- 5-methoxytryptophol
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- $1.60
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2026-08-25
- CAS:712-09-4
- Min. Order: 1kg
- Purity: 99%
- Supply Ability: 100kg
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| | 5-Methoxytryptophol Basic information |
| Product Name: | 5-Methoxytryptophol | | Synonyms: | 5-methoxy-1h-indole-3-ethano;5-methoxy-1h-indole-3-ethanol;2-(5-METHOXY-1H-INDOL-3-YL)-1-ETHANOL;5-methoxy-indole-3-ethano;5-METHOXY-3-(2-HYDROXYETHYL)INDOLE;5-METHOXYINDOLE-3-ETHANOL;2-(5-Methoxy-1H-indole-3-yl)ethanol;3-(2-Hydroxyethyl)-5-methoxy-1H-indole | | CAS: | 712-09-4 | | MF: | C11H13NO2 | | MW: | 191.23 | | EINECS: | 211-919-3 | | Product Categories: | Indoles and derivatives | | Mol File: | 712-09-4.mol |  |
| | 5-Methoxytryptophol Chemical Properties |
| Boiling point | 326.97°C (rough estimate) | | density | 1.224 | | refractive index | 1.5220 (estimate) | | storage temp. | Sealed in dry,2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Viscous Liquid | | pka | 14.90±0.10(Predicted) | | color | Dark Yellow to Very Dark Brown | | Major Application | forensics and toxicology
pharmaceutical (small molecule)
veterinary | | InChI | 1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3 | | InChIKey | QLWKTGDEPLRFAT-UHFFFAOYSA-N | | SMILES | COc1ccc2[nH]cc(CCO)c2c1 | | CAS DataBase Reference | 712-09-4(CAS DataBase Reference) |
| Hazard Codes | Xi | | WGK Germany | 3 | | RTECS | NL8513000 | | HazardClass | IRRITANT | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids |
| | 5-Methoxytryptophol Usage And Synthesis |
| Description | 5-methoxy Tryptophol (5-MTOH) is a natural indole that is produced by the pineal gland. It is a product of melatonin metabolism that may be biologically active. The levels of 5-MTOH in plasma vary in a diurnal pattern in rodents and humans. | | Uses | 5-Methoxytryptophol is a compound known to play a significant role in bone metabolism. 5-Methoxytryptophol can inhibit osteoclastogenesis and promote osteoblast differentiation. | | Definition | ChEBI: 5-Methoxytryptophol is a member of indoles. | | Synthesis | General procedure for the synthesis of 5-methoxychromanol from 2,3-dihydrofuran and 4-methoxyphenylhydrazine hydrochloride:
1. dissolve 4-methoxyphenylhydrazine hydrochloride (1.214 g, 6.95 mmol) in a mixture of 10 mL of 0.72 M H2SO4 and 10 mL of DMA and heat to 55°C.
2. 2,3-dihydrofuran (0.525 mL, 6.95 mmol) was added slowly over 2 minutes.
3. the reaction mixture was stirred at 55 °C for 2 h and subsequently cooled to room temperature.
4. The reaction mixture was extracted with isopropyl acetate (2 x 25 mL).
5. The organic layers were combined and washed sequentially with H2O (3 x 20 mL) and saturated NaCl solution (1 x 20 mL).
6. The organic layer was dried with Na2SO4, filtered and concentrated.
7. The crude product was purified by fast chromatography (eluent: 50:50 ethyl acetate/hexane) to afford 3-(2-hydroxyethyl)-5-methoxy-1H-indole (5-methoxytryptophan) (11) as an orange-red oil. | | IC 50 | Human Endogenous Metabolite | | References | [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 23, p. 6888 - 6891
[2] Angew. Chem., 2018, vol. 130, # 23, p. 7004 - 7007,4
[3] Organic Letters, 2017, vol. 19, # 7, p. 1504 - 1507
[4] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5489 - 5491
[5] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 363 - 367 |
| | 5-Methoxytryptophol Preparation Products And Raw materials |
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