117-10-2 Usage
Description
Danthron, 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.
Chemical Properties
Different sources of media describe the Chemical Properties of 117-10-2 differently. You can refer to the following data:
1. orange-brown or brown powder
2. Red-orange to orange crystalline powder or
reddish-brown crystalline solid.
Uses
Different sources of media describe the Uses of 117-10-2 differently. You can refer to the following data:
1. Important intermediate in the manufacture of alizarin and indanthrene dyestuffs; forms insoluble Ca, Ba, Pb lakes. Antioxidant in synthetic lubricants; fungicide.
2. Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.
3. cathartic
4. 1,8-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.
Definition
ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.
Brand name
Dorbane
(3M Pharmaceuticals); Istizin (Sterling Winthrop);Doss;Normax;Regulex-d.
World Health Organization (WHO)
Dantron, an anthroquinone derivative, has been available for over
twenty years and is widely used as a laxative. The results of two chronic toxicity
studies in rodents, published in 1985 and 1986, have shown that administration of
high doses is associated with the development of intestinal and liver tumours.
General Description
Orange crystalline powder. Almost odorless and tasteless.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
1,8-Dihydroxyanthraquinone is incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides.
Fire Hazard
Flash point data for 1,8-Dihydroxyanthraquinone are not available; however, 1,8-Dihydroxyanthraquinone is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic data.
Moderately toxic by intraperitoneal route.
An eye irritant. Questionable carcinogen
with experimental carcinogenic and
neoplastigenic data. Human mutation data
reported. A laxative. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Potential Exposure
A potential liver carcinogen and
possible narcotic, this compound is no longer sold or
marketed in the United States Nervous system toxin-acute
effects; Respiratory toxin-acute effects other than severe or
moderate irritation; Liver-acute effects; Eye irritant-mild.
Carcinogenicity
Danthron is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Danthron can cause DNA damage particularly at guanines in the
5'-GG-3', 5'-GGGG-3', 5'-GGGGG-3' sequences in the presence
of Cu(II), cytochrome P450 reductase and the nicotinamide
adenine dinucleotide phosphate (NADPH)-generating system.
H2O2 and Cu(I) may also be involved because this DNA
damage can be inhibited by catalase and bathocuproine. The
further mechanism is danthron is reduced by P450 reductase
and generate reactive oxygen species through the redox cycle,
leading to extensive Cu(II)-mediated DNA damage. The DNA
damage also comes from similar topoisomerase II inhibitor
behavior of danthron.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
Purification Methods
Crystallise Danthrone from EtOH and sublime it in a vacuum. [Beilstein 8 IV 3217.]
Toxicity evaluation
Danthron is discovered in several species of plants and insects.
It has been isolated from dried leaves and stems of Xyris semifuscata
harvested in Madagascar, and roots of Da Huang,
a Chinese traditional herbal medicine. Danthron also appears
to be biosynthesized by some insects. The presence of danthron
in insects may be a way of protection from predators. Danthron
can be manually synthesized by many countries. In the United
States, danthron was available from 12 suppliers.
If released to the atmosphere, danthron will exist in both
the vapor phase and the particulate phase. Vapor phase danthron
has an estimated half-life of 11 days. Particulate phase
danthron can be physically removed from air by wet and dry deposition. It is expected to biodegrade with 68% degradation
within 3 months.
If released to water, danthron is expected to adsorb to the
surface of solid particle and sediment. Biodegradation is also
a major pathway processed in water. It was reported that 82%
of the added danthron was degraded by fresh water within
3 days. If added to seawater, 91% of danthron was reported as
degraded. Danthron may bioconcentrate in aquatic organisms,
such as fish and shrimps.
Incompatibilities
Keep away from strong reducing agents,
such as hydrides, nitrides, alkali metals, and sulfides.
Waste Disposal
It is inappropriate and
possibly dangerous to the environment to dispose of
expired or waste drugs and pharmaceuticals by flushing
them down the toilet or discarding them to the trash.
Household quantities of expired or waste pharmaceuticals
may be mixed with wet cat litter or coffee grounds, double-
bagged in plastic, discard in trash. Larger quantities shall
carefully take into consideration applicable DEA, EPA, and
FDA regulations. If possible return the pharmaceutical to
the manufacturer for proper disposal being careful to prop-
erly label and securely package the material. Alternatively,
the waste pharmaceutical shall be labeled, securely
packaged and transported by a state licensed medical waste
contractor to dispose by burial in a licensed hazardous or
toxic waste landfill or incinerator.
