None
H-C=:0 ^CH/ The reaction is of somewhat more than usual interest^ since it indicates very clearly that acridine contains a para union between the nitrogen and carbon atoms of the central nucleus, and, by analogy, points to a similar structure for anthracene. Acridine is also found in coal-tar. It is a very stable substance, melting at 107°, and boiling at a tem- perature above 360°, without decomposition. It is a weak base. Potassium permanganate oxidizes it to acridic add (2, yquinoiine dkarboxylic acid)^ N CO Acridone, CeH4<-.„>CeH4, may be prepared by the oxidation of acridine with bleaching powder and cobalt nitrate. It is also formed when o-aminobenzophenone. LABORATORY EXERCISES. 50I is heated to 355° with lead oxide. Acridone crystallizes in needles, which melt at 354°. By distilling with zinc dust it is reduced to acridine. Other heterocyclic compounds in great numbers, and of a great variety of types, are known. Some of those given are no more important than others which might have been selected. It does not seem advisable, however, to extend the list, as it is not possible, in a work of the present scope, to include representatives of all of the types which have been discovered. Laboratory Exercises. Preparation of the following compounds : — . I. Thiophene. 2. Antipyrine. 502 ORGANIC CHEMISTRY. CHAPTER XXIV. ALKALOIDS. Many plants contain basic compounds of nitrogen to which the general name alkaloids has been given. The plants containing such compounds belong almost exclusively to the class of dicotyledons. In many cases the same plant contains several different alkaloids ; but, when this is the case, the different bases are almost invariably closely related in structure. Different plants of the same family often edn- tain the same or closely related alkaloids, while a given alkaloid is rarely found in plants belonging to different families. Most of the alkaloids exert a powerful physiological action on the animal organism. Many of them are valuable medi- cal agents, and some of them are very powerful poisons. Most of the alkaloids form, with acids, well characterised salts. In many cases they can be extracted from aqueous alkaline solutions by means of immiscible solvents, as ether, amyl alcohol, chloroform, or benzene, while acids, in turn, extract them from solution in such solvents. Many of the alkaloids give, with acids and other reagents, highly characteristic color reactions which are of great value in toxicology. All alkaloids give precipitates with phospho- molybdic and phosphotungstic acids, and many of them, with tannin and with potassium mercuric iodide. The alkaloids are generally optically active, and are usually laevorotatory. PYRIDINE GROUP. S03 The number of the alkaloids is very large, and many of them have been carefully studied and their structure estab- lished with a good degree of certainty. Only a very few have been prepared synthetically. They are best classified in accordance with the characteristic group which each contains. Only a few of the more important can be mentioned. I. Pyridine Group. The alkaloids of this group are derivatives of pyridine, ( CH / CH CH II CH 1 CH \ ^ N Pilocarpine, CuHigNgOg, is the most important alkaloid of Jaborandi leaves {Pilocarpus pentafolius). Its chloride is CiiHieNgOa • HCl. The base somewhat resembles nicotine in its physiological properties. Coniine, CgHj^N, the alkaloid of hemlock {Conium macu- iatuni), has been considered (p. 435), as has also piperine^ C17H19NO8, the alkaloid of pepper (p. 434). The former is a monacid base, but the latter forms a chlorplatinate of the remarkable formula, (C^Hi^NOeX . H^PtCl,. Nicotine (C10H14N2), the principal alkaloid of tobacco (see p. 438), is sixteen times more poisonous than coniine. Atropine, C17H28NO8, is the chief alkaloid of the deadly nightshade, Atropa belladonna^ and is found also in Datura 504 ORGANIC CHEMISTRY. stramonium and in several other plants. Atropine is a powerful poison. It causes a widening of the pupil of the eye, and is often used by oculists, for that purpose. This effect is called mydriasis^ and is also produced by some other alkaloids, and by some artificial bases. Atropine is a men- acid base. Cocaine, C„HnN04, is found in cocoa leaves {Erythroxo- Ion coca). It is a monacid base. Cocaine i$ much used to produce local anaesthesia for surgical operations upon the eyes or teeth, but it is so poisonous that great care is re- quired in its administration. According to recent researches, atropine and cocaine are derivatives, not of pyridine, but of pyrrolidine^ CH,-CH, I >NH. Cxlj — CH2 Connectioii Between Structure and PhysioIogUd Effect of Cocaine. — The structure assigned to cocaine is, CH,-CH CH-CO-OCH, I I N - CHgCH - O - COCeH.. I I CJxij — CH— — OHj According to this formula, it is an ester of benzoic acid, CjHbCOOH, and a study of other esters of that acid has led to the conclusion that its peculiar physiological action is dependent largely on that portion of its structure. This has led to the synthesis of two compounds which can replace cocaine for some purposes of local anaesthesia, but which are far less poisonous than that base. These are : QUINOLINB GROUP. 