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2D Structure
Also known as: 2-methyl-2,4-pentanediol, 107-41-5, 2-methylpentane-2,4-diol, Diolane, 2,4-pentanediol, 2-methyl-, 2,4-dihydroxy-2-methylpentane
Molecular Formula
C6H14O2
Molecular Weight
118.17  g/mol
InChI Key
SVTBMSDMJJWYQN-UHFFFAOYSA-N
FDA UNII
KEH0A3F75J

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methylpentane-2,4-diol
2.1.2 InChI
InChI=1S/C6H14O2/c1-5(7)4-6(2,3)8/h5,7-8H,4H2,1-3H3
2.1.3 InChI Key
SVTBMSDMJJWYQN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(CC(C)(C)O)O
2.2 Other Identifiers
2.2.1 UNII
KEH0A3F75J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-methyl-2,4-pentanediol

2. 2-methylpentane-2,4-diol

3. Hexylene Glycol, Titanium(4+) Salt

2.3.2 Depositor-Supplied Synonyms

1. 2-methyl-2,4-pentanediol

2. 107-41-5

3. 2-methylpentane-2,4-diol

4. Diolane

5. 2,4-pentanediol, 2-methyl-

6. 2,4-dihydroxy-2-methylpentane

7. Isol

8. Pinakon

9. 4-methyl-2,4-pentanediol

10. 1,1,3-trimethyltrimethylenediol

11. 2-methyl Pentane-2,4-diol

12. Hexyleneglycol

13. 2-methyl-2,4-pentandiol

14. Hexylene Glycol [nf]

15. Nsc-8098

16. Alpha,alpha,alpha'-trimethyltrimethylene Glycol

17. Keh0a3f75j

18. 1,3-dimethyl-3-hydroxybutanol

19. Chebi:62995

20. 1,3,3-trimethyl-1,3-propanediol

21. Mfcd00004547

22. Hexylene Glycol (nf)

23. Nsc 8098

24. Dsstox_cid_1885

25. Dsstox_rid_76384

26. Dsstox_gsid_21885

27. Caswell No. 574

28. Cas-107-41-5

29. 2-methylpentan-2,4-diol

30. Hsdb 1126

31. 2-methyl-pentane-2,4-diol

32. (+-)-2-methyl-2,4-pentanediol

33. Einecs 203-489-0

34. Unii-keh0a3f75j

35. Epa Pesticide Chemical Code 068601

36. Brn 1098298

37. Ai3-00919

38. Ccris 9439

39. Hexylene Glycol, 99%

40. R-(-)-2-methyl-2,4-pentanediol

41. 2methyl-2,4-pentanediol

42. 2-methyl-2-4-pentanediol

43. Ec 203-489-0

44. Hexylene Glycol, >=99%

45. Hexylene Glycol, 99.5%

46. Schembl19379

47. Hexylene Glycol [ii]

48. Hexylene Glycol [mi]

49. 1,3-trimethyltrimethylenediol

50. 4-01-00-02565 (beilstein Handbook Reference)

51. Hexylene Glycol [hsdb]

52. Hexylene Glycol [inci]

53. Chembl2104293

54. Dtxsid5021885

55. Hexylene Glycol [mart.]

56. Hexylene Glycol [usp-rs]

57. Nsc8098

58. (?)-2-methyl-2,4-pentanediol

59. Hms3264e19

60. 1,1,3-trimethyl-1,3-propanediol

61. Hy-b0903

62. Hexylene Glycol, Analytical Standard

63. Tox21_201975

64. Tox21_302818

65. (+/-)-2-methyl-2,4-pentanediol

66. S3588

67. Akos015901459

68. Ccg-213719

69. Wln: Qy1 & 1xq1 & 1

70. Ncgc00249143-01

71. Ncgc00256494-01

72. Ncgc00259524-01

73. (+/-)-2,4-dihydroxy-2-methyl Pentane

74. Ac-13749

75. As-58339

76. Hexylene Glycol, Bioxtra, >=99% (gc)

77. (+/-)-2-methyl-2,4-pentanediol, Mpd

78. (^+)-2-methyl-2,4-pentanediol, 98%

79. Db-057767

80. Ft-0605050

81. Ft-0605756

82. Ft-0613069

83. Hexylene Glycol, Puriss., >=99.0% (gc)

84. M0384

85. .alpha.,.alpha.'-trimethyltrimethylene Glycol

86. Hexylene Glycol, Bioultra, >=99.0% (gc)

87. D04439

88. Ab01563179_01

89. J-640306

90. J-660006

91. Q2792203

92. W-108748

93. Hexylene Glycol, United States Pharmacopeia (usp) Reference Standard

94. Hexylene Glycol, Pharmagrade, Usp/nf, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 118.17 g/mol
Molecular Formula C6H14O2
XLogP30.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass118.099379685 g/mol
Monoisotopic Mass118.099379685 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count8
Formal Charge0
Complexity68.9
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

