Basic information
- Standard SMILES
O=C1c2cccc(O)c2C(=O)c2c(O)cccc21- InChIKey
QBPFLULOKWLNNW-UHFFFAOYSA-N- Molecular formula
- C14H8O4
- Average molar mass
- 240.21 g/mol
- Monoisotopic mass
- 240.04225873
Names & identifiers
- Preferred name
- 1,8-Dihydroxyanthraquinone
- IUPAC
- 1,8-dihydroxyanthracene-9,10-dione
- English name
- 1,8-Dihydroxyanthraquinone
- Molecular formula
- C14H8O4
- Molecular weight
- 240.21
Names & synonyms
Show more names
Database identifiers
- CAS
117-10-2- PubChem CID
- 2950
- DTXSID
DTXSID9020328- ChEMBL
CHEMBL53418- ChEBI
CHEBI:3682- UNII
- Z4XE6IBF3V
- EC Number
- 204-173-5
- Nikkaji
- J2.905J
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 346
Physicochemical properties
- Melting point
- 191 · 191-193 °C (lit.)
- Boiling point
- 342.92 °C · 342.92°C (rough estimate)
- Density
- 1.3032 · 1.3032 (rough estimate)
- bulk density
- 600 kg/m3 · 600kg/m3
- refractive index
- 1.543 · 1.5430 (estimate)
- Flash point
- 200 °C · >200°C
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- very faint turbidity in hot Acetic acid
- form
- Powder
- pka
- 6.27 · 6.27±0.20(Predicted)
- color
- Orange-brown or brown
- Water Solubility
- insoluble
- Merck
- 14 · 14,2815
- BRN
- 2054727 · 2054727
- Henry's Law Constant
- 1.8 · 1.8×105 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
- InChIKey
- QBPFLULOKWLNNW-UHFFFAOYSA-N
- SMILES
- Oc1cccc2C(=O)c3cccc(O)c3C(=O)c12
- LogP
- 4.57 · 4.570 (est)
- CAS DataBase Reference
- 117 · 117-10-2(CAS DataBase Reference)
- FDA 21 CFR
- 310.545 · 310.545
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 4 XE6IBF3V · Z4XE6IBF3V
- Proposition 65 List
- Dantron (Chrysazin; 1,8-Dihydroxyanthraquinone)
- ATC code
- 6 AB03,A06AB53,A06AG03 · A06AB03,A06AB53,A06AG03
- IARC
- 2 B · 2B (Vol. 50) 1990
- NIST Chemistry Reference
- 1 · 1,8-Dihydroxyanthraquinone(117-10-2)
- EPA Substance Registry System
- Danthron (117-10-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335-H351
- Precautionary statements
- 201 · P201-P302+P352-P305+P351+P338-P308+P313
- target organs
- Respiratory system
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40
- Safety Statements
- 36 · 36/37-36-22
- RIDADR
- 2811 · 2811
- WGK Germany
- 1 · 1
- RTECS
- 6650000 · CB6650000
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29146990 · 29146990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Eye · Carc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 117 · 117-10-2(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in mice: <7 g/kg (Case)
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- CB6650000
- ridadr
- 2811
- hs_code
- 29146990
- Toxicity
- LD50 orally in mice: <7 g/kg (Case)
- risk_code
- 40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 36/37-36-22
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H351
- Hazard Classifications
- Carc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P201-P302+P352-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 117-10-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionDanthron, a natural product, was originally extracted from the roots and rhizome of Polygonaceae plant, also called Da Huang in traditional Chinese herbal medicine. Now it is synthesized in many countries, such as Germany, India, Japan, Poland, the United Kingdom, and the United States. Danthron is reasonably anticipated to be a human carcinogen. Danthron is an anthraquinone that exists at room temperature as a red or orange crystalline powder.It is practically insoluble in water, but soluble in a variety of solvents (acetone, chloroform, diethyl ether, ethanol) and alkaline hydroxide solutions. The stability of danthron is generally good. It is stable under room temperatures and normal pressures.
UsesUsed as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.
Usescathartic
UsesImportant intermediate in the manufacture of alizarin and indanthrene dyestuffs; forms insoluble Ca, Ba, Pb lakes. Antioxidant in synthetic lubricants; fungicide.
Uses1,8-Dihydroxyanthraquinone can be used:To prepare an inclusion complex with β-cyclodextrin, applicable as a sensor in the estimation of Cu2+ions in an aqueous solution.As a starting material in the synthesis of 1,4,5,8-tetramethoxyanthracene.As an aromatic scavenger in the modification of lignin, which acts as a corrosion inhibitor for steel.
General DescriptionOrange crystalline powder. Almost odorless and tasteless.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 1,8-Dihydroxyanthraquinone is a dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8. It has a role as an apoptosis inducer and a plant metabolite.
Related reactions
Linked notes
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