3-Indoleacetic acid 3-吲哚乙酸

CAS 87-51-4 MFCD00005636

化学结构图

87-51-4
SMILES: O=C(O)Cc1c[nH]c2ccccc12

化学属性

Mol. FormulaC10H9NO2
Mol. Weight175.18
Melting Point165-169°C
Density1.354
Flash Point171°(339°F)
TSCAYes
Stability对光敏感
SolubilityH2O: soluble
Appearance 白色结晶性粉末。熔点165-166℃（168-170℃）。易溶于丙酮和乙醚，微溶于氯仿，不溶于水。 crystalline
Boiling Point415°C at 760 mmHg

别名和识别编码

Chemical Name3-Indoleacetic acid
CAS Number87-51-4
Alfabeta NameINDOLYLACETICACID H13---
MDL NumberMFCD00005636
Synonym 3-Indoleacetic acid {LY} 3-Indoleacetic acid {} {LY} 3-Indoleacetic acid {} {} {LY} 3-Indoleacetic acid {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 3-Indoleacetic acid {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID802
Beilstein Registry Number143358
EC Number201-748-2
Merck Number4964
Chemical Name Translation3-吲哚乙酸
Reaxys-RN143358
Wiswesser Line NotationT56 BMJ D1VQ
LabNetwork Molecule IDLN00007733
InChIInChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
Canonical SMILESOC(CC1=CNC2=C1C=CC=C2)=O
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分类

  • {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
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Chromatography, Environmental Standards,
  • Auxins, Plant Biotechnology, Plant Growth Regulators, Plant Tissue Culture
  • {SNA} Auxins, Plant Biotechnology, Plant Growth Regulators, Plant Tissue Culture
  • {SNA} Building Blocks, C10, Carbohydrates A to Z, Carbohydrates H-L, Chemical Synthesis, Heterocyclic Building

产品应用

  • 吲哚乙酸 (IAA) 是一种吲哚类具有生长素活性的广谱性植物生长调节剂;调控细胞膜电子通道和质子通道。

相关文献及参考

  • Lata H, Chandra S, Khan IA, Elsohly MA., High frequency plant regeneration from leaf derived callus of high Δ9-tetrahydrocannabinol yielding Cannabis sativa L. Planta Med. 76 , 1629-1633, (2010) 摘要
  • Deb CR, Temjensangba., In vitro propagation of threatened terrestrial orchid, Malaxis khasiana Soland ex. Swartz through immature seed culture. Indian J. Exp. Biol. 44 , 762-767, (2006) 摘要
  • Farkya S, Bisaria VS., Exogenous hormones affecting morphology and biosynthetic potential of hairy root line (LYR2i) of Linum album. J. Biosci. Bioeng. 105 , 140-146, (2008) 摘要
  • Merck: 14,4964
  • Merck 14 ,4964
  • Jahan AA, Anis M, Aref IM., Assessment of factors affecting micropropagation and ex vitro acclimatization of Nyctanthes arbor-tristis L. Acta Biol. Hung. 62 , 45-56, (2011) 摘要
  • Merck: 14,4964 Beilstein:22,66
  • Kun-Hua W, Shan-Lin G, He-Ping H., Tissue culture and generation of autotetraploid plants of Sophora flavescens Aiton. Pharmacogn. Mag. 6 , 286-292, (2010) 摘要
  • Koshiba, T., et al., Transcriptional regulation of PS-IAA4/5 and PS-IAA6 early gene expression by indoleacetic acid and protein synthesis inhibitors in pea ( Pisum sativum ). J. Mol. Biol. 253 , 396-413, (1995)

安全信息

Warnings IRRITANT
RTECSNL3150000
WGK Germany3
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Signal word Warning
GHS Symbol
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • 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；
  • 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；
  • S37 Wear suitable gloves 戴适当手套；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
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。
  • 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。
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • 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
Storage condition 2-8°C {LY} 2-8°C Light 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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {}
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
Hazard Codes Xi 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2000 mg/kg/20W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumor types after systemic administration not seen
   spontaneously
REFERENCE :
   AICCA6 Acta Unio Internationalis Contra Cancrum.  (Louvain, Belgium) V.1-20,
   1936-64.  For publisher information, see IJCNAW. Volume(issue)/page/year:
   19,660,1963

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           : 150 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD691-490

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Fish - salmon Sperm
DOSE/DURATION           : 250 umol/L
REFERENCE :
   PYTCAS Phytochemistry.  An International Journal of Plant Biochemistry.
   (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-
      1961-  Volume(issue)/page/year: 11,3135,1972

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 241,109,1990

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 1150 umol/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

TYPE OF TEST            : Gene conversion and mitotic recombination
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 1150 umol/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            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 250 umol/L
REFERENCE :
   PYTCAS Phytochemistry.  An International Journal of Plant Biochemistry.
   (Pergamon Press Inc., Ma

