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Zeatin

HCID 178653647
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Grundinformationen

CAS
1637-39-4
Standard-SMILES
C/C(=C\CNc1ncnc2[nH]cnc12)CO
InChIKey
UZKQTCBAMSWPJD-FARCUNLSSA-N
Summenformel
C10H13N5O
Durchschnittliche Molmasse
219,24 g/mol
Monoisotopische Masse
219,11201006

Überblick

Zeatin is a 6-isopentenylaminopurine. It has a role as a cytokinin.

Namen und Bezeichner

Bevorzugter Name
Zeatin
IUPAC
(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol

Namen und Synonyme

trans-Zeatin1637-39-4Zeatin(E)-ZeatinZeatine(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol(E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-olN6-(4-Hydroxyisopentenyl)adenine2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-7I6OOJ9GR62-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (E)-DTXSID9040631
Weitere Namen anzeigen
(E)-2-Methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol(E)-2-methyl-4-(purin-6-ylamino)-2-buten-1-ol(2E)-2-methyl-4-(1H-purin-6-ylamino)-2-buten-1-olCHEBI:15333CHEBI:165222-BUTEN-1-OL, 2-METHYL-4-(PURIN-6-YLAMINO)-, (E)-(2E)-2-methyl-4-((7H-purin-6-yl)amino)but-2-en-1-ol(2E)-2-methyl-4-[(7H-purin-6-yl)amino]but-2-en-1-ol

Datenbank-Bezeichner

CAS
1637-39-4
PubChem CID
449093
ChEMBL
CHEMBL525239
ChEBI
CHEBI:15333
UNII
7I6OOJ9GR6
EC Number
605-343-5
Nikkaji
J3.243.127E、J7.540J

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,7
Polarare Oberfläche (TPSA)
86,7 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
16
Formalladung
0
Komplexität
258

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Color/FormCrystals from water
Melting Point207-208 °C
Physical DescriptionSolid

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Informationtrans-Zeatin: Does not have an individual approval but may be used under an appropriate group standard
Special Reports · 1 Eintrag

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.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Interactions · 1 Eintrag

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

Verwendung und Herstellung

UsesInhibition of mitochondrial function...
General Manufacturing Information · 2 Einträge

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.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung

... 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...

Natural Pollution SourcesNaturally occurring plant growth hormone; cytokinin originally isolated from sweet corn kernels, Zea mays L. Gramineae.
Antidote and Emergency Treatment · 3 Einträge

/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/

Non-Human Toxicity Values · 2 Einträge

LD50 Rat oral >5 g/kg /from table/ /Cytokinin/

LD50 Rabbit dermal >2 g/kg /from table/ /Cytokinin/