4-Chloroindole-3-acetic Acid
(Synonyms: 4-氯吲哚-3-乙酸) 目录号 : GC49801
An auxin plant growth regulator
Cas No.:2519-61-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
4-Chloroindole-3-acetic acid (4-Cl-IAA) is a halogenated plant auxin plant growth regulator that has been found in P. sativum.1 It induces tobacco callus growth and biologically active alkaloid production in Duboisia root cultures when used at a concentration of 0.1 mg/ml. 4-Cl-IAA (1 µM) reduces heat stress-induced grain loss in wheat (T. aestivum).2
1.Reinecke, D.M.4-Chloroindole-3-acetic acid and plant growthPlant Growth Regul.273-13(1999) 2.Abeysingha, D.N., Ozga, J.A., Strydhorst, S., et al.The effect of auxins on amelioration of heat stress-induced wheat (Triticum aestivum L.) grain lossJ. Agron. Crop. Sci.207(6)970-983(2021)
| Cas No. | 2519-61-1 | SDF | Download SDF |
| 别名 | 4-氯吲哚-3-乙酸 | ||
| Canonical SMILES | O=C(CC1=CNC2=CC=CC(Cl)=C21)O | ||
| 分子式 | C10H8ClNO2 | 分子量 | 209.6 |
| 溶解度 | DMF: 16 mg/mL,DMSO: 14 mg/mL,Ethanol: 16 mg/mL,PBS (pH 7.2): 0.20 mg/mL | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.771 mL | 23.855 mL | 47.7099 mL |
| 5 mM | 0.9542 mL | 4.771 mL | 9.542 mL |
| 10 mM | 0.4771 mL | 2.3855 mL | 4.771 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Biosynthesis of the halogenated auxin, 4-Chloroindole-3-acetic Acid
Plant Physiol 2012 Jul;159(3):1055-63.PMID:22573801DOI:10.1104/pp.112.198457.
Seeds of several agriculturally important legumes are rich sources of the only halogenated plant hormone, 4-Chloroindole-3-acetic Acid. However, the biosynthesis of this auxin is poorly understood. Here, we show that in pea (Pisum sativum) seeds, 4-Chloroindole-3-acetic Acid is synthesized via the novel intermediate 4-chloroindole-3-pyruvic acid, which is produced from 4-chlorotryptophan by two aminotransferases, TRYPTOPHAN AMINOTRANSFERASE RELATED1 and TRYPTOPHAN AMINOTRANSFERASE RELATED2. We characterize a tar2 mutant, obtained by Targeting Induced Local Lesions in Genomes, the seeds of which contain dramatically reduced 4-Chloroindole-3-acetic Acid levels as they mature. We also show that the widespread auxin, indole-3-acetic acid, is synthesized by a parallel pathway in pea.
Synthesis and biological activities of 4-Chloroindole-3-acetic Acid and its esters
Biosci Biotechnol Biochem 2000 Apr;64(4):808-15.PMID:10830497DOI:10.1271/bbb.64.808.
4-Chloroindole-3-acetic Acid (4-Cl-IAA) and its esters were synthesized from 2-chloro-6-nitrotoluene as the starting material. The biological activities of 4-CI-IAA and its esters were determined by four bioassays. Except for the tert-butyl ester, 4-Cl-IAA and its esters had stronger elongation activity toward Avena coleoptiles than had indole-3-acetic acid. The biological activities of the methyl, ethyl and allyl esters were as strong as the activity of the free acid. All the esters, except for the tert-butyl, inhibited Chinese cabbage hypocotyl growth more than the free acid did, and all the esters induced severe swelling and formation of numerous lateral roots in black gram seedlings even at a low concentration. Furthermore, adventitious root formation was strongly promoted in Serissa japonica cuttings by all the esters. The root formation-promoting activities of the ethyl and allyl esters were about three times the value for indole-3-butyric acid which is used to promote and accelerate root formation in plant cuttings.
A mutation affecting the synthesis of 4-Chloroindole-3-acetic Acid
Plant Signal Behav 2012 Dec;7(12):1533-6.PMID:23073010DOI:10.4161/psb.22319.
