| Identification | Back Directory | [Name]
ACETYLSALICYLSALICYLIC ACID | [CAS]
530-75-6 | [Synonyms]
2-(Ace
Acesalum
Diplosalacetat
DIPLOSALSALATE
Diplosal Acetate
Aspirin IMpurity D
Aspirin Impurity 4
Aspirin EP IMpurity D
ACETYLSALISYLIC ACID IMP D
Acetylsalicylsalicyic acid
SALICYLACETYLSALICYLIC ACID
ACETYLSALICYLSALICYLIC ACID
(Acetysalicylsalicyclic acid)
Acetylsalicylsalicylic acid,97%
2-carboxyphenyl o-acetylsalicylate
2-(2-Acetoxybenzoyloxy)benzoic acid
o-(o-Acetoxybenzoyloxy)benzoic acid
2-[[2-(Acetyloxy)benzoyl]oxy]benzoic acid
2-((2-Acetoxybenzoyl)oxy)benzoic acid,95+%
2-(Acetyloxy)benzoic Acid 2-Carboxyphenyl Ester
2-[[(2-Acetyloxyphenyl)carbonyl]oxy]benzoic acid
Benzoic acid, 2-(acetyloxy)-, 2-carboxyphenyl ester
2-HYDROXYBENZOIC ACID ACETATE 2-CARBOXYPHENYL ESTER
Acetylsalicylic Acid IMpurity D (Aspirin IMpurity D) | [EINECS(EC#)]
208-493-6 | [Molecular Formula]
C16H12O6 | [MDL Number]
MFCD00143537 | [MOL File]
530-75-6.mol | [Molecular Weight]
300.26 |
| Chemical Properties | Back Directory | [Appearance]
white to almost white fine crystalline powder | [Melting point ]
153-160 °C
| [Boiling point ]
361.5°C (rough estimate) | [density ]
1.346 | [refractive index ]
1.4600 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly) | [form ]
neat | [pka]
2.94±0.36(Predicted) | [color ]
White to Off-White | [Water Solubility ]
20mg/L(21 ºC) | [Major Application]
pharmaceutical (small molecule) | [InChI]
InChI=1S/C16H12O6/c1-10(17)21-14-9-5-3-7-12(14)16(20)22-13-8-4-2-6-11(13)15(18)19/h2-9H,1H3,(H,18,19) | [InChIKey]
DDSFKIFGAPZBSR-UHFFFAOYSA-N | [SMILES]
C(OC1=CC=CC=C1C(O)=O)(=O)C1=CC=CC=C1OC(C)=O | [EPA Substance Registry System]
2-Carboxyphenyl 2-(acetyloxy)benzoate (530-75-6) |
| Hazard Information | Back Directory | [Chemical Properties]
white to almost white fine crystalline powder | [Uses]
Acetylsalicylic Acid Impurity C | [Uses]
analgesic, antipyretic | [Uses]
Antiinflammatory;Cyclooxygenase inhibitor | [Definition]
ChEBI: 2-[(2-acetyloxyphenyl)-oxomethoxy]benzoic acid is a carbonyl compound. | [Synthesis]
To a solution of 2-((2-hydroxybenzoyl)oxy)benzoic acid (5.0 g, 19.37 mmol) in ethanoic anhydride (15.0 mL, 147.0 mmol) was added 3 drops of concentrated hydrochloric acid. The reaction mixture was stirred at room temperature for 16-20 hours. After completion of the reaction, the mixture was diluted with ice-cold water (50 mL) and the precipitated solid was collected by filtration. The solid was washed sequentially with water (2 x 10 mL) and hexane (20 mL) and dried to give 2-((2-acetoxybenzoyl)oxy)benzoic acid (5.5 g) as a white solid. Thin layer chromatography (TLC) Rf value was 0.3 (unfolding agent: 50% ethyl acetate/hexane). | [Purification Methods]
Crystallise the analgesic from dilute AcOH or EtOH (m 161-162o), MeOH (m 165-168o), and *C6H6/EtOH (m 163-165o). Its solubilities in boiling Et2O, *C6H6 and EtOH are 1.4%, 2.2% and 33%, respectively. [Baker et al. J Chem Soc 201 1951, Garrett et al. J Am Pharm Soc 48 684 1959, Beilstein 10 I 41, 10 II 54, 10 IV 165.] | [References]
[1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 5, p. 2158 - 2161
[2] Patent: US2014/357680, 2014, A1. Location in patent: Paragraph 0135-0136
[3] Patent: WO2014/195961, 2014, A1. Location in patent: Paragraph 00125; 00126 |
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