Check Digit Verification of cas no
The CAS Registry Mumber 117-10-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117-10:
(5*1)+(4*1)+(3*7)+(2*1)+(1*0)=32
32 % 10 = 2
So 117-10-2 is a valid CAS Registry Number.
InChI:InChI=1/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
117-10-2Relevant articles and documents
Oxygenation of Dithranol by complexes of transition elements
Mueller, Klaus,Duchstein, Hans-Juergen
, p. 35 - 38 (1989)
The oxygen activation in the dark by complexes of transition metals in the presence of the antipsoriatic compound dithranol (1a) is described.With the system CuCl/O2 an electron transfer oxygenation occurs, which simulates a 1O2-reaction, without an attack of 1O2.In the presence of Co-Salen/O2 the mechanism depends on the solvent and substrate, as already shown in the naphthalene-series.In methylenchloride dantrone (2), the radical product bisanthrone 3 and 1,8,10-trihydroxy-9-anthrone (4) are identified.The mechanistic particularity of this reaction in methylenchloride is discussed.
Segal,A. et al.
, p. 1152 - 1154 (1971)
The Synthesis and Diels-Alder Reactions of 2-Prop-2-enylidene-1,3-dioxolan
Ley, Steven V.,Mitchell, William L.,Radhakrishnan, Tarur V.,Barton, Derek H. R.
, p. 1582 - 1584 (1981)
The synthesis and regiospecific Diels-Alder reactions of 2-prop-2-enylidene-1,3-dioxolan (1) are described.Reactions with 1,4-naphthoquinones (5) gave tetrahydroanthraquinones (6).The adduct of (1) with juglone (5d) could be further hydrolysed to 1,8-dihydroxy-9,10-anthraquinone (7).
The Formal Oxidative Addition of Electron-Rich Transoid Dienes to Bromonaphthoquinones
Grunwell, John R.,Karipides, Anastas,Wigal, Carl T.,Heinzman, Stephen W.,Parlow, John,et al.
, p. 91 - 95 (1991)
This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond.The addition of the electron-rich end of a transoid diene to a bromojuglone dervative occurred exclusively at the unsubstituted carbon of the quinone.Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57percent or 71percent yield.Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77percent yield.
Inhibition of the prototropic tautomerism in chrysazine by p-sulfonatocalixarene hosts
Gharat, Poojan Milan,Maity, Dilip Kumar,Pal, Haridas,Dutta Choudhury, Sharmistha
, p. 5178 - 5187 (2018)
This study explores the interesting effect of p-sulfonatocalix[n]arene hosts (SCXn) on the excited-state tautomeric equilibrium of Chrysazine (CZ), a model antitumour drug molecule. Detailed photophysical investigations reveal that conversion of CZ from its more dipolar, excited normal form (N*) to the less dipolar, tautomeric form (T*) is hindered in SCXn-CZ host-guest complexes, which is quite unexpected considering the nonpolar cavity of the hosts. The atypical effect of SCXn is proposed to arise due to the partial inclusion or external binding of CZ with the hosts, which facilitates H-bonding interactions between CZ and the sulfonate groups present at the portals of the hosts. The intermolecular H-bonding subsequently leads to weakening of the pre-existing intramolecular H-bond network within CZ, and thus hinders the tautomerizaion process. Our results suggest that rather than the binding affinity, it is the orientation of CZ in the SCXn-CZ complexes, and its proximity to the portals of the host that plays a predominant role in influencing the tautomeric equilibrium. These observations are supported by quantum chemical calculations. Thermodynamic studies validate that SCXn-CZ interaction is essentially enthalpy driven and accompanied by small entropy loss, which is consistent with the binding mechanisms.
A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability
Das, Kiran,De, Arijit,Husain, Syed Masood,Maity, Biswanath,Mondal, Amit,Rajput, Anshul
, p. 3087 - 3090 (2022/02/21)
Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.
Efficient and selective iron-mediated reductive Claisen rearrangement of propargyloxyanthraquinones to anthrafurandiones in ionic liquids
Nadali, Samaneh,Aghapour, Ghasem,Rafieepour, Zahra
, p. 1045 - 1051 (2017/10/03)
An efficient and rapid method is described for the reductive Claisen rearrangement of different propargyloxyanthraquinones to anthra[1,2-b]furan-6,11-diones for first time using iron powder in a mixture of two ionic liquids, namely 1-methylimidazolium tetrafluoroborate [Hmim]BF4 and 1-benzyl-3-methylimidazolium chloride [Bzmim]Cl. The present method is able to execute single or double Claisen rearrangements of 1,4-or 1,5-bispropargyloxyanthraquinones selectively, so that the desired anthra(mono)furandiones or anthra(bis)furandiones are produced, respectively, as the major product.
