Molecular Formula | C10H9NO2 |
Molar Mass | 175.18 |
Density | 1.1999 (rough estimate) |
Melting Point | 165-169 °C (lit.) |
Boling Point | 306.47°C (rough estimate) |
Flash Point | 171°C |
Water Solubility | Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water. |
Solubility | Soluble in acetone and ether, slightly soluble in chloroform, insoluble in water. |
Vapor Presure | 1.24E-07mmHg at 25°C |
Appearance | White crystalline powder |
Color | off-white to tan |
Merck | 14,4964 |
BRN | 143358 |
pKa | 4.75(at 25℃) |
Storage Condition | -20°C |
Stability | Stable. Incompatible with strong oxidizing agents. Light sensitive. |
Sensitive | Light Sensitive |
Refractive Index | 1.5460 (estimate) |
MDL | MFCD00005636 |
Physical and Chemical Properties | melting point 165-169°C |
Use | Used as plant growth stimulating hormone and reagent |
Hazard Symbols | Xi - Irritant![]() |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
RTECS | NL3150000 |
FLUKA BRAND F CODES | 8-10-23 |
TSCA | Yes |
HS Code | 29339990 |
Hazard Note | Irritant |
Toxicity | LD50 intraperitoneal in mouse: 150mg/kg |
Reference Show more | 1. Zhou Ying, Wu Yuxiang, Li Yongxia, etc. Determination of endogenous hormones in blueberry leaves by high performance liquid chromatography [J]. China fruit tree, 2018, No.191(03):94-97 100. 2. Liu Xu, Zhou Wennan, Chen Zhao, et al. Effects of growth-promoting rhizobacteria on aging seed germination and seedling growth of Brome [J]. Heilongjiang Journal of Animal Husbandry and Veterinary Medicine, 2018, 000(011):24-31. 3. Chen Jie, Liu Jinhang, Li Yongyu, etc. Media and plant growth regulators on oil? Effect of embryo culture [J]. Fujian Journal of Agricultural Sciences, 2020, v.35;No.196(03):65-70. 4. He Xueqing Shaya helati Zhang yfan et al. Effects of different plant growth substances on seed germination characteristics of switchgrass [J]. Journal of Grassland Science 2018(3):684-690. 5. Zhao Luzhou, Xin Fang, Sun Tianzun, et al. Physiological Analysis of overwintering bud development of Panax ginseng -- Analysis of endogenous plant hormones based on HPLC-MS/MS [J]. Journal of Northeast Normal University: natural science edition 2020(1):127-135. 6. Zhang Dan, Sun Ping, Chen Si-jin, Xing Hua, Rui Shi-Li, cow premature Xia, Li Meng-Fei. Simultaneous determination of six plant hormones by liquid chromatography-tandem mass spectrometry [J]. Journal of Gansu Agricultural University, 2020,55(04):98-103. 7. Wang Jin, Dai Lin, Wang Anqi, Lu Yaping. Determination of 10 plant endogenous hormones by ultra performance liquid chromatography-high resolution mass spectrometry [J]. Journal of Analytical Sciences, 2021,37(01):81-87. 8. Yao, Yaming, et al. "Effect of 2, 4-epibrassinolide treatment on the postharvest quality and physiological metabolism of fresh daylily flower buds during storage." Scientia Horticulturae 226 (2017): 110-116.https://doi.org/10.1016/j.scienta.2017.08.039 9. Zhipeng Wang, Hong Jiang, Xujiao Chen, Xinhua Song, Fengjing Xu, Fangchao Chen, Zhiguo Mao, Shouhong Gao Wansheng Chen,A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: applica 10. [IF=3.463] Yaming Yao et al."Effect of 2,4-epibrassinolide treatment on the postharvest quality and physiological metabolism of fresh daylily flower buds during storage."Sci Hortic-Amsterdam. 2017 Dec;226:110 11. [IF=7.271] Gangzheng Wang et al."Transcriptome and proteome analyses reveal the regulatory networks and metabolite biosynthesis pathways during the development of Tolypocladium guangdongense."Comput Struct Biotec. 2020 Jan;18:2081 12. [IF=5.537] Hui Liu et al."Mechanism of early germination inhibition of fresh walnuts (Juglans regia) with gamma radiation uncovered by transcriptomic profiling of embryos during storage."Postharvest Biol Tec. 2021 Feb;172:111380 13. [IF=5.279] Li-Ming Wang et al."1H NMR and UHPLC/Q-Orbitrap-MS-Based Metabolomics Combined with 16S rRNA Gut Microbiota Analysis Revealed the Potential Regulation Mechanism of Nuciferine in Hyperuricemia Rats."J Agr Food Chem. 2020;68(47):14059-14070 14. [IF=4.411] Jian-Hui Ye et al."Effects of Light Intensity and Spectral Composition on the Transcriptome Profiles of Leaves in Shade Grown Tea Plants (Camellia sinensis L.) and Regulatory Network of Flavonoid Biosynthesis."Molecules. 2021 Jan;26(19):5836 15. [IF=4.215] Ahmad Husain et al."Impact of water deficit on the development and senescence of tomato roots grown under various soil textures of Shaanxi, China."Bmc Plant Biol. 2021 Dec;21(1):1-16 16. [IF=4.128] Jia Yin et al."Dose-Dependent Beneficial Effects of Tryptophan and Its Derived Metabolites on Akkermansia In Vitro: A Preliminary Prospective Study."Microorganisms. 2021 Jul;9(7):1511 17. [IF=4.046] Yiwei Zhou et al."Effect of heterocystous nitrogen-fixing cyanobacteria against rice sheath blight and the underlying mechanism."Appl Soil Ecol. 2020 Sep;153:103580 18. [IF=3.935] Zhipeng Wang et al."A rapid and sensitive method for simultaneous determination of eight protein-bound uremic toxins in human serum by UHPLC-MS/MS: application in assessing peritoneal dialysis."J Pharmaceut Biomed. 2020 Jul;186:113312 19. [IF=2.419] Shanshan Gao et al."Development and validation of a sensitive and reliable targeted metabolomics method for the quantification of cardiovascular disease-related biomarkers in plasma by using UPLC-MS/MS."Rapid Communications In Mass Spectrometry. 2022 Mar 20. [IF=8.34] Li Ying et al."Transcriptome and miRNAome analysis reveals components regulating tissue differentiation of bamboo shoots."Plant Physiol. 2022 Mar;188(4):2182-2198 21. [IF=3.739] Liming Wang et al."Metabolomic Study on Iohexol-Induced Nephrotoxicity in Rats Based on NMR and LC-MS Analyses."Chem Res Toxicol. 2022;XXXX(XXX):XXX-XXX 22. [IF=4.169] Amin Bakht et al."Biochemical and Physiological Responses of Cucumis sativus Cultivars to Different Combinations of Low-Temperature and High Humidity."J Plant Growth Regul. 2022 Jan;:1-17 |
white crystalline powder. Melting point 168~170 deg C; Pk4.75. Soluble in acetone and ether, chloroform-soluble, insoluble in water.
The indole is reacted with glycolic acid, filtered, washed with cold water, and dried.
used as plant growth stimulating hormone and assay reagent.
Decomposition | 167 ºC |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Use | is used as a plant growth stimulating hormone and an analytical reagent. 3-indole acetic acid and 3-indole acetaldehyde, 3-indole acetonitrile, ascorbic acid and other long hormone substances naturally exist in nature, 3-indole acetic acid in the plant body biosynthesis of the precursor is tryptophan. The basic function of auxin is to regulate the growth of plants, not only to promote growth, but also to inhibit growth and organ building. In plant cells, auxin not only exists in a free state, but also can exist in the binding of the bound type of the biological polymer and the like, and also have the combination with the special material, such as indole acetyl asparagine, indole acetic acid pentose sugar and indole acetyl glucose etc. This may be a kind of storage of auxin in the cell, but also to remove the excess toxin detoxification of auxin. used as plant growth stimulating hormone and reagent used as plant growth regulator, can promote cell division, accelerate root formation, prevention of fruit drop indole acetic acid (IAA) is a kind of indole with auxin activity of broad-spectrum plant growth regulator; Regulation of cell membrane electron channels and proton channels. |
production method | is obtained by reacting indole with glycolic acid. In a 3L stainless steel autoclave were added 4.1g (85% mol) of potassium hydroxide, 3.3g(3mol) of indole, and then 70% G (mol) of a aqueous glycolic acid solution. The mixture was closed and heated to 250 °c and stirred for 18h. Cool to below 50 °c, add 100 ml of water, and stir at °c for 30min to dissolve potassium indole 3-acetate. After cooling to 25 °c, the autoclave contents were poured into water and water was added to a total volume of 3L. The mixture was extracted with 500ml of ether, and the aqueous layer was separated and acidified by adding hydrochloric acid at 20-30 ° C. To precipitate indole -3-acetic acid. Filtration, washing with cold water, and drying in the dark yielded 455-490g of product. |