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Chemistry

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Also known as: 2-propanone, 67-64-1, Propanone, Dimethyl ketone, Propan-2-one, Methyl ketone
Molecular Formula
C3H6O
Molecular Weight
58.08  g/mol
InChI Key
CSCPPACGZOOCGX-UHFFFAOYSA-N
FDA UNII
1364PS73AF

Acetone
A colorless liquid used as a solvent and an antiseptic. It is one of the ketone bodies produced during ketoacidosis.
1 2D Structure

Acetone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propan-2-one
2.1.2 InChI
InChI=1S/C3H6O/c1-3(2)4/h1-2H3
2.1.3 InChI Key
CSCPPACGZOOCGX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)C
2.2 Other Identifiers
2.2.1 UNII
1364PS73AF
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 2-propanone

2. 67-64-1

3. Propanone

4. Dimethyl Ketone

5. Propan-2-one

6. Methyl Ketone

7. Pyroacetic Ether

8. Dimethylformaldehyde

9. Beta-ketopropane

10. Dimethylketal

11. Chevron Acetone

12. Ketone Propane

13. Aceton

14. Pyroacetic Acid

15. Ketone, Dimethyl

16. Dimethylketone

17. Fema No. 3326

18. .beta.-ketopropane

19. Rcra Waste Number U002

20. Dimethyl Formaldehyde

21. Taimax

22. Aceton [german, Dutch, Polish]

23. Ketone, Dimethyl-

24. Acetone [nf]

25. Nsc 135802

26. Mfcd00008765

27. Nsc-135802

28. (ch3)2co

29. Chebi:15347

30. 1364ps73af

31. Acetone (nf)

32. Ncgc00091179-01

33. Dsstox_cid_1482

34. Dsstox_rid_76176

35. Acetone (natural)

36. Dsstox_gsid_21482

37. Caswell No. 004

38. 3-methyl-4-(2,2-dimethyl-6-methylenecyclohexyl)-3-buten-2-one

39. Acetone, For Hplc, >=99.8%

40. Acetone, For Hplc, >=99.9%

41. Acetone, Acs Reagent, >=99.5%

42. Cas-67-64-1

43. Hsdb 41

44. Ccris 5953

45. Acetone (1,1,1,3,3,3-d6)

46. Einecs 200-662-2

47. Un1090

48. Rcra Waste No. U002

49. Epa Pesticide Chemical Code 004101

50. Dimethylcetone

51. Isopropanal

52. Methylketone

53. Dimethylketon

54. Propanon

55. Sasetone

56. Methyl-ketone

57. 2propanone

58. B-ketopropane

59. Unii-1364ps73af

60. Ai3-01238

61. 2-propanal

62. Acetone Hp

63. Acetone Acs

64. Acetone, Puriss.

65. Acetone P.a.

66. Acetone (tn)

67. Acetone Hplc Grade

68. Methyl Methyl Ketone

69. Acetone, For Hplc

70. Acetone, Acs Reagent

71. Acetone, Hplc Grade

72. Acetone [vandf]

73. Acetone [fhfi]

74. Acetone [hsdb]

75. Acetone [inci]

76. Acetone Acs Low Benzene

77. Acetone, Technical Grade

78. Acetone [fcc]

79. Acetone [mi]

80. Acetone Oil (salt/mix)

81. Ch3coch3

82. Acetone [mart.]

83. Acetone [usp-rs]

84. Acetone [who-dd]

85. Acetone Reagent Grade Acs

86. Acetone, Histological Grade

87. Ec 200-662-2

88. Acetone, Analytical Standard

89. Acetone, Environmental Grade

90. Acetone, Semiconductor Grade

91. Acetone, Lr, >=99%

92. Acetone, Natural, >=97%

93. Un 1091 (salt/mix)

94. Aceton (german, Polish)

95. Acetone [ep Impurity]

96. Acetone, Puriss., 99.0%

97. Chembl14253

98. Acetone [ep Monograph]

99. Dimethylketone, Pyroacetic Acid

100. Wln: 1v1

101. Acetone, Ar, >=99.5%

102. Dtxsid8021482

103. Acetone, Spectrophotometric Grade

104. Citronellidene Acetone; Baccartol

105. Zinc895111

106. Acetone, Gc, For Residue Analysis

107. Acetone, >=99.5%, Acs Reagent

108. Tox21_111096

109. Tox21_202480

110. C0556

111. Lmfa12000057

112. Nsc135802

113. Acetone 5000 Microg/ml In Methanol

114. Acetone, Purum, >=99.0% (gc)

115. Akos000120890

116. Acetone 100 Microg/ml In Acetonitrile

117. Un 1090

118. Acetone, Saj First Grade, >=99.0%

119. Acetone [un1090] [flammable Liquid]

120. Acetone, For Chromatography, >=99.8%

121. Acetone, Histological Grade, >=99.5%

122. Acetone, Jis Special Grade, >=99.5%

123. Acetone, Laboratory Reagent, >=99.5%

124. Ncgc00260029-01

125. Acetone, For Hplc, >=99.8% (gc)

126. Acetone, Uv Hplc Spectroscopic, 99.8%

127. Acetone, >=99.5%, For Residue Analysis

128. Acetone, For Residue Analysis, >=99.5%

129. Isoflurane Impurity F [ep Impurity]

130. A0054

131. Acetone, For Luminescence, >=99.5% (gc)

132. Ft-0621803

133. Acetone, Suitable For Determination Of Dioxins

134. Chlorobutanol Impurity B [ep Impurity]

135. Acetone, Glass Distilled Hrgc/hplc Trace Grade

136. C00207

137. D02311

138. Q49546

139. Acetone, Acs Spectrophotometric Grade, >=99.5%

140. Acetone, Reagentplus(r), Phenol Free, >=99.5%

141. Acetone, >=99%, Meets Fcc Analytical Specifications

142. Acetone, Acs Reagent, >=99.5%, <=2 Ppm Low Benzene

143. Acetone, Contains 20.0 % (v/v) Acetonitrile, For Hplc

144. Acetone, For Residue Analysis, Suitable For 5000 Per Jis

145. Acetone, For Uv-spectroscopy, Acs Reagent, >=99.7% (gc)

146. Acetone, United States Pharmacopeia (usp) Reference Standard

147. Acetone Solution, Contains 20.0 % (v/v) Acetonitrile, For Hplc

148. Acetone, Hplc Plus, For Hplc, Gc, And Residue Analysis, >=99.9%

149. Acetone, Semiconductor Grade Mos Puranal(tm) (honeywell 17921)

150. Acetone, Semiconductor Grade Ulsi Puranal(tm) (honeywell 17014)

151. Acetone, Semiconductor Grade Vlsi Puranal(tm) (honeywell 17617)

152. Acetone, Pharmaceutical Secondary Standard; Certified Reference Material

153. Acetone Solution, Certified Reference Material, 2000 Mug/ml In Methanol: Water (9:1)

154. Acetone, Puriss. P.a., Acs Reagent, Reag. Iso, Reag. Ph. Eur., >=99.5% (gc)

155. Acetone, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Nf, >=99% (gc)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 58.08 g/mol
Molecular Formula C3H6O
XLogP3-0.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass58.041864811 g/mol
Monoisotopic Mass58.041864811 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count4
Formal Charge0
Complexity26.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Solvents

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)


4.2 Absorption, Distribution and Excretion

In rats receiving acetone in drinking water (7.5% v/v) for 11 consecutive days, plasma concentrations of acetone on day 1 were in the range of 315-800 ug/mL. The plasma concentration appeared to plateau at about 1,200 ug/mL by day 4.

DHHS/ATSDR; Addendum to the Toxicological Profile for Acetone p.? (August 2011). Available from, as of January 7, 2015: https://www.atsdr.cdc.gov/toxprofiles/index.asp


Physiologically based toxicokinetic (PBTK) modeling of human experimental data suggests difficulties to simultaneously describe the time courses of inhaled polar solvents in blood and breath, especially if exposures occur during physical exercise. We attribute this to the washin-washout effect in the airways. The aim was to develop a PBTK-model that explains the behavior of acetone in blood and exhaled air at different levels of physical exercise. The model includes exchange of inhaled solvent vapor with the blood flow via the mucosa and separate compartments to describe working and resting muscles. The developed model was contrasted to a traditional PBTK-model where the conducting airways were regarded as an inert tube. Our model predictions agrees well with experimentally observed acetone levels in both arterial blood and end- and mixed-exhaled air from 26 inhalation experiments conducted with 18 human volunteers at 0, 50, 100 and 150 W workload. In contrast, the inert-tube model was unable to describe the data. The developed model is to our knowledge the first which explains the toxicokinetics of acetone at such various levels of physical exercise. It may be useful in breath monitoring and to obtain more accurate estimates of absorbed dose during inhalation of polar volatiles.

PMID:16364574 Mork AK, Johanson G; Toxicol Lett 164 (1): 6-15 (2006)


Patients with severe diabetic ketoacidosis can have plasma acetone levels as high as 750 mg/L, which is up to 300 times the normal limit.

European Chemicals Bureau; IUCLID Dataset, ACETONE (67-64-1). Available from, as of January 22, 2007: https://esis.jrc.ec.europa.eu/


Acetone is one of the least hazardous industrial solvents, but is highly volatile and may be inhaled in large quantities. It may be absorbed into the blood through the lungs and diffused throughout the body. Small quantities may be absorbed through the skin.

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 38


For more Absorption, Distribution and Excretion (Complete) data for ACETONE (19 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

... The role of CYP2E1 in acetone catabolism /was assessed/ by measuring acetone levels at different time points in rats that had been treated with diallyl sulfide (DAS, a CYP2E1 inhibitor) at a variety of dose levels. The study noted DAS dose-dependent increases in the time to peak blood acetone level and in the time to return to pre-dose levels, suggesting an important role of CYP2E1 in acetone catabolism.

DHHS/ATSDR; Addendum to the Toxicological Profile for Acetone p.6 (August 2011). Available from, as of January 7, 2015: https://www.atsdr.cdc.gov/toxprofiles/index.asp


Acetone, one of the principal ketone bodies elevated during treatment with the ketogenic diet, exhibits anticonvulsant properties that may contribute to the seizure protection conferred by the diet. The anticonvulsant mechanism of acetone is unknown, but it is metabolized to several bioactive substances that could play a role. Acetone and its major metabolites-acetol, 1,2-propanediol, methylglyoxal, and pyruvic acid-were assessed for anticonvulsant activity in two mouse seizure models. Various doses of the substances administered intraperitoneally were characterized for their ability to elevate the threshold for clonic seizures induced by intravenous infusion of pentylenetetrazol (PTZ) and for protection against tonic seizures induced by subcutaneous bolus administration of 4-aminopyridine (4-AP). The inverted-screen test was used to assess acute neurological toxicity. Acetone (1-32 mmol/kg, i.p.), in a dose-dependent fashion, elevated the PTZ threshold and conferred protection against 4-AP seizures (ED(50), 26.3 mmol/kg). Effective doses of acetone (10-32 mmol/kg) did not cause motor impairment in the inverted-screen test (TD(50), 45.7 mmol/kg). In doses 10-fold greater than the minimally effective dose ofacetone (3.2 mmol/kg), the metabolites acetol, 1,2-propanediol, and pyruvic acid were inactive in the PTZ model. At higher doses that produced motor impairment, acetol and 1,2-propanediol (but not pyruvic acid) did elevate the PTZ threshold. Methylglyoxal had both proconvulsant and anticonvulsant actions, and had substantial toxicity, producing respiratory distress, motor impairment, and death. None of the acetone metabolites protected against 4-AP seizures. This study confirms the broad-spectrum anticonvulsant properties of acetone and indicates that the seizure protection conferred is unlikely to result from its major metabolic products.

PMID:17386058 Gasior M et al; Epilepsia 48 (4): 793-800 (2007)


Two pathways for the conversion of acetone to glucose are proposed, the methylglyoxal & the propanediol pathways. The methylglyoxal pathway is responsible for the conversion to acetol, acetol to methylglyoxal, & subsequent conversion of methylglyoxal to glucose. The propanediol pathway involves the conversion of acetol to L-1,2-propanediol by an as yet unknown process. L-1,2-propanediol is converted to L-lactaldehyde by alcohol dehydrogenase, & L-lactaldehyde is converted to L-lactic acid by aldehyde dehydrogenase. Expression of these metabolic pathways in rat appears to be dependent on the induction of /acetone/ oxygenase & acetol monooxygenase by acetone.

PMID:6706932 Casazza JP et al; J Biol Chem 259 (1): 231-6 (1984)


Hepatic NAD-dependent alcohol dehydrogenase... enzyme is capable of catalyzing reverse reaction in which... acetone.../is reduced to alcohol/.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 310


For more Metabolism/Metabolites (Complete) data for ACETONE (8 total), please visit the HSDB record page.


4.4 Biological Half-Life

Blood: 3 hours; whole body: 19-31 hours; [TDR, p. 17]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 17


Half-times for blood elimination of 3-3.9 hrs have been estimated in humans exposed to 100-500 ppm for 2-4 hrs. Elimination half-times of 3.9 hrs and 6.2 hrs have been estimated for arterial and venous blood, respectively. No differences in elimination half-times were found between men and women.

DHHS/ATSDR; Toxicological Profile for Acetone p. 79 (1994)


Tissue distribution of 2(14)C-acetone following inhalation exposure to 1,200 mg/cu m (500 ppm) was studied in mice. .... Half-times for acetone elimination were 2-3 hr for blood, kidney, lung, brain, and muscle, and greater than 5 hr for subcutaneous adipose tissue. By 24 hr after exposure, acetone concentrations had returned to endogenous levels in all tissues.

European Chemicals Bureau; IUCLID Dataset, ACETONE (67-64-1). Available from, as of January 22, 2007: https://esis.jrc.ec.europa.eu/


Two instances of finding abnormally high concentrations of acetone in urine (0.10 g/dL and 0.052 g/dL) without any measurable amounts of ethanol (<0.005 g/dL) or isopropanol (<0.005 g/dL) prompted a survey of the elimination kinetics of isopropanol and its metabolite acetone in humans. In a hospital patient who had ingested denatured alcohol, the elimination half-life (t(1/2)) of acetone during detoxification was 27 hr and not 3-5 hr as reported by other workers. Several other literature reports of individuals who had ingested isopropanol as well as controlled studies after administration of moderate amounts of acetone and/or isopropanol support the notion of a long elimination half-life of 17-27 hr for acetone compared with a t(1/2) of 1-3 hr for isopropanol.

PMID:10654562 Jones AW; J Anal Toxicol 24 (1): 8-10


The elimination half life in mice for acetone in various tissues was between 2 and 5 hr, with the subcutaneous adipose tissue showing the slowest release of acetone. Daily exposure of mice to 500 ppm acetone for 6 hr did not result in any day-to-day accumulation of acetone.

European Chemicals Bureau; IUCLID Dataset, ACETONE (67-64-1). Available from, as of January 22, 2007: https://esis.jrc.ec.europa.eu/


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04-Jan-2021
30-Oct-2024
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South Africa

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Pharmtech & Ingredients
Not Confirmed

Acetone

Brand Name : Merthiolate

Dosage Form : SPR

Dosage Strength : 10ml

Packaging : 2500X1mg

Approval Date :

Application Number :

Regulatory Info : Generic

Registration Country : South Africa

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Pharmtech & Ingredients
Not Confirmed

Acetone

Brand Name : Merthiolate Spray

Dosage Form : SPO

Dosage Strength : 10ml

Packaging : 30X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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DATA COMPILATION #PharmaFlow

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Excipient Market Overview: Roquette, Seqens, Evonik make strategic moves; new guidelines deal with contamination
The pharmaceutical industry has long recognized the critical role excipients or inactive ingredients play in drug formulation and delivery. Excipients can comprise up to 90 percent of a medicine's total ingredients and serve crucial functions as binders, disintegrants, coatings, preservatives, colors, and flavorings. According to recent market research, the pharmaceutical excipients market was valued at US$ 9.27 billion in 2023. It is growing at a compound annual growth rate (CAGR) of 7.03 percent and is projected to reach US$ 18.48 billion by 2032. The main factors driving market growth is an increased demand for multifunctional excipients, coupled with the expanding use of generic medications. The development in the biologics sector and advancements in nanotechnology are also contributing significantly to market growth. Major excipient providers include BASF, Evonik, Merck KGaA owned MilliporeSigma, Gangwal Healthcare, Roquette Frères, DuPont, Croda International, Seqens, Boai NKY Pharmaceuticals, PMC Isochem, Minakem, Kewpie Corporation, Ashland Global, SPI Pharma, Pfanstiehl, Nanjing Well Pharmaceutical, ICE Pharma, Anhui Ribobay Pharmaceutical and Nippon Fine Chemical.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available) WHO, India’s CDSCO tighten regulations; new GMP guidelines implemented to curb contamination Last year, the World Health Organization (WHO) issued a health alert linking at least 300 child deaths in the Gambia, Uzbekistan, and Indonesia to the ingestion of contaminated cough syrups containing unacceptable levels of diethylene glycol (DEG) and ethylene glycol (EG). In response to the tragic events, the WHO released two draft appendices to its guideline on good manufacturing practices (GMPs) for excipients this year. Manufacturers are now required to use suitable risk assessment tools to identify and mitigate potential hazards.  Since India-made cough syrups had been linked to the deaths, India’s drug regulator — Central Drugs Standard Control Organization (CDSCO) — took steps to prevent contamination, and advised drugmakers to only use pharmaceutical-grade excipients from approved sources. Furthermore, the Indian Health Ministry proposed amendments to the Drugs and Cosmetics Rules, 1945 to include details of excipients on drug labels. While listing all excipients on every strip of medicine may be challenging, the ministry suggested mentioning those causing hypersensitivity on the label. Applicants now mandatorily need to submit evidence of stability and safety of excipients. These regulatory developments have significant implications for excipient manufacturers and pharmaceutical companies worldwide. Leading pharmaceutical excipient firms like Gangwal Healthcare, Sigachi Industries, and Nitika Pharmaceuticals are well-positioned to meet these heightened quality and safety standards, given their long-standing commitment to producing high-quality, compliant excipients.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Roquette buys IFF’s pharma unit for US$ 2.85 bn; Evonik opens new spray-drying facility in Darmstadt In a significant industry move, France-based Roquette entered into an agreement to acquire IFF's pharma solutions business in a deal valued at US$ 2.85 billion. This acquisition is set to rebalance family-owned Roquette’s portfolio around health and nutrition. The deal is expected to accelerate Roquette’s growth and significantly strengthen its presence in the excipients market. Evonik has opened a new facility for drying aqueous dispersions of its Eudragit polymers at its site in Darmstadt, Germany. The facility will help Evonik meet increasing demand from drugmakers for its oral drug delivery solutions. The plant uses green energy solutions. The company has also partnered University of Mainz to commercialize a new class of polyethylene glycols (PEG) lipids for nucleic acid delivery. Evonik’s Health Care business has been growing its nucleic acid drug and vaccine delivery portfolio.  Germany’s Johannes Gutenberg University of Mainz was the first to develop randomized polyethylene glycols (rPEGs). This collaboration aims to expand Evonik’s toolbox of technologies for nucleic acid-based medicines, offering an improved immunogenicity profile for lipid nanoparticle carriers used in mRNA vaccines and therapeutics. Asahi Kasei made significant strides in addressing a pressing industry concern that emerged in 2018 when potentially carcinogenic nitrosamine impurities were detected in several pharmaceuticals. Guided by regional authorities, such as the European Medicines Agency and the US Food and Drug Administration, the pharmaceutical industry has been carrying out extensive assessments and research to identify the cause of these impurities. In response to this challenge, Asahi Kasei developed its Ceolus microcrystalline cellulose with extremely low nitrite levels. The Japanese company achieved nitrite concentrations of 0.1 micrograms per gram or less, which is equivalent to 0.1 parts per million (ppm). The company also started full commercial operation of its second manufacturing facility for Ceolus in Japan, enhancing supply capacity and stability. JRS Pharma and Gujarat Microwax opened a state-of-the-art cotton-based croscarmellose sodium plant in Mehsana, Gujarat (India). This facility aims to produce high-quality excipients that meet global standards, potentially reducing India's dependency on imports and boosting its presence in the global excipient market. The Indian excipient industry accounts for less than 1 percent of the global market share.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Seqens to advance innovative polymer; biologics, personalized medicine create demand for specialized excipients Recent industry collaborations highlight the ongoing innovation in novel excipients. France’s Seqens, with over 20 years of polymer development experience, was chosen by Pleryon Therapeutics to advance its leading osteoarthritis candidate – an innovative GMP polymer. This collaboration leverages Seqens’ newly expanded and modernized cGMP plant in Aramon, France, demonstrating the industry’s commitment to investing in advanced manufacturing capabilities for novel excipients.  The rise of biologics and personalized medicine has created a demand for specialized excipients capable of stabilizing complex molecules and enabling targeted drug delivery. Roquette’s launch of Lycagel Flex, a hydroxypropyl pemix for nutraceutical and pharmaceutical softgel capsules, exemplifies this trend. Built on Roquette’s market-first Lycagel pea starch technology, this plant-based alternative to gelatin offers manufacturers the flexibility to customize formulations for a range of production and end-user needs. The innovative pea starch foundation also underscores the industry’s move towards sustainable bio-based excipients. The trend towards patient-centric drug development has also influenced excipient innovation. Excipients that can improve palatability, ease of swallowing, or enable novel dosage forms (such as orally disintegrating tablets) are in high demand. For example, IFF brought a super disintegrant Ac-Di-Sol, that supports faster disintegration and drug dissolution in oral disintegrating tablets, improving patient experience.  View Our Dashboard on Major Excipient Companies in 2024 (Free Excel Available)   Our view The heightened regulatory scrutiny on excipients due to product contamination incidents has created a high risk perception and uncertainty around the regulatory acceptance of novel excipients. That said, novel excipients are central to the development of new drug modalities and therapies. Going forward, sustainability will also become an increasingly important factor in excipient selection and development. As the industry innovates towards biologics, personalized therapies, and patient-centric formulations, the role of high-quality, multifunctional excipients will only grow more vital in ensuring drug stability, bioavailability, and patient compliance. Companies that can navigate the complex regulatory landscape, invest in R&D, and offer high-quality, multifunctional excipients will be well-positioned to succeed in this evolving market.   

Impressions: 1619

https://www.pharmacompass.com/radio-compass-blog/excipient-market-overview-roquette-seqens-evonik-make-strategic-moves-new-guidelines-deal-with-contamination

#PharmaFlow by PHARMACOMPASS
12 Sep 2024

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