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Also known as: Terpineol, 98-55-5, 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol, P-menth-1-en-8-ol, 8000-41-7, Dl-alpha-terpineol

Molecular Formula

C₁₀H₁₈O

Molecular Weight

154.25 g/mol

InChI Key

WUOACPNHFRMFPN-UHFFFAOYSA-N

FDA UNII

21334LVV8W

2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

Alpha-Terpineol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propan-2-ol

2.1.2 InChI

InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3

2.1.3 InChI Key

WUOACPNHFRMFPN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CCC(CC1)C(C)(C)O

2.2 Other Identifiers

2.2.1 UNII

21334LVV8W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-alpha-terpineol

2. Alpha-terpineol, Sodium Salt

3. D-alpha-terpineol

4. Dl-alpha-terpineol

5. P-menth-1-en-8-ol

2.3.2 Depositor-Supplied Synonyms

1. Terpineol

2. 98-55-5

3. 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol

4. P-menth-1-en-8-ol

5. 8000-41-7

6. Dl-alpha-terpineol

7. 1-p-menthen-8-ol

8. .alpha.-terpineol

9. Terpineol 350

10. 1-menthene-8-ol

11. Carvomenthenol

12. Terpineols

13. Fema No. 3045

14. 1-methyl-4-isopropyl-1-cyclohexen-8-ol

15. Alpha,alpha,4-trimethyl-3-cyclohexene-1-methanol

16. 2-(4-methyl-3-cyclohexenyl)-2-propanol

17. Terpineol Schlechthin

18. Terpenol

19. Alpha-terpinenol

20. 1-methyl-4-isopropyl-1-cyclohexene-8-ol

21. Mfcd00001557

22. 8006-39-1

23. Chebi:22469

24. 1-alpha-terpineol

25. 21334lvv8w

26. Nsc-21449

27. Nsc-403665

28. 3-cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-

29. Ncgc00164431-01

30. Nsc 21449

31. Pc 593

32. Dsstox_cid_6625

33. Dsstox_rid_79596

34. Dsstox_gsid_40775

35. Terpilenol, Alpha-

36. Terpene Alcohol

37. Fema Number 3045

38. Alpha-terpineol, Analytical Standard

39. Alpha-terpineol (natural)

40. Menth-1-en-8-ol

41. 2-(4-methylcyclohex-3-enyl)propan-2-ol

42. Cas-8000-41-7

43. Ccris 3204

44. 3-cyclohexene-1-methanol,.alpha.4-trimethyl-

45. Caswell No. 823

46. Hsdb 5316

47. Mixture Of P-methenols

48. Einecs 202-680-6

49. Einecs 219-448-5

50. 3-cyclohexene-1-methanol, Alpha,alpha,4-trimethyl-

51. Brn 1906604

52. Unii-r53q4zwc99

53. Alfa_terpineol

54. Unii-21334lvv8w

55. Ai3-00275

56. Terpineol Normal

57. Alpha -terpineol

58. Dl A-terpineol

59. Menthen-8-ol

60. Einecs 232-268-1

61. Epa Pesticide Chemical Code 067005

62. Alfa-terpineol

63. 1-p-menthen-8-

64. Terpineol Or

65. .alpha.terpineol

66. Terpineol, Alpha

67. D-1-p-menthen-8-ol

68. Terpineol, Mixed Isomers

69. Monocyclic Terpenealcohols

70. (+)-.alpha.-terpineol

71. 3-cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl-

72. Ec 202-680-6

73. Ec 232-268-1

74. Alpha-terpineol, Aldrichcpr

75. Dsstox_rid_78167

76. Dsstox_gsid_26625

77. Pine Oil-593

78. Schembl28466

79. Alpha-terpineol [fcc]

80. 3-cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (s)-

81. Alpha-terpineol [hsdb]

82. (1)-alpha,alpha,4-trimethylcyclohex-3-ene-1-methanol

83. Chembl449810

84. R53q4zwc99

85. .alpha.-terpineol [ii]

86. .alpha.-terpineol [mi]

87. Alfa-terpineol [who-dd]

88. Dtxsid5026625

89. Mil-350

90. .alpha.-terpineol [fhfi]

91. Hy-n5142

92. Nsc21449

93. Tox21_112118

94. Tox21_200112

95. Tox21_302298

96. C0669

97. Nsc403665

98. Pc-593

99. 3-cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, Sodium Salt, (1s)-

100. Akos015840815

101. Alpha-terpineol, 90%, Technical Grade

102. Sb45068

103. Cas-98-55-5

104. Ncgc00248528-01

105. Ncgc00255464-01

106. Ncgc00257666-01

107. Db-059206

108. Alpha-terpineol 1000 Microg/ml In N-hexane

109. Cs-0032554

110. Ft-0622202

111. Ft-0627680

112. Ft-0698995

113. Ft-0772029

114. T0022

115. T0984

116. 2-(4-methyl-1-cyclohex-3-enyl)-propan-2-ol

117. D70165

118. (1r)-a,a,4-trimethyl-3-cyclohexene-1-methanol

119. Sr-01000944873

120. J-500272

121. Sr-01000944873-1

122. Terpin Monohydrate Impurity A [ep Impurity]

123. W-100076

124. Q27109437

125. F0001-2319

126. Alpha-terpineol, Primary Pharmaceutical Reference Standard

127. 3-cyclohexene-1-methanol, Alpha., .alpha., 4-trimethyl-

128. 22347-88-2

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₈O
Molecular Weight	154.25 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	154.135765193 g/mol
Monoisotopic Mass	154.135765193 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	168
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

