3-Indolebutyric acid 吲哚-3-丁酸

CAS 133-32-4 MFCD00005664

化学结构图

133-32-4
SMILES: O=C(O)CCCc1c[nH]c2ccccc12

化学属性

Mol. FormulaC12H13NO2
Mol. Weight203.24
Melting Point124.0-125.5°C
TSCAT
Density1.252
Stability对光敏感
Appearance 3-吲哚丁酸(133-32-4)为白色晶体,小鼠急性经口LD50为100毫克/公斤;急性经皮LD50 大鼠为5000毫克/公斤,小鼠为1760毫克/公斤。小鼠腹腔内注射LD50150毫克/公斤鲤鱼LC50 (48小时)180ppm,水蚤>40ppm。对蜜蜂无毒
Boiling Point341.55 °C at 760 mmHg

别名和识别编码

Chemical Name3-Indolebutyric acid
CAS Number133-32-4
Alfabeta NameINDOLEBUTYRICACID 3--
MDL NumberMFCD00005664
Synonym Indole-3-butyric acid {LY} Indole-3-butyric acid {} {LY} Indole-3-butyric acid {} {} {LY} Indole-3-butyric acid {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyric acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Indole-3-butyri
PubChem Substance ID87571435
Beilstein Registry Number22(2)54
EC Number205-101-5
Reaxys-RN171120
Merck Number4965
Chemical Name Translation吲哚-3-丁酸
Wiswesser Line NotationT56 BMJ D3VQ
LabNetwork Molecule IDLN00139659
Canonical SMILESO=C(O)CCCC1=CNC2=C1C=CC=C2
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分类

  • {Chemicalbook} 农药: 植物生长
  • {SNA} Auxins, Plant Biotechnology, Plant Growth Regulators, 分子生物学, 植物组织培养
  • {SNA} Auxins, 分子生物学, 植物生物技术, 植物生长调节剂, 植物组织培养
  • Auxins, Plant Biotechnology, Plant Growth Regulators, Plant Tissue Culture
  • {SNA} Auxins, Plant Biotechnology, 分子生物学, 植物生长调节剂, 植物组织培养
  • {SNA} Auxins, Plant Biotechnology, Plant Growth Regulators, Plant Tissue Culture
  • {SA} Alpha sort, Alphabetic, Analytical Standards, Analytical/Chromatography, Chromatography, Environmental Standards,

产品应用

  • 吲哚丁酸(IBA)是一种广谱的吲哚类植物生长调节剂,是良好的生根剂,可促进草本和木本观赏植物插枝的生根。还可用于瓜果的座果,提高座果率。

相关文献及参考

  • Steinitz B, Barr N, Tabib Y, et. al., Control of in vitro rooting and plant development in Corymbia maculata by silver nitrate, silver thiosulfate and thiosulfate ion. Plant Cell Rep. 29 , 1315-1323, (2010) 摘要
  • Merck: 14,4965 Beilstein:22(2)54
  • Leljak-Levanić D, Ježić M, Cesar V, et. al., Biochemical and epigenetic changes in phytoplasma-recovered periwinkle after indole-3-butyric acid treatment. J. Appl. Microbiol. 109 , 2069-2078, (2010) 摘要
  • Ruzicka K, Strader LC, Bailly A, Yang H, et. al., Arabidopsis PIS1 encodes the ABCG37 transporter of auxinic compounds including the auxin precursor indole-3-butyric acid. Proc. Natl. Acad. Sci. U. S. A. 107 , 10749-10753, (2010) 摘要
  • Epstein, E. and Ludwigmuller, J., Indole-3-butyric Acid in Plants - Occurrence, Synthesis, Metabolism and Transport Physiol. Plant. 88 , 382-389, (1993)
  • Merck: 14,4965
  • Handa, A., et al.: Plant Physiol., 69, 514
  • Merck 14 ,4965

安全信息

Warnings IRRITANT, MOISTURE SENSITIVE
RTECSNL5250000
GHS Symbol
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P310
  • P301+P310+P330
  • P302+P352+P332+P313+P362+P364
  • P305+
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Hazard Codes T T,Xi
WGK Germany3
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Signal word
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S38 In case of insufficient ventilation wear suitable respiratory equipment 通风不良时,佩带适当的呼吸器;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
Risk Statements
  • R25 Toxic if swallowed 吞咽有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
UN Number 2811 UN 2811 6.1/PG 3
Storage condition 2-8°C {LY} 2-8°C Air Sensitive {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Packing GroupIII
Hazard Class6.1
TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCNSA6 National Academy of Sciences, National Research Council,
   Chemical-Biological Coordination Center, Review.  (Washington, DC)
   Volume(issue)/page/year: 5,7,1953

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85JFAN "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd,
   eds., Nottingham, Royal Soc. of Chemistry, 1983-86 Volume(issue)/page/year:
   A231,1983

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ARAE "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson
   Publications, 1976/77 revision  Volume(issue)/page/year: 3,76,1976/1977

TYPE OF TEST            : Gene conversion and mitotic recombination
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 4,1409,1983

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 1 mmol/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 4,1409,1983

