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Zeatin

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Zeatin
Names
IUPAC name (E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+Key: UZKQTCBAMSWPJD-FARCUNLSSA-N
  • InChI=1/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+Key: UZKQTCBAMSWPJD-FARCUNLSBM
SMILES
  • C/C(=C\CNC1=NC=NC2=C1NC=N2)/CO
Properties
Chemical formula C10H13N5O
Molar mass 219.248 g·mol
Appearance Off-white to yellow crystalline powder
Melting point 208 to 210 °C (406 to 410 °F; 481 to 483 K)
Solubility in 1M NaOH Soluble
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose) 2200 mg/kg (mouse, transperitoneal)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Zeatin is a cytokinin derived from adenine, which occurs in the form of a cis- and a trans-isomer and conjugates. Zeatin was discovered in immature corn kernels from the genus Zea. It promotes growth of lateral buds and when sprayed on meristems stimulates cell division to produce bushier plants.

Occurrence

Zeatin and its derivatives occur in many plant extracts and are the active ingredient in coconut milk, which causes plant growth.

6-(γ,γ-Dimethylallylamino)purine is a zeatin precursor.

Application

Zeatin has a variety of effects including:

  1. Promotes callus initiation when combined with auxin, concentration 1 ppm.
  2. Promotes fruit set. Zeatin 100 ppm + GA3 500 ppm + NAA 20 ppm, sprayed at 10th, 25th, 40th day after blossom.
  3. Retards yellowing for vegetables, 20 ppm, sprayed.
  4. Causes auxiliary stems to grow and flower.

Zeatin can also be applied to stimulate seed germination and seedling growth.

Zeatin has also been shown to promote the resistance of tobacco against the bacterial pathogen Pseudomonas syringae, in which trans-zeatin has a more prominent effect than cis-zeatin.

The two isomers of Zeatin are found to have different effects biologically, as trans-zeatin is found to be bioactive while cis-zeatin has a weak impact. This distinct bioactivity is not a result of difference in uptake and accumulation of trans-Zeatin as opposed to cis-Zeatin. In the tobacco callus bioassay, cis-Zeatin was found to be less active than trans-Zeatin. There is no evidence of cis↔trans isomerization in plant tissues.

References

  1. David W. S. Mok; Machteld C. Mok (1994). Cytokinins: Chemistry, Activity, and Function. CRC Press. p. 8. ISBN 0-8493-6252-0.
  2. "6-(γ,γ-Dimethylallylamino)purine BioReagent, suitable for plant cell culture, 1 mg/mL". MilliporeSigma | United States. Retrieved 2021-10-12.
  3. Großkinsky, D.K.; Edelsbrunner, K.; Pfeifhofer, H.; van der Graaff, E. & Roitsch, T. (2013). "Cis- and trans-zeatin differentially modulate plant immunity". Plant Signaling & Behavior. 8 (7): e24798. Bibcode:2013PlSiB...8E4798G. doi:10.4161/psb.24798. PMC 3906432. PMID 23656869.
  4. Gajdošová, Silvia; Spíchal, Lukáš; Kamínek, Miroslav; Hoyerová, Klára; Novák, Ondřej; Dobrev, Petre I.; Galuszka, Petr; Klíma, Petr; Gaudinová, Alena; Žižková, Eva; Hanuš, Jan; Dančák, Martin; Trávníček, Bohumil; Pešek, Bedřich; Krupička, Martin (May 2011). "Distribution, biological activities, metabolism, and the conceivable function of cis-zeatin-type cytokinins in plants". Journal of Experimental Botany. 62 (8): 2827–2840. doi:10.1093/jxb/erq457. ISSN 1460-2431. PMID 21282330. Retrieved December 7, 2023.
  5. Jameson, Paula Elizabeth (2023-05-02). "Zeatin: The 60th anniversary of its identification". Plant Physiology. 192 (1): 34–55. doi:10.1093/plphys/kiad094. ISSN 0032-0889. PMC 10152681. PMID 36789623.

External links

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