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Chemistry

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Also known as: Hexane, 110-54-3, Esani, Skellysolve b, Gettysolve-b, Hexanes
Molecular Formula
C6H14
Molecular Weight
86.18  g/mol
InChI Key
VLKZOEOYAKHREP-UHFFFAOYSA-N
FDA UNII
2DDG612ED8

Hexane
Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.
1 2D Structure

Hexane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
hexane
2.1.2 InChI
InChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
2.1.3 InChI Key
VLKZOEOYAKHREP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCC
2.2 Other Identifiers
2.2.1 UNII
2DDG612ED8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hexane

2. Hexanes

3. Isohexane

4. Isohexanes

2.3.2 Depositor-Supplied Synonyms

1. Hexane

2. 110-54-3

3. Esani

4. Skellysolve B

5. Gettysolve-b

6. Hexanes

7. Hexyl Hydride

8. Hexan

9. Dipropyl

10. Heksan

11. Hexanen

12. Butane, Ethyl-

13. 92112-69-1

14. Normal Hexane

15. Nci-c60571

16. Nsc 68472

17. Chebi:29021

18. N-c6h14

19. Naphtha Solvent

20. Naptha Solvent

21. 2ddg612ed8

22. Ch3-[ch2]4-ch3

23. Nsc-68472

24. N-hexan

25. Esani [italian]

26. Heksan [polish]

27. Hexanen [dutch]

28. Hexane, For Hplc, >=95%

29. Normal-hexane

30. Mfcd00009520

31. 1-hexane

32. Hexane, Branched And Linear

33. Hsdb 91

34. Hydrocarbons, C>3

35. Ccris 6247

36. Einecs 203-777-6

37. Un1208

38. Unii-2ddg612ed8

39. Hexane Solution

40. Ai3-24253

41. Hexane, Hplc Plus, For Hplc, Gc, And Residue Analysis, >=95%

42. Hexh

43. N-hexane Solution

44. Hexane, For Hplc

45. Hexane, P.a.

46. N-hexane, Anhydrous

47. N-hexane, P.a.

48. N-hexane Hplc Grade

49. N-hexane, Acs Grade

50. Hexane Fraction, Purum

51. Hexane, Technical Grade

52. N-hexane, Hplc Grade

53. Hexane (solvent Grade)

54. Hexane [inci]

55. Hexane [usp-rs]

56. N-hexane [hsdb]

57. Hexane [ii]

58. Dsstox_cid_1917

59. Hexane, Anhydrous, 95%

60. N-hexane [mi]

61. Epitope Id:116866

62. Exxsol Hexane (salt/mix)

63. Hexanes Reagent Grade Acs

64. Un 1208 (related)

65. Ec 203-777-6

66. Hexane, Analytical Standard

67. Hexane, P.a., 95%

68. N-hexane [mart.]

69. Dsstox_rid_76401

70. Dsstox_gsid_21917

71. Hexane, Ar, >=99%

72. Wln: 6h

73. 68476-44-8

74. Hexane, Acs Reagent, 99%

75. Chembl15939

76. N-hexane, Environmental Grade

77. Hexane, P.a., 95.0%

78. Ligroine, Hexane (laboratory)

79. Dtxsid0021917

80. Hexane, For Hplc, >=99%

81. Hexane, Purification Grade, 95%

82. N-hexane, Spectrophotometric Grade

83. N-hexane Gc, For Residue Analysis

84. Amy22305

85. Hexane, Reagentplus(r), >=99%

86. Nsc68472

87. Zinc1532209

88. Hexane, Puriss., >=95% (gc)

89. Tox21_200777

90. Lmfa11000007

91. Stl445663

92. Hexane, Laboratory Reagent, >=95%

93. Hexane, Purum, >=98.0% (gc)

94. N-hexane 100 Microg/ml In Methanol

95. Akos000269046

96. Hexane, Uv Hplc Spectroscopic, 97%

97. Hexane, Saj First Grade, >=95.0%

98. N-hexane 1000 Microg/ml In Methanol

99. Hexane, Jis Special Grade, >=96.0%

100. Hexanes [un1208] [flammable Liquid]

101. Ncgc00248828-01

102. Ncgc00258331-01

103. Cas-110-54-3

104. Hexane, For Hplc, >=97.0% (gc)

105. Hexane, Spectrophotometric Grade, >=95%

106. Ft-0627031

107. Ft-0657006

108. H0394

109. H0405

110. H0490

111. H1197

112. Hexane, Suitable For Determination Of Dioxins

113. A802211

114. Q150440

115. J-002443

116. Hexane, Vetec(tm) Reagent Grade, Anhydrous, >=95%

117. Hexane, Puriss. P.a., Acs Reagent, >=99.0% (gc)

118. 680af2ee-a7b6-479b-bfb3-0f5354069f72

119. Hexane, >=96.0%, Suitable For Residual Phthalate Analysis

120. Hexane, For Residue Analysis, Suitable For 5000 Per Jis

121. N-hexane, 95% Min. Glass Distilled Hrgc/hplc Trace Grade

122. Hexanes, Mixture Of Isomers, For Spectroscopy, 95+%

123. Hexane, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99% (gc)

124. Hexane, Suitable For 1000 Per Jis, >=96.0%, For Residue Analysis

125. Hexane, Suitable For 300 Per Jis, >=96.0%, For Residue Analysis

126. Hexane, Pharmaceutical Secondary Standard; Certified Reference Material

127. Hexane, Commercial Grade (52% N-hexane, 16% 3-methylpentane, 16% Methylcyclopentane)

128. Hexane, Puriss., Absolute, Over Molecular Sieve (h2o <=0.01%), >=99.0% (gc)

129. 50981-41-4

130. Hexane, Commercial Grade (52% N-hexane, 16% 3-methylcyclopentane, 16% Methylcyclopentane)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 86.18 g/mol