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Leukocyte
DOSE/DURATION           : 100 nmol/L
REFERENCE :
   EXPEAM Experientia.  (Birkhaeuser Verlag, POB 133, CH-4010 Basel,
   Switzerland)  V.1-    1945-  Volume(issue)/page/year: 32,29,1976

其他信息

  • Acr
  • 用途二:
  • Alfa Aesa
  • 毒性:对人畜低毒。大鼠急性经口LD 50 5000mg/kg、小鼠为1760mg/kg。鲤鱼LC 50 180mg/L(48h)。对蜜蜂低毒。
  • 3-吲哚丁酸价格(试剂级):
  • 制备方法:实验室通过将吲哚、氢氧化钾、聚乙二酸和干燥过的四氢萘混合物与γ-丁内酯加热回流得吲哚丁酸。反应式如下: 在反应器中加入吲哚、氢氧化钾、聚乙二酸和干燥过的四氢萘,混和物在室温搅拌半小时后,加入γ-丁内酯。然后加热回流4小时。反应体系中的水分由分水器除去。冷却后用水将固体全部溶解,分出有机层用盐酸酸化,析出大量灰白色固体。抽滤、水洗,干燥后得吲哚丁酸粗品,粗产率为92.6%。经乙醇水重结晶后,得白色鳞片状晶体
  • 制备方法:实验室通过将吲哚、氢氧化钾、聚乙二酸和干燥过的四氢萘混合物与γ-丁内酯加热
  • 微有特殊气味。溶于乙醇、乙醚、苯、DMSO、石油醚和丙酮,几乎不溶于水和氯仿。有毒,半数致死量(小鼠,经口)100mg/kg。有刺激性。水中溶解度:250 mg/l (20°C)。
  • 敏感性:Air Sensitive
  • 植物生长调节剂:植物生长调节剂是人工合成的具有生理活性,类似植物激素并能调节植物的生理过程、控制植物的生长和繁殖的有机化合物,吲哚丁酸(IBA)与萘乙酸(NAA)是两种常用的插枝生根的植物生长调节剂,其中以吲哚丁酸效果最好,因它在植物体内运转较少,容易保留在使用部位附近。此外,如将一种促根生长调节剂与另一有利于生长调节剂发挥作用的物质混合使用,则可表现出增效或加合作用,可能使难以生根的植物得到较满意的效果。吲哚丁酸促进生根作用强,但产生的不定根细而长,而萘乙酸(NAA)的促根作用是根少而粗,因此,将两者混合使用,往往可获得更好的效果。 1928年,温特(F.W.Went)首次分离出这种引起胚芽鞘弯曲的化学信使,命名为生长素。1934年,凯格(F.Kogl)等确定它为吲哚乙酸。因此,习惯上常把吲哚乙酸作为生长素的同义词。在认识到吲哚乙酸具有调节生长的效应后不久,科学家又发现吲哚丙酸(IPA)和吲哚丁酸(IBA)也有类似生长素的生理效应。以后又发现萘乙酸(NAA)、2,4-二氯苯氧乙酸(2,4-D)、2,4,6-三氯苯甲酸与4-氨基-3,5,6-三氯吡啶羧酸及它们的一些衍生物(包括盐、酯、酰胺,如萘乙酸钠、2,4-D丁酯、萘乙酰胺等),都有生长素的活性。 3-吲哚丁酸在植物体内不易被氧化,传导性能差。具有类似吲哚乙酸的生理效应,能作用于植物的细胞分裂和细胞生长,但不如吲哚乙酸明显,主要用于促进插条发根,有效地促进形成层的细胞分裂。维持药效时间较长,形成不定根多而细长,与萘乙酸混合施用效果更佳。 3-吲哚丁酸可用于菊花和其他观赏植物的扦插和插条,以促进生根,浓度为0.5~1.0mg/L,但勿用于植物的叶部。降解和代谢:土壤中能迅速降解。 以上信息由Chemicalbook的晓楠编辑整理。
  • 方法一:制备方法一 由吲哚与γ-丁内酯在四氢萘的回流温度下缩合得到。操作方法是:将1.17g吲哚、1.4g氢氧化钾、0.2g相转移催化剂聚乙二醇和干燥的四氢萘3mL混合后在室温下搅拌30min,加γ-丁内酯1.12g,在大于200℃回流4h。反应体系中的水分由分水器除去。冷却后用15mL水将固体全部溶解,分出有机层用盐酸酸化则析出大量灰白色固体。抽滤,水洗,干燥后得1.88g产物,粗品收率92.6%。 本法具有反应条件温和、操作简便、产率高的优点。 制备方法二 由吲哚与格氏试剂及α-氯代丙腈反应,制得3-丁腈吲哚,再由NaOH水解并与盐酸反应制得。
  • Sigma Aldrich:133-32-4(sigmaald
  • 用途四:吲哚丁酸(IBA)是一种广谱的吲哚类植物生长调节剂,是良好的生根剂,可促进草本和木本观赏植物插枝的生根。还可用于瓜果的座果,提高座果率。
  • Acros Organics:3-吲哚丁酸 3-Indolebutyric acid, 98%(133-32-4)
  • 用途一:用作植物生长刺激素,促进植物主根生长,提高发芽率、成活率
  • 用途三:植物
  • MSDS 信息:Seradix(133-

系列性分类


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