... After iv injection of 0.1 mL/kg, death due to massive pulmonary edema occurred within minutes. In this animal blood and tissue levels of alpha-terpineol of between 150 and 300 ppm were observed. After smaller doses of pine oil (0.033 mL/kg), horses survived until euthanized up to 48 hr later. Blood levels of alpha-terpineol became undetectable in one of these animals after 2 hr, and no tissue levels were detected at postmortem....

PMID:981787 Tobin T et al; Res Commun Chem Pathol Pharm 15 (2): 291 (1976)

4.2 Metabolism/Metabolites

The metabolic fate of alpha-terpineol administered orally to male albino-rats was investigated, and its effects on the liver microsomal cytochrome-P-450 system were studied. For metabolic studies, alpha-terpineol was given once daily for 20 days at a dose of 600mg/kg bw; cytochrome-P-450 studies involved dosing for up to 9 days. ...The neutral fraction isolated showed the presence of one major (alpha-terpineol) and two minor compounds. One of the minor compounds was identified as p-menthane-1,2,8-triol. Further study revealed the presence of the methyl esters of oleuropeic-acid and dihydrooleuropeic-acid. Allylic oxidation of C-1 methyl esters appeared to be the major metabolic pathway. It was considered likely that the allylic methyl group at C-7 was oxidized prior to the reduction of the 1,2-double bond. Administration of alpha-terpineol increased the levels of liver microsomal cytochrome-P-450 by 72, 104, 90, 54, and 52% after 1, 2, 3, 6, and 9 days of dosing, respectively. A moderate incr was noted in the levels of liver microsomal NADPH-cytochrome-c-reductase during the first 3 days of repeated dosing. No significant effect was noted on cytochrome-b5 and NADH-cytochrome-c-reductase. The authors conclude that the allylic methyl oxidation of alpha-terpineol is the major route for its metabolic transformation in the rat. The reduction of the endocyclic double bond was specifically noted in the formation of dihydrooleuropeic-acid from oleuropeic-acid.

PMID:3179523 Madyastha KM, Srivatsan V; Bulletin of Environmental Contamination and Toxicology 41 (1): 17-25 (1988)

Biotransformation of alpha-terpineol by the common cutworm (Spodoptera litura) larvae was investigated. alpha-Terpineol was mixed in an artificial diet, and the diet was fed to the larvae (fourth-fifth instar) of S. litura. Metabolites were isolated from the frass and analyzed spectroscopically. Main metabolites were 7-hydroxy-alpha-terpineol (p-menth-1-ene-7,8-diol) and oleuropeic acid (8-hydroxy-p-menth-1-en-7-oic acid). Intestinal bacteria from the frass of larvae did not participate in the metabolism of alpha-terpineol. alpha-Terpineol was preferentially oxidized at the C-7 position (allylic methyl group) by S. litura larvae.

PMID:12166982 Miyazawa M, Ohsawa M; J Agric Food Chem 50 (17): 4916-8 (2002)

Details of the metabolism of alpha-terpineol by Pseudomonas incognita are presented. Degradation of alpha-terpineol by this organism resulted in the formation of a number of acidic and neutral metabolites. Among the acidic metabolites, beta-isopropyl pimelic acid, 1-hydroxy-4-isopropenyl-cyclohexane-1-carboxylic acid, 8-hydroxycumic acid, oleuropeic acid, cumic acid, and p-isopropenyl benzoic acid have been identified. Neutral metabolites identified were limonene, p-cymene-8-ol, 2-hydroxycineole, and uroterpenol. ... /I/t appears that P. incognita degrades alpha-terpineol by at least three different routes. While one of the pathways seems to operate via oleuropeic acid, a second may be initiated through the aromatization of alpha-terpineol. The third pathway may involve the formation of limonene from alpha-terpineol and its further metabolism.

PMID:6525582 Madyastha KM, Renganathan V; Can J Microbiol 30 (12): 1429-36 (1984)

In a minor pathway, the endocyclic alkene of alpha-terpineol is epoxidized and then hydrolysed to yield a triol metabolite 1,2,8-trihydroxy- para-menthane, which was also reported in humans after inadvertent oral ingestion of a pine-oil disinfectant containing alpha-terpineol.

FAO/WHO Joint Expert Committee on Food Additives; WHO Food Additives Series 42: 943. Aliphatic Acyclic and Alicyclic Terpenoid Tertiary Alcohols and Structurally Related Substances (1999). Available from, as of July 14, 2015: https://inchem.org/pages/jecfa.html

Metabolized primarily by conjugation with glucuronic acid and excreted in urine. Oxidation of the allylic methyl group followed by hydrogenation to yield the corresponding saturated acid may occur.

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