Echitamine

Title: Echitamine
CAS Registry Number: 6871-44-9
CAS Name: (3b,16R)-3,17-Dihydroxy-16-(methoxycarbonyl)-4-methyl-2,4(1H)-cyclo-3,4-secoakuammilanium
Additional Names: ditaine
Molecular Formula: [C22H29N2O4]+
Literature References: From the bark of Alstonia scholaris (L.) R.Br., A. congensis Engl., Apocynaceae; A. neriifolia: Hesse, Ann. 203, 150 (1880); Goodson, Henry, J. Chem. Soc. 127, 1640 (1925); Goodson, ibid. 1932, 2626; Chakravarti et al., Bull. Calcutta Sch. Trop. Med. 16, 81 (1968), C.A. 71, 3529f (1969); Roy, Chatterjee, J. Indian Chem. Soc. 45, 21 (1968). Structure: Hamilton et al., Proc. Chem. Soc. London 1961, 63; J. Chem. Soc. 1962, 5061. Abs config: Manohar, Ramaseshan, Tetrahedron Lett. 1961, 814. Synthetic studies: Fritz, Fischer, Tetrahedron 20, 1737 (1964); Dolby, Esfandiari, J. Org. Chem. 37, 43 (1972). Review: Govindachari, J. Indian Chem. Soc. 45, 945-957 (1968).
Derivative Type: Hydroxide
Molecular Formula: C22H30N2O5
Molecular Weight: 402.48
Percent Composition: C 65.65%, H 7.51%, N 6.96%, O 19.88%
Properties: White crystals, mp 206°. [a]D20 -29° (alcohol). Sol in water, alcohol, chloroform, ether.
Melting point: mp 206°
Optical Rotation: [a]D20 -29° (alcohol)
Derivative Type: Chloride
Molecular Formula: C22H29O4N2+Cl-
Properties: Long needles from water, mp 295°. [a]D15 -58°. uv max (ethanol): 235, 295 nm (log e 3.93, 3.55).
Melting point: mp 295°
Optical Rotation: [a]D15 -58°
Absorption maximum: uv max (ethanol): 235, 295 nm (log e 3.93, 3.55)
Echothiophate Iodide Ecteinascidins ECTEOLA-Cellulose Ectoine Ectylurea