . . . . . . . . . .. 39.5 Loss (water soluble) . . . . . . . . . . . . . . . . . .. 75.7 The average digestibility of the total chloroform extract and of the total ether extract agree closely. There is also some agreement between the individual hays and fodders, though not always close. The greatest difference is peanut l1ay, of which the ether extract is much more readily digested, but this contains more fats and oils than ordinary fodders, on account of the presence of the peanuts. The average digestibility of the unsaponifiable matter are also not so very far apart, though the unsaponifiable _in the chloroform extract is less easily digested. The saponifiable matter is much less easily digestai from the chloroform extract than from the ether extract. It "appears prob- able that the fatty acids extracted by the chloroform are present in the- feerl in a different form of combination from those in the ether extract, A. _. ‘t ._. i , .. _.. .~_ .. _..._ _...m.r_ ___._ >|- .. -r .._._.v 12 TEXAS AGRICULTURAL EXPERIMENT STATIONS. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..OWN.~U>< 0.0. 0.0m v.00 ~00 0.00 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .............nwn 03> w film” Ono ¢ - ¢ ¢ ¢ - - ¢ - - - ¢ ¢ ¢ - ¢ - ¢ - - ¢ Q . - ¢ ¢ » ~ ~ » | - ~ ¢ u | I nllullnhwx N c nha.$@ N. . . . . . . . . . . . . . . . . a . . . . . . . . . . . . . . . . . . .AWNM:@QOEQ amhfim QUwm m.¢q . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .........¢cNQN&-v k/Whfim Unix R. 0.00 0.0 wmwm 0.0 0.0m . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .........>mn0:cmom 0H 0.000 000 0.5 0.0 0.00 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12m: 33m 95m 0; olfim Y w: - ¢ - . . - - - - ~ - - _ - . . . ~ - - ~ . » . - > ¢ - . - - ¢ - - - ¢ - - - - . < ~ - - ~ ¢ nn>wn m. v.00 0.0 000 0.0m 0.00 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 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Dissolve 3 grams caustic potash in about 25 c.c. warm alcohol and add to the alcohol. Shake, allow the precipitate to settle, pour otf the alcohol and distill. Do not let stand longer than three days before pouring oif. Caustic Sodam-Dissolve 40 grams caustic soda, pure by alcohol, in 500 c.c. purified alcohol, filter and dilute to 1000 c.c. Titrate 10 c.c. Will! N /5 hydrochloric acid. Ten c.c. should require 25 c.c. or more of the acid. Extracti0n.—-Use 10 grams of the substance which has previously been extracted for sixteen hours with ether. Extract for sixteen hours with redistilled chloroform, transfer to a tared flask, evaporate, dry, and weigh. Haponification.—'llransfer to 500 c.c. Jena erlenmeyer with hot chlo- roform and evaporate off the solvent on water bath. Use 5 c.c. of the alcoholic soda for each Q; gram of the chloroform extract, and 20 c.c. alcohol. Saponify by boiling with a reflux condenser for five hours, shaking gently from time to time, a11d using great care that the caustic comes in contact with all the fat which may be present in the flask. Add 0.25 grams sodium bicarbonate for every 5 c.c. of alcoholic soda used, and stir well. E-vaporate off all alcohol in steam bath. Dry thirty minutes in a water oven. Extraction of Un.sap0nifiect.-—Heat the soap prepared above with 50 c.c. petroleum ether, which dist-ills below 80° C., for twenty minutes on water bath under reflux condenser with shaking. Add 25 c.c. Water and heat for thirty minutes longer, Draw off the clear petroleum ether and filter through a filter paper previously extracted with ether, if it contains any suspended matter. lf the solution is not clear, wash with 25 c.c. of 1 to 1 alcohol. By the use of a pear shaped separatory funnel and allowing the extract to stand, the insoluble matter will usually separate and fall to the bottom of the funnel, where it can be separated and returned to the original mixture. In case it is necessary to filter and use the alcohol wash, evaporate the. alcohol washings in a porcelain dish after adding the products of extraction of the filter with alcohol and ether, and return to the soap solution by means of hot Water and a steel spatula, laefore extracting the soap solution With ether. Extract twice with 50 c.c. petroleum ether by heating thirty minutes as above, wash with wrater threes times to remove traces of soap and inorganic substances, returning the