Yojiro Tsuzuki Science University o f Tokyo Kagurazaka 1-3, T O ~ Y O (162) Japan
Some Japanese Organic Chemists Who Discovered Remarkable Substances
Discoverers are often left unquoted when they published their works in local publications. After their death their names are more liable to disappear, even when they were once known, k i n g obscured by later investigators. A few notable examples of Japanese chemists to whom this has happened will be discussed in this paper. Ephedrine
I n 1885, the active ingredient of dBa Huang (Ephedra Sinica or Ephedra vulgaris Rich. var. helvetica Hook et Thomp.) used in China as a cough remedy and antifebric for 5000 years was isolated in the crystalline state (mp 216-217°C) by NagayoshiNagai (1845-1929)) who designated it "Ephedrin" (1). Nagai, born near Toliushima in 1845, originally learned Dutch medicine a t Nagasaki from foreign teachers, but later studied organic chemistry in Berlin under August Wilhelm von Hofmanil and Ferdinand Tiemann during the years 1872-84. After returning to his native country, he was appointed professor of pharmacy of Tokyo Imperial University in 1893 in place of Johan Frederili Eyliman (1851-1915) noted for studies on shiliimic acid and molecular weight determination. Nagai was one of the founders of pharmaceutical chemistry in Japan and was respected as an autrhorit8y in this field. His numerous papers were mostly pubThe discovery of ephedrine has usually been dat,ed 1887 (for Chemie," example, WALDI~:N, P.: "Geschichte der orga~lische~l Jnlius Spriirger, Berlin, 1941, p. 752) because K. Miurn (of the chirurgic-ophthalmological department of Tokyo Imperial. University) published ill 1887 (Berlin. Klin. Wochcnschr., 19, 707) his re%earcheson the physiological effect of ephedrine ment i o ~ l i l ~t>he g discovery of Nagai, but it should be corrected to be 1885 according t>ot,he researches of Yamashit.a (2). Reference (4) is on the relat,io~lbetween molecular st,ructure and taste (especially sweet.~~ess) of perfumes, particularly aldehydes, ket,olies, and their derivatives. Appendix: 011sweet perfume, see Furukawa, S., J. Chcm. Soc., 41, 706 (1920). Chcn~. Abstr., 15, 1145 (1921). La Forge, ct al. described i11their review, "The Determination of t.he Structure of Rotello~le" [Chcm. Revs.,17, 181 (1933)] that "It appears t,hat rotenone was first isolated ill 1895 by Geoffroy from a plant native t o French Guiana and called Robinia nicou. The substarlce was reported t o melt a t 160°C, and named by the author nicoulinc." Geoffroy gave no description of the crystalline state. However, Nagai gave the first detailed description of t,he crystalli~lestate, the chemical and physiological properties, and the toxic effect on fishes of rotenolle. Kariyone, et al. found in 1923 [J.P h a ~ n Soc. ~ . Japan, 43, [491], 10, 7391 that rote~lorle by Nagai was almost ider~t~ical with t,he insect,icide "Tubotoxill" (mp 163.S°C) isolated by Takeo Ishikawa (1916) from D. elliptica native t o Borneo and with some fish poiso~lssuch as "Pachyrhizid" obtained earlier by van Sillevoldt (1899) from Pachyrhizus angulatus Rich. native t o Java, arrd with "Timboin" obtained by F. Pfaff (1891) from Tephrosia toxicaria native tfoBrazil.
lished in Japanese. His later studies on ephedrine ( 2 ) appeared in ten papers (1892-1930). He married a German woman named Therese Schumacher in lSSG, and had a daughter and two sons. His second son Willy was also an organic chemist ( 3 ) . Perillartine
I n 1919, Furuliawwra isolated perillaldehyde CgH1,CHO from the oil of Aoshiso Perylla nankinensis, described its a-anti-oxime CloHl~ON(mp 102OC) to be 2000 times sweeter than sucrose, and named it "Perillnrtine." It is curious that although a-anti-perillnldoxin~c is 2000 times as sweet as sucrose, its syn-isomer (mp 129°C) is tasteless (4).% Seiji Furulia~w~a (1SSG-1955) graduated in 1911 from the department of agricultural chemistry of Tokyo Imperial University. His life and 1~0r1iwere studied by Yamashita ( 5 ) . In Holiliaido, perillartine has been produced from a natural source since the prewar days for the purpose of supplyirlg the Ilonopoly Bureau with a s~veetening perfume for tobacco. Even after the war I~uruliaw~n made a notable ~ontribut~ion to the perfumiilg of tobacco as a nonregulnr staff member of the office. Soon after the war Tamurn, ef al. ( 6 ) succeeded in synthesizing perillartine from a-pinene, and for its production a unique plant called Yul;i Gosei Koqyo Co. (Organic Synthetic I~ldust~ries Co.) has been established in the suburbs of Tokyo. Rotenones
I11 1902, Icazuo Nagai (1873-1923) isolated, as a crystalline compou~ld(mp 163OC), the active principle from the root of Afilletia taircaniana Hayata whose narcotic effect wvns used for fishing by the aborigines in the mountainous district of Taiwan (Formosa) ( 7 ) . I
