Title: Chrysanthemic Acid
CAS Registry Number: 10453-89-1
CAS Name: 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid
Synonyms: chrysanthemummonocarboxylic acid; chrysanthemumic acid
Molecular Formula: C10H16O2
Molecular Weight: 168.23
Percent Composition: C 71.39%, H 9.59%, O 19.02%
Literature References: Occurs as esters in pyrethrum flowers,
see Pyrethrin I and Cinerin I,
also Allethrin (a synthetic product). Isoln and structure: Staudinger, Ruzicka,
Helv. Chim. Acta 7, 177, 201 (1924). Synthesis: Staudinger
et al., ibid. 390; Campbell, Harper,
J. Chem. Soc. 1945, 283; M. J. Devos, A. Krief,
Tetrahedron Lett. 1978, 1845;
1979, 1891; O. A. Nesmeyanova
et al., Synthesis 1982, 296. Asymmetric synthesis: T. Aratani
et al., ibid. 1977, 2599. Stereoselective synthesis of
dl-trans-chrysanthemic acid: Mills
et al., Chem. Commun. 1971, 555;
eidem, J. Chem. Soc. Perkin Trans. 1 1973, 133; S. C. Welch, T. A. Valdes,
J. Org. Chem. 42, 2108 (1977); J. P. Genet
et al., Tetrahedron Lett. 21, 3183 (1980); of
dl-cis-form: J. Mann, A. Thomas,
ibid. 27, 3533 (1986). Synthesis of (-)-
cis- and (+)-
trans-forms: Gopichand
et al., Indian J. Chem. 13, 433 (1975).
Derivative Type: dl-cis-Form
CAS Registry Number: 2935-23-1
Properties: Cubic prisms from ethyl acetate, mp 115-116°.
Melting point: mp 115-116°
Derivative Type: dl-trans-Form
CAS Registry Number: 705-16-8
Properties: Long prisms, mp 54°. Very sol in ethyl acetate. Exhibits a marked negative heat of soln in ethyl acetate or in methanol.
Melting point: mp 54°
Derivative Type: l-trans-Form
CAS Registry Number: 2259-14-5
Properties: Elongated prisms, mp 17-21°. [a]D25 -14.01° (c = 1.535 in abs alc).
Melting point: mp 17-21°
Optical Rotation: [a]D25 -14.01° (c = 1.535 in abs alc)
Derivative Type: d-trans-Form
CAS Registry Number: 4638-92-0
Properties: Elongated prisms, mp 17-21°. [a]D25 +14.16° (c = 1.554 in abs alc).
Melting point: mp 17-21°
Optical Rotation: [a]D25 +14.16° (c = 1.554 in abs alc)
