| Identification | More | [Name]
trans-Zeatin | [CAS]
1637-39-4 | [Synonyms]
6-(4-HYDROXY-3-METHYL-2-BUTENYLAMINO)PURINE
6-[4-HYDROXY-3-METHYLBUT-2-ENYLAMINO]PURINE
6-[4-HYDROXY-3-METHYLBUT-2-ENYLAMINO]PURINE TRANS ISOMER
6-[(E)-4-HYDROXY-3-METHYL-2-BUTENYLAMINE]PURINE
6[(E)-4-HYDROXY-3-METHYL-2-BUTENYLAMINO] PURINE
6-(HYDROXY-3-METHYL-BUT-2-ENYLAMINO)PURINE
(E)-2-METHYL-4-(1H-PURIN-6-YLAMINO)-2-BUTEN-1-OL
N6-(4-HYDROXY-3-METHYL-2-BUTEN-1-YL)ADENINE
TRANS-2-METHYL-4-(1H-PURIN-6-YLAMINO)-BUT-2-EN-1-OL
TRANS-6-(4-HYDROXY-3-METHYLBUT-2-ENYLAMINO)PURINE
TRANS-ZEATIN
trans-Zeatin (synthetic)
ZEATIN
ZEATIN TRANS ISOMER
(e)-2-buten-1-o
(E)-Zeatin
2-Buten-1-ol,2-methyl-4-(purin-6-ylamino)-,(E)-
2-methyl-4-(1H-purin-6-ylamino)-,(E)-2-Buten-1-ol
2-methyl-4-(purin-6-ylamino)-,(E)-2-Buten-1-ol
Zeatine | [EINECS(EC#)]
605-343-5 | [Molecular Formula]
C10H13N5O | [MDL Number]
MFCD00213654 | [Molecular Weight]
219.24 | [MOL File]
1637-39-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
207 °C | [Boiling point ]
395.0±52.0 °C(Predicted) | [density ]
1.40±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
H2O: soluble
| [form ]
powder
| [pka]
14.77±0.10(Predicted) | [color ]
off-white to yellow
| [Merck ]
10117 | [BRN ]
616241 | [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+ | [InChIKey]
UZKQTCBAMSWPJD-FARCUNLSSA-N | [SMILES]
C(O)/C(/C)=C/CNC1=C2C(=NC=N1)NC=N2 | [CAS DataBase Reference]
1637-39-4(CAS DataBase Reference) | [EPA Substance Registry System]
1637-39-4(EPA Substance) |
| Hazard Information | Back Directory | [Description]
trans-Zeatin is a cytokinin plant growth regulator with antioxidant and neuroprotective activities.1,2,3,4 It binds to the cytokinin receptor Arabidopsis histidine kinase 3 (AHK3) with a KD value of 1.3 nM.3 trans-Zeatin increases chlorophyll levels in etiolated Cucumus sativus cotyledons in a concentration-dependent manner.1 It increases callus growth and shoot formation in N. tabacum calluses when used at concentrations of 5 and 50 μM.2 trans-Zeatin (25-100 μM) reduces production of reactive oxygen species (ROS) induced by amyloid β (25-35) (Aβ25-35) in PC12 cells.4 It reduces scopolamine-induced spontaneous alternations in the Y-maze, indicating enhanced spatial memory, in mice when administered at doses of 1.5, 3, and 4.5 mg/kg per day. | [Chemical Properties]
white to light yellow crystal powder | [Physical properties]
Trans-zeatin is freely soluble in acetic acid and water.
| [Uses]
Labelled Zeatin. It is purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form
-induced matrix metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging. | [Uses]
Zeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form
metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging. | [Definition]
ChEBI: The trans-isomer of zeatin. | [General Description]
trans-Zeatin contains a hydroxylated isoprenoid side chain. | [Biochem/physiol Actions]
Zeatin upon reduction forms zeatin O-glucoside, which is widely present in plants. It possesses transportation and storage functions, along with defence against zeatin oxidases. | [Purification Methods]
Purify zeatin by recrystallisation from EtOH or H2O. The UV has max at 207 and 275nm ( 1,400 and 14,650) in 0.1N aqueous HCl; 212 and 270nm ( 17,050 and 16,150) in aqueous buffer pH 7.2; 220 and 276nm ( 15,900 and 14,650) in 0.1N aqueous NaOH. The picrate has m 192-194o (from H2O) from which zeatin can be recovered by treatment with Dowex-1 x 8 (200-400 mesh, OH-form). [Letham et al. Aust J Chem 22 205 1969, Proc Chem Soc (London) 230 1964, Shaw & Wilson Proc Chem Soc (London) 231 1964.] It is a cell division factor (plant growth regulator) [Letham & Palni Ann Rev Plant Physiol 34 163 1983] and inhibits mitochondrial function [Miller Plant Physiol 69 1274 1982]. The commercially available trans -9-riboside derivative, [6025-53-2], M 351.4,is a cytokine which separates from aqueous AcOH with m 177-179o. It solubility in AcOH is ~5%. [McDonald & Morris Methods Enzymol 100 347 1985]. | [References]
[1] Dominik K Gro?kinsky. “Cis- and trans-zeatin differentially modulate plant immunity.” Plant Signaling Behavior 8 7 (2013): e24798. |
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