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 4500 mg/kg
SEX/DURATION            : female 7-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Effects on Embryo or Fetus - fetal death
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 19,321,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 450 mg/kg
SEX/DURATION            : female 7-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 19,321,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 4500 mg/kg
SEX/DURATION            : female 7-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 19,321,1979

{hazard_com

其他信息

  • 方法一:由吲哚与羟基乙酸反应而得。在3L不锈钢高压釜中，加入270g（4.1mol）85%在氢氧化钾，351g（3mol）吲哚，然后慢慢地加入360g（3.3mol）70%的羟基乙酸水溶液。密闭加热至250℃，搅拌18h。冷却至50℃以下，加入500ml水，再在100℃搅拌30min以溶解吲哚3-乙酸钾。冷却至25℃，将高压釜物料倒入水中，加水至总体积为3L。用500ml乙醚萃取，分取水层，在20-30℃加盐酸酸化，析出吲哚-3-乙酸沉淀。过滤，冷水洗涤，避光干燥，得产品455-490g。
  • 上游原料:吲哚 --> 乙酸钾 --> 乙醇酸
  • Hazard Note:Irritant
  • Decomposition:167 °C
  • Sigma Aldrich:87-51-4(sigmaaldrich)
  • F:8-10-23
  • 易溶于无水乙醇，溶于乙醚和丙酮，微溶于水和氯仿，水中溶解度:8 g/L (20°C)。其水溶液能被紫外线分解，但对可见光稳定。
  • MOL 文件:87-51-4.mol
  • color:off-white to tan
  • 海关编码:29339990
  • 下游产品:1-甲基-3-吲哚乙酸
  • 敏感性:Light Sensitive
  • TCI Shanghai:3-吲哚乙酸 3-Indoleacetic Acid,>;98.0%(T)(87-51-4)
  • 用途三:用作植物生长刺激素及分析试剂。3-吲哚乙酸以及3-吲哚乙醛、3-吲哚乙腈、抗坏血酸等茁长素类物质在自然界天然存在，3-吲哚乙酸在植物体内生物合成的前体是色氨酸。茁长素的基本作用在于调节植物的生长，不仅能促进生长，而且具有抑制生长和器官建成的作用。茁长素在植物细胞内不仅以游离状态存在，还可以与生物高分子等牢固结合的束缚型茁长素存在，也有与特殊物质形成结合物的茁长素，例如吲哚乙酰基天门冬酰胺、吲哚乙酸阿戊糖和吲哚乙酰葡萄糖等。这可能是茁长素在细胞内的一种贮藏方式，也是解除过剩茁长素毒害的解毒方式。
  • 用途四:吲哚乙酸 (IAA) 是一种吲哚类具有生长素活性的广谱性植物生长调节剂;调控细胞膜电子通道和质子通道。
  • 用途二:用作植物生长调节剂，能促进细胞分裂、加速根的形成，可增加座果，防止落果
  • 检测方法:HPLC
  • 图谱信息:3-吲哚乙酸(87-51-4)质谱(MS) 3-吲哚乙酸(87-51-4)核磁图( 1 HNMR) 3-吲哚乙酸(87-51-4)核磁图( 13 CNMR) 3-吲哚乙酸(87-51-4)红外图谱(IR2) 3-吲哚乙酸(87-51-4)红外图谱(IR1)
  • MSDS 信息:1H-Indole-3-acetic acid(87-51-4).msds
  • 3-吲哚乙酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30105621 吲哚-3-乙酸 1g 8元 2011/08/23 30105680 吲哚-3-乙酸 1g 111.2元 2011/04/16 I0022 3-吲哚乙酸 3-Indoleacetic Acid 25G 330元
  • 用途一:用作植物生长刺激素及试剂
  • MOL 文件:6505-45-9.mol
  • 存储注意事项:空气敏感;光敏感
  • Alfa Aesar:吲哚-3-乙酸,98+% Indole-3-acetic acid, 98+%(87-51-4)
  • Acros Organics:3-吲哚乙酸/IAA 1H-Indole-3-acetic acid, 99+%(87-51-4)
  • Sigma Aldrich:6505-45-9(sigmaaldrich)

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indazoles 吲唑
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indoles 吲哚
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indolines 吲哚啉
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Environmental Standards - Chromatography
  5. Pesticides & Metabolites - Environmental Standards
  6. Alpha sort - Pesticides & Metabolites
  7. H-M - Alpha sort
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Indoles 吲哚
  5. C10 - Indoles
  1. Life Science 生命科学
  2. Plant Biotechnology 植物生物技术
  3. Plant Tissue Culture - Plant Biotechnology
  4. Plant Growth Regulators - Plant Tissue Culture
  5. Auxins - Plant Growth Regulators
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Aromatic acids
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Indoles
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Heterocyclic Acids 杂环酸
  5. Indole Acids
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Molecular Biology
  4. Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Plant Biotechnology
  4. Plant Tissue Culture
  5. Plant Growth Regulators
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Substrates
  5. Substrates by Enzyme
  6. Glucosidase, alpha
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Glycobiology
  4. Inhibitors and Substrates
  5. Substrates
  6. Galactoside
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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