5,6-二羟基吲哚
5,6-dihydroxyindole
CAS: 3131-52-0
Molecular Formula: C8H7NO2
5,6-二羟基吲哚 - Names and Identifiers
| Name | 5,6-dihydroxyindole |
| Synonyms | Dopamine lutine 1H-Indole-5,6-diol 5,6-dihydroxyindole 5,6-Dihydroxyindole |
| CAS | 3131-52-0 |
| EINECS | 412-130-9 |
| InChI | InChI=1/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H |
5,6-二羟基吲哚 - Physico-chemical Properties
| Molecular Formula | C8H7NO2 |
| Molar Mass | 149.15 |
| Density | 1.51g/cm3 |
| Melting Point | 140 °C (decomp) |
| Boling Point | 411.2°C at 760 mmHg |
| Flash Point | 202.5°C |
| Vapor Presure | 2.38E-07mmHg at 25°C |
| Appearance | Solid |
| pKa | 9.81±0.40(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.802 |
| Use | 5, 6-dihydroxyindole is a permanent hair dye with non-toxic and side effects, and is gradually replacing aniline compounds as the best choice for synthetic hair dyes. 5, 6-dihydroxyindole is an important intermediate of melanogen, which was first found in a plant in nature. |
5,6-二羟基吲哚 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R41 - Risk of serious damage to eyes R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| RTECS | NL7858000 |
5,6-二羟基吲哚 - Upstream Downstream Industry
5,6-二羟基吲哚 - Hair dyeing mechanism
As a permanent hair dye, 5, 6-dihydroxyindole has the same hair dyeing mechanism as p-phenylenediamine and its derivatives. It acts on hair keratin fibers, making the dyeing effect very obvious, and it enters the hair inside the hair pulp. After dyeing, washing is not easy to fade and will not be greatly affected by sunlight.
For a long time, the effective blackening ingredients in hair dyes are p-phenylenediamine and its derivatives. These substances have carcinogenic, teratogenic, and allergic adverse effects on the human body, and affect the health of users. As an effective substitute, 5, 6-dihydroxyindole is originally produced by the organism itself, which is non-toxic and side effects to the body.
Last Update：2024-04-10 22:29:15
5,6-二羟基吲哚 - Synthesis method
At present, there are many common synthesis methods to synthesize 5, 6-dihydroxyindole, which are generally protected by hydroxyl, nitrification, deprotection, and cyclization. According to the different starting materials, protection can be divided into The following three methods.
1. Benzaldehyde method
2. phenylacetonitrile method
3. phenethylamine method
Using 3,4 dimethoxyphenylacetonitrile as the main raw material, 5, 6-dihydroxyindole was synthesized by four steps of demethyl, hydroxyl protection, nitration and reductive cyclization. In the demethyl reaction, hydrogen chloride/pyridine is used as ether bond cleavage reagent, and the yield is 90.2%. With benzyl gasification as hydroxyl protection reagent and potassium carbonate as acid binding agent, the reaction yield of protecting hydroxyl is 87.8%. The yield of nitration with concentrated nitric acid is 86.9%. When reducing the cyclization, 10% Pd/C is a suitable catalyst, the cyclization is diluted as a hydrogen donor, and the cyclization yield is 85.2%. The comprehensive yield of 5, 6-dihydroxyindole was 58.6% based on 3, 4-dimethoxyphenylacetonitrile.
Last Update：2024-04-10 22:29:15
5,6-二羟基吲哚 - Introduction
Biological activity 5,6-Dihydroxyindole is a precursor of melanin with broad-spectrum antibacterial, antifungal, antiviral, and antiparasitic activities. 5,6-Dihydroxyindole has cytotoxic effects and is highly toxic to various pathogens.
Target
Human Endogenous Metabolite
In vitro study
5,6-Dihydroxyindole (1, 10, 20, 50, 100 μM; for 4 hours) dose-dependently decreases OD 492 values. Pretreatment of Sf9 cells with 1.0 mM 5,6-Dihydroxyindole for 4 hours results in 97% mortality, and LC 50 values of 20.3 μM in buffer and 131.8 μM in a culture medium.
Preincubation of a baculovirus stock with 1.25 mM 5,6-Dihydroxyindole for 3 hours near fully disables recombinant protein production. The LC 50 for lambda bacteriophage and eggs of the wasp Microplitis demolitor are 5.6 and 111.0 μM, respectively.
5,6-Dihydroxyindole and its spontaneous oxidation products are also active against viruses and parasitic wasps.
Last Update：2024-04-09 20:52:54
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Raw Materials for 5,6-二羟基吲哚