100 



SCIENCE 



[N. S. Vol. XLII. No. 1072 



salts of ortho-coumaric acid. These reactions af- 

 ford a very convenient method for converting cou- 

 marin into coumaric aeid. 



By the action of acetic anhydride at the ordinary 

 temperature, the sulphonate of hydro-coumaric acid 

 reverts to the hydro-coumarin sulphonate, so that 

 by this series of smooth reactions it is possible to 

 pass at will from coumarin to coumaric acid, or 

 vice versa. 



An analogous compound of Limettin (di- 

 methoxy-coumarin) with sodium bi-sulphite is de- 

 scribed. 



The author also calls attention to the character- 

 istic behavior of the coumarins on hydrolysis, 

 which may be of diagnostic value for compounds 

 of unknown constitution. 



L. F. AuGSPURGEE: The Isolation of a Blue Hy- 



drooarbon from Milfoil Oil. 



The blue color of certain volatile oils has long 

 attracted attention, but thus far appears to have 

 escaped rational chemical investigation. Thanks 

 to the distillation of more than a liter of volatile 

 oil of Achillea millefolium by Professor E. R. 

 Miller last summer, the writer had several hun- 

 dred cubic centimeters of the high boiling in- 

 tensely blue fraction placed at bis disposal. 

 Thanks also to the observation made by Mr. A. E. 

 Sherndal in the laboratory of Dodge and Oleott, 

 that an artificial blue oil combines with phosphoric 

 acid to form a labile addition product from which 

 the blue hydrocarbon oil can be recovered by the 

 addition of water, it became possible for the first 

 time to isolate the blue substance of a natural oil 

 in a pure state. 



Analysis of the compound thus isolated revealed 

 the composition CwHjs. It will be seen at once that 

 whereas this hydrocarbon has the same number of 

 carbon atoms as have the sesquiterpenes, CibH,,,, 

 its hydrocarbon content is much lower, hence it is 

 less saturated. The most interesting observation of 

 the investigation thus far is that the blue color is 

 lost upon additions to the molecule. Apparently 

 it makes no difference whether hydrogen is added 

 (reduction with palladium hydrogen), phosphoric 

 acid, or possibly other substances still to be tested. 



Nellie Wakeman: A Possible New Terpene 



from, Monarda Punctata. 



Although Schumann in 1896 reported the pres- 

 ence of eymene, and Hendricks in 1899 that of 

 limonene as results of the preliminary investiga- 

 tion of this oil, the subsequent study of larger 

 amounts seemed to add to the complexity of the 



chemical study of the oldest of the Monarda oils. 



A large amount of the non-phenol constituents 

 of horsemint oil having been placed at the dis- 

 posal of the writer, a more careful study was made 

 of the hydrocarbon fractions than before. All en- 

 deavors to make the hydrocarbon which yields a 

 nitroso chloride correspond with one of the known 

 terpenes have failed. The melting point of its 

 nitrol piperidine differs by 103 and 87 degrees 

 respectively from that of limonene and dipentene 

 and by 78 degrees from that of pinene. The 

 benzylamine base shows no such striking differ- 

 ences. With aniline, however, it does not react as 

 does limonene but resembles pinene. 



As soon as new material that is now being pre- 

 pared for further nitroso chloride experiments is 

 ready, a third attempt to identify this hydrocar- 

 bon with known terpenes will be made. For a 

 summary of the chemical studies of the Monarda 

 see Bulletin 448 of the University of Wisconsin. 



C. H. Hertt and D. H. Killepper: The So-called 

 Alpha and Beta Isomeric Sesin Acids. 



Oliver Kamm and C. G. Deeick: The Structure 



of Certain Hydronaphthoio Acids. 



The evidence previously advanced for the struc- 

 ture of the isomeric dihydro-j3-naphthoie acids was 

 based upon the reactions of their dibromides. A 

 study of the oxidation products from these unsat- 

 urated acids has verified the conclusions previously 

 advanced. 



C. Gr. Derick and Oliver K4.MM: The Correlation 

 of Ionization and Structure in Unsaturated 

 Acids. 



Conclusions are drawn chiefly from acids having 

 the unsaturation in a ring structure, thus elimina- 

 ting the possibilities of cis-trans isomerism. The 

 effect of conjugation of double unions is shown 

 and the method of determining the constitution of 

 acids of unknown structure is indicated. The 

 possibility of obtaining a quantitative expression 

 for conjugation of Thiele's partial valences is ex- 



Oliver Kamm: Some Tests for Qualitative Or- 

 ganic Analysis. 

 Several tests used in the courses in qualitative 



organic analysis at the University of Illinois are 



mentioned. 



1. The identification of the volatile fatty acids 



by means of a method based upon that advanced 



by Duclaux for quantitative work. 