Molecular Formula C6H14
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count3
Exact Mass86.109550447 g/mol
Monoisotopic Mass86.109550447 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count6
Formal Charge0
Complexity12
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

Concentrations of about 50 g may be fatal to humans. ...

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V4 36


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

Hexane is absorbed through the lungs and relatively poorly absorbed through the intact skin.

Rom, W.N. (ed.). Environmental and Occupational Medicine. 2nd ed. Boston, MA: Little, Brown and Company, 1992., p. 566


Accumulation in the tissues depends on lipid content in these tissues. n-/Hexane/ is oxidized in the liver. Excretion occurs via the lungs and kidneys. ... Excretion of /hexane/ is related to dose.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 740


The pharmacokinetics of inhaled n-hexane in rat and man were compared. In the rat metabolism was saturable. Up to 300 ppm, the metabolic rate was directly proportional to the concentration in the atmosphere, reaching 47 umol/(hr X kg). Only 17% of n-hexane was exhaled unchanged. Above 300 ppm, the amount of n-hexane in the body rose with increasing atmospheric concentrations from 1.6 up to a limiting value of 9.6, which corresponded to the thermodynamic distribution coefficient of n-hexane between the organism and the atmosphere. Up to 3000 ppm, the rate of metabolism increased to 245 umol/(hr X kg); only a slow further increase was found up to 7000 ppm (285 umol/(hr X kg). In man the steady-state concentrations of n-hexane were about 1 ppm. The metabolic clearance was 132 1/hr, and n-hexane accumulated to a factor of 2.3 in the organism. The thermodynamic distribution coefficient was calculated to be 12. Twenty per cent of n-hexane in the body was exhaled unchanged. At low concentrations the rate of metabolism of n-hexane is limited in both species by transport to the enzyme system. Under these conditions the rate of metabolism of n-hexane should not be influenced by xenobiotics which induce the n-hexane metabolizing enzyme system.

PMID:3619648 Filser JG et al; Arch Toxicol 60 (1-3): 77-80 (1987)


... Male Fischer 344 rats were exposed to 500, 1000, 3000 or 10,000 ppm (14)C-n-hexane for 6 hr and the elimination of radioactivity followed for 72 hr after exposure. The disposition of radioactivity was dose-dependent, with 12, 24, 38 and 62% of the acquired body burden excreted as n-hexane by the lung with increasing exposure concentration. In contrast, 38, 31, 27 and 18% of the body burden of radioactivity was recovered as expired (14)CO2 and 35, 40, 31 and 18% was recovered in the urine with increasing n-hexane concentration. Radioactivity remaining in the tissues and carcass 72 hr after exposure represented 6.1, 8.8, 7.4 and 5.4% of the body burden for the respective exposures. The dose-dependent elimination of radioactivity was apparently due in part to an inhibition of n-hexane metabolism, reflected by a decrease in total 14CO2 and urinary 14C excretion after 10,000 ppm exposure compared to the 3000 ppm exposure.

PMID:6821041 Bus JS, Deyo D, Cox M; Fundam Appl Toxicol 2 (5): 226-9 (1982)


For more Absorption, Distribution and Excretion (Complete) data for N-HEXANE (6 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

Different levels of physical activity, namely, rest, 25 W, and 50 W (for 12 hr followed by 12 hr at rest) were simulated to assess the impact of work load on the recommended biological exposure indices: ...free (nonhydrolyzed) 2,5-hexanedione (a metabolite of n-hexane) at the end of the shift at the end of the workweek. ... Urinary 2,5-hexanedione predicted for 50 ppm was 1.07 mg/L at 50 W and 0.92 mg/L at rest (+16%). ...

PMID:19384711 Sari-Minodier I et al; J Occup Environ Hyg 6 (7): 415-32 (2009)


Phenobarbital pre-treatment induces 2- and 3-hydroxylation /of n-hexane/ six-fold; 3,4-benzopyrene suppresses 2- and stimulates 3-hydroxylation.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 270


The major urinary metabolite in rat is 1-hexanol.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 740


...2,5-Hexanedione is principal metabolite of this and other 6-carbon compounds... .

Schaumburg HH, Spencer PS; Ann NY Acad Sci 329 (Public