32771-64-5

Usage

Uses

Used in Plant Growth Regulation:
cis-Zeatin is used as a plant growth regulator to promote cell division, differentiation, and elongation in plants. It helps in the overall growth and development of plants, leading to increased crop yields and improved plant health.
Used in Cytokinin Standard:
cis-Zeatin has been used as a cytokinin standard in the ultra-violet (UV) spectrum and gas chromatogram measurements to characterize N-glucoside of cis-Zeatin from potato tuber sprouts. This helps in the accurate identification and quantification of cytokinins in plant samples.
Used in Legume Pseudonodules Formation:
cis-Zeatin has been used as a cytokinin to treat legume M. atropurpureum to test its effect on pseudonodules formation. This research helps in understanding the role of cytokinins in the formation of nodules, which are essential for nitrogen fixation in leguminous plants.

Biochem/physiol Actions

cis-Zeatin displays a low affinity to cytokinin receptors (CK) and lower activity in the classical CK bioassays compared to the trans isomer. cis-Zeatin (cZ) and its riboside (cZR) regulate plant development and stress. cZ also plays a key role in the growth and development of rice. It may also have a role in mediating plant-pathogen interactions and plant immunity.

InChI:InChI=1/2C2H4O2.2H2O.Zn/c2*1-2(3)4;;;/h2*1H3,(H,3,4);2*1H2;/q;;;;+2/p-2

Upstream product

• 1838-94-4 isoprene epoxide 
• 87-42-3 6-chloropurine 
• 71866-93-8 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-[(Z)-2-methyl-4-(9H-purin-6-ylamino)-but-2-enyloxy]-tetrahydro-pyran-3,4,5-triol 
• 145428-43-9 (Z)-4-amino-2-methyl-2-buten-1-ol oxalate (2:1) 

Downstream Products

• 1795-76-2 (Z)-4-amino-2-methyl-2-buten-1-ol 
• 68-94-0 hypoxanthine 

Relevant academic research and scientific papers

A hetero diels-alder access to (Z)-zeatin and (Z)-isozeatin

(Z)-6-(4-Hydroxy-3-methylbut-2-en-1-ylamino)purine, (Z)-zeatin, and the isomeric (Z)-isozeatin, both free from the E isomers, were prepared using the cycloaddition of the in situ generated tert-butyl nitrosoformate on isoprene. A mixture of tert-butyl 5(and 4)-methyl-3,6-dihydro-2H-1,2-oxazine-2-carboxylates thus formed was deprotected and reductively cleaved to (Z)-4-amino-2(and 3)-methylbut-2-en-1-ols, which were chromatographically separated and finally alkylated with 6-chloropurine to give the title compounds.

Syntheses of cis-zeatin and its 9-(2-deoxy-β-D-ribofuranosyl) derivative: A novel synthetic route to the side chain at C(6), and cytokinin activity

cis-Zeatin (3a) and its 9-(2-deoxy-β-D-ribofuranosyl) derivative (3c) have been synthesized from N-[(1,1-dimethylethoxy)carbonyl]glycine methyl ester (5) in 5 steps by adopting the 'α-amino aldehyde/olefination' technology. The new cis-zeatin derivative (3c), its trans isomer (1c), and known trans-zeatin 9-β-D-riboside (1b) were tested for cytokinin activity in the stimulation of chlorophyll biosynthesis in etiolated cucumber cotyledons. The ribeside 1b turned out to be the most active cytokinin among them, while the deoxyribosides 1c and 3c showed a marked decrease and a total loss, respectively, of cytokinin activity.

Cytokinin metabolism and the modulation of cytokinin activity in radish

The metabolism of zeatin, N6-(Δ2-isopentenyl) adenine, dihydrozeatin, zeatin-O-glucoside and dihydrozeatin-O-glucoside has been studied using derooted radish seedlings. The metabolites were identified by UV and GC/MS. The patterns of metabolism are compared and provide evidence that the O-glucosyl conjugates may be storage forms of the cytokinins.