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Chemistry

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Also known as: 1,3,5-trimethylbenzene, 108-67-8, Sym-trimethylbenzene, Benzene, 1,3,5-trimethyl-, 3,5-dimethyltoluene, Fleet-x
Molecular Formula
C9H12
Molecular Weight
120.19  g/mol
InChI Key
AUHZEENZYGFFBQ-UHFFFAOYSA-N
FDA UNII
887L18KQ6X

Trimethylbenzol
mesitylene is a natural product found in Lepidium meyenii and Ferulago nodosa with data available.
1 2D Structure

Trimethylbenzol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,3,5-trimethylbenzene
2.1.2 InChI
InChI=1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3
2.1.3 InChI Key
AUHZEENZYGFFBQ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=CC(=C1)C)C
2.2 Other Identifiers
2.2.1 UNII
887L18KQ6X
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 1,3,5-trimethylbenzene

2. 108-67-8

3. Sym-trimethylbenzene

4. Benzene, 1,3,5-trimethyl-

5. 3,5-dimethyltoluene

6. Fleet-x

7. Trimethylbenzol

8. S-trimethylbenzene

9. 2,4,6-trimethylbenzene

10. 1,3,5-trimethyl-benzene

11. Nsc 9273

12. Trimethylbenzene, 1,3,5-

13. Chebi:34833

14. 887l18kq6x

15. Nsc-9273

16. Dsstox_cid_6797

17. Dsstox_rid_78217

18. Dsstox_gsid_26797

19. Cas-108-67-8

20. Hsdb 92

21. Einecs 203-604-4

22. Un2325

23. Unii-887l18kq6x

24. Ai3-23973

25. Ccris 8147

26. Mesitylene, 98%

27. Mesitylene [mi]

28. Mesitylene [hsdb]

29. Mesitylene [inci]

30. Trimethylbenzol (related)

31. Trimethylbenzene (related)

32. 1,3, 5-trimethylbenzene

33. Ec 203-604-4

34. Bidd:er0286

35. Mesitylene (acd/name 4.0)

36. Mesitylene, Analytical Standard

37. Chembl1797281

38. Dtxsid6026797

39. Wln: 1r C1 E1

40. Mesitylene, Reagent Grade, 97%

41. Nsc9273

42. Benzene,1,3,5-trimethyl

43. Str03436

44. Zinc1699890

45. Tox21_201452

46. Tox21_300341

47. Mfcd00008538

48. Stl268905

49. 1,3,5-trimethylbenzene (mesitylene)

50. Akos000120144

51. Mesitylene, Purum, >=98.0% (gc)

52. Un 2325

53. Ncgc00247999-01

54. Ncgc00247999-02

55. Ncgc00254430-01

56. Ncgc00259003-01

57. Ft-0606520

58. S0658

59. T0470

60. A801911

61. Q425161

62. 1,3,5-trimethylbenzene 100 Microg/ml In Methanol

63. J-002179

64. J-521685

65. 1,3,5-trimethylbenzene [un2325] [flammable Liquid]

66. F0001-0175

67. Mesitylene, Certified Reference Material, Tracecert(r)

68. Z1262253023

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 120.19 g/mol
Molecular Formula C9H12
XLogP33.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass120.093900383 g/mol
Monoisotopic Mass120.093900383 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count9
Formal Charge0
Complexity55
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

The objective of this study was to determine the uptake and disposition of inhaled trimethylbenzenes (TMBs) in man. The toxicokinetics were studied in 10 male, healthy volunteers exposed to TMB vapor in an exposure chamber for 2 hr during a work load of 50 W. The subjects were exposed on four occasions to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, and to 2 ppm of 1,2,4-TMB. The TMB isomers were analyzed in blood, urine, and exhaled air by gas chromatography. The relative respiratory uptake was in the range 56-64%. The elimination of TMBs was moderate compared to other aromatic solvents, with a total blood clearance of 0.6-1.0 L per hr per kg. Large volumes of distribution (30-39 liters/kg) and long terminal half-lives of the TMBs in blood (78-120 hr) imply extensive accumulation in adipose tissue. Exhalation during and postexposure accounted for 20-37% of the absorbed amount, whereas the urinary excretion of unchanged TMBs was low (< or = 0.002%). The kinetics of 1,2,4-TMB seemed linear up to 25 ppm. ...

