HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Zeatin

HCID 449093
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
1637-39-4
Standard SMILES
C/C(=C\CNc1ncnc2nc[nH]c12)CO
InChIKey
UZKQTCBAMSWPJD-FARCUNLSSA-N
Molecular formula
C10H13N5O
Average molar mass
219.24 g/mol
Monoisotopic mass
219.11201006

Overview

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

Names & identifiers

Preferred name
Zeatin
IUPAC
(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
English name
trans-Zeatin
Molecular formula
C10H13N5O
Molecular weight
219.24

Names & synonyms

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
Show more names
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

Database identifiers

CAS
1637-39-4
PubChem CID

Properties

Computed structural properties

XLogP
0.7
Topological polar surface area
86.7 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
16
Formal charge
0
Complexity
258

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
207 °C · 207 °C
Boiling point
395 · 395.0±52.0 °C(Predicted)
Density
1.4 · 1.40±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
2 O: · H2O: soluble
form
powder
pka
14.77 · 14.77±0.10(Predicted)
color
off-white to yellow
Merck
14 · 14,10117
BRN
616241 · 616241

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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.

Hazard information

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

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%)

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Interactions · 1 item

... 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...

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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.

Uses & manufacturing

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

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.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
449093
DTXSID
DTXSID9040631
ChEMBL
CHEMBL525239
ChEBI
CHEBI:15333
UNII
7I6OOJ9GR6
EC Number
605-343-5
Nikkaji
J3.243.127E、J7.540J
Major Application
agriculture
Cosmetics Ingredients Functions
SKIN CONDITIONING
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 · 1637-39-4(CAS DataBase Reference)
FDA UNII
7 I6OOJ9GR6 · 7I6OOJ9GR6
EPA Substance Registry System
Zeatin (1637-39-4)
UNSPSC Code
10171502 · 10171502
NACRES
72 · NA.72
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
9506000 · EM9506000
F
8 · 8-10-23
HS Code
29335990 · 29335990
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
1637 · 1637-39-4(Hazardous Substances Data)
Natural Pollution SourcesNaturally occurring plant growth hormone; cytokinin originally isolated from sweet corn kernels, Zea mays L. Gramineae.
Antidote and Emergency Treatment · 3 items

/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 items

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

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

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
EM9506000
hs_code
29335990
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazardous Substances Data
1637-39-4(Hazardous Substances Data)
Applications · 3 items

Descriptiontrans-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.

UsesZeatin, 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. Trans-Zeatin inhibits UVB-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.

General Descriptiontrans-Zeatin contains a hydroxylated isoprenoid side chain.

Upstream & downstream products

Upstream raw materials

2-Buten-1-ol, 4-amino-2-methyl-6-ChloropurineEthanol1H-Isoindole-1,3(2H)-dione, 2-[(2E)-4-(acetyloxy)-3-methyl-2-buten-1-yl]-Triethylamine

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
沧州辉映医药科技有限责任公司15532866377 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
北京绿百草科技发展有限公司010-61136123 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
泰州凯美迪生物医药技术有限公司0523-86200218 18994667082 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
TransMIT GmbH PlantMetaChem+49-172-1024293 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海厚博生物科技有限公司+21-18501659228 18501659228 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
上海裕兰生物科技有限公司021-57171705 13817537615 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海鑫圭生物科技有限公司15121041756 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
北京翔宇恒天医药技术有限公司010-88755821 13911359480;18612220856 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
AN PharmaTech Co Ltd86(21)68097365 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
Additional notes · 2 items

DefinitionIncreased 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].

DefinitionChEBI: The trans-isomer of zeatin.