1H-Indole-5,6-diol

Names

[ Name ]:
1H-Indole-5,6-diol

[Synonym ]:
5,6-Dihydroxyindoline
5,6-Dihydroxy-1H-indole
5,6-dihydroxyindol
5,6-Dihydroxyindole
dhi
indole-5,6-diol
Dopamine lutine
Indol-5,6-diol
1H-Indole-5,6-diol
3H-INDOLE-5,6-DIOL
3ID
5,6-dihydroxy-indole

Biological Activity

[Description]:

5,6-Dihydroxyindole, a melanin precursor, has a broad-spectrum antibacterial, antifungal, antiviral, antiparasitic activity. 5,6-Dihydroxyindole has cytotoxic effects and is strongly toxic against various pathogens[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Human Endogenous Metabolite

[In Vitro]

5,6-Dihydroxyindole (1, 10, 20, 50, 100 μM; for 4 hours) dose-dependently decreases OD492 values. Pretreatment of Sf9 cells with 1.0 mM 5,6-Dihydroxyindole for 4 hours results in 97% mortality, and LC50 values of 20.3 μM in buffer and 131.8 μM in a culture medium[1]. Preincubation of a baculovirus stock with 1.25 mM 5,6-Dihydroxyindole for 3 hours near fully disables recombinant protein production. The LC50 for lambda bacteriophage and eggs of the wasp Microplitis demolitor are 5.6 and 111.0 μM, respectively[1]. 5,6-Dihydroxyindole and its spontaneous oxidation products are also active against viruses and parasitic wasps[1].

[References]

[1]. Zhao P, et al. Antiviral, anti-parasitic, and cytotoxic effects of 5,6-dihydroxyindole (DHI), a reactive compound generated by phenoloxidase during insect immune response. Insect Biochem Mol Biol. 2011 Sep;41(9):645-52.

[2]. Heiduschka P, et al. Melanin precursor 5,6-dihydroxyindol: protective effects and cytotoxicity on retinal cells in vitroand in vivo. Toxicol Pathol. 2007 Dec;35(7):1030-8.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
411.2±25.0 °C at 760 mmHg

[ Molecular Formula ]:
C₈H₇NO₂

[ Molecular Weight ]:
149.147

[ Flash Point ]:
202.5±23.2 °C

[ Exact Mass ]:
149.047684

[ PSA ]:
56.25000

[ LogP ]:
0.37

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.802

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn: Harmful;N: Dangerous for the environment;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
22-26-36/37/39-61

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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