trans-Zeatin

Names

[ Name ]:
trans-Zeatin

[Synonym ]:
(2z)-2-methyl-4-(9h-purin-6-ylamino)but-2-en-1-ol
2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-
cis-zeatin
trans-Zeatin (synthetic)
(2E)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol
2-Buten-1-ol, 2-methyl-4-(3H-purin-6-ylamino)-, (2Z)-
(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
oxyenadenine
(2E)-2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
ZEATIN TRANS ISOMER
(2Z)-2-Methyl-4-(3H-purin-6-ylamino)-2-buten-1-ol
2-Buten-1-ol, 2-methyl-4-(3H-purin-6-ylamino)-, (2E)-
6-(4-Hydroxy-3-methyl-2-butenylamino)purine
(E)-zeatin
(2E)-2-Methyl-4-(3H-purin-6-ylamino)-2-buten-1-ol
MFCD00213654
(2E)-2-Methyl-4-(1H-purin-6-ylamino)but-2-en-1-ol
trans-Zeatin
(2E)-2-Methyl-4-(9H-purin-6-ylamino)but-2-en-1-ol
2-Buten-1-ol, 2-methyl-4-(purin-6-ylamino)-, (E)-
N6-(4-Hydroxy-3-methyl-2-buten-1-yl)adenine
Zeatin
6-(4-Hydroxy-3-methylbut-2-enylamino)purine (N6-(4-Hydroxy-3-methyl-2-buten-1-yl)adenine
Zeatine
(2Z)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol
TRANS ISOMER-ZEATIN
ZEATINRESEARCH GRADE
2-Buten-1-ol, 2-methyl-4-(7H-purin-6-ylamino)-, (2Z)-
6-(4-Hydroxy-3-methylbut-2-enylamino)purine
2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (E)-
ZEATIN,CRYSTALLIZED

Biological Activity

[Description]:

trans-Zeatin is a plant cytokinin, which plays an important role in cell growth, differentiation, and division; trans-Zeatin also inhibits UV-induced MEK/ERK activation.

[Related Catalog]:

Research Areas >> Others

Natural Products >> Others

[Target]

MEK

ERK

[In Vitro]

trans-Zeatin is a plant cytokinin, which plays an important role in cell growth, differentiation, and division[1]. trans-Zeatin (20, 40 or 80 μM) inhibits UV-induced MEK/ERK activation, upregulates AQP3 in a time- and dose-dependent manner, and attenuates UV induced loss of AQP3 in keratinocytes (HaCaT cells). UV-induced AQP3 downregulation is blocked by MEK/ERK inhibitors. Trans-Zeatin (80 μM) attenuates UV-induced downregulation of wound healing and water permeability in HaCaT cells[2].

[References]

[1]. Li Q, et al. Endogenous trans-zeatin content in plants with different metal-accumulating ability: a field survey. Environ Sci Pollut Res Int. 2016 Dec;23(23):23422-23435. Epub 2016 Sep 9.

[2]. Ji C, et al. Trans-Zeatin attenuates ultraviolet induced down-regulation of aquaporin-3 in cultured human skin keratinocytes. Int J Mol Med. 2010 Aug;26(2):257-63.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
395.0±52.0 °C at 760 mmHg

[ Melting Point ]:
207 °C

[ Molecular Formula ]:
C₁₀H₁₃N₅O

[ Molecular Weight ]:
219.243

[ Flash Point ]:
192.7±30.7 °C

[ Exact Mass ]:
219.112015

[ PSA ]:
86.72000

[ LogP ]:
-1.02

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.684

[ Storage condition ]:
−20°C

[ Water Solubility ]:
H2O: soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EM9506000

CHEMICAL NAME :: 2-Buten-1-ol, 2-methyl-4-(purin-6-ylamino)-, (E)-

CAS REGISTRY NUMBER :: 1637-39-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C10-H13-N5-O

MOLECULAR WEIGHT :: 219.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 100 umol/L

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 32,29,1976

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
EM9506000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Silicon induces resistance to the brown spot fungus Cochliobolus miyabeanus by preventing the pathogen from hijacking the rice ethylene pathway.

New Phytol. 206(2) , 761-73, (2015)

Although numerous studies have shown the ability of silicon (Si) to mitigate a wide variety of abiotic and biotic stresses, relatively little is known about the underlying mechanism(s). Here, we have ...

High-internal-phase-emulsion polymeric monolith coupled with liquid chromatography-electrospray tandem mass spectrometry for enrichment and sensitive detection of trace cytokinins in plant samples.

Anal. Bioanal. Chem 407 , 6071-9, (2015)

High-internal-phase-emulsion polymers (polyHIPEs) show great promise as solid-phase-extraction (SPE) materials because of the tremendous porosity and highly interconnected framework afforded by the hi...

Physiological response to drought in radiata pine: phytohormone implication at leaf level.

Tree Physiol. 32(4) , 435-49, (2012)

Pinus radiata D. Don is one of the most abundant species in the north of Spain. Knowledge of drought response mechanisms is essential to guarantee plantation survival under reduced water supply as pre...