50$ The methyl ester of p-amin(Hhhydroxy4>enzoic acid (" Ortho- form "), / COaCH, I C,H3~OH 2, \ NH, 4 and the methyl ester of diethylglycocoU-aminosalicyclic add (" Nirvanine "), /NH-CO-CH2-N(CaH6)a 5 CeHs-OH 2 \ COaCHg I (Einhom, Ann, d, Chem, (Liebig), 31 z, 26 and 154). Ecgonine, CjHigNOg+HaO, is formed by the saponifica- tion of cocaine, either by dilute acids or by barium hydrox- ide. The structure is evident from the formula of cocaine. As an amino-acid it combines both with acids and with bases to form well-characterized salts. Other esters of ecgonine are found along with cocaine in cocoa-leaves. The ecgonine can be obtained from these by saponification, and can be then converted into cocaine, — facts of very considerable technical importance. 2. QuiNOLiNE Group. The alkaloids of this group are derivatives of quinolinci CH CH CH C CH 1 CH II c 1 CH •^ CH 4' N Qninine, CjoHaiNjOj, is the most important alkaloid of "Peruvian bark," the bark of several varieties of trees 506 ORGANIC CHEMISTRY, belonging to the genus Cinchona. It forms salts with one or with two molecules of a bibasic acid. The fomler are called the neutral salts, as the latter have an acid reaction. The "neutral" sulphate, (CaoHa4Nj02)jH2S04+8HjO (or, crys- tallized from alcohol, with 2H2O), is much used in medicine as an antipyretic. It is a specific in cases of malarial fever. Cinchonine, Qy^^J^fi^ is usually, if not always, associated with quinine. It possesses similar chemical properties, and has a similar physiological effect Quinidine, C^Hg^NgO^ and cinchonidme, Q^HssNgO^ are isomeric with quinine and cinchonine, and can be prepared from them by a molecular rearrangement They are also found in nature. ' '■ Strychnine, CnHsgN^Os, is foimd in St Ignatius' bean, in Strychnos mix vomica^ and in some other plants^ Strycb- nine has an intensely bitter taste. It is a violent poison, 50 milligrams being a fatal dose. In very small doses it acts as a powerful stimulant, in larger doses it produces tetanu3. Bnidne, CaHajNjO^, is always found with strychnine in plants, and is probably closely related to it in structure. It resembles strychnine in its physiological effects, but is a less violent poison. 3. ISOQUINOLINE GROUP. The alkaloids of this group are derivatives of isoquinoline, CH CH CH C CH. 1 CH II C 1 N CH CH BERBERINE. 507 When incisions are made in the green seed capsules of the white poppy {Fapaver somniferum JO)y a milk-like sap exudes, which dries to a gummy mass, and is called opium. Opium contains a number of alkaloids, of which the most im- portant, with their average proportion, are the following : Morphine, CijH^aNOg-hHjO . . , .10 percent Narcotine, C,,H,«NO, 6 " " Papaverine, C,,H,^NO, i « « Codeine, C,sH„NO, ....... 0.3 " " Narceiney C„H,,N08+3H,0 . .... 0.2 " " Thebaine, C^^H^NO, 0.15 " " Of these alkaloids only narcotine, papaverine, and nar- ceine are derivatives of isoquinoline, while morphine, codeine, and thebaine are derivatives of phenanthrene. All of these alkaloids are monacid bases, and all produce a hypnotic effect, though the different individuals vary greatly in power. Morphine and codeine are most used in medicine. Laudanum is an alcoholic extract of opium. Paregoric is a more dilute extract of opium, containing also camphor. Hydrastine, CgiHaiNOe, is the principal alkaloid of golden seal {^Hydrastis Canadensis Z.). It has a strong styptic effect, causing a contraction of the blood-vessels. It is a monacid base. Berberine, C20H17NO4, is also found in golden seal, and is found in a considerable number of other plants. It crystallizes in yellowish brown needles, and its aqueous solu- tion is yellow, while almost all other pure alkaloids are colorless. It is a monacid base. Berberine has a toxic effect on dogs, producing paresis and interfering with the respiration. Upon men it seems to have little toxic effect; even in considerable doses. S08 ORGANIC CHEMISTRY. 4« Alkaloids op Unknown Structure. Veratrine, C^HnNOu, is a poisonous alkaloid found in white hellebore (^Veratrum album)^ and in sabadilla seeds ( Veratrum sabadiHd), Jenrine, Q,H,tNQ„ is found in the same plants, and' especially in white hellebore. It also is a violent poison. Gelaemine, CJR^fi^, is an alkaloid found in the yellow jasmine {Gelsemium sempervirens). It is a monacid base. Its poisonous effects resemble those of strychnine in part, and partly those of curarine^ the alkaloid of "curare," a substance used by the Indians of South America in poison- ing their arrows. Aconitine, C,4H47NOii, is the alkaloid of aconite (Acorn- turn napellus). It is one of the most violent poisons. In very minute quantity it produces a prickly sensation on the tongue. It widens the pupil of the eye in the same manner as atropine. Emetine, CjoH^NjOj, is the chief active principle of ipecac {CephaiHo Ipecacuanha). It is a diacid base. Its emetic effect depends on the local irritation which it causes. Lobeline, CigHjgNOa, is found in Lobelia inflata. The pure alkaloid is a viscous liquid having a yellow color. As a poison it affects the respiratory organs, inhibiting their action. Solanine, CgaHggNOu. See p. 378. Laboratory Exercises. Study the general alkaloid al reactions, and the reactions used for the identification of some of the more imp(»rtant alkaloids. PROTEINS. 509 CHAPTER XXV. COMPOUNDS OF INTEREST IN PHYSIOLOGY AND IN PATHOLOGY. Proteins. — This general name is given to a large class of compounds which are most intimately associated with the life processes of plants and animals. All of them except the protamines contain carbon, hydrogen, oxygen and nitro- gen ; most of them contain sulphur and many, phosphorus. A few contain iron, and copper, chlorine, iodine, manganese and zinc have been found in rare cases. The percentage composition of the more important pro- teins falls within the following limits : c .. • • • 5°' ~SS- ^^^ cent H . , ... 6.-7.3 " " 0 .. ... 