玉米素 | 13114-27-7

• 物质功能分类: 化学农药原药 - 植物生长调节剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 玉米素
• 英文名称: zeatin
• 英文别名: 2-methyl-4-(7H-purin-6-ylamino)but-2-en-1-ol
• CAS: 13114-27-7
• 化学式: C₁₀H₁₃N₅O
• 分子量: 219.246
• InChiKey: UZKQTCBAMSWPJD-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211°C
• 沸点：
  395.0±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Zeatin
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 13114-27-7
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 6-(4-Hydroxy-3-methylbut-2-enylamino)purine
Formula : C10H13N5O
Molecular Weight : 219,24 g/mol
CAS-No. : 13114-27-7
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

玉米素（Zeatin）是一种天然植物细胞分裂素（cytokinins, CKs），最初是在幼嫩的玉米芯中被发现和分离出来的，后来也在椰汁中发现了该物质及其衍生物。作为植物生长调节剂，玉米素不仅促进侧芽生长，刺激细胞分化（侧端优势），还能够促进愈伤组织和种子发芽。此外，它还能防止叶片衰老、逆转因毒素造成的伤害并抑制过度根部形成。在高浓度下，玉米素还能诱导不定芽的分化。这些特性使得玉米素能促进植物细胞分裂、阻止叶绿素和蛋白质降解、减慢呼吸作用、保持细胞活力，并延缓植株衰老。

用途

玉米素通过促进植物细胞分裂、阻止叶绿素和蛋白质降解、减慢呼吸作用以及保持细胞活力，从而延缓植株衰老。

作用机制

玉米素具有促进细胞分裂、促进侧芽发育、延缓叶片衰老及蔬菜贮藏保鲜的作用。根部是合成玉米素的重要场所，幼叶、芽、幼果和正在发育的种子中也能形成这些物质。

作用机理

通过喷施该制剂，可以使植株矮化、茎秆增粗、根系发达、叶夹角变小，并延长绿叶功能期及提高光合效率。这最终有助于提升作物产量。

反应信息

• 作为反应物：
  描述：

  玉米素 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 反式玉米素核糖甙
  参考文献：
  名称：

  Peroxide-Shunt Substrate-Specificity for the Salmonella typhimurium O₂-Dependent tRNA Modifying Monooxygenase (MiaE)

  摘要：

  Post-transcriptional modifications of tRNA are made to structurally diversify tRNA. These modifications alter noncovalent interactions within the ribosomal machinery, resulting in phenotypic changes related to cell metabolism, growth, and virulence. MiaE is a carboxylate bridged, nonheme diiron monooxygenase, which catalyzes the O-2-dependent hydroxylation of a hypermodified-tRNA nucleoside at position 37 (2-methylthio-N-6-isopentenyl-adenosine(37)-tRNA) [designated ms(2)i(6)A(37)]. In this work, recombinant MiaE was cloned from Salmonella typhimurium, purified to homogeneity, and characterized by UV-visible and dual-mode X-band EPR spectroscopy for comparison to other nonheme diiron enzymes. Additionally, three nucleoside substrate-surrogates (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) and their corresponding hydroxylated products (io(6)A, Cl(2)io(6)A, and ms(2)io(6)A) were synthesized to investigate the chemo- and stereospecificity of this enzyme. In the absence of the native electron transport chain, the peroxide-shunt was utilized to monitor the rate of substrate hydroxylation. Remarkably, regardless of the substrate (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) used in peroxide-shunt assays, hydroxylation of the terminal isopentenyl-C4-position was observed with >97% E-stereoselectivity. No other nonspecific hydroxylation products were observed in enzymatic assays. Steady-state kinetic experiments also demonstrate that the initial rate of MiaE hydroxylation is highly influenced by the substituent at the C2-position of the nucleoside base (v(0)/[E] for ms(2)i(6)A > i(6)A > Cl(2)i(6)A). Indeed, the >3-fold rate enhancement exhibited by MiaE for the hydroxylation of the free ms(2)i(6)A nucleoside relative to i(6)A is consistent with previous whole cell assays reporting the ms(2)io(6)A and io(6)A product distribution within native tRNA-substrates. This observation suggests that the nucleoside C2-substituent is a key point of interaction regulating MiaE substrate specificity:

