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1-Hydroxyanthraquinone

1-Hydroxyanthraquinone structure

1-Hydroxyanthraquinone 

structure
  • CAS No:

    129-43-1

  • Formula:

    C14H8O3

  • Chemical Name:

    1-Hydroxyanthraquinone

  • Synonyms:

    9,10-Anthracenedione,1-hydroxy-;Anthraquinone,1-hydroxy-;1-Hydroxy-9,10-anthracenedione;1-Hydroxyanthraquinone;1-Hydroxy-9,10-anthraquinone;α-Hydroxyanthraquinone;Erythroxyanthraquinone;NSC 8640;1-Hydroxy-9,10-dihydroanthracene-9,10-dione

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Orange-red needles, orange-red to fine yellow crystals


1-hydroxyanthraquinone is a monohydroxyanthraquinone.

1-Hydroxyanthraquinone Basic Attributes

224.215

224.21

204-946-7

LFU129OE9H

8640

DTXSID1020722

Orange red needles|Red-orange needles from ethyl alcohol|Orange-red to fine yellow crystals in ethanol

2914690090

Characteristics

54.4

3.52

Red-orange to fine yellow crystals

1.4±0.1 g/cm3

193.8 °C

sublimes

365°F

1.695

In water, 8.5 mg/L @ 25 deg C

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

2.09 mmHg

1.44

Henry's Law constant = 7.2X10-9 atm-cu m/mole @ 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 1.4X10-11 cu cm/molecul-sec @ 25 °C /Estimated/

Safety Information

III

R36/37/38:Irritating to eyes, respiratory system and skin .

S26-S36/37/39

CB7178000

Xn

P201, P202, P264, P281, P305+P351+P338, P308+P313, P337+P313, P405, P501

H320

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 1-HYDROXYANTHRAQUINONE (6 total), please visit the HSDB record page.

|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P280, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 1-HYDROXYANTHRAQUINONE (10 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

An eye irritant.

Toxicity

... In addition, 1-HAQ has a synergistic effect with methylazoxymethaol (MAM) acetate on colon carcinogenesis.

1-Hydroxyanthraquinone's former production and use as a dye(1) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(SRC), determined from a log Kow of 3.52(2) and a regression-derived equation(3), indicates that 1-hydroxyanthraquinone is expected to have slight mobility in soil(SRC). Volatilization of 1-hydroxyanthraquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.09X10-7 mm Hg(4), and water solubility, 8.5 mg/l(5). 1-Hydroxyanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon it's vapor pressure(4). Biodegradation in soil is not expected to be an important environmental fate process based on a 1-5% theoretical BOD using activated sludge and the Japanese MITI test(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(SRC), determined from a log Kow of 3.52(2) and a regression-derived equation(3), indicates that 1-hydroxyanthraquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.09X10-7 mm Hg(4), and water solubility, 8.5 mg/l(5). According to a classification scheme(6), BCFs ranging from 55-318(7), suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation in water is not expected to be an important environmental fate process based on a 1-5% theoretical BOD using activated sludge and the Japanese MITI test(8). However, in most anoxic sediments, uncharged simple anthraquinone dyes exhibit half-lives of less than 10 days(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-hydroxyanthraquinone, which has a vapor pressure of 2.09X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1-hydroxyanthraquinone 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 28 hrs(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-hydroxyanthraquinone may be removed from the air by wet and dry deposition(SRC). 1-Hydroxyanthraquinone isomers photodecomposed under irradiation with visible light in aerated alkaline solution, with phthalic acid as the main product(4).

The rate constant for the vapor-phase reaction of 1-hydroxyanthraquinone with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 28 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Hydroxyanthraquinone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 1-Hydroxyanthraquinone isomers photodecomposed under irradiation with visible light in aerated alkaline solution, with phthalic acid as the main product(3).

177.83|BCF ranges of 55-318 and 62-297 at test chemical concns of 50 and 5 mg/l, respectively, were measured for 1-hydroxyanthraquinone using orange-red killifish (Oryzias latipes) which were exposed over an 8-week period(1). According to a classification scheme(2), BCF values of 30 to 100 are moderate and from 100 to 1,000 are high.

