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    Technical details about MolPort-002-042-108, learn more about the structure, uses, toxicity, action, side effects and more

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    MolPort-002-042-108

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    DOSSIERs // Finished Dosage Forms

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    PharmaCompass

    Minakem offers CDMO services for API & HPAPI, generics, regulatory expertise, track record performance & FDA & GMP certifications.

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    2D Structure
    1. 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

    2D Structure

    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 Weight 154.25 g/mol
    Molecular Formula C10H18O
    XLogP31.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count1
    Exact Mass154.135765193 g/mol
    Monoisotopic Mass154.135765193 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity168
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

    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://www.inchem.org/pages/jecfa.html

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