  DOI：

  10.1021/bi4000832
• 作为产物：
  描述：

  4-[(2-chloro-7H-purin-6-yl)amino]-2-methylbut-2-en-1-ol 在 二氯二茂钛 、 异丙基溴化镁 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以46%的产率得到玉米素
  参考文献：
  名称：

  Peroxide-Shunt Substrate-Specificity for the Salmonella typhimurium O₂-Dependent tRNA Modifying Monooxygenase (MiaE)

  摘要：

  Post-transcriptional modifications of tRNA are made to structurally diversify tRNA. These modifications alter noncovalent interactions within the ribosomal machinery, resulting in phenotypic changes related to cell metabolism, growth, and virulence. MiaE is a carboxylate bridged, nonheme diiron monooxygenase, which catalyzes the O-2-dependent hydroxylation of a hypermodified-tRNA nucleoside at position 37 (2-methylthio-N-6-isopentenyl-adenosine(37)-tRNA) [designated ms(2)i(6)A(37)]. In this work, recombinant MiaE was cloned from Salmonella typhimurium, purified to homogeneity, and characterized by UV-visible and dual-mode X-band EPR spectroscopy for comparison to other nonheme diiron enzymes. Additionally, three nucleoside substrate-surrogates (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) and their corresponding hydroxylated products (io(6)A, Cl(2)io(6)A, and ms(2)io(6)A) were synthesized to investigate the chemo- and stereospecificity of this enzyme. In the absence of the native electron transport chain, the peroxide-shunt was utilized to monitor the rate of substrate hydroxylation. Remarkably, regardless of the substrate (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) used in peroxide-shunt assays, hydroxylation of the terminal isopentenyl-C4-position was observed with >97% E-stereoselectivity. No other nonspecific hydroxylation products were observed in enzymatic assays. Steady-state kinetic experiments also demonstrate that the initial rate of MiaE hydroxylation is highly influenced by the substituent at the C2-position of the nucleoside base (v(0)/[E] for ms(2)i(6)A > i(6)A > Cl(2)i(6)A). Indeed, the >3-fold rate enhancement exhibited by MiaE for the hydroxylation of the free ms(2)i(6)A nucleoside relative to i(6)A is consistent with previous whole cell assays reporting the ms(2)io(6)A and io(6)A product distribution within native tRNA-substrates. This observation suggests that the nucleoside C2-substituent is a key point of interaction regulating MiaE substrate specificity:

  DOI：

  10.1021/bi4000832

文献信息

• Isolation and partial purification of an enzyme catalyzing the formation of <i>O</i> -xylosylzeatin in <i>Phaseolus vulgaris</i> embryos
  作者：Janet E. Turner、David W. S. Mok、Machteld C. Mok、Gordon Shaw

  DOI：10.1073/pnas.84.11.3714

  日期：1987.6

  ribonucleoside. The enzyme (UDP-xylose:zeatin O-xylosyltransferase, EC 2.4.2.-) has high affinity for trans-zeatin (K(m) 2 muM) and dihydrozeatin (K(m) 10 muM) but does not recognize cis-zeatin or ribosylzeatin. The molecular weight of the enzyme is approximately 50,000 and the pH optimum of the reaction is 8-8.5. Under comparable isolation and reaction conditions, similar enzyme activity could not

  催化细胞分裂素代谢物的形成的酶，玉米素的O-戊糖基衍生物[Lee，YH，Mok，MC，Mok，DWS，Griffin，DA＆Shaw，G.（1985）植物生理学。77，635-641]是从菜豆胚中分离出来的。在所有测试的潜在戊糖供体中，UDP-木糖是酶识别的唯一底物。这表明先前获得的O-戊糖基衍生物是O-木糖基玉米蛋白及其核糖核苷。该酶（UDP-木糖：玉米素O-木糖基转移酶，EC 2.4.2.-）对反式玉米素（K（m）2 muM）和二氢玉米素（K（m）10 muM）具有高亲和力，但不识别顺式玉米蛋白或核糖基玉米蛋白。该酶的分子量约为50,000，反应的最佳pH为8-8.5。在可比的分离和反应条件下，
• An Enzyme Mediating the Conversion of Zeatin to Dihydrozeatin in <i>Phaseolus</i> Embryos
  作者：Ruth C. Martin、Machteld C. Mok、Gordon Shaw、David W. S. Mok