The Koc of 1-hydroxyanthraquinone is estimated as 2,000(SRC), using a log Kow of 3.52(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-hydroxyanthraquinone is expected to have slight mobility in soil.

The Henry's Law constant for 1-hydroxyanthraquinone is estimated as 7.25X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.09X10-7 mm Hg(1), and water solubility, 8.5 mg/l(2). This Henry's Law constant indicates that 1-hydroxyanthraquinone is expected to be essentially nonvolatile from water surfaces(3). 1-Hydroxyanthraquinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure and general population exposure should be low or non-existent since 1-hydroxyanthraquinone is no longer produced or used. (SRC)

Drug Information

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)

1-Hydroxyanthraquinone was found to be absorbed when continuously administered to rats (strain not specified) by stomach tube (50 mg suspended in aqueous gum arabic), and its metabolites were identified by paper chromatography. Urine and feces were collected during 48 hours after treatment and extracted with diethyl ether. Of the 1-hydroxyanthraquinone originally present, 2.49% and 0.74% were converted into alizarin (1,2-dihydroxyanthraquinone), in urine and feces, respectively. The alizarin was then excreted after sulfation and glucuronidation.

... 1-Hydroxyanthraquinone was found to be absorbed when continuously administered to rats (strain not specified) by stomach tube (50 mg suspended in aqueous gum arabic), and its metabolites were identified by paper chromatography. Urine and feces were collected during 48 hours after treatment and extracted with diethyl ether. Of the 1-hydroxyanthraquinone originally present, 2.49% and 0.74% were converted into alizarin (1,2-dihydroxyanthraquinone), in urine and feces, respectively. The alizarin was then excreted after sulfation and glucuronidation.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

1-hydroxy-9,10-anthraquinone

1-Hydroxyanthraquinone Use and Manufacturing

Methods of Manufacturing

A general method for synthesis of anthraquinones, including 1-hydroxy-anthraquinone, has been developed. The anthraquinones were obtained under mild conditions from ortho-dicarboxylic acid chlorides and suitable aromatic substrates via a FriedelCrafts process.|1-Hydroxyanthraquinone has been synthesized by diazotization of 1-aminoanthraquinone and heating the diazonium salt with concentrated sulfuric acid. After dilution with water, the precipitated crude product was diluted with acetone and purified by preparative thin-layer chromatography (TLC) in toluene:ethyl formate:formic acid (75:24:1).|1-Hydroxyanthraquinone has also been prepared in 96.4% yield by reacting 1-nitroanthraquinone with sodium formate in dimethylformamide at 130 C for 17 hours.

Uses

1-Hydroxyanthraquinone can be used as an intermediate in the production of dyes and drugs.

9,10-Anthracenedione, 1-hydroxy-: INACTIVE|1-Hydroxyanthraquinone has been isolated from the roots of Rubia cordifolia, Morinda officinalis and Damnacanthus indicus, from the heartwood of Tabebuia avellanedae and the herb Cassia occidentalis.

The following method has been used to determine hydroxyanthraquinones in experimental laboratory animal diet containing madder. Hydroxyanthraquinones were isolated by Soxhlet extraction with ethyl acetate, evaporation of the solvent, and dissolution in methanol. Separation of the hydroxyanthraquinones was accomplished by HPLC with spectrometric detection at 410 nm. /Hydroxyanthraquinones/|A method using reversed-phase high-performance liquid chromatography (HPLC) has been described that allows the separation of 13 naturally occurring naphthoquinones and anthraquinones, including 1-hydroxyanthraquinone. The separation was achieved under isocratic and gradient conditions.

Pyrrolizidine alkaloids may be estimated in animal tissues and fluids by removing protein, chromatographing on Florisil and estimating colorimetrically with methyl orange. /Pyrrolizidine Alkaloids/

Computed Properties

Molecular Weight:224.21
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:224.047344113
Monoisotopic Mass:224.047344113
Topological Polar Surface Area:54.4
Heavy Atom Count:17
Complexity:349
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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