19. -24. *♦ " N. ... 15. -19. « « S .. . . . 0.3- 2.5 " « When phosphorus is present it seldom exceeds 0.8 per cent. For the albumin from the white of an egg the formula CyjHjjjSOjj has been given, but the formula cannot be con- sidered as established or important. This formula gives a molecular weight of 16 12. Determinations by the freezing- point method have given, approximately, 15,000. Osborne has discussed the question on the basis of the amount and character of the sulphur present, and gives evidence in support of a similar value for the molecular weight. He also assigns definite formula to a considerable number of proteins (/. Am, Chem^ Soc, 24, 160). 512 ORGANIC CHEMISTRY. ClAMification of Proteins. — The following classification of the proteins has been proposed by the American Society of Biological Chemists and the American Physiological Society. (See " Chemical Abstracts," 2, 1286 ; also " Practical Physio- logical Chemistry " by P. B. Hawk, p. 86.) A classification based on the structure of the proteins is not now possible. I. Simple Pk,oteVns. a. Albumini. Egg albumin^ serum albumin^ lactaibumin^ vegetable albumins, b. Globalins. Serum globulin^ egg globulin^ edestin^ amandin^ and other vegetable globulins, c. Glutelins. Glutenin. d. Alcohol-soluble proteins. ZeiUy gliadin^ hordein^ bynin, e. Albuminoids. Elastin^ collagen^ keratin. f. Histones. Globitiy thymus histone^ scombrone, g. Protamines. SalmifUy sturine^ clupeine^ scombrine. II. Conjugated Proteins. a. Nucleoproteins. CytoglobuUny nucleohistone, b. Glycoproteins. Mucins and mucoids {osseomucoid^ tendomucoid, ichthulin, kelicoprotehi). c. Phosphoprote'ins. Casein^ vitellin. * d. Haemoglobins. ^ Haemoglobin^ haemocyanin, , . • • • ' * e. Lecithoprote'ins. Lecithans^ phosphatides. SIMPLE PROTEINS. S13 III. Derived Proteins. 1. Primary Protein Derivatives. a. Proteans. Myosan^ edestan, b. Metaproteins. Acid metaprotein {acid albuminate)^ alkali tnetaprotein {alkali albuminate). c. Coagulated Proteins. 2. Secondary Protein Derivatives. a. Proteoses. Ptotoproteose^ deuteroproteose, \ b. Peptones. Antipeptone^t amphopeptone» c. Peptides. Albumins are soluble in pure water and are not precipi- tated by a small amount of acid or alkali, apparently because they possess both basic and acid properties. A larger amount of a mineral acid precipitates them, and they are also precipitated by heat when their solutions contain a neutral salt. Globulins. — These are simple proteins, insoluble in pure water, but soluble in neutral solutions of salts of strong bases with strong acids. (The precipitation limits with ammonium sulphate should not be made the basis for distinguishing the albumins from the globulins.) Glutelins are simple proteins insoluble in all neutral sol- vents, but readily soluble in very dilute acids and alkalies. They are found in the seeds of cereals. Alcohol-soluble Proteins. — These are soluble in alcohol: of 70 to 80 per cent as well as in dilute acids and alkalies, but ar-e insoluble in water, absolute alcohol or other neutral solvents. They occur principally in the seeds of cereals : zein in maize, gladin in wheat flour, hordein in barley, bynin in malt. -> $14 ORGANIC CHEMISTRY. Altmminoids have essentially the same composition as other proteins, but are very insoluble in all neutral solvents. The group includes collagens, keratins, and elastins. CoUagen is a constituent of such forms of connective tissue as tendon, ligament, cartilage, and bone. It is present in maximum amount (3 1 per cent) in tendon and constitutes the major portion of this form of tissue. The organic portion of bone, the so-called ossein, is practically identical with collagen. By boiling with water, especially in the presence of a little acid, collagen is converted into gelatine. Gelatine absorbs cold water and swells up, but does not dissolve. It dissolves in hot water to a colloidal solution, which does not diffuse through parchment, and which solidifies on cooling, if not too dilute. Keratins form the principal constituent of the epidermis, hair, nails, hoofs, horns, and feathers. They differ from the other albuminoids in containing a large amount of sulphur. A portion of this sulphur is in so loose a state of combination as to give a precipitate of lead sulphide on boiling with an alkaline solution of a lead salt. The kera- tins are all extremely insoluble and are non-digestible. They give on hydrolysis a larger amount than usual of tyrosine. Elastin is the principal solid constituent of yellow elastic connective tissue, or ligament, e. g. ligamentum nuckae, Elastih resembles keratins and collagen in being insoluble. It differs from keratin in being digestible and in containing only a small amount of sulphur (about 0.14 per cent. Rich- ards and Gies, Am, /. Physiol, 7). Histones are soluble in water but insoluble in very dilute ammonia and, in the absence of ammonium salts, even in an excess of ammonia. They yield precipitates with solu- tions of other proteins and are coagulated by heat, but the coagulum is easily soluble in dilute acids. HAEMOGLOBIN. 