2380-82-7

Usage

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 academic research and scientific papers

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.

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.

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.

Process for dyeing keratinous fibres with a hydroxyindole in combination with a quinone derivative; and novel 1,4-benzoquinones

Process for dyeing keratinous fibres, comprising the step of applying to these fibres at least one composition A containing, in a medium appropriate for dyeing, at least one mono- or di-hydroxyindole the application of the composition A being preceded or followed by the application of a composition B containing, in a medium appropriate for dyeing, at least one quinone derivative chosen from ortho- or para-benzoquinones, monoimines or diimines of ortho- or para-benzoquinones, 1,2- or 1,4-naphthoquinones, sulphonimides of ortho- or para-benzoquinones, α, ω-alkylene-bis-1,4-benzoquinones, or 1,2- or 1,4-naphthoquinone-monoimines or -diimines; the mono- or di-hydroxyindoles and the quinone derivatives being chosen such that the oxidation-reduction potential difference ΔE between the oxidation-reduction potential Ei of the mono- or di-hydroxyindoles, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the oxidation-reduction potential Eq of the quinone derivative determined at pH 7 in a phosphate medium by polarography on a mercury electrode and relative to a saturated calomel electrode is such that

Process for dyeing keratinous fibres with indole derivatives combined with an iodide

Process for dyeing human keratinous fibres, consisting in applying on these fibres at least least one composition (A) containing, in a cosmetically acceptable medium, one or more indole derivatives corresponding to the formula (I) STR1 in which: R1/

Improved Synthesis of 6-Hydroxy-5-methoxy- and 5-Hydroxy-6-methoxyindoles and Their O-Acetates, Analogs of Natural Eumelanin Precursors.

Improved routes for syntheses of gram quantities of the isomeric 5,6-acetoxymethoxyindoles, and milligram amounts of the 5,6-hydroxymethoxyindoles, have been developed.They depend on regiospecific nitration of the benzyl ethers of vanillin and isovanillin