PMID:8887444 Jarnberg J et al; Toxicol Appl Pharmacol 140 (2): 281-8 (1996)


Absorption takes place most readily by inhalation of the vapor, but the liquid can be absorbed from the gastro-intestinal tract, and probably, though slowly, by the intact skin.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 112


... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 112


... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. About 22% of the inhaled amount of 1,2,4-TMB was excreted as DMHAs within 24 hr, mainly as 3,4-DMHA. The 24-hr recovery of 1,2,3-TMB as DMHAs was 11%. Only 3% of the absorbed amount of 1,3,5-TMB was excreted as 3,5,-DMHA. ... In addition to analysis of DMHAs, the excretion of unconjugated dimethylbenzoic acids in urine was estimated to account for approximately 3% of the dose of all TMBs. In conclusion, the urinary excretion of DMHA isomers may serve as a good indicator of TMB exposure. In this controlled short-term-exposure study the sum of excretion rate of several DMHA isomers reflected exposure more closely than did the excretion rate of any single DMHA.

PMID:9215938 Jarnberg J et al; Int Arch Occup Environ Health 69 (6): 491-7 (1997)


4.2 Metabolism/Metabolites

... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.

Browning, E. Toxicity and Metabolism of Industrial Solvents. New York: American Elsevier, 1965., p. 112


Mesitylene yields 2,4,6-trimethylphenol in rat. /from table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. M-5


Approximately 78% of oral dose of mesitylene was excreted as 3,5-dimethylhippuric acid; additional 7.6 and 8.2% were excreted as glucuronic and sulfuric acid conjugates.

PMID:1129786 Mikulski PI, Wiglusz R; Toxicol Appl Pharmacol 31 (1): 21-31 (1975)


Toxicity of Tri- and Tetramethylbenzenes: Material: 1,3,5-trimethylbenzene; Route of entry: oral (subacute); Species: rat; Dose or concentration: 1.2 g/kg/day; Results or Effects: Metabolites: 3,5-dimethylhippuric acid 78.0%, 3,5-dimethylbenzoic glucuronide 7.6%, and 3,5-dimethylbenzoic sulfate 1.2%. /From table/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:271


The possibility of evaluating occupational exposure to mesitylene /depending/ on the determination of unchanged solvent in capillary blood or 3,5-dimethylbenzoic acid in urine was investigated. The volunteers were exposed to mesitylene in a toxicological chamber (range 10-150 mg/cu m). Concn of the solvent or its metabolite in biological material were determined by gas chromatography. The toxicokinetic data concerning retention in the lung, absorption and elimination of mesitylene and its metabolite in biological fluids were obtained. The highest correlation coefficient value was obtained for the relationship between the absorbed dose of mesitylene and the excretion rate of 3,5-dimethylbenzoic acid in urine (r= 0.95). ...

Kostrewski P, Wiaderna-Brycht A; Tox Lett 77 (1-3): 259-64 (1995)


4.3 Biological Half-Life

... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. ... The half-times of the different DMHA isomers ranged from 4 to 16 hr.

PMID:9215938 Jarnberg J et al; Int Arch Occup Environ Health 69 (6): 491-7 (1997)


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Trimethylbenzol

About the Company : SAINTSUN PHARMA, we are engaging mainly in the manufacturing and distributing APIs, Pharmaceutical Intermediates, Chemicals, Formulations, Medical supplies, etc... With a self-owne...

SAINTSUN PHARMA, we are engaging mainly in the manufacturing and distributing APIs, Pharmaceutical Intermediates, Chemicals, Formulations, Medical supplies, etc... With a self-owned brand of "SAINTSUN PHARMA", after more than 12 years efforts, our products are successfully expanded to different continents like Asia, South America, Africa more than 35 countries and regions.
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