trans-Zeatin
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trans-Zeatin
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CAS No:
1637-39-4
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Formula:
C10H13N5O
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Chemical Name:
trans-Zeatin
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Synonyms:
(e)-2-buten-1-o;(E)-Zeatin;2-Buten-1-ol,2-methyl-4-(purin-6-ylamino)-,(E)-;ZEATIN, CRYSTALLIZED;TRANS-6-(4-HYDROXY-3-METHYLBUT-2-ENYLAMINO)PURINE(ZEATIN);TRANS-ZEATIN [TRANS-6-(4-HYDROXY-3-METHYLBUT-2-ENYLAMINO)PURINE];(2E)-2-METHYL-4-(1H PURIN-6-YLAMINO)-2-BUTEN-1-OL;2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-
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CAS No:
Description
white to light yellow crystal powderChEBI: The trans-isomer of zeatin.
Solid
Zeatin is a 6-isopentenylaminopurine. It has a role as a cytokinin.|An aminopurine factor in plant extracts that induces cell division. (Grant & Hackh's Chemical Dict, 5th ed)|An aminopurine factor in plant extracts that induces cell division. (Grant and Hackh's Chemical Dict, 5th ed)
trans-Zeatin is a cytokinin plant growth regulator with antioxidant and neuroprotective activities. It binds to the cytokinin receptorArabidopsishistidine kinase 3 (AHK3) with a KDvalue of 1.3 nM.trans-Zeatin increases chlorophyll levels in etiolatedCucumus sativuscotyledons in a concentration-dependent manner. It increases callus growth and shoot formation inN. tabacumcalluses when used at concentrations of 5 and 50 μM.trans-Zeatin (25-100 μM) reduces production of reactive oxygen species (ROS) induced by amyloid β (25-35) (Aβ25-35) in PC12 cells. 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.
white to light yellow crystal powder
trans-Zeatin Basic Attributes
219.24
219.24
616241
605-343-5
7I6OOJ9GR6
DTXSID9040631
off-white to yellow
29335990
Characteristics
86.7
Trans-zeatin is freely soluble in acetic acid and water.
0.16 (est)
off-white to yellow powder
1.40±0.1 g/cm3(Predicted)
207 °C
395.0±52.0 °C(Predicted)
192.7±30.7 °C
1.684
H2O: soluble
−20°C
2.02X10-11 mm Hg at 25 deg C (est)
14.77±0.10(Predicted)
Henry's Law constant = 1.82X10-17 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 2.99X10-10 cu cm/molec-sec at 25 °C (est)|Ozone radical reaction rate constant = 4.3X10-16 cu cm/molec-sec at 25 °C (est)
-20°C
Safety Information
NONH for all modes of transport
3
Xi
22-24/25
EM9506000
Xi
Stable under normal temperatures and pressures.
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
H315
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Cytokinin p.v EPA 738-R-95-025 (December 1995). Available from the Database Query page at http://www.epa.gov/pesticides/reregistration/status.htm as of February 9, 2009.
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Toxicity
... Zeatin mitigated cognitive deficits and showed AChE inhibition in scopolamine (Scop)-induced mice following 21 days of zeatin treatment. After administration of Scop for 30 min, each mouse performed Y-maze and step-down latency tasks as a check on immediate against cognitive function. The results showed that zeatin administration attenuated Scop-induced memory damage and decreased AChE activity in the mice...
LD50 Rat oral >5 g/kg /from table/ /Cytokinin/|LD50 Rabbit dermal >2 g/kg /from table/ /Cytokinin/
Naturally occurring plant growth hormone; cytokinin originally isolated from sweet corn kernels, Zea mays L. Gramineae.
Drug Information
/EXPL THER/ In this study, our aim was to clarify the ameliorative effects of zeatin, a development hormone in plants. Zeatin mitigated cognitive deficits and showed AChE inhibition in scopolamine (Scop)-induced mice following 21 days of zeatin treatment. After administration of Scop for 30 min, each mouse performed Y-maze and step-down latency tasks as a check on immediate against cognitive function. The results showed that zeatin administration attenuated Scop-induced memory damage and decreased AChE activity in the mice. This suggests that zeatin might be useful for protecting cognitive dysfunction, as well as for reducing the activation of AChE in dementia.
Any of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins. (See all compounds classified as Plant Growth Regulators.)
Kinetin stimulated phosphorylation of protein in floated Chinese-cabbage leaf discs, but inhibited protein phosphorylation in nuclei+chloroplast extracts from Chinese-cabbage or tobacco leaves. Kinetin also inhibited protein phosphorylation in isolated tobacco nuclei or nuclei from carrot secondary-phloem tissue. Purified Chinese-cabbage leaf ribosomes exhibited protein kinase activity which was inhibited by kinetin and zeatin. The ribosome-associated kinase responded to kinetin and zeatin differently from that associated with nuclei+chloroplast preparations. Protein phosphorylation in vitro was not affected by adenosine 3':5'-cyclic monophosphate, indol-3-ylacetic acid or gibberellic acid. It was only inhibited by N(9)-unsubstituted purines, among which the known cytokinins were the most effective inhibitors. The results are discussed in relation to possible similarities between the effects of cytokinins in plant tissues and the effects of adenosine 3':5'-cyclic monophosphate in animal tissues. Both compounds appear to modify the activity of protein kinases and both affect many different cellular processes.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Zeatin
trans-Zeatin Use and Manufacturing
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.
Naturally occurring plant growth hormone; cytokinin originally isolated from sweet corn kernels, Zea mays L. Gramineae.|Cytokinin is a group of plant regulators that promote cell division, leaf expansion and retard leaf aging. Cytokinin is comprised of four naturally occurring cytokinins (derived from aqueous extract of seaweed meal) -- zeatin [6-(4-hydroxy-3-methylbut-trans-2-enylamino)-purine], N6-methylaminopurine, N6-dimethylaminopurine, N6-isopentenylaminopurine, and synthetic cytokinin -- kinetin [6-(furfurylamino)purine]. Cytokinins (i.e. naturally occurring) in aqueous extracts of seaweed meal, are derived from the following algae: Laminaria digitata, Laminaria hyperborea, Fucus serratus and Ascophyllum nodosum.
Computed Properties
Molecular Weight:219.24
XLogP3:0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:219.11201006
Monoisotopic Mass:219.11201006
Topological Polar Surface Area:86.7
Heavy Atom Count:16
Complexity:258
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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