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2D Structure
Also known as: 78-70-6, 3,7-dimethylocta-1,6-dien-3-ol, Linalol, Linalyl alcohol, 3,7-dimethyl-1,6-octadien-3-ol, Allo-ocimenol
Molecular Formula
C10H18O
Molecular Weight
154.25  g/mol
InChI Key
CDOSHBSSFJOMGT-UHFFFAOYSA-N
FDA UNII
D81QY6I88E

3,7-Dimethyl-1,6-octadien-3-ol 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
3,7-dimethylocta-1,6-dien-3-ol
2.1.2 InChI
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
2.1.3 InChI Key
CDOSHBSSFJOMGT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=CCCC(C)(C=C)O)C
2.2 Other Identifiers
2.2.1 UNII
D81QY6I88E
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3,7-dimethyl-1,6-octadien-3-ol

2. 7-methyl-3-methyleneocta-4,6-dien-2-ol

3. Allo-ocimenol

4. Linalool, (+-)-isomer

5. Linalool, (r)-isomer

6. Linalool, (s)-isomer

7. Linalool, Titanium (4+) Salt

8. Muguol

2.3.2 Depositor-Supplied Synonyms

1. 78-70-6

2. 3,7-dimethylocta-1,6-dien-3-ol

3. Linalol

4. Linalyl Alcohol

5. 3,7-dimethyl-1,6-octadien-3-ol

6. Allo-ocimenol

7. Beta-linalool

8. 1,6-octadien-3-ol, 3,7-dimethyl-

9. (+-)-linalool

10. P-linalool

11. Linanool

12. Linolool

13. Phantol

14. 2,6-dimethyl-2,7-octadien-6-ol

15. 2,6-dimethylocta-2,7-dien-6-ol

16. .beta.-linalool

17. (+/-)-linalool

18. 2,6-dimethyl-2,7-octadiene-6-ol

19. Fema No. 2635

20. Nsc 3789

21. (rs)-linalool

22. (1)-3,7-dimethyl-1,6-octadien-3-ol

23. Chebi:17580

24. 3,7-dimethyl-octa-1,6-dien-3-ol

25. D81qy6i88e

26. Nsc3789

27. Nsc-3789

28. Dsstox_cid_5502

29. Coriandrol

30. Dsstox_rid_77812

31. Dsstox_gsid_25502

32. Licareol

33. Linalool (natural)

34. Caswell No. 526a

35. (s)-linalol

36. Dl-linalool

37. Fema Number 2635

38. Cas-78-70-6

39. Ccris 6557

40. Hsdb 645

41. Linalool (+)

42. Einecs 201-134-4

43. Einecs 245-083-6

44. Epa Pesticide Chemical Code 128838

45. Brn 1721488

46. Unii-d81qy6i88e

47. Ai3-00942

48. Linalool B

49. Howood Oil

50. Natural Linalool

51. Linalool, .beta.

52. Linalool,(s)

53. ( )-linalool

54. Linalool Ex Ho Oil

55. Mfcd00008906

56. Diabexall

57. Linalool, 97%

58. 2,7-octadien-6-ol, 2,6-dimethyl-

59. Linalool Ex Orange Oil

60. 3,6-octadien-3-ol

61. 2,7-octadiene-6-ol

62. Linalool [fhfi]

63. Linalool [hsdb]

64. Linalool [inci]

65. Linalool [fcc]

66. 2,7-dien-6-ol

67. 3,6-dien-3-ol

68. Dl-3,7-dimethyl-3-hydroxy-1,6-octadiene

69. Linalool [mi]

70. Linalool, Dl-

71. Linolool (d)

72. (.+/-.)-linalool

73. Linalool [usp-rs]

74. Linalool [who-dd]

75. Ec 201-134-4

76. Linalool Oil [ndi]

77. L 260-2

78. Schembl20316

79. Linalool Ex Bois De Rose Oil

80. Linalool, Analytical Standard

81. 0-01-00-00462 (beilstein Handbook Reference)

82. 22564-99-4

83. Mls002152908

84. Chembl25306

85. Pentaerythritoltetramethacrylate

86. Gtpl2469

87. Ndi 595 [fdms]

88. Dtxsid7025502

89. Linalool Ex Bois De Rose

90. Linalool, (+/-)-

91. Fema 2635

92. ((c)i)-linalool-d3(vinyl-d3)

93. Hms2268e18

94. Hms3886g07

95. Linalool, >=97%, Fcc, Fg

96. 1, 3,7-dimethyl-, (-)-

97. Hy-n0368

98. Wln: 1u1xq1&3uy1&1

99. Tox21_201658

100. Tox21_303037

101. Ac-551

102. Bbl027734

103. Bdbm50459894

104. Mfcd09025547

105. S4957

106. Stl373777

107. 3,7-dimethyl-1, 6-octadien-3-ol

108. Akos015901617

109. ( Inverted Exclamation Marka)-linalool

110. Ccg-266253

111. Linalool 1000 Microg/ml In Isopropanol

112. Ncgc00091688-01

113. Ncgc00091688-02

114. Ncgc00091688-03

115. Ncgc00091688-04

116. Ncgc00257060-01

117. Ncgc00259207-01

118. (?)-3,7-dimethyl-1,6-octadien-3-ol

119. As-56047

120. Smr000112394

121. Sy264412

122. Wln: 1y1&u3xq1&1u1 -,-

123. Db-062552

124. Cs-0008916

125. Ft-0614785

126. Ft-0772303

127. L0048

128. C03985

129. F17676

130. Linalool, Primary Pharmaceutical Reference Standard

131. Q410932

132. Cu-01000013132-2

133. Q-201306

134. Linalool, Certified Reference Material, Tracecert(r)

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 Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Exact Mass154.135765193 g/mol
Monoisotopic Mass154.135765193 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count11
Formal Charge0
Complexity154
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 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)