5 1 5 Protamines are easily soluble, strongly basic polypeptides containing no sulphur. They have been obtained especially from the spermatozoa of eels and fishes. They are not coagulated by heat and form stable salts with strong mineral acids. They precipitate aqueous solutions of other proteins. Conjugated proteins contain the protein molecule united with some other molecule or molecules otherwise than as a salt ; as with nucleic acid (nucleo-proteins), a carbohydrate (glycoproteins), some as yet undefined phosphorus com- pound (phosphoproteins) with haematin (haemoglobin) or with lecithin (p. 433) (lecithoproteins). Casein is the most important protein of milk. Whether the casein from different kinds of milk is identical or not has not been fully determined, but the caseins from different sources differ in some of their properties. The casein is coagulated by dilute acids or by the enzyme found in rennet and m the gastric juice. It separates in the form of a cal- cium salt. When some lactic acid is formed in the milk by the fermentation which naturally occurs in unsterilized milk, the casein will coagulate on heating the milk. Haemoglobin is the chief coloring matter of the blood. It is also the substance which directly absorbs the oxygen of the air in the lungs, combining with it to form oxy haemo- globin. In the passage from the arterial to the venous sys- tem, through the capillaries, in the circulation of the blood, this absorbed oxygen enters into combination with other substances, oxidizing them, and thereby furnishing heat and energy for the body. Haemoglobin contains iron, and both its color and its property of combining with oxygen are sup- posed to be due to this element. By means of acids haemoglobin is decomposed into globin and haematin. The latter is a coloring matter which con- Sl6 ORG j4 NIC CHEMISTRY, tains iron, and can be separated in the form of its chloride, which is called haemin. Primary protein deriyatiyes are formed, apparently, through hydrolytic changes which involve only slight changes in the molecule. Proteans result from the incipient action of water, very dilute acids, or enzymes. Meta-proteins result from the further action of acids or alkalies and are soluble in dilute acids or alkalies, but insoluble in neutral fluids. The sub- stances called " acid proteins " and " alkali proteins " are included in the group, but not the salts of proteins with acids. Coagulated proteins are formed by the action either of heat or alcohol on solutions of proteins. Secondary protein deriyatives result from the further hydro- lytic changes of proteins by acids or enzymes. Proteoses are soluble in water, are not coagulated by heat, but are precipitated by saturating their solutions with am- monium or zinc sulphate. Peptones are formed by the action of proteolytic enzymes (pepsin and trypsin, see below) upon albumins, and other proteins. They have a much smaller molecular weight than the albumins, are easily soluble in water, are not coagulated by heat, and are not precipitated by acids or by potassium ferrocyanide. In the process of digestion they seem to be intermediate between the proteins of the food and those of the living body, being formed by the decomposition of the former, and, in turn, uniting with themselves, or with other substances, to form the latter. Peptones are closely related in their properties to the pep- tides, and the two classes of proteins are not distinguished from each other by characteristic reactions. The distinc- ENZYMES. '51^ .tion is, for the present, based chiefly on the difference in origin. Peptides are definite compounds formed by the union of two or more amino acids in such a way that the carboxyl group of one molecule condenses with the amino group of another with the elimination of water. The simplest is glycylglycine, CHgNH^CONHCHjCOjH, which was first NH-CH2-CO obtained from glycine anhydride | | by hydrol- CO^CHj-NH ysis with concentrated hydrochloric acid (E. Fischer, Ber. d, chem, Ges, 34, 2868). Later {Ibid, 37, 2500) the same author showed that by treating glycylglycine with chloracetyl chloride, ClCHjCOCl, and sodium hydroxide, chloracetyl- glycylglycine, C1CH2C0NHCH,C0NHCH2C02H, can be prepared. This gives, when treated with ammonia, a tripep- tide, di-glycylglycine, NH2CH2CONHCH2CONHCH2C02H-. In a similar manner tetrapeptides and pentapeptides have been prepared. He points out (Ber. d, chem. Ges, 37, 2489) that these synthetic polypeptides resemble the peptones in many of [their properties ; especially they give the biuret •reaction,* give precipitates with phosphotungstic acid, and are hydrolyzed by trypsin. Enzymes. The name enzyme is applied to a class of bodies which are soluble in water, which are not endowed with the capa- bility of propagating themselves, nor with any of the other properties distinctly characteristic of life, and which yet produce many effects closely related to those that are * The purplbh violet or pinkish violet color produced when equal volumes of a protein solution and a strong solution of potassium hydroxide are treated with a to 5 drops of a very dilute solution of copper sulphate. K^-i* •1 -^' .^ . ' W -- a ^/r^ -jjj^« •-•■I' &- 1 * ^f^ >» PTOMAINES. 519 5* Enzymes which Decompose Amides, as urease^ which de- composes urea into carbonic acid and ammonia. 6. Protein-Coagulating, as rennin^ found especially in rennet, an infusion of the mucous membrane of the stomach of the calf. It coagulates casein. 7. Enzymes which Form Alcohols, as zymase^ an enzyme found in yeast (p. 131). 