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THE MERCK INDEX on CD-ROM / Version 12:3 / 1999 =============================================== Monograph number: 7620. Title: Piperic Acid.

CAS Registry number: [5285-18-7] CAS name(s): 5-(1,3-Benzodioxol-5-yl)-2,4-penta dienoic acid; 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid. Molecular formula: C12H10O4 ; Molecular weight: 218.21. Percent Composition: C 66.05%, H 4.62%, O 29.33%. Literature references: Early literature treats the title compound without specifying stereochemistry; however, four isomers exist: piperinic acid (E,E); isochavicinic acid (E,Z); isopiperinic acid (Z,E); chavicinic acid (Z,Z). Physical constants given in early references for piperic acid agree with those of piperinic acid. See Beilstein 19, 281; suppl. II, 300. Synthesis of (E,E)- form: L. von Babo, E. Keller, J. Prakt. Chem. 72, 53 (1857); A. Ladenburg, M. Sholtz, Ber. 27, 2958 (1894); of (E,Z)- form: H. Lohaus, H. Gall, Ann. 517, 278 (1935); of (Z,E)- form: E. Ott, F. Eichler, Ber. 55, 2653 (1922); of (Z,Z)- form: idem, loc. cit.; H. Lohaus, H. Gall, loc. cit.; of all isomers: R. Grewe et al., Ber. 103, 3752 (1970); R. De Cleyn, A. Verzele, Bull. Soc. Chim. Belg. 81, 529 (1972). Derivative: (E,E)- Form, CAS Registry: [136-72-1] Additional name(s): piperinic acid, piperinsaumlure (German). Properties: Nee dles from alc. Colorless when freshly prepd, rapidly turns yellow on exposure to light. mp 216-217 . Sublimes as yellow needles with partial decompn. uv max (methanol): 340 nm (epsi 28800) . Sol in 50 parts boiling alcohol, 275 parts abs alcohol at 25. Practically insol in water, ether, benzene, carbon disulfide. Melting Point: 216-217 UV Maxima: 340 Derivative: (E,Z)- Form, CAS Registry: [495-87-4] Additional name(s): isochavicinic acid. Properties: Yellow crystals from methanol/water, sublimes as needles. mp 134-136 (Lo haus, Gall); 143 (Grewe) . uv max (methanol): 335 nm (epsi 14500) . Sol in methanol, benzene. Melting Point: 134-136 (Lo haus, Gall); 143 (Grewe) UV Maxima: 335 Derivative: (Z,E)- Form, CAS Registry: [495-88-5] Additional name(s): isopiperinic acid. Properties: Needles from benzene. mp 145 (Ott, Eichler); 153 (Grewe); 138 (DeCleyn, Verzele) . uv max (methanol): 328 nm (epsi 22000) . Sol in benzene. Melting Point: 145 (Ott, Eichler); 153 (Grewe); 138 (DeCleyn, Verzele) UV Maxima: 328 Derivative: (Z,Z)- Form, CAS Registry: [495-89-6] Additional name(s): chavicinic acid. Properties: Amorphous yellow granules from benzene. Wide disparities in mp have been reported: 200-202 (Ott, Eichler); 130 (Grewe); 120 (De Cleyn,

Verzele) . uv max (methanol): 335 nm (epsi 17500) . 0.55 g sol in 16 g boiling 95% alcohol, and in 65 g boiling benzene. Melting Point: have been reported: 200-202 (Ott, Eichler); 130 (Grewe); 120 (De Cleyn, Verzele) UV Maxima: 335