2380-82-7

Basic information

• Product Name: 6-hydroxy-5-methoxyindole
• Synonyms: 6-hydroxy-5-methoxyindole;5-methoxy-1H-indol-6-ol
• CAS NO: 2380-82-7
• Molecular Formula: C9H9 N O2
• Molecular Weight: 163.17
• Mol File: 2380-82-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 359.9°Cat760mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.312g/cm³
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 6-hydroxy-5-methoxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-hydroxy-5-methoxyindole(2380-82-7)
• EPA Substance Registry System: 6-hydroxy-5-methoxyindole(2380-82-7)

Safety Data

• Hazardous Substances Data: 2380-82-7(Hazardous Substances Data)

Usage

Description

6-Hydroxy-5-methoxyindole, also known as 5-methoxyindole-6-ol, is an organic compound that belongs to the indole family. It is characterized by the presence of a hydroxyl group at the 6th position and a methoxy group at the 5th position on the indole ring. 6-hydroxy-5-methoxyindole is known for its role in promoting melanin synthesis, which is essential for skin pigmentation.

Uses

Used in Cosmetics Industry:
6-Hydroxy-5-methoxyindole is used as an active ingredient in the cosmetics industry for its ability to promote melanin synthesis. This property is utilized to create a tanned look in cosmetic products, similar to the effect produced by dihydroxyacetone. The compound is claimed to yield a pigmentation quality equivalent to that obtained from natural tanning, making it a valuable addition to tanning and self-tanning products.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 941, 1987 DOI: 10.1002/jhet.5570240410

InChI:InChI=1/C9H9NO2/c1-12-9-4-6-2-3-10-7(6)5-8(9)11/h2-5,10-11H,1H3

Upstream product

• 112919-69-4 6-acetoxy-5-methoxy indole 
• 98258-76-5 (E)-4-hydroxy-5-methoxy-2,β-dinitrostyrene 
• 98258-74-3 1-benzyloxy-2-methoxy-5-nitro-4-(2-nitrovinyl)benzene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 2426-84-8 4-(benzyloxy)-5-methoxy-2-nitrobenzaldehyde 
• 121-33-5 vanillin 
• 2454-72-0 6-nitrovanillin 
• 84333-01-7 4-acetoxy-5-methoxy-2-nitro-benzaldehyde 
• 112919-67-2 4-acetoxy-5-methoxy-2,β-dinitrostyrene 

Relevant articles and documents

Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.

Product based on inorganic or organic lamellar particles, containing a melanotic pigment, process for preparing it and its use in cosmetics

The invention relates to a product in powder form consisting of organic or inorganic particles having a lamellar structure, having a size of less than 50 microns and containing at least one synthetic melanotic pigment formed in situ by oxidation of an indole compound, and to its use for the protection of the human epidermis, in make-up products and for dyeing hair.

Dyeing process employing indole dyes and oxidation dye precursors and dyeing agents employed

A process for dyeing keratinous fibers comprises a two-step operation in which in the first step the fibers are contacted with an indole dye in a medium suitable for dyeing the fibers, the medium being free from any oxidation catalyst and oxidation catalyst. Thereafter, in the second step the fibers are contacted with a para type oxidation dye precursor in a medium which is also suitable for dyeing the fibers and is free from any oxidation catalyst and oxidation agent. A multi-compartment kit housing the indole dye and para type oxidation dye precursor is also provided.