5311. Kinetin

Nomenclature

CAS number: 525-79-1
N-(2-Furanylmethyl)-1H-purin-6-amine; N6-furfuryladenine; 6-furfurylaminopurine.
C10H9N5O; mol wt 215.21.
C 55.81%, H 4.22%, N 32.54%, O 7.43%.

Description and references

A cell division factor found in various plant parts and in yeast. Isoln from autoclaved water slurries of deoxyribonucleic acid: Miller et al., J. Am. Chem. Soc. 77, 1392 (1955). Structure and synthesis from furfurylamine and 6-methylmercaptopurine: Miller et al., ibid. 2662; 78, 1375 (1956); US 2903455 (1959 to Wisc. Alumni Res. Found.). Physiologically active at very great dilutions, but only in presence of auxin, see Indoleacetic Acid. Crystal structure: M. Soriano-Garcia, R. Parthasarathy, Acta Crystallogr. 33B, 2674 (1977). Review: Miller, Annu. Rev. Plant Physiol. 12, 395 (1961).

Chemical structure

Properties

Platelets from abs ethanol, mp 266-267° (sealed tube). Sublimes at 220°. pKa1 2.7; pKa2 9.9. uv max (ethanol): 268 nm (ε 18,650). Slightly soluble in cold water, methanol, ethanol. Freely soluble in dil aq HCl or NaOH. Can be extracted from neutral aq solns by shaking with ether.

Note

Kinetin is also a brand of hyaluronidase, q.v.

Use

Plant growth regulator. To augment growth of microbial cultures: BE 632589 (1963 to Hoechst).