InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H

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Search term: RGCKGOZRHPZPFP-UHFFFAOYAG
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Inherent Properties, Identifiers and References

ChemSpider ID:	6056
Empirical Formula:	C₁₄H₈O₄
Molecular Weight:	240.2109
Nominal Mass:	240 Da
Average Mass:	240.2109 Da
Monoisotopic Mass:	240.042259 Da

Systematic Name:

1,2-dihydroxyanthracene-9,10-dione

SMILES:

O=C2c1ccccc1C(=O)c3c2ccc(O)c3O

InChI:

InChI=1/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H

InChIKey:

RGCKGOZRHPZPFP-UHFFFAOYAG

Std. InChI:

InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H

Std. InChIKey:

RGCKGOZRHPZPFP-UHFFFAOYSA-N

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Wikipedia Article(s)

Alizarin or 1,2-dihydroxyanthraquinone is an organic compound with formula that is historically important as a prominent dye, originally derived from the roots of plants of the madder genus. Alizarin was used as a red dye for the English parliamentary "new model" army. The distinctive red color would continue to be worn for centuries, giving English and later British soldiers the nickname of "redcoat". In 1869, it became the first natural pigment to be duplicated synthetically. Alizarin is the main ingredient for the manufacture of the madder lake pigments know to painters as Rose Madder and Alizarin Crimson. The term is also part of the name for a variety of related dyes, such as Alizarine Cyanine Green G and Alizarine Brilliant Blue R, and gave its name to alizarin crimson, a particular shade of red. The word derives from the Arabic al-usara "juice". Read more... or Edit at Wikipedia...

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Supplemental Information

Links & References

Igor V. Tetko, Vsevolod Yu. Tanchuk, Tamara N. Kasheva, and Alessandro E. P. Villa. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices, J. Chem. Inf. Comput. Sci., 2001, 41 (6), pp 1488–1493

[DOI: 10.1021/ci000392t]

The molecular weight and electrotopological E-state indices were used to estimate by Artificial Neural Networks aqueous solubility for a diverse set of 1291 organic compounds. The neural network with 33-4-1 neurons provided highly predictive results with r2 = 0.91 and RMS = 0.62.

E. L. Willighagen, H. M. G. W. Denissen, R. Wehrens, and L. M. C. Buydens. On the Use of 1H and 13C 1D NMR Spectra as QSPR Descriptors, J. Chem. Inf. Model., 46 (2), 487-494, 2006

[PubMed: 16562976] [DOI: 10.1021/ci050282s]

User Data

experimental physchem properties

Melting Point: 286-290

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Melting Point: 279 - 283 C

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Boiling Point: ca 430 subl.

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Boiling Point: 430 C

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Solubility: -2.78

No description available

miscellaneous

Appearance: orange-red crystals or powder

Visual appearance of the given substance.

Stability: Stable. Incompatible with strong oxidizing agents, strong bases.

Chemical stability occurs when a substance is in a (dynamic) chemical equilibrium with its environment. See also: Chemical Stability

Toxicity: ORL-BWD LD50 316 mg kg-1

Toxicity is the degree to which something is able to produce illness or damage to an exposed organism. See also: Toxicity and list of used abbreviations.

Safety: Harmful and irritating. Possible irreversible damage risk

See Chemical Safety

Safety: Minimize exposure.

See Chemical Safety

Source: Rubia tinctorum

No description available

Drug Status: experimental

No description available

Chemical Class: anthraquinone

No description available

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ALIZARIN RED

1,2-Dihydroxy-9,10-anthrachinon

1,2-Dihydroxy-9,10-anthraquinone

1,2-Dihydroxyanthracen-9,10-dion

1,2-dihydroxyanthracene-9,10-dione

1,2-Dihydroxy-anthraquinone

72-48-0 [RN]

9,10-anthracenedione, 1,2-dihydroxy-

Acid Metachrome Red B

Acid Mordant Red B

More...

Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

ACD/Labs Predicted Properties

ACD/LogP:	4.10	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	4.07	ACD/LogD (pH 7.4):	3.37
ACD/BCF (pH 5.5):	723.76	ACD/BCF (pH 7.4):	144.24
ACD/KOC (pH 5.5):	3819.44	ACD/KOC (pH 7.4):	761.19
#H bond acceptors:	4	#H bond donors:	2
#Freely Rotating Bonds:	2	Polar Surface Area:	52.6 Å²
Index of Refraction:	1.732	Molar Refractivity:	62.43 cm³
Molar Volume:	155.9 cm³	Polarizability:	24.74 10^-24cm³
Surface Tension:	79.2 dyne/cm	Density:	1.54 g/cm³
Flash Point:	228 °C	Enthalpy of Vaporization:	71.19 kJ/mol
Boiling Point:	430 °C at 760 mmHg	Vapour Pressure:	5.34E-08 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.16

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  433.26  (Adapted Stein & Brown method)
    Melting Pt (deg C):  181.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.15E-011  (Modified Grain method)
    MP  (exp database):  289.5 deg C
    BP  (exp database):  430 deg C
    VP  (exp database):  8.76E-10 mm Hg at 25 deg C
    Subcooled liquid VP: 3.62E-007 mm Hg (25 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  15.79
       log Kow used: 3.16 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  400 mg/L ( deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  255.83 mg/L
    Wat Sol (Exper. database match) =  400.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.33E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.431E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.16  (KowWin est)
  Log Kaw used:  -11.752  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  14.912
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8785
   Biowin2 (Non-Linear Model)     :   0.6245
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7361  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5361  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4107
   Biowin6 (MITI Non-Linear Model):   0.2603
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3588
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.83E-005 Pa (3.62E-007 mm Hg)
  Log Koa (Koawin est  ): 14.912
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0622 
       Octanol/air (Koa) model:  200 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.692 
       Mackay model           :  0.833 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   9.8450 E-12 cm3/molecule-sec
      Half-Life =     1.086 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    13.037 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.762 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  507.7
      Log Koc:  2.706 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.894 (BCF = 7.834)
       log Kow used: 3.16 (estimated)

 Volatilization from Water:
    Henry LC:  4.33E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.096E+010  hours   (8.732E+008 days)
    Half-Life from Model Lake : 2.286E+011  hours   (9.526E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               7.30  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     7.17  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.000117        26.1         1000       
   Water     12.3            900          1000       
   Soil      87.3            1.8e+003     1000       
   Sediment  0.403           8.1e+003     0          
     Persistence Time: 1.8e+003 hr