8. Deamidizing Enzymes, such as adenase^ which converts adenine into hypoxanthine, and guanase, which converts guanine into xanthine. r 9. Oxidizing Enzymes, such as xanthooxidase , which oxi- dizes xanthine and hypoxanthine to uric acid. 10. A Uricolytic Enzyme, which has the property of de- stroying uric acid, possibly with the formation of urea and glycocoU with allantoin as an intermediate product. Ptomaines. When albumin, flesh, or other animal or vegetable nitro- genous substances decay under the influence of bacteria, basic substances cdW^di ptomaines are often formed. Similar compounds seem to be formed in living animals and men dur- ing the progress of some diseases caused by pathogenic bac- teria, and may play a part in the progress of such diseases. The study of the ptomaines has acquired an especial in- terest, also, because a number have been discovered which give color reactions resembling some of the reactions of well- known poisonous alkaloids, a fact which has greatly increased the difiiculty of the toxicological search for these poisons. Some of the ptomaines are poisonous, others are not. Neurine(p, 433) and Cadaverine {\^ ^-diatninopentane (^, 433), have been mentioned. Methyl amine, dimethyl amine, and trimethyl amine have all been found in herring brine. C520 ORGANIC CHEMISTRY. Tetanine, CjjH^NjO^, is formed when cultures of the bac- teria of tetanus, or lockjaw, are made in horse-fiesh. It is very poisonous. Typhotozine, C^H^^NOj, is obtained in a similar manner with the bacteria of typhoid fever. It is poisonous. Erysipeline, CjiHjjNO,, has been found in the urine of persons affected with erysipelas. The list might be considerably extended. Toxins. In some, and perhaps in most of those diseases which are caused by bacteria, there are generated poisonous compounds which appear to be closely related to the enzymes in their general character. These have been called toxalbumins by some authors, while other writers claim that they are not albumins^ and prefer the more general name toxins. The latter term, in its broader sense, would include poisonous ptomaines as well. The poison of serpents, and the two vegetable poisons, abrin and ricin^ which are of a protein nature, seem, also, to be closely related to the toxins. Some of these bodies are very virulent. The lethal dose of tetanus toxin has been shown by Brieger and Cohn (^'Cellular Toxins,'* Vaughan and Novy, 4th edition, p. 61) to be 0.0033 of a milligram per kilogram body weight, or 0.00023 gram for a man weighing 70 kilograms, whereas others have deter- mined that ^V o^ ^ milligram of ricin per kilogram of body weight is fatal. Such results recall the fact that one part of rennin will coagulate two million parts of casein. None of the toxins of this class have been isolated in a pure con- dition, and the study of their chemical nature is attended with very great difficulty. FATS. 521 Antitoxins. At the same time with the development of toxins under the influence of bacteria the animal organism appears to produce compounds which serve, in some manner which is little understood, as their antidotes. These are called anti- toxins. In a few cases, by inoculating animals with a particular disease, a blood serum can, later, be obtained which acts as a specific curative for that disease. The first of the antitoxins prepared in this manner was the antitoxin of tetanus. The one which has,*thus far, been most success- ful, is the antitoxin of diphtheria. Fats. From the physiological standpoint, the fats seem to be of value chiefly as a source, or for the storage of energy which can be converted into muscular work or heat. While the fatty acids are among th'e most stable of organic compounds, and are attacked only by very vigorous agents, the animal organism finds no difficulty, apparently, in securing their complete oxidation to carbon dioxide and water. INDEX. Aa asterisk after the number indicates that the compound is mentioned only in a table. Abrin» 520 "Ac" as a prefix, 445 Acenaphtene, 114* Acetal, 285 Acetaldehyde, 175 Acetaldehyde cyanhydrin, 178 Acetamide, 299 Acetanilide, 440 Acetates, 227 Acetic anhydride, 277 Acetoacetic ester, 347 Acetone, 187. Acetone ethylmercaptol, 485 Acetonitrile, 299 Acetonyl acetone, 207 Acetophenone, 198 Acetoxime, 189 Acetylacetone, 206 Acetyl chloride, 276. Acid, Terephthalic, 265 Tetrahydrobenzoic, 340* Tetrahydroterephthalic, 267 Tetrolic, 240* Tiglic, 23a* Toluic, 240* Transbutenoic, 234 Triazoacetic, 463 Trichloracetic, 408 Trichlorcyclopentenediolcarboz- ylic, 146 Tridecylic, 222* Trimethylcyclopcntanccarbox- ylic, 232* Trimcthylcyclopcntcnoic, 240* Trimethylsuccinic, 259 Trimethyltricarballylic, 196 Undecylic, 222* Uric, 293 Valeric, 230 Vanillic, 340 Xylic, 241* Acid anhydrides, 276 Acid chlorides, 273 Acid decomposition, 351 Acids, 220; preparation of, 270 Aconitine, 508 Acridine, 499 Acridone, 500 Acrolein, 180 Acrose, 174 Adenase, 519 Adipic ester, 256 Adipic ketone, 171* Adjective dyes, 481 Aesculetin, 375 Aesculin, 375 Alanine, 450, 511 Albumins, 512, 513 Albuminoids, 512, 5x4 Alcohol, 129 ff Alcohol, absolute, 132 Alcohols, 124, 126 preparation of, i6z Aldehyde acids, 344 Aldehyde ammonia. 179 Aldehydes, 170, 218 preparation of, 215 Aldohexoses, 357 Aidol, 177 AlicycUc compounds, 1x7 Aliphatic compounds, 93 Alizarin, 212 Alkaloids, 299, 502 Alloisomerism, 235 Alloxan, 293 AUoxantin, 294 Allyl alcohol, 140 Ally I bromide, 400 Allylene, 87 ♦ Allyl ether, 164* Allyl isothiocyanate, 310 Allylmethoxyt)enzene, 334 Allylpyridine, 435 Amide chlorides, 310 Amides, 286 Amidines, 311 Amido group, 288 ^ Amidoximes, 311 Amines, 420 Aminoazobenzene, 467 Aminoazo compounds, 466 Aminocyclopentane, 424 Amino group, 289 Aminophenol, 209 Aminouracil, 296 Ammonium thiocyanate, 308 Amphopeptone, 513* Amygdalin, 182, 302, 376 Amyl alcohols, 136 Amylan, 358* Amylases, 518 ♦ Amylopsin, 518 Amylum, 373 Anaesthetics, 397 Analysis, 19 Anethol, 324 Anhydrides, acid, 276 Aniline, 439 Aniline yellow, 468 Anisol, 166 Anthracene, 117 Anthrahydroquinone, 2x4 Anthranoi, 149, 214 Anthranone, 214 Anthrapurpurin, 215 Anthraquinone, 211 INDEX. 