Basic information
- CAS
3131-52-0- Standard SMILES
Oc1cc2cc[nH]c2cc1O- InChIKey
SGNZYJXNUURYCH-UHFFFAOYSA-N- Molecular formula
- C8H7NO2
- Average molar mass
- 149.15 g/mol
- Monoisotopic mass
- 149.04767847
Names & identifiers
- Preferred name
- 5,6-Dihydroxyindole
- IUPAC
- 1H-indole-5,6-diol
- English name
- 5,6-DIHYDROXYINDOLE
- Molecular formula
- C8H7NO2
- Molecular weight
- 149.15
Names & synonyms
5,6-Dihydroxyindole3131-52-01H-Indole-5,6-diolDopamine lutine3H-INDOLE-5,6-DIOLZ3OC8499KGIMEXINE OAYDTXSID20185242CHEBI:27404RefChem:587786CHEBI:23781DTXCID30107733
Show more names
3IDJACS-3131-52-0Indol-5,6-diolINDOLE-5,6-DIOL5,6-DIYDROXYINDOLE5.6-Dihydroxy Indol
412-130-9DihydroxyindoleMFCD00798933dhi5,6-Dihydroxy-1H-indole5,6-dihydroxy indoleCHEMBL92636BDBM50028548
Database identifiers
- CAS
3131-52-0- PubChem CID
- 114683
- DTXSID
DTXSID20185242- ChEMBL
CHEMBL92636- ChEBI
CHEBI:27404- UNII
- Z3OC8499KG
- EC Number
- 412-130-9
- Nikkaji
- J434.158I
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 56.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 151
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 140 °C · 140 °C (decomp)
- Boiling point
- 411.2 · 411.2±25.0 °C(Predicted)
- Density
- 1.51 · 1.510±0.06 g/cm3(Predicted)
- RTECS
- 7858000 · NL7858000
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
- form
- Solid
- pka
- 9.81 · 9.81±0.40(Predicted)
- color
- Off-white to light brown
- Cosmetics Ingredients Functions
- HAIR DYEING
- InChI
- InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
- InChIKey
- SGNZYJXNUURYCH-UHFFFAOYSA-N
Safety & regulation
GHS classification
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]；H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]；H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, and P501 (click each P-code to see the statement)
Danger
Hazard information
Regulatory InformationStatus: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/2544
Hazard Classes and Categories
Acute Tox. 4 (100%)；Eye Dam. 1 (97.4%)；Aquatic Chronic 2 (97.4%)
Acute toxicity - category 4；Eye damage - category 1；Hazardous to the aquatic environment (chronic) - category 2
Acute Tox. 4 *；Eye Dam. 1；Aquatic Chronic 2
Regulatory information
Regulatory InformationStatus: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/2544
Safety data
- wgk
- WGK 3
- hs_code
- 2933998090
- risk_code
- 22-41-51/53
- Signal word
- Warning
- Symbol(GHS)
- GHS05,GHS07,GHS09
- hazard_code
- Xn,N
- safety_code
- 22-26-36/37/39-61
- Storage Class
Chemistry & industry
Pharmacology
Metabolism/MetabolitesDihyroxy-1H-indole has known human metabolites that include Dihyroxy-1H-indole glucuronide I.
MeSH Pharmacological Classification
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Compounds and drugs that inhibit or block the activity of CATECHOL O-METHYLTRANSFERASE enzymes. Drugs in this class are used in management of central nervous system disorders such as PARKINSON DISEASE.
Metabolite PathwaysAlkaptonuria；Disulfiram Action Pathway；Dopamine beta-hydroxylase deficiency；Hawkinsinuria；Monoamine oxidase-a deficiency (MAO-A)；Tyrosine metabolism；Tyrosinemia Type I；Tyrosinemia, transient, of the newborn
Uses & manufacturing
Use ClassificationCosmetics -> Hair dyeing
Applications
Description5,6-Dihydroxyindole is a melanin precursor. It is one of the toxic compounds in the melanin biosynthetic pathway. 5,6-Dihydroxyindole is an indole derivative that contains two hydroxyl groups attached to the 5th and 6th positions of the indole ring. It is an intermediate in the biosynthesis of melanin, a pigment responsible for the coloration of hair, skin, and eyes in humans and other organisms.
Uses5,6-Dihydroxyindole is an intermediate in melanogenesis, the production of melanin which is found in our skin, eyes, hair, and inner ear.
Upstream & downstream products
Upstream raw materials
Related reactions
21 records
Compound notes
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