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Menthone
Also known as: (-)-menthone, 14073-97-3, L-menthone, Trans-menthone, (2s,5r)-2-isopropyl-5-methylcyclohexanone, P-menthone
Molecular Formula
C10H18O
Molecular Weight
154.25  g/mol
InChI Key
NFLGAXVYCFJBMK-BDAKNGLRSA-N
FDA UNII
5F709W4OG4

Menthone is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Menthone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one
2.1.2 InChI
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
2.1.3 InChI Key
NFLGAXVYCFJBMK-BDAKNGLRSA-N
2.1.4 Canonical SMILES
CC1CCC(C(=O)C1)C(C)C
2.1.5 Isomeric SMILES
C[C@@H]1CC[C@H](C(=O)C1)C(C)C
2.2 Other Identifiers
2.2.1 UNII
5F709W4OG4
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. (-)-menthone

2. 14073-97-3

3. L-menthone

4. Trans-menthone

5. (2s,5r)-2-isopropyl-5-methylcyclohexanone

6. P-menthone

7. L-menthan-3-one

8. Neomenthone

9. Menthone Racemic

10. Trans-menthan-3-one

11. 89-80-5

12. Trans-p-menthan-3-one

13. (1r,4s)-(-)-p-menthan-3-one

14. Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2s,5r)-

15. Dl-menthone

16. P-menthan-3-one, Trans-

17. Fema No. 2667

18. (2s,5r)-5-methyl-2-(propan-2-yl)cyclohexanone

19. (-)-(2s,5r)-menthone

20. (1r,4s)-p-menthan-3-one

21. (2s,5r)-5-methyl-2-(1-methylethyl)cyclohexanone

22. (2s,5r)-5-methyl-2-propan-2-ylcyclohexan-1-one

23. (2s-trans)-5-methyl-2-(1-methylethyl)cyclohexanone

24. Cyclohexanone, 5-methyl-2-(1-methylethyl)-, Trans-

25. (-)-(1r,4s)-menthone

26. (2s,5r)-5-methyl-2-(1-methylethyl)-cyclohexanone

27. Chebi:15410

28. (-)-5-methyl-2-(1-methylethyl)cyclohexanone

29. 5f709w4og4

30. Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2s-trans)-

31. Dsstox_cid_24384

32. Dsstox_rid_80188

33. Dsstox_gsid_44384

34. Menthone (natural)

35. P-menthan-3-one Racemic

36. L-p-menthan-3-one

37. (dl)-menthone

38. 5-methyl-2-(1-methylethyl)cyclohexanone

39. Cas-14073-97-3

40. Ccris 5747

41. Hsdb 1268

42. P-menthan-3-one, Dl-

43. Einecs 201-941-1

44. Einecs 214-049-2

45. Unii-9nh5j4v8fn

46. Menthon

47. Unii-5f709w4og4

48. Ai3-11106

49. Menthone G

50. Trans-p-menthone

51. 1-menthone

52. (-)menthone

53. 5-methyl-2-(1-methylethyl)cyclohexanone, Trans-

54. Ncgc00095606-01

55. Cyclohexan-1-one, 2-isopropyl-5-methyl-, Racemic

56. Einecs 237-926-1

57. Mfcd00001634

58. Menthan-3-one, Trans

59. Spectrum_001299

60. Rel-(2r,5s)-2-isopropyl-5-methylcyclohexanone

61. (-)-menthone,(s)

62. Menthone [fhfi]

63. Specplus_000437

64. Menthone, L-

65. L-menthone [mi]

66. Spectrum2_000691

67. Spectrum3_001272

68. Spectrum4_001648

69. Spectrum5_000495

70. (2s,5r)-2-isopropyl-5-methyl-cyclohexanone

71. Bmse000375

72. (-)-menthone, 90%

73. Ec 237-926-1

74. 9nh5j4v8fn

75. Schembl21709

76. Bspbio_002864

77. Kbiogr_002115

78. Kbioss_001779

79. Menthone, (-)-

80. Spectrum300564

81. Divk1c_006533

82. Spbio_000841

83. (1s)-trans-p-menthan-3-one

84. (-)-menthone [fcc]

85. (2s,5r)-5-methyl-2-(propan-2-yl)cyclohexan-1-one

86. Chembl276311

87. Dtxsid2044478

88. Dtxsid3044384

89. Kbio1_001477

90. Kbio2_001779

91. Kbio2_004347

92. Kbio2_006915

93. Kbio3_002364

94. Cyclohexanone, 5-methyl-2-(1-methylethyl)-, Trans-(+/-)-

95. Zinc967796

96. (-)-menthone, Analytical Standard

97. Hy-n7916

98. Tox21_111510

99. Tox21_302153

100. Ccg-38562

101. Mfcd00136033

102. Akos006343213

103. Tox21_111510_1

104. Lmpr0102090004

105. Sdccgmls-0066582.p001

106. 2-isopropyl-5-methylcyclohexanone, Trans

107. Ncgc00095606-02

108. Ncgc00178425-01

109. Ncgc00255957-01

110. As-17440

111. (2s,5r)2-isopropyl-5-methylcyclohexanone

112. Cs-0138798

113. 1-methyl-4-isopropylcyclohexan-3-one

114. C00843

115. (2s,5r)-2-isopropyl-5-methylcyclohexan-1-one

116. (2s, 5r)-trans-2-isopropyl-5-methylcyclohexanone

117. Q424902

118. Sr-05000002387

119. 5-methyl-2-(1-methylethyl)-(2s,5r)-cyclohexanone

120. L-menthone, Mixture Of Isomers, >=96%, Fcc, Fg

121. Sr-05000002387-1

122. W-108194

123. 5-methyl-2-(1-methylethyl)-(2s-trans)-cyclohexanone

124. (-)-menthone, Primary Pharmaceutical Reference Standard

125. Cyclohexanone, 5-methyl-2-(1-methylethyl)-, Trans-(.+/-.)-

126. 1/c10h18o/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9h,4-6h2,1-3h3/t8-,9+/m1/s

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 154.25 g/mol
Molecular Formula C10H18O
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass154.135765193 g/mol
Monoisotopic Mass154.135765193 g/mol
Topological Polar Surface Area17.1 Ų
Heavy Atom Count11
Formal Charge0
Complexity149
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

...KETONES (EG CARVONE & MENTHONE) ARE REDUCED TO SECONDARY ALCOHOLS WHICH ARE THEN EXCRETED AS GLUCURONIDES. MENTHONE, ASYMMETRIC REDUCTION /TO/ NEO-MENTHOL, GLUCURONIDE CONJUGATION /TO/ MENTHYL GLUCURONIDE.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 149


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