Between toxicity ratings 2 or 3. 2= Slightly toxic: probable oral lethal dose (human) 5-15 g/kg, between 1 pint & 1 qt for 70 kg person (150 lb). 3= Moderately toxic: probable oral lethal dose (human) 0.5-5 g/kg; between 1 oz & 1 pint (or 1 lb) for 70 kg person (150 lb).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-179


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

... Mice /were fed hexylene glycol/ orally 20 mg/day in 2 mL of whole milk for up to 81 days ... . approximately 40% of the hexylene glycol was accounted for in the urine, but only 4% of the amount excreted was free glycol; the other 36% was conjugated with glycuronic acid.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 50


... Not readily absorbed through the skin ... .

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 49


Eliminated in urine, partly (20-25%) in conjugated forms.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-179


... Oral administration of hexylene glycol to rats & rabbits resulted in a substantial increase in the amt of hexuronates in the plasma & in the urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 50


For more Absorption, Distribution and Excretion (Complete) data for 2-METHYL-2,4-PENTANEDIOL (8 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

...Five human subjects ... /had/ both free & conjugated hexylene glycol in the urine after single or repeated oral doses. ...

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 50


(14)C-hexylene glycol fed to rabbits... urine contained 7 metabolites incl glucuronide of hexylene glycol (46% of dose), unchanged hexylene glycol (2.5%), diacetone alcohol (1.4%) & an unidentified glucuronide which could be conjugate of diacetone alcohol. ...Converted into diacetone alc by incubation with rat liver slices.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 166


... Oral administration of hexylene glycol to rats & rabbits resulted in a substantial increase in the amt of hexuronates in the plasma & in the urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 50


It was also shown that approximately 40% of the hexylene glycol was accounted for in the urine, but only 4% of the amount excreted was free glycol; the other 36% was conjugated with glycuronic acid.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 50


5.3 Biological Half-Life

...after a single oral (gavage) administration of Hexylene glycol at the dose-level of 590 mg/kg to male Sprague-Dawley rats ...t1/2 21.2 hr

European Chemicals Agency (ECHA); REACH Registration for 2-methylpentane-2,4-diol (CAS 107-41-5); Available from, as of May 29, 2014: https://echa.europa.eu/


5.4 Mechanism of Action

Some effects of gravity on early morphogenesis are correlated with microtubule locations within cells. During first cleavage in Ilyanassa obsoleta embryos, a transitory polar lobe constriction forms and then relaxes, allowing the polar lobe to merge with one daughter cell. If the polar lobe is equally divided or removed, morphogenesis is severely disrupted. To examine microtuble locations during early Ilyanassa development, eggs were fixed and stained for polymerized alpha-tubulin during first cleavage. The mitotic apparatus assembles at the animal pole. The cleavage furrow forms between the asters, constricting to a stabilized intercellular bridge encircling midbody-bound microtubules, whereas the polar lobe constriction forms below and parallel to the spindle, constricting to a transitory intercellular bridge encircling no detectable microtubules. At metaphase an alpha-tubulin epitope is distributed throughout the spindle, whereas a beta-tubulin epitope is present predominantly in the asters. Incubation in hexylene glycol, a drug that increases microtubule polymerization, during mitosis causes the polar lobe constriction to tighten around polymerized alpha-tubulin and remain stably constricted. If hexylene glycol is removed, alpha-tubulin staining disappears from the polar lobe constriction, which relaxes, whereas microtubules remain in the cleavage furrow, which remains constricted. These observations suggest that asymmetric distribution of microtubules affects early Ilyanassa cleavage patterns, and that continued presence of microtubules extending through an intercellular bridge is important for stabilization of the bridge constriction prior to completion of cytokinesis. These data provide the basis for further analysis of the role of microtubules in possible microgravity disruptions of Ilyanassa development.

PMID:11536633 Conrad AH et al; J Exp Zool 269 (3): 188-204 (1994)