529 Diazoaminobenzene, 466 Diazobenzene, 479 Diazobenzene imide, 479 Diazobenzene potassium, 457 Diazo compounds, 456 Diazo group, replacement of, 459 Diazoimides, 478 Diazonium salts, 456 Dibenzalacetone, 190 Dibrombutanediols, 156 Dibrompropane, 401 Dichlorethanes, 78, 398 Dichlorhydrin, 405 Dichlorpropanol, 405 Dicyclic compounds, 90 Diethyl carbonate, 284 Diethyl ketone, 171 * Diethylsulphone, 486 Diethylsulphone-dimethylme- thane, 486 Diformin, 140 Digitalein, 376 Digitaliretin, 376 Dihydroresorcinol, 207 Dihydroxyanthracene, 214 Dihydroxyanthraquinones, 215 Dihydroxybenzene, 158 Dihydroxyxylene, 211 Diiodomethane, 395 Dimethyl amine, 429 Dimethyl aminoazobenzene, 468 Dimethyl aniline, 429, 442 Dimethyl azole, 208 Dimethyl butanes, 56 *, 75 * Dimethyl butanone, 189 Dimethyl cyclohexanes, 82 * Dimethylene imine, 432 Dimethyl furane, 208 Dimethyl furfurane, 208 Dimethyl heptane, 56 * Dimethyl hexane, 56 * Dimethyl ketone, 187 Dimethyloctadienal, 181 Dimethyl octanes, 56 * Dimethyl pentane, 56 * Dimethyl propane, 68 Dimethyl pyridines, 438 Dimethyl pyrrol, 208 Dimethyl thiofurane, 208 Dimethyl thiophene, 208 Dimethyl xanthine, 298 Diminished pressure, distillation under, 16 Dinitrobenzene, 414 Dioxindol, 451 Dioxyanthracene, 214 Dioxyanthraquinones, 215 Dioxyterephthalic ester, 355 Dioxyuracil, 296 Di phenyl, 114 * Diphenylethanedione, 172 * Diphenylethanes, 114* Diphenylfurazane, 185 Diphenylmethane, 114* Diphenylquinoxaline, 203 Diphenylsulphone, 486 Diphenyl urea, 304 Dipropargyl, 87 * Disaccharides, 367 Disazo compounds, 472 Dissociation constants, 409, 417, 424 Distillation, 12 fiF. Dithioethyldimethylmethane, 485 Double unions, 79 Dumas's method, 23 Dulcite, 158 Durene, 107 * Dyes, 479 Dynamite, 154 Ecgonine, 505 Edestan, 513 * Egg albumin, 512 * Eikosane, 70 Elastin, 512, 514 Emetine, 5oi8 Empirical formulae, 2X Emulsin, 302, 518 "Enol" form, 205 Enzymes, 517 Eosin, 265 Erysipeline, 520 Erythrol, 154 Esterification, law of, 280 Esters, 278 Ethanal, 175 Ethane, 6z 530 INDEX. Ethanediol, 150 Ethanethioli 483 Ethanol, 129 Ethanoyl cyclopropane, 171 * Ethene, 76 Ethenol, 139 Ethers, 164 Ethoxyacetic ester, 315 Ethyl acetate, 278 Ethyl amines, 431 Ethyl alcohol, 129 Ethyl benzene, 109 Ethyibenzyl hydroxylamine, 448 Ethyl bromide, 399 Ethyl butyrate, 284 Ethyl carbamate, 292 Ethyl carbonimide, 307 Ethyl chloride, 398 Ethyl cyanate, 396 Ethylene, 76 Ethylene bromide, 399 Ethylene chloride, 398 Ethylene oxide, 168 Ethylene series, 75 Ethyl ether, 165 Ethyl glycollate, 315 Ethyl hydroxylamine, 448 Ethylidene acetone, 171 * Ethylidene chloride, 398 Ethylidenediethyl ether, 285 Ethyl iodide, 400 Ethyl isocyanate, 307 Ethyl mercaptan, 483 Ethyl nitrite, 411 Ethylol trimethyl ammonium hy- droxide, 433 Ethylonephen, 172 * Ethylpentane, 56 * Ethyl phenyl ether, 166 Ethylphenyl ketone, 172 * Ethyl pseudocarbostyril, 454 Ethyl pyridines, 438 Ethyl quinolone, 454 Ethyl sulphide, 484 Ethyl sulphuric acid, 76 Ethyl thiocyanate, 308 Eugenol, 186 Fast colors, 482 Fatty acids, 222 Fats, 230, 521 Fehling's solution, 363 Fenchone, 197 Fermentation, 130 Fittig's synthesis, iii Flavol, 214 Flavopurpurin, 215 Flashing-point, 73 Fluorene, 114* Fluorescein, 264 Formaldehyde, 173 Formaline, 174 Formation, heat of, 45 Formulae, graphical, 65 Fractional distillation, 13 Freezing point lowering, 26 ff. Friedel-Craft reaction, 112 Fructose, 365 Fruit sugar, 365 Fuchsine, 442 Furfural, 360 Furfurane, 496 Galactose, 357 * Gasoline, 73 Gelatine, 514 Gelatine, explosive, 154 Gelsemine, 508 Geranial, 181 Geraniol, 181 Gliadin, 512, 513 Globin, 512, 515 Globulins, 512, 513 Glucoheptose, 358* Gluconic anhydride, 364 Glucononose, 358 * Glucosazone, 364 Glucose, 361 Glucosides, 357, 375 Glutaric anhydride, 256 Glutelins, 512, 513 Glutenin, 512 * Glycerine, 152 Glycerol, 152 Glyceryl trinitrate, 154 Glycine, 448 Glycocoll, 448, 511 Glycogen, 374 Glycol, 150 Glycol chlorhydrin, 168, 404 ] INDEX. 531 GlycoUc acetate, 315 Glycolic aldehyde, 151 Glycolid, 315 Glycol monacetate, 168 Glycoproteins, 512 Glyoxal, 152 Grape sugar, 361 Grignard's reaction, 162 Guaiacol, 186 Guanine, 299 Gulose, 366 Gun-cotton, 372 Haematin, 515 Haemin, 516 Haemoglobins, 512, 515 Haemocyanin, 512* Halogen compounds, 380 Halogens, determination, 21 Helianthin, 468 Helicin, 378 Hemellithene, 107 * Heptanal, 170* Heptane, 56 * Heterocyclic compounds, 495 Hexachlorethane, 398 Hexadiines, 87 * Hexahydropyridine, 434 Hexahydroxycyclohexane, 367 Hexamethylene amine, 174 Hexanal, 170* Hex&nedione, 207 Hexanehexols, 158 Hexanes, 68 Hexanetrione, 160 Hexaphenylethane, 78, 115 Hexazane, 434 Hexenes, 75 * Hexoses, 357 Hexoxyhexahydrobenzene, 367 Histones, 512*, 514 Hofmann's method, 26 Homology, 56 Hordein, 512, 513 Hydrastine, 507 Hydrazines, 476 • Hydrazobenzene, 476 Hydrazo compounds, 473 Hydrazones, 179, 478 Hydrindene, 114 * Hydroanthranol, 214 Hydrocarbons, 55 Hydrocarbostyril, 453 Hydrocinnamic aldehyde, 170 * Hydropyrone, 190 Hydroquinone, 160 Hydroxy acids, 313 Hydroxyanthraquinone, 212 Hydroxyazobenzene, 470 Hydroxyazo compounds, 469 Hydroxybenzaldehydes, 185 Hydroxybenzyl alcohol, 378 Hydroxydisazo compounds, 470 Hydroxylamine derivatives, 447 Hydroxyl group, 129 Hydroxyquiholine, 453 Hydroxytoluene, 147 Hystazarin, 215 Imide chlorides, 310 Imides, 289 Imido esters, 310 Inactive compounds, 137 Indene, 114 * Indican, 376 Indiglucin, 377 Indigo, 451 Indol, 452 Indophenin reaction, 495 Indurite, 373 Inosite, 367 Inulin, 374 Invertases, 518 Invert