4.2 Absorption, Distribution and Excretion

Linalool may permeate porcine (and by extension also human) buccal mucosa in function of its concentration (14.46% w/w) and of formulation /as in the essential oil of Salvia desoleana Atzei & Picci/

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.95 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


Based on experiments with rats using (14)C-labelled substance, linalool is rapidly absorbed from the intestinal tract following oral uptake ... judging from the delay in fecal excretion, intestinal absorption is complete. Subsequent to absorption, linalool is metabolized rapidly, with urinary excretion of (14)C activity starting without delay. Several hours after gavage, substantial amounts of radioactivity were detected in the expired air as (14)CO2, evidencing complete intermediary metabolism. Fecal excretion of radioactivity was delayed and found mostly between 36 and 48 hours after dosing, suggesting entero-hepato-biliary re-circulation; this re-circulation was confirmed in a second experiment involving cross-linking a treated and an untreated rat with a biliary-to-intestinal cannula and subsequent radio-analysis. Overall, approximately 60% of the total excreted dose was found in urine over 72 hours after administration; approximately 23% of activity was detected in exhaled air and approximately 15% was found in the feces; there is no indication of tissue accumulation of linalool whatsoever. The study suggests that large doses of oral linalool will be metabolized in the rat by conjugation and excretion in urine and bile, while a substantial proportion will enter intermediary metabolisms up to the formation of carbon dioxide and pulmonary excretion. Entero-hepato-biliary re-circulation may have the effect of enhancing the metabolic load on the liver over a certain period.

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.12 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


After a 1 hour inhalation of 27 mg linalool ... /mouse/ plasma levels of linalool 30, 60 and 90 min after exposure: about 1, 2.7 and 2.9 ng/mL.

European Chemicals Bureau; IUCLID Dataset, Linalool (78-70-6) p.46 (2000 CD-ROM edition).


Linalool applied to mouse skin was not absorbed within two hours.

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.100 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


4.3 Metabolism/Metabolites

... Metabolites isolated from urine of rats after oral administration of linalool (VII) were 8-hydroxy-linalool (VIII) and 8-carboxy-linalool (IX). After three days of feeding rats with either geraniol or linalool, liver-microsomal cytochrome P-450 was increased. Both NADH- and NADPH-cytochrome c reductase activities were not significantly changed during the six days of treatment. Oral administration of these two terpenoids did not affect any of the lung-microsomal parameters measured.

PMID:6475100 Chadha A, Madyastha KM; Xenobiotica 14 (5): 365-74 (1984)


Based on experiments with rats using (14)C-labelled substance ... subsequent to absorption, linalool is metabolized rapidly, with urinary excretion of (14)C activity starting without delay. Several hours after gavage, substantial amounts of radioactivity were detected in the expired air as (14)CO2, evidencing complete intermediary metabolism. Fecal excretion of radioactivity was delayed and found mostly between 36 and 48 hours after dosing, suggesting entero-hepato-biliary re-circulation ... Entero-hepato-biliary re-circulation may have the effect of enhancing the metabolic load on the liver over a certain period.

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.12 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


For the induction study 600 mg linalool/kg bw was administered /to male IISc strain rats/ once daily for 6 days by gastric tube as a suspension in 1% methyl cellulose solution. Control rats were only given the vehicle. For the identification of metabolites, 800 mg linalool/kg bw was administered once daily for 20 days ... . 8-Hydroxy-linalool and 8-carboxy-linalool were identified in the urine, showing selective oxidation of the C8-methyl in linalool. The 8-hydroxylase present in both lung and liver microsomes was shown to be mediated by a cytochrome P-450 (CYP450) system. After 3 days of dosing, liver and lung microsomal CYP450 was increased; on the other hand, both NADH- and NADPH-cytochrome c reductase activities were not significantly changed during the 6 days of treatment. /Purity > 99.5%/

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.97 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


... Hydrolysis occurs more rapidly at the low pH of gastric fluids. The reaction products are linalool and acetic acid (ester hydrolysis). This is supported by the findings of the hydrolysis study ... at pH 4, 7 and 9. Therefore it is expected that linalool is the substance that will enter the systemic circulation after oral uptake of linalyl acetate. Linalool is probably converted to geraniol and its metabolites, 1,5-dimethyl-hexadiene-1,6-dicarboxylic acid and 7-carboxy-5-methylocto-6-enoic acid ... /linalool acetate/

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALYL ACETATE (115-95-7) p.10 (March 2002). Available from, as of July 14, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html


For more Metabolism/Metabolites (Complete) data for LINALOOL (7 total), please visit the HSDB record page.


4.4 Mechanism of Action

... The specific toxic effect of linalool on animals is therefore likely to be caused by its neurotoxic respectively neuropharmacological mode of action. In turn, this may explain the use of linalool-containing natural products (aromatic herbs and spices or their essential oils respectively extracts) in traditional medicinal systems, specifically for their sleep-inducing and anticonvulsant purposes. Moreover, it also accounts for the widespread traditional use of herbs containing linalool for stored-food pest control for the use of linalool-containing extracts as a pet flea insecticide.

Organization for Economic Cooperation and Development; Screening Information Data Set for LINALOOL (78-70-6) p.20 (March 2002). Available from, as of July 15, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html