Traditionally, schemes depicting auxin biosynthesis in plants have been notoriously complex. They have involved up to four possible pathways by which the amino acid tryptophan might be converted to the main active auxin, indole-3-acetic acid (IAA), while another pathway was suggested to bypass tryptophan altogether. It was also postulated that different plants use different pathways, further adding to the complexity. In 2011, however, it was suggested that one of the four tryptophan-dependent pathways, via indole-3-pyruvic acid (IPyA), is the main pathway in Arabidopsis thaliana, although concurrent operation of one or more other pathways has not been excluded. We recently showed that, for seeds of Pisum sativum (pea), it is possible to go one step further. Our new evidence indicates that the IPyA pathway is the only tryptophan-dependent IAA synthesis pathway operating in pea seeds. We also demonstrated that the main auxin in developing pea seeds, 4-Chloroindole-3-acetic Acid (4-Cl-IAA), which accumulates to levels far exceeding those of IAA, is synthesized via a chlorinated version of the IPyA pathway.
Regulation of ethylene-related gene expression by indole-3-acetic acid and 4-Chloroindole-3-acetic Acid in relation to pea fruit and seed development
J Exp Bot 2017 Jul 10;68(15):4137-4151.PMID:28922757DOI:10.1093/jxb/erx217.
In pea, the auxins 4-Chloroindole-3-acetic Acid (4-Cl-IAA) and indole-3-acetic acid (IAA) occur naturally; however, only 4-Cl-IAA stimulates pericarp growth and gibberellin (GA) biosynthesis, and inhibits the ethylene response in deseeded ovaries (pericarps), mimicking the presence of seeds. Expression of ovary ethylene biosynthesis genes was regulated similarly in most cases by the presence of 4-Cl-IAA or seeds. PsACS1 [which encodes an enzyme that synthesizes 1-aminocyclopropane-1-carboxylic acid (ACC)] transcript abundance was high in pericarp tissue adjacent to developing seeds following pollination. ACC accumulation in 4-Cl-IAA-treated deseeded pericarps was driven by high PsASC1 expression (1800-fold). 4-Cl-IAA, but not IAA, also suppressed the pericarp transcript levels of PsACS4. 4-Cl-IAA increased PsACO1 and decreased PsACO2 and PsACO3 expression (enzymes that convert ACC to ethylene) but did not change ACO enzyme activity. Increased ethylene was countered by a 4-Cl-IAA-specific decrease in ethylene responsiveness potentially via modulation of pericarp ethylene receptor and signaling gene expression. This pattern did not occur in IAA-treated pericarps. Overall, the effect of 4-Cl-IAA and IAA on ethylene biosynthesis gene expression generally explains the ethylene evolution patterns, and their effects on GA biosynthesis and ethylene signaling gene expression explain the tissue response patterns in young pea ovaries.
Seed and 4-Chloroindole-3-acetic Acid regulation of gibberellin metabolism in pea pericarp
Plant Physiol 1995 Dec;109(4):1213-7.PMID:8539289DOI:10.1104/pp.109.4.1213.
In this study, we investigated seed and auxin regulation of gibberellin (GA) biosynthesis in pea (Pisum sativum L.) pericarp tissue in situ, specifically the conversion of [14C]GA19 to [14C]GA20. [14C]GA19 metabolism was monitored in pericarp with seeds, deseeded pericarp, and deseeded pericarp treated with 4-Chloroindole-3-acetic Acid (4-CI-IAA). Pericarp with seeds and deseeded pericarp treated with 4-CI-IAA continued to convert [14C]GA19 to [14C]GA20 throughout the incubation period (2-24 h). However, seed removal resulted in minimal or no accumulation of [14C]GA20 in pericarp tissue. [14C]GA29 was also identified as a product of [14C]GA19 metabolism in pea pericarp. The ratio of [14C]GA29 to [14C]GA20 was significantly higher in deseeded pericarp (with or without exogenous 4-CI-IAA) than in pericarp with seeds. Therefore, conversion of [14C]GA20 to [14C]GA29 may also be seed regulated in pea fruit. These data support the hypothesis that the conversion of GA19 to GA20 in pea pericarp is seed regulated and that the auxin 4-CI-IAA can substitute for the seeds in the stimulation of pericarp growth and the conversion of GA19 to GA20.