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Z0750

Sigma-Aldrich

cis-Zeatin

≥90% (HPLC)

Synonyme(s) :

6-(4-Hydroxy-3-methyl-cis-2-butenylamino)purine

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About This Item

Formule empirique (notation de Hill):
C10H13N5O
Numéro CAS:
32771-64-5
Poids moléculaire :
219.24
Numéro MDL:
MFCD00070217
Code UNSPSC :
41106305
ID de substance PubChem :
24902168
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Pureté

≥90% (HPLC)

Forme

powder

Solubilité

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

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

UZKQTCBAMSWPJD-UQCOIBPSSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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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