Basic information
- Standard SMILES
O=C1c2ccccc2Cc2ccccc21- InChIKey
RJGDLRCDCYRQOQ-UHFFFAOYSA-N- Molecular formula
- C14H10O
- Average molar mass
- 194.23 g/mol
- Monoisotopic mass
- 194.07316494
Overview
Anthrone is a member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9. It has a role as a radical scavenger. It is a tautomer of a 9-anthrol.
Names & identifiers
- Preferred name
- Anthrone
- IUPAC
- 10H-anthracen-9-one
- English name
- Anthrone
- Molecular formula
- C14H10O
- Molecular weight
- 194.23
Names & synonyms
Show more names
Database identifiers
- CAS
90-44-8- PubChem CID
- 7018
- DTXSID
DTXSID1049431- ChEMBL
CHEMBL124440- ChEBI
CHEBI:33835- UNII
- FP0FJ7K744
- EC Number
- 201-994-0
- Nikkaji
- J3.916K
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 234
Experimental & physicochemical properties
LogP
Log Kow = 3.66
3.46
Color/Form
ORTHORHOMBIC NEEDLES FROM BENZENE AND PETROLEUM ETHER
COLORLESS NEEDLES
Solubility
SOL IN MOST ORG SOLVENTS WITHOUT FLUORESCENCE
SOL IN ACETONE, HOT BENZENE, CONCN SULFURIC ACID, HOT DIL ALKALI
Other Experimental Properties
ANY FLUORESCENCE PRESENT IS DUE TO ANTHRANOL
ADDITION CMPD WITH 4 MOLECULES DESOXYCHOLIC ACID, C110-H170-O17, MP 179 °C
EQUIL IN ABSOLUTE ALCOHOL: 89% ANTHRONE; 11% ANTHRANOL; TENDENCY TO CHANGE TO ANTHRAQUINONE
Physicochemical properties
- Melting point
- 154 · 154-157 °C (lit.)
- Boiling point
- 721 °C · 721 °C
- Density
- 1.055 · 1.0550 (rough estimate)
- bulk density
- 450 kg/m3 · 450kg/m3
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- INSOLUBLE
- form
- Powder
- color
- Yellow
- Water Solubility
- INSOLUBLE
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,691
- BRN
- 1910173 · 1910173
- Henry's Law Constant
- 1.2 · 1.2×101 mol/(m3Pa) at 25℃, HSDB (2015)
- Stability
- Stable. Incompatible with strong oxidizing agents. Combustible.
- Major Application
- diagnostic assay manufacturinghematologyhistology
- InChI
- 1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-8H,9H2
- InChIKey
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N
- SMILES
- O=C1c2ccccc2Cc3ccccc13
- CAS DataBase Reference
- 90 · 90-44-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 FJ7K744 · FP0FJ7K744
- NIST Chemistry Reference
- Anthrone(90-44-8)
- EPA Substance Registry System
- 9 · 9(10H)-Anthracenone (90-44-8)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-20/21/22
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 8925500 · CB8925500
- F
- 8 · 8
- TSCA
- TSCA listed
- HS Code
- 29143990 · 29143990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 90 · 90-44-8(Hazardous Substances Data)
- Toxicity
- 60 mg/plate · mmo-sat 60 mg/plate MUREAV 157,149,85
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.9% (2 of 51) of reports.
Warning
H315 (96.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 9(10H)-Anthracenone
9(10H)-Anthracenone: Does not have an individual approval but may be used under an appropriate group standard
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that anthrone will have only slight mobility in soil(SRC). Biodegradation of anthrone is expected based on limited data and may be a major fate process for this compound in soil(SRC). A mixed bacterial population, isolated from a hydrocarbon-polluted creek, degraded 40% of anthrone to traces of anthrone and to anthraquinone in 30% yield(4). Anthrone's estimated values for vapor pressure(5) and Henry's Law constant(6,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that anthrone should adsorb to sediment and suspended solids(SRC). Anthrone may volatilize slowly from water surfaces based on an estimated Henry's Law constant of 7.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 65 and 480 days, respectively(3,SRC). An estimated BCF value of 360(3,SRC), from a measured log Kow(2), suggests that anthrone will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(2,SRC) indicates that anthrone will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase anthrone is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 40 hours(3,SRC). Particulate-phase anthrone may be physically removed from the air by dry deposition(SRC).
Effluent Concentrations
Several unspecified isomers of anthrone were detected in chlorinated coal-tar leachate at unreported concentrations(1). A heavy-duty diesel exhaust particulate sample, NBS SRM 1650, contained anthrone at unreported concentrations(2). Diesel emission particulates, collected from a Volkswagen Rabbit contained anthrone(3). Fine particle emissions from the combined exhaust of a vented natural gas-fired residential space heater plus a water heater contained 21.4 pg/kJ anthrone(4).
Soil Adsorption/Mobility
The Koc of anthrone is estimated as approximately 2300(SRC), using a measured log Kow of 3.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that anthrone has only slight mobility in soil(SRC).
Sediment/Soil Concentrations
Superficial marine sediments of Cortiou Creek, in the sewage area of Marseilles, France, are contaminated with anthrone at concentrations ranging from non-detectable to 300 ng/g (9 of 10 sites had measurable quantities of anthrone; detection limit not given)(1).
Environmental Bioconcentration
An estimated BCF value of 360 was calculated for anthrone(SRC), using a measured log Kow of 3.66(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be an important fate process(SRC).
Volatilization from Water/Soil
The Henry's Law constant for anthrone is estimated as 7.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that anthrone will slowly volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 65 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 480 days(2,SRC). Anthrone's values for vapor pressure(3) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces is not likely to be a major fate process for this compound(SRC).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of anthrone with photochemically produced hydroxyl radicals has been estimated as 9.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 40 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CB8925500
- hs_code
- 29143990
- Toxicity
- mmo-sat 60 mg/plate MUREAV 157,149,85
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 90-44-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used in the colorimetric determination of sugar and animal starch in body fluids, as a general reagent for carbohydrates, in the determination of animal starch in liver tissue, and in organic synthesis; [HSDB]
IN COLORIMETRIC DETERMINATION OF SUGAR AND ANIMAL STARCH IN BODY FLUIDS; IN ORG SYNTHESIS
GENERAL REAGENT FOR CARBOHYDRATES; DETERMINATION OF ANIMAL STARCH IN LIVER TISSUE
Derivatives: melitracen
Applications
UsesUsed for determination of carbohydrates Anthrone is used for the determination of carbohydrates. It is used as a general reagent in the colorimetric determination of carbohydrates in yeast and plant extracts. It is involved in organic synthesis. It is utilized for the determination of sugar in body fluids. It finds application as a laxative.
UsesAnthrone is a tricyclic aromatic ketone and related compound of anthracene. Anthrone is used as a reagent in the colorometric determination of carbohydrates.
General DescriptionAnthrone has the ability to reduce aldehyde containing reducing sugars such as streptose and N-acetyl glucosamine present in streptomycin, into acids. It develops a red- violet color. Therefore, it is used to determine streptomycin quantitatively. Anthrone has been used to detect carbohydrate containing lipids and to measure sugar content such as sucrose and trehalose in the liquid medium.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A member of the class of anthracenes that is 9,10-dihydroanthracene carrying an oxo group at C-9.
Related reactions
Linked notes
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