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117-10-2 molecular structure
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1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione

ChemBase ID: 4360
Molecular Formular: C14H8O4
Molecular Mass: 240.21092
Monoisotopic Mass: 240.04225874
SMILES and InChIs

SMILES:
O=C1c2c(C(=O)c3c1c(O)ccc3)cccc2O
Canonical SMILES:
Oc1cccc2c1C(=O)c1c(C2=O)cccc1O
InChI:
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

Cite this record

CBID:4360 http://www.chembase.cn/molecule-4360.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
IUPAC Traditional name
altan
danthron
1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
Brand Name
Altan
Antrapurol
Bancon
Chrysazin
Chrysazine
Criasazin
Danivac
Dantron
Diaquone
Dionone
Dorbane
Dorbanex
Dorbantyl
Duolax
Istan
Istin
Istizin
LTAN
Laxanorm
Laxanthreen
Laxipur
Laxipurin
Modane
Neokutin s
Pastomin
Prugol
Regulin
Roydan
Scatron d
Zwitsalax
Synonyms
Altan
Antrapurol
Chrysazin
Danthrone
Dantron
Diaquone
Dionone
Dorbane
Istin
Istizin
Laxanorm
Laxanthreen
Laxipur
Laxipurin
Modane
NSC 38626
NSC 646568
NSC 7210
Zwitsalax
1,8-dihydroxyanthracene-9,10-dione
Dantron
1,8-Dihydroxyanthra-9,10-quinone
Chrysazine
1,8-Dihydroxyanthraquinone
Danthron
1,8-DIHYDROXYANTHRAQUINONE
CHRYSAZIN PRACTICAL GRADE
1,4,5,8-Tetroxyantraquinone
1,8-Dihydroanthraquinone
1,8-Dihydroxy-9,10-anthracenedione
1,8-Dihydroxy-9,10-anthraquinone
1,8-Dihydroxyanthra-9,10-quinone
1,8-dihydroxyanthracene-9,10-dione
1,8-Dihydroxyanthrachinon
1,8-Dihydroxyanthrachinon [Czech]
1,8-Dihydroxyanthraquinone
Dantrona [inn-spanish]
Dantrone [inn-french]
Dantronum [inn-latin]
DHAQ
Dihydroxyanthraquinone
Dioxyanthrachinonum
Usaf nd-59
Danthron
Danivac
Dantron
丹蒽醌
二羟蒽醌
1,8-二羟基蒽醌
CAS Number
117-10-2
EC Number
204-173-5
MDL Number
MFCD00001211
Beilstein Number
2054727
Merck Index
142815
PubChem SID
46509077
160967792
24893346
PubChem CID
2950
CHEBI ID
3682
ATC CODE
A06AG03
A06AB03
CHEMBL
53418
Chemspider ID
2845
DrugBank ID
DB04816
KEGG ID
D07107
Unique Ingredient Identifier
Z4XE6IBF3V
Wikipedia Title
Dantron

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.890132  H Acceptors
H Donor LogD (pH = 5.5) 3.6098228 
LogD (pH = 7.4) 3.483305  Log P 3.6115754 
Molar Refractivity 65.1128 cm3 Polarizability 24.523813 Å3
Polar Surface Area 74.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.98  LOG S -2.9 
Solubility (Water) 3.05e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol (Slightly and Sparingly) expand Show data source
Apperance
Orange powder expand Show data source
Yellow Solid expand Show data source
Melting Point
191-193 °C(lit.) expand Show data source
191-193°C subl. expand Show data source
193-195°C expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
CB6650000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
40 expand Show data source
R:45 expand Show data source
Safety Statements
36/37 expand Show data source
S:28-36/37/39-45-53 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319-H351 expand Show data source
H351 expand Show data source
GHS Precautionary statements
P281-P201-P202-P308+P313-P405-P501A expand Show data source
P281-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Admin Routes
Oral, rectal (enema) expand Show data source
Mechanism of Action
alters electrolyte-secretion expand Show data source
alters water-secretion expand Show data source
Direct action on intestinal mucosa expand Show data source
stimulates myenteric-plexus expand Show data source
Purity
~95% expand Show data source
95% expand Show data source
96% expand Show data source
Grade
PRACTICAL expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Biological Source
Occurs in roots of Rheum palmatum, leaves and stems of Xyris semifuscata, tissue culture of Cinchona ledgeriana and leaves of Pyrrhalta luteola expand Show data source
Application(s)
Laxative expand Show data source
Empirical Formula (Hill Notation)
C14H8O4 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02157739 external link
Crystalline
Purity: ~95%
MP Biomedicals - 05204925 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB04816 external link
Item Information
Drug Groups withdrawn
Description Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.
External Links
Wikipedia
Sigma Aldrich - D108103 external link
Packaging
100, 500 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D108103.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - D450150 external link
Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed.

REFERENCES

REFERENCES

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  • • Grocholski, T., et al.: Biochem., 49, 934 (2009)
  • • Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 87D, (ir)
  • • Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 91B, (nmr)
  • • Naylor, C.A. et al., J.A.C.S., 1931, 53, 4112
  • • Aoyama, S. et al., Yakugaku Zasshi, 1932, 52, 17
  • • Lish, P.M. et al., J. Am. Pharm. Assoc., 1958, 47, 371, (pharmacol)
  • • Kido, H. et al., Anal. Chim. Acta, 1960, 23, 116, (ir)
  • • Beynon, J.H. et al., Appl. Spectrosc., 1960, 14, 156, (ms)
  • • Ruggieri, R., Anal. Chim. Acta, 1961, 25, 145, (use)
  • • Prakesh, A., Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem., 1965, 122, 272, (cryst struct)
  • • Fairbairn, J.W. et al., J. Pharm. Pharmacol., 1970, 22, 584, (pharmacol)
  • • Idris, K.A. et al., Egypt. J. Chem., 1973, 67, (uv)
  • • Morley, J.O. et al., J.C.S. Perkin 2, 1973, 1626, (pmr)
  • • Fournier, G. et al., Phytochemistry, 1975, 14, 2099, (isol)
  • • Breimer, D.D. et al., Pharmacology, 1976, 14, 30, (metab)
  • • Case, M.T. et al., Drug Chem. Toxicol., 1978, 1, 89, (tox)
  • • Berger, Y. et al., Org. Magn. Reson., 1978, 11, 375, (cmr)
  • • Cameron, A.W. et al., Aust. J. Chem., 1982, 35, 2095, (synth)
  • • Howard, D.F. et al., Naturwissenschaften, 1982, 69, 91, (isol)
  • • Roman Ceba, M. et al., Mikrochim. Acta, 1983, 2, 85, (detn, Mg)
  • • Mueller, K. et al., Arch. Pharm. (Weinheim, Ger.), 1984, 317, 120, (synth)
  • • Gattuso, J.M. et al., Drug Saf., 1984, 10, 47, (rev)
  • • Khanapure, S.P. et al., J.O.C., 1987, 52, 5685, (deriv, synth, pmr, ir)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2970, (synonyms)
  • • IARC Monog., 1990, 50, 265, (rev, tox)
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  • • Kahr, B. et al., Angew. Chem., Int. Ed., 1992, 31, 1, (tautom)
  • • Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1215
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DMH400
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PATENTS

PATENTS

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INTERNET

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