ChemicalBook Product Catalog Analytical Chemistry Standard Forensic and veterinary standards 5-Methoxytryptophol

5-Methoxytryptophol

Product Name5-Methoxytryptophol
CAS712-09-4
MFC11H13NO2
MW191.23
EINECS211-919-3
MOL File712-09-4.mol

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)

Safety Information

Hazard Codes	Xi
WGK Germany	3
RTECS	NL8513000
HazardClass	IRRITANT
HS Code	2933998090
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

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

1191-99-7

19501-58-7

712-09-4

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

5-Methoxytryptophol Supplier

5-Methoxytryptophol manufacturers

Related Product Information