  DOI：10.1104/pp.90.4.1630

  日期：1989.8.1

  chromatography. NADPH was the only cofactor required for enzyme activity, and the pH optimum was 7.5 to 8.0. The enzyme did not recognize compounds closely related to zeatin, such as ribosylzeatin, cls-zeatin, O-xylosylzeatin, N(6)-(Delta(2)-isopentenyl)adenine, or N(6)-(Delta(2)-isopentenyl)adenosine. No conversion of dihydrozeatin to zeatin by the enzyme was observed. Two forms of the reductase could

  在未成熟的菜豆胚的可溶性部分中检测到催化玉米素转化为二氢玉米素的还原酶。该酶通过硫酸铵分级分离和亲和、凝胶过滤和阴离子交换层析进行部分纯化。NADPH 是酶活性所需的唯一辅因子，最适 pH 值为 7.5 至 8.0。该酶无法识别与玉米素密切相关的化合物，例如核糖基玉米素、cls-玉米素、O-木糖基玉米素、N(6)-(Delta(2)-异戊烯基)腺嘌呤或 N(6)-(Delta(2)-异戊烯基）腺苷。没有观察到二氢玉米素被酶转化为玉米素。两种形式的还原酶可以通过凝胶过滤或阴离子交换高效液相色谱分离。高分子量同工酶 (M(r) 55,000 +/- 5, 000) 作为阴离子交换柱的第二个峰洗脱，而低分子量同工酶 (M(r) 25,000+/- 5000) 带负电荷较少。结果表明侧链减少发生在游离碱水平。此外，菜豆胚胎可用于检测玉米素特异性代谢酶。
• Mitigation of alternate bearing
  申请人：The Regents of the University of California

  公开号：US10292393B2

  公开（公告）日：2019-05-21

  Described are compositions and methods to mitigate alternate bearing of perennial crops by use of a natural metabolite. In particular, the present disclosure provides a natural metabolite in the presence or absence of an auxin transport inhibitor to increase floral intensity (flower number) of the return bloom in the spring following the setting of a heavy on-crop to increase the yield of the putative off-crop year and, thus, increase cumulative crop yield. Additionally the present disclosure provides a natural metabolite in combination with one or both of a growth promoting type of plant growth regulator, and a hormone biosynthesis, transport or function inhibiting type of plant growth regulator.

  描述了通过使用天然代谢物减轻多年生作物交替开花的组合物和方法。特别是，本公开提供了一种天然代谢物，在存在或不存在辅助素转运抑制剂的情况下，可提高重茬作物种植后春季返青开花的花朵强度（花朵数量），从而提高假定非重茬年的产量，进而提高作物累积产量。此外，本公开还提供了一种天然代谢物与一种促进生长类型的植物生长调节剂和一种抑制激素生物合成、运输或功能类型的植物生长调节剂中的一种或两种结合使用。
• Use of 9-beta-D-adenosine to increase crop production
  申请人：The Regents of the University of California

  公开号：US10321684B2

  公开（公告）日：2019-06-18

  Described are compositions and methods to increase bud break in order to increase aspects of one or both of plant vegetative and reproductive growth, by use of a natural metabolite. In particular, the present disclosure provides a natural metabolite either alone or as part of a fertilizer blend to increase crop production. Additionally the present disclosure provides a natural metabolite in combination with one or both of a plant growth regulator and a biostimulant to increase crop production.

  本发明描述了通过使用天然代谢物来增加花芽分化以提高植物无性和生殖生长的一个或两个方面的组合物和方法。特别是，本公开提供了一种天然代谢物，可单独使用或作为混合肥料的一部分使用，以提高作物产量。此外，本公开还提供了一种天然代谢物，与植物生长调节剂和生物刺激剂中的一种或两种结合使用，可提高作物产量。
• USE OF A NATURAL METABOLITE TO INCREASE CROP PRODUCTION
  申请人：The Regents of the University of California

  公开号：EP2519105B1

  公开（公告）日：2017-05-03