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Z0750

Sigma-Aldrich

cis-Zeatin

≥90% (HPLC)

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Synonym(s):
6-(4-Hydroxy-3-methyl-cis-2-butenylamino)purine
Empirical Formula (Hill Notation):
C10H13N5O
CAS Number:
32771-64-5
Molecular Weight:
219.24
MDL number:
MFCD00070217
PubChem Substance ID:
24902168
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

100

Assay

≥90% (HPLC)

form

powder

solubility

glacial acetic acid: 10 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

C\C(CO)=C\CNc1ncnc2nc[nH]c12

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-

InChI key

UZKQTCBAMSWPJD-UQCOIBPSSA-N

General description

cis-Zeatin is an isoprenoid cytokinin (CK)(2) present in plants and some bacteria.

Application

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. It has also been used as a cytokinin to treat legume M. atropurpureum to test its effect on pseudonodules formation.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Martin Schäfer et al.
Journal of experimental botany, 66(16), 4873-4884 (2015-05-23)
Cytokinins (CKs) are well-established as important phytohormonal regulators of plant growth and development. An increasing number of studies have also revealed the function of these hormones in plant responses to biotic and abiotic stresses. While the function of certain CK
Christopher Gauthier-Coles et al.
Frontiers in plant science, 9, 1901-1901 (2019-01-24)
Root nodule symbiosis (RNS) is a feature confined to a single clade of plants, the Fabids. Among Fabids capable of RNS, legumes form root cortex-based nodules in symbioses with rhizobia, while actinorhizal species form lateral root-based nodules with actinomycetes. Cytokinin
Raju Bheemanahalli et al.
Physiologia plantarum, 169(4), 501-514 (2020-04-22)
Unraveling the metabolic and phytohormonal changes in anthers exposed to heat stress would help identify mechanisms regulating heat stress tolerance during the sensitive reproductive stage. Two spring wheat genotypes contrasting for heat tolerance were exposed to heat stress during heading
Dominik K Großkinsky et al.
Plant signaling & behavior, 8(7), e24798-e24798 (2013-05-10)
Phytohormones are essential regulators of various processes in plant growth and development. Several phytohormones are also known to regulate plant responses to environmental stress and pathogens. Only recently, cytokinins have been demonstrated to play an important role in plant immunity.
Toru Kudo et al.
Plant physiology, 160(1), 319-331 (2012-07-20)
cis-Zeatin (cZ) is generally regarded as a cytokinin with little or no activity, compared with the highly active trans-zeatin (tZ). Although recent studies suggested possible roles for cZ, its physiological significance remains unclear. In our studies with rice (Oryza sativa)

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