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trans-ゼアチン

Zeatin

HCID 449093
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1637-39-4
標準SMILES
C/C(=C\CNc1ncnc2nc[nH]c12)CO
InChIKey
UZKQTCBAMSWPJD-FARCUNLSSA-N
分子式
C10H13N5O
平均分子量
219.24 g/mol
単同位体質量
219.11201006

概要

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

名称と識別子

優先名称
Zeatin
IUPAC
(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
現地名
trans-ゼアチン
英語名
trans-Zeatin
分子式
C10H13N5O
分子量
219.24

名称と別名

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
名称をさらに表示
trans-ゼアチン(E)-2-メチル-4-(9H-プリン-6-イルアミノ)-2-ブテン-1-オール(E)-2-メチル-4-[(9H-プリン-6-イル)アミノ]-2-ブテン-1-オール(E)-2-メチル-4-[(1H-プリン-6-イル)アミノ]-2-ブテン-1-オール6-(4-ヒドロキシ-3-メチル-2-ブテニルアミノ)プリンTRANS‐ゼアチンTRANS-ゼアチン (6-((E)-4-ヒドロキシ-3-メチルブト-2-エニルアミノ)プリン), >98%(2E)-2-メチル-4-[(1H-プリン-6-イル)アミノ]ブタ-2-エン-1-オールアミノアップ6-[(E)-4-ヒドロキシ-3-メチル-2-ブテニルアミノ]-9H-プリンrans-zeatinZeatin (7CI)(e)-2-buten-1-otrans-ZEATIN (Z)Trans-Zeatin HCltrans-ZEATIN (tZ)TRANS ISOMER-ZEATIN
(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

物性

構造計算による物性

XLogP
0.7
極性表面積
86.7 Ų
水素結合供与体数
3
水素結合受容体数
5
回転可能結合数
4
重原子数
16
形式電荷
0
複雑度
258

実験および物理化学的性質

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

物理化学的性質

融点
207 °C · 207 °C
沸点
395 · 395.0±52.0 °C(Predicted)
比重(密度)
1.4 · 1.40±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
2 O: · H2O: 可溶
外見
粉
酸解離定数(Pka)
14.77 · 14.77±0.10(Predicted)
色
オフホワイトからイエロー
Merck
14 · 14,10117
BRN
616241 · 616241
主な用途
農業
化粧品成分の機能
スキンコンディショニング
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+

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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

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%)

安全と保護具

Disposal Methods · 1 件

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.

毒性情報

Interactions · 1 件

... 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...

化学と産業

薬理情報

Mechanism of Action · 1 件

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.

用途と製造

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

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.

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
1637-39-4
PubChem CID
449093
DTXSID
DTXSID9040631
ChEMBL
CHEMBL525239
ChEBI
CHEBI:15333
UNII
7I6OOJ9GR6
EC Number
605-343-5
Nikkaji
J3.243.127E、J7.540J
InChIKey
UZKQTCBAMSWPJD-FARCUNLSSA-N
SMILES
C(O)/C(/C)=C/CNC1=C2C(=NC=N1)NC=N2
CAS データベース
1637 · 1637-39-4(CAS DataBase Reference)
EPAの化学物質情報
Zeatin (1637-39-4)

化学的性質

化学的特性white to light yellow crystal powder

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

/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 件

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

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

安全データ

F
8-10-23
wgk
3
rtecs
EM9506000
hs_code
29335990
hazard_code
Xi
safety_code
22-24/25
ストレージクラス
11 - Combustible Solids
有毒物質データの
1637-39-4(Hazardous Substances Data)
応用分野 · 3 件

用途植物培養培地添加用。

説明trans-Zeatin is a cytokinin plant growth regulator with antioxidant and neuroprotective activities. It binds to the cytokinin receptor Arabidopsis histidine kinase 3 (AHK3) with a KD value of 1.3 nM. trans-Zeatin increases chlorophyll levels in etiolated Cucumus sativus cotyledons in a concentration-dependent manner. It increases callus growth and shoot formation in N. tabacum calluses 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.

一般的な説明trans-Zeatin contains a hydroxylated isoprenoid side chain.

調製方法 · 1 件

純化方法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].

上流・下流製品情報

上流原料

2-Buten-1-ol, 4-amino-2-methyl-6-クロロプリンエタノール1H-Isoindole-1,3(2H)-dione, 2-[(2E)-4-(acetyloxy)-3-methyl-2-buten-1-yl]-トリエチルアミン

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補足説明 · 2 件

定義Increased levels of cytokinins such as trans-zeatin, which are considered highly active, induced resistance against mainly (hemi)biotrophic pathogens in different plant species. In contrast, cis-zeatin is commonly regarded as a cytokinin exhibiting low or no activity [1].

定義ChEBI: The trans-isomer of zeatin.