32771-64-5

Basic information

• Product Name: 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE
• Synonyms: 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE;6-[4-HYDROXY-3-METHYLBUT-2-ENYLAMINO]PURINE CIS-ISOMER;CIS-ZEATIN;ZEATIN CIS-ISOMER;cis-ZEATIN (cZ);cis-Zeatin,6-(4-Hydroxy-3-methyl-cis-2-butenylamino)purine;(Z)-4-((7H-Purin-6-yl)amino)-2-methylbut-2-en-1-ol
• CAS NO: 32771-64-5
• Molecular Formula: C₁₀H₁₃N₅O
• Molecular Weight: 219.24
• EINECS: 209-170-2
• Product Categories: Miscellaneous Natural Products
• Mol File: 32771-64-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 206-208 °C
• Boiling Point: 117.1°C at 760 mmHg
• Flash Point: 40°C
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• Vapor Pressure: 13.9mmHg at 25°C
• Storage Temp.: −20°C
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE(32771-64-5)
• EPA Substance Registry System: 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE(32771-64-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 1
• Hazardous Substances Data: 32771-64-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 32771-64-5 differently. You can refer to the following data:
1. cis-Zeatin is a member of the cytokinin family.
2. 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.

General Description

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

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 articles and documents

A Novel Method for Synthesis of cis-Zeatin and Its Valuable Precursor (Z)-4-Chloro-2-methyl-but-2-en-1-ol

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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.