Zeatin

Zeatin
Names
	IUPAC name (E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
Identifiers
CAS Number	1637-39-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16522 ;
ChemSpider	395716 ;
PubChem CID	449093;
UNII	7I6OOJ9GR6 ;
	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−1
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 [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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.[1]

6-(γ,γ-Dimethylallylamino)purine is a zeatin precursor.[2]

Toxicology

Zeatin has several anti-aging effects on human skin fibroblasts.[3] Zeatin riboside has an immunomodulatory effect by agonizing the mammalian adenosine A2A receptor.[4]

Application

Zeatin has a variety of effects including:

Promotes callus initiation when combined with auxin, concentration 1 ppm.
Promotes fruit set. Zeatin 100 ppm + GA3 500 ppm + NAA 20 ppm, sprayed at 10th, 25th, 40th day after blossom.
Retards yellowing for vegetables, 20 ppm, sprayed.
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. [5]

References

David W. S. Mok; Machteld C. Mok (1994). Cytokinins: Chemistry, Activity, and Function. CRC Press. p. 8. ISBN 0-8493-6252-0.
http://www.sigmaaldrich.com/catalog/product/sigma/d7660
Rattan, S.I.S. & Sodagam, L. (2005). "Gerontomodulatory and youth-preserving effects of zeatin on fibroblasts of human skin". Rejuvenation Research. 8 (1): 46–57. doi:10.1089/rej.2005.8.46. PMID 15798374.
CM Lappas (2015), "The plant hormone zeatin riboside inhibits T lymphocyte activity via adenosine A2A receptor activation", Cellular & Molecular Immunology, 12 (1), doi:10.1038/cmi.2014.33, PMC 4654369, PMID 24813229
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). doi:10.4161/psb.24798. PMC 3906432. PMID 23656869.

External links

Cytokinins

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[1] David W. S. Mok; Machteld C. Mok (1994). Cytokinins: Chemistry, Activity, and Function. CRC Press. p. 8. ISBN 0-8493-6252-0.

[2] ttp://www.sigmaaldrich.com/catalog/product/sigma/d7660

[3] Rattan, S.I.S. & Sodagam, L. (2005). "Gerontomodulatory and youth-preserving effects of zeatin on fibroblasts of human skin". Rejuvenation Research. 8 (1): 46–57. doi:10.1089/rej.2005.8.46. PMID 15798374.

[4] CM Lappas (2015), "The plant hormone zeatin riboside inhibits T lymphocyte activity via adenosine A2A receptor activation", Cellular & Molecular Immunology, 12 (1), doi:10.1038/cmi.2014.33, PMC 4654369, PMID 24813229

[5] 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). doi:10.4161/psb.24798. PMC 3906432. PMID 23656869.