wash water to the flask containing the soap. Heat the extracted soap with 50 c.c. ethyl ether as before, separate the clear ether, and wash three times with 15 c.c. water. Allow any emulsion to go back into the flask with the soap. Return the washing to the flask also. Extract with ether in this way 14 TEXAS AGRICULTURAL EXPERIMENT STATIONS. four times. If any emulsion is then present, heat till the ether is all gone. Make a fifth extraction and evaporate separately as a test of completeness of the extraction. If this extraction weighs more than 1 per cent of the original chloroform extract, continue the extraction with ether until it is less than that amount. Put the ethyl ether ex- tracts in the flask with the petroleum ether extracts and evaporate during ‘the progress of the extraction. After completion of the ether extraction, evaporate off the rest of "the petroleum ether and ethyl ether, adding alcohol to aid in the removal of the petroleum ether if necessary. TFranstcr to a tared 100 e.c. erlenmeyer by means of hot chloroform. Evaporate and dry to constant weight. Correction. for Fatty Acids in T71isa-ponifiabZe.—Heat unsaponifiable for 15 minutes with 20 e.c. of N/5 hydrochloric acid and 100 e.c. water. Let cool and pour off the water, through a filter if necessary. Heat to laoiling Wlill 5O e.c. water, let cool and pour off again. The substance usually sticks to the flask, and the use of a filter is not necessary. Wash four times with water,.dissolve in alcohol, and titrate with N/5 caustic soda and phenolphthalein, making a iblainl: test on the alcohol. Calculate to palinitic acid. Extraction 0f Fatty Acids.~Heat the soap solution, after the re- moval of the unsaponified, on a steam bath to remove ether in solution. Heat until the ether is all gone. Cool and acidity with acetic acid, testing with litmus paper. Extract with 5O e.c. petroleum ether three times by shaking the slightly warmed mixture in a separatory funnel and combine the extracts in a 500 e.c. erlenmeyer flask. Extract a fourth time as described in the removal of the unsaponified, wash with 2x15 e.c. water, dry and weigh separately. This extraction should Weigh less than 1 per cent of the original chloroform extract. Wash the combined extracts with 2x50 e.c. of water to remove inorganic salts. Return to the erlenmeyer and evaporate to dryness, transfer to a tared 100 e.c. erlenmeyer with hot chloroform, evaporate and dry to constant weight. _ Extraction 0f the Ohlorop-liy/ZZ, etc.——Aci-dify-_~thepresidue from the above extraction further with hydrochloric acid, and add a few cubic centimeters of alcohol. Flxtract xvith ethyl ether just as described in the extraction of the fatty acids. Wash with water and complete as described in the extraction of the fatty acids. References.——Acetic acid acid method for chlorophyll, Beilstein III, 657, “Alkachlorophyll CMHMNTOT . . . (is) difficulty soluble in absolute ether, easily in alcohol, insoluble in Water . . . and ligroin.” GHLOROFORM EXTRACT OF HAYS AND Fonmm. 0901:. 25G... .2... 2.... I... i... u... .... ..C.........w....=2=.z....m 0...... m... 5... :... i... 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(1) Chloroform extracts comparatively large percentages of ma- tc-rial from hays and fodders which have previously been extracted with ether. (2) The chloroform extract contains wax alcohols, fatty acids, chloroplruvll and unknown substances. (3) The chloroform extract is different in quantitative composition from the ether extract, containing less unsaponifiable "matter, more saponifiable matter, and with a greater loss. It contains high percent- ages of substances related in their properties to chlorophyll. (it) The average digestibility of the total chloroform extract and the total ether extract, are in fairly close agreement. (5) The unsaponifiable material in ‘the chloroform extract is di- gested to a less extent than that in the ether extract. The digestibility of both i.s low. (6) The saponifiahle material. of the chloroform extract is digested ‘to a much greater extent than the unsaponifialale material. It is di- gested to a much less extent than the saponifiahle material of the ether extract, which latter contains larger proportions of true fats. (7) A method is given for separating the chloroform extract into several groups of constituents.