sugar, 365 Iodoform, 396 lodopropane, 400 lonone, 182, 197 Iridin, 377 Irigenin, 377 Irone, 197, 377 Isatin, 451 Isoamyl acetate, 284 Isoamyl alcohol, 136 Isoamyl ether, 164 * Isoamyl isovalerate, 284 Isobutane, 66 Isobutyl alcohol, 135 Isobutyric aldehyde, 170* Isocaprolactone, 320 Isocyanates, 306 532 INDEX, Isocyanides, 304 Isodiazobenzene potassium, 457 Isomaltose, 358 * Isomerism, 64 Isomerism, geometrical, 156 Isonit riles, 304 Isonitrosoketones, 201 Isopentane, 68 Isopropyl alcohol, 135 Isopropyl benzenes, 107 ♦ Isopropyl ether, 164 ♦ Isopropyl iodide, 400 Isoquinoline group, 506. Isothiocyanates, 309, 428 Isovaleric aldehyde, 170* Jervine, 508 Kekul^'s formula, 103 Keratins, 512, 514 Kerosene, 73 Ketohexoses, 357 Ketones, 170, 218 Ketones, preparation of, 216 Ketonic acids, 344 Ketonic decomposition, 202, 351 Kjeldahl method, 20 « Lactalbumin, 512 * Lactid, 317 Lactones, 218, 319 Lactose, 370 Lactosin, 358 * Ladenburg's formula, loi Laevo compounds, 137 Lakes, 213 Laudanum, 507 Lecithans, 512 * Lecithoproteins, 512* Lecithin, 433 Leucine, 450, 511 Leuco compounds, 473 Liebermann's reaction, 427 Ligroin, 73 Lipase, 518 Lobeline, 508 Lutidines, 438 Lysine, 511 Magnetic rotation, 49 Malefc anhydride, 257 Malonic ester, 251 Maltose, 370 Mannite, 158 Mannoheptose, 358 * Mannononose, 358 * Manno-octose, 358* Mannose, 363 Marsh-gas, 58 Marsh-gas series, 55 Melibiose, 358 ♦ Melitose, 371 Meiitriose, 371 Melezitose, 358 * Melting-point determinations, 10 Menthone, 195 Mercaptans, 483 Mesitylene, no, 191 Mesityl oxide, 192 Metaformaldehyde, 174 Metaldehyde, 176 Meta position, 105 Metaproteins, 513, 516 Methanal, 173 Methane, 58 Methanol, 126 Metho-ethylphenmethylal, 171 ♦ Methyl alcohol, 126 Methylalcyclopentane, 170* Methylalcyclopentene, 170* Methyl amine, 429 Methyl aniline, 441 Methyl benzamide, 201 Methylbenzimidazole, 443 Methylbenzyl ketone, 172 * Methyl butanal, 170* Methyl butane, 68 Methyl-butanolst 136 Methyl butanone, 171 * Methyl butenal, 170* Methylbutenes, 75 * Methyl butenone, 171 * Methylcarboxethylcyclopenta- none, 353 Methyl cyanide, 299 Methyl cyclobutane, %^ Methyl cyclohexane, 82 * Methyl cyclopentane, 86 INDEX. 533 Methyl cyclopentenone, 171 * Methyl cyclopropane, 82 * Methylene, 76 Methylene iodide, 395 Methyl ether, 164 * Methyl ethyl ether, 164 * Methyl ethyl ketone, 171 * Methylethylthetin, 488 Methylethylthetin bromide, 487 Methylglycocoll, 449 Methyl hezanes, 56 * Methyl hexazane, 435 Methyl hydroxy lamine, 447 Methyl iodide, 395 Methyl isopropylbenzene, 196 Methyl isopropyl ketone, 171 * Methyl nonane, 56 * Methyl orange, 468 Methyl pentanes, 56 * Methyl pentanolid, 320 Methyl pentenes, 75 * Methyl pentenone, 171 * Methyl phenmethylal, 170* Methyl phenyl ether, 166 Methylpiperidine, 435 Methyl propanal, 170* Methyl propane, 66 Methyl propanol, 135 Methyl propargyl ether, 164 * Methyl propene, 75 * Methyl propyl cyclohexanone, 171 ♦ Methyl propyl ether, 164 * Methyl propyl ketone, 171 * Methyl pyridines, 438 Methyl salicylate, 323 Methyl uracil, 295 Methyl violet, 442 Meyer's law of esterification, 280 Meyer's vapor density method, 25 Milk sugar, 370 Molecular dispersion, 47 Molecular refraction, 46 Molecular volume, 40 Molecular weight, determination, 22 fiF. Monochlorhydrin, 404 Monoethyl carbonate, 284 Monoformin, 224 Mordants, 213, 481 Morphine, 507 Mucins, 512 * Mucoids, 512* Multirotation, 362 Mustard oils, 309 Myosan, 513 * Naphtha, 73 Naphthaldehyde, 171 * Naphthalene, 116 Naphthenemethylal, 171 * Naphthols, 149 NaphtHbqui nones, 173 * Naphthylamine, 444 Naphthyl ether, 164 ♦ Narceine, 507 Narcotine, 507 Natural gas, 58 Nervanine, 505 Neurine, 433 Nicotine, 438, 503 Nitriles, 300 Nitrobenzene, 413 Nitrobenzene diazonium chloride, 458 Nitrocellulose, 372 Nitro compounds, 411 Nitroethane, 411 Nitrogen, determination, 20 Nitroglycerine, 154 Nitronaphthalene, 416 Nitrophenols, 416 Nitrosamines, 426 Nitrosophenol, 210 Nitrosopiperidine, 434 Nitrotoluenes, 414, 415 Nitrourea, 419 Nitroxylenes, 415 Nonane, 56 * Nucleohistone, 512* Nucleoproteins, 512 Octane, 70 Octyl acetate, 284 Oenanthaldehyde, 170* Official nomenclature, 68 Oil of anise, 324 Oil of winteigreen, 323 Olefiant gas, 77 534 INDEX. Oleln, 152, 238 Opium, 506 Optical activity, 137 Orange III, 468 Ornitnine, 511 Orthocarbonic ester, 285 Orthoform, 505 Orthoformic ester, 285 Ortho position, 105 Osazones, 364, 478 Ossein, 514 Overcooling, 10, 30 Oxalates, 250 Oximes, 179 Oxindol, 451 Oxyanthraquinone, 214 Oxyanthrarufin, 215 Oxyazobenzene, 470 Oxyazo compounds, 469 Oxy methylene, 174 Oxy uracil, 296 Palmitin, 152, 230 Papaverine, 507 Papayotin, 518 Paraffin, 7*3 Paraffin oils, 73 Paraffins, 56, 70 Paraldehyde, 176 Para position, 105 Paregoric, 507 Pentachlorethane, 398 Pentamethylene diamine, 433 Pentamethylene oxide, 164 * Pentanedione, 206 Pentanes, 67 Pentanol, 124 * Pentanone, 171 * Pentazane, 437 Pentenes, 75 * Pentenone, 171 * Pentosans, 375 Pentoses, 357 Pentylene oxide, 164 * Pepsin, 518 Peptides, 513, 517 Peptones, 513, 516 Perbromethylene, 399 Perkin's synthesis, 244 Petroleum, 71 Petroleum ether, 73 Phenanthrene, 119 Phenanthrertequinone, 204 Phendiols, 158, 160 Phenethylal, 170* Phenetol, 166 Phenmethylal, 170* Phenmethylol, 125* Phenol, 142 Phenoldisazobenzene, 470 Phenolphthalein, 263 Phenpropenylal, 171 * Phenpropylal, 170* Phenthiol, 484 Phentriols, 160 Phenyl acetaldehyde, 170* Phenyl acetamide, 440 Phenyl acetylene, 247 Phenyl alanine, 511 Phenyl carbonimide, 307 Phenyl cyclotriazine, 479 Phenyl cyanide, 241 Phenyldimethyl pyrazole, 206 Phenyldrmethyl pyrazolone, 499 Phenylene diamines, 443, 444 Phenyl ether, 164 * Phenyl hydrazine, 477 Phenyl isocyanate, 307 Phenyl isocyanide chloride, 304 Phenyl isothiocyanate, 305 Phenyl methylamine, 441 Phenyl methyl ketone, 198 Phenyl methylpyrazolone, 499 Phenyl mustard oil, 305 Phenyl nitromethane, 415 Phenyl pyrazole, 498 Phenyl sulphide, 485 Phenyl thioformamide, 305 Phenyl tolyl ketoxime, 201 Phenyl urethane, 293 Phloretin, 377 Phlorizin, 377 Phloroglucinol, 160 Phorone, 192 Phosphatides, 512* Phosphoproteins, 512* Phthalic anhydride, 262, 278 Phthalid, 262, 32$ INDEX. 535 Phthalimide, 289 Phthalyl chloride, 262 * Picoline, 438 Pilocarpine, 503 Pimelic ester, 354 Pimelic ketone, 171 * Pinacoline, 189 Pinacone, 188 Pinene hydrochloride, 401 Pipecoline, 435 Piperidine, 434 Piperine, 503 Piperonal, 187 Polarization, rotatory, 47 Potassium cyanide, 302 Potassium ferrocyanide, 303 Potassium thiocyanate, 308 Prism formula, loi Propadi^ne, 87 * Propanal, 170 Propane, 62 Propanediol, 152 Propanetriol, 152 Propanols, 134, 135 Propanone, 187 Propargyl alcohol, 125 * Propenal, 180 Propene, 75 * Propenol, 124 * Propinol, 125 * Propionic aldehyde, 170* Propionyl chloride, 275 Propyl alcohol, 134 Propylene glycol, 152 Propylene oxide, 164 * Propyl ether, 164 * Propyl iodide, 400 Propylonephen, 172 * Propyl piperidine, 435 Protamine, 510* Protamines, 512, 515 Proteans, 513, 516 Proteases, 518 Protein derivatives, primary, 513, Protein derivatives, secondary, 513, 516 Proteins, 509, 51 a Proteins, alcohol-gglubj^ 513, 513 Proteins, classification, 512 Proteins, coagulated, 513, 516 Proteins, conjugated, 512, 515 Proteoses, 513, 516 Pseudo acids, 411 Pseudo compounds, 454 Pseudocumene, no Ptomaines, 433, 519 Ptyalin, 518 Pulegone, 197 Purification, 9 Purpurin, 215 Purpuroxanthin, 215 Putrescine, 512 "Py" as a prefix, 453 Pyrazole, 497 Pyrazolone, 498 Pyridine, 437 Pyridine group, 503 Pyrocatechol, 158 Pyrogallol, 160 Pyrone, 190 Pyroterebic ester, 394 Pyroxylin, 372 Pyrrol, 436 Pyrrolidine,  noline group, 505 noline iodoethylate, 455 none monoxime, 210 nones, 209 Racemic compounds, 138 Raffinose, 371 Reimer-Tiemann reaction, 186 Rennin, 519 Resorcinol, 158 Resorcinoldisazobenzene, 47a Rhammoheptose, 358 * Rhamnohexose, 358 ♦ Rhamnose, 357 * Rhigolene, 73 Ricin, 520 536 INDEX. RingS) formation of, 193 Rochelle salt, 335 Rosaniline, 442 Rufol, 214 Saccharates, 369 Saccharin, 492 Saccharose, 367 Salicin, 378 Salicylic aldehyde, 185 Saligenin, 186 Sandmeyer's reaction, 460 Sapogenin, 378 Saponification, 152, 283 Saponin, 378 Sarcosine, 449 Schotten-Baumann reaction, 282 Schweitzer's reagent, 372 Scombrone, 512 * Semicarbazones, 179 Semidines, 474 Serum albumin, 512 * Sinigrin, 377 Soap, 152, 230 Sodium glycolate, 151 Solanidine, 378 Solanine, 378 Sorbinose, 357 * Sorbite, 158 Space arrangement, 66 Specific gravity, 39 Starch, 373 Starch sugar, 361 Steam distillation, 17 Steapsin, 518 Stearin, 152, 230 Stereoisomerism, 156, 183, 236, 239 Strychnine, 506 Styrene, 114 * Suberone, 192 Substantive dyes, 481 Succinimide, 289 Succinylosuccinic ester, 354 Sulfonal, 486 Sulphides, 484 Sulphobenzenazonaphthylamine, 445» 469 Sulphodihydroxyazobenzene, 471 Sulphodimethy laminoazobenzene , 468 Sulphones, 486 Sulphonic acids, 488 Sulphonium bases, 487 Sulphotoluene, 491 Sulphur compounds, 483 Sulphur, determination, 21 Sulphur ethers, 484 Surface tension, 43 ^ Syn-benzaidozime, 183 Tanacetone, 197 Tannins, 341, 376 Tartar emetic, 335 Tautomerism, 297 Terpenes, 91 Tetanine, 520 Tetrabromfluoresceln, 265 Tetrachiorethane, 398 Tetrahydronapbthylamines, 445 Tetramethyl ammonium iodide 431 Tetramethyl benzene, 107 * Tetramethylene aldehyde, 170* Tetramethyl methane, 68 Tetrethyl ammonium hydroxide, 431 Tetrose, 359 Tetroxalates, 250 Thebaine, 507 Theine, 298 Theobromine, 298 Thetin compounds, 487 Thioalcohols, 483 Thiocyanates, 308- Thioformanilide, 305 Thiophene, 495 Thiophenol, 484 Thiotolene, 495 Thioxene, 495 Thujone, 197 Thymol, 148 Tiglic aldehyde, 170* Toluene, 108 Toluene sulphamide, 493 Toluene sulphochloride, 492 Toluic aldehyde, 170* Toluic anilide, 201 Toluidines, 442 Toxalbumins, 520 Toxins, 520 INDEX. 537 Trans forms, 236 Trehalose, 358 * Triaminoazobenzene, 468 Triazobenzene, 479 Tribrommethane, 396 Tribrom phenol, 405 Trichloracetaldehyde, 405 Trichlorethane, 398 Trichlorhydrin, 405 Trichlormethane, 396 Trichlorpropane, 405 Triethyl sulphonium hydroxide, 487 Triethyl sulphonium iodide, 487 Triiodomethane, 396 Trimethyl amine, 430 Trimethyl benzenes, 107 * Trimethyl cyclopentanone, 260 Trimethylene bromide, 401 Trimethylene glycol, 132 Trimethyl glycocoll, 449 Trimethyl pyridine, 438 Trimethylxanthine, 298 Trinitrobenzene, 414 Triphenylcarbinol, 263 Triphenylchlormethane, 403 Triphenylmethane, 115 Triphenylmethyl, 115 Trioxyanthraquinones, 215 Trisaccharides, 371 TropaSlin D, 468 Tropaolin O, 471 Trypsin, 518 Tryptophane, 511 Turanose, 358 * Turkey red, 212 Typhotoxine, 520 Tyrosine, 511 Unsaturated hydrocarbons, 75, 77 Uracil, 294 Uramidocrotonic ester, 295 Urea, 290 Urea chloride, 292 Urease, 519 Urethane, 292 Valeric aldehyde, 170* Valerolactone, 394 Valylene, 87 * Vanillin, 186 Vapor density, determination, 23 Vaseline, 73 Veratrine, 508 Vinegar, 226 Vinyl alcohol, 139 Vinyl amine, 432 Vinyl bromide, 399 Vinyl ether, 164 * Vinyl trimethyl ammonium hydrox- ide, 433 Viscosity, 43 Vitellin, 512 * Wood alcohol, 126 Xanthine, 298 Xanthooxidase, 519 Xylan, 360, 375 Xylene diazonium chloride, 458 Xylenes, 109 Xyli dines, 442 Xyloquinone, 211 Xylose, 360 Zein, 512, 515 Zymase, 131, 518, 519 SEP 2 0 1920 { I t n. 