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2D Structure
Also known as: 1-phenylpropan-2-one, 1-phenyl-2-propanone, 103-79-7, Benzyl methyl ketone, Methyl benzyl ketone, Phenyl-2-propanone
Molecular Formula
C9H10O
Molecular Weight
134.17  g/mol
InChI Key
QCCDLTOVEPVEJK-UHFFFAOYSA-N
FDA UNII
O7IZH10V9Y

Phenylacetone is a natural product found in Streptomyces and Gossypium hirsutum with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-phenylpropan-2-one
2.1.2 InChI
InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3
2.1.3 InChI Key
QCCDLTOVEPVEJK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)CC1=CC=CC=C1
2.2 Other Identifiers
2.2.1 UNII
O7IZH10V9Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-phenyl-2-propanone

2. Benzyl Methyl Ketone

2.3.2 Depositor-Supplied Synonyms

1. 1-phenylpropan-2-one

2. 1-phenyl-2-propanone

3. 103-79-7

4. Benzyl Methyl Ketone

5. Methyl Benzyl Ketone

6. Phenyl-2-propanone

7. 2-propanone, 1-phenyl-

8. 3-phenyl-2-propanone

9. 1-phenylacetone

10. Phenylmethyl Methyl Ketone

11. Phenyl Acetone

12. 1-phenyl-propan-2-one

13. 136675-26-8

14. Phenylaceton

15. O7izh10v9y

16. Chembl3800510

17. Nsc-9827

18. Nsc 9827

19. Phenylacetone, 99%

20. Einecs 203-144-4

21. Unii-o7izh10v9y

22. (phenyl)acetone

23. Ai3-02938

24. Dea No. 8501

25. Methylbenzyl Ketone

26. Phenyl 2-propanone

27. 1-phenylpropane-2-one

28. Phenylacetone [mi]

29. Schembl43943

30. Ghl.pd_mitscher_leg0.660

31. Dtxsid1059280

32. Schembl13341529

33. Chebi:52052

34. Hsdb 8385

35. Nsc9827

36. Phenylacetone, Analytical Standard

37. Bcp22277

38. Bdbm50167968

39. Stl373560

40. Akos004905656

41. Ft-0673719

42. A800807

43. Q418831

44. Amfetamine Sulfate Impurity B [ep Impurity]

45. Inchi=1/c9h10o/c1-8(10)7-9-5-3-2-4-6-9/h2-6h,7h2,1h

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 134.17 g/mol
Molecular Formula C9H10O
XLogP31.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count2
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area17.1
Heavy Atom Count10
Formal Charge0
Complexity112
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 Metabolism/Metabolites

Marked differences were observed, in the ability of fortified 9000 g liver homogenate supernatants from three species to reduce 1-phenyl-2-propanone to the corresponding alcohol. This metabolic keto-reduction was negligible in homogenates from the rat and extensive in the rabbit; guinea-pig liver homogenates had intermediate ability. Metabolic oxidation of 1-phenyl-2-propanol was negligible in all three species. The amount of deamination of amphetamine and of N-n-propylamphetamine was approximately equal, in vitro, in rats and guinea-pigs but two to three times greater in liver homogenates from rabbits. Approximately three times more deaminated products were formed from the in vitro metabolism of N-n-propylamphetamine than from amphetamine metabolism by all three species.

PMID:27606 Coutts RT et al; J Pharm Pharmacol 30 (7): 415-8 (1978)


Phenylacetone was found to be the major metabolite formed when 2-nitro-1-phenylpropane was incubated with rabbit liver microsomes. The enzymatic character of the reaction was demonstrated by the increase of product with microsomal protein and dependency on NADPH and oxygen. Furthermore, phenobarbital induction markedly increased the formation of phenylacetone. Carbon monoxide decreased the reaction indicating the involvement of a metalloenzyme. Experiments with H2(18)O indicated that the carbonyl oxygen originated from water. It is suggested that the microsomal metabolism of 2-nitro-1-phenylpropane involves an enzymatic step followed by chemical hydrolysis of an intermediate, possibly a secondary nitronic acid.

PMID:905635 Jonsson J et al; Res Commun Chem Pathol Pharmacol 18 (1): 75-82 (1977)


Amphetamine is deaminated oxidatively by highly purified rat liver mitochondria. This monoamineoxidase (MAO) is an enzyme of the mitochondrial outer membrane and its activity is about two times higher than that of the microsomal MAO. Anaerobic incubations with mitochondria reduce phenylacetone, an important metabolite of amphetamine, to phenylisopropanol. The ketoreductase is localized in the mitochondrial inner membrane or its matrix.

PMID:7196246 Blume H; Arzneimittelforschung 31 (6): 994-7 (1981)


Fenetylline is metabolized in humans on two pathways. In addition to previously described degradation to amphetamine and 7-oxyethyltheophylline fenetylline undergoes moreover oxydative N-dealkylation to yield 7-aminoethyltheophylline and phenylacetone.

PMID:6742951 Goenechea S, Brzezinka H; Arch Kriminol 173 (3-4): 7-102 (1984)