| Identification | More | [Name]
5-METHOXYTRYPTOPHOL | [CAS]
712-09-4 | [Synonyms]
2-(5-METHOXY-1H-INDOL-3-YL)-1-ETHANOL
5-METHOXY-3-(2-HYDROXYETHYL)INDOLE
5-METHOXYINDOLE-3-ETHANOL
5-METHOXYTRYPTOPHOL
5-methoxy-1h-indole-3-ethano
5-methoxy-1h-indole-3-ethanol
5-methoxy-indole-3-ethano
2-(5-methoxy-1H-indol-3-yl)ethanol
methoxytryptophol
2-(5-Methoxy-1H-indole-3-yl)ethanol
3-(2-Hydroxyethyl)-5-methoxy-1H-indole | [EINECS(EC#)]
211-919-3 | [Molecular Formula]
C11H13NO2 | [MDL Number]
MFCD00047196 | [Molecular Weight]
191.23 | [MOL File]
712-09-4.mol |
| Chemical Properties | Back Directory | [Boiling point ]
326.97°C (rough estimate) | [density ]
1.224 | [refractive index ]
1.5220 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [WGK Germany ]
3
| [RTECS ]
NL8513000
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
5-methoxy Tryptophol (5-MTOH) is a natural indole that is produced by the pineal gland.1,2 It is a product of melatonin metabolism that may be biologically active.3,4 The levels of 5-MTOH in plasma vary in a diurnal pattern in rodents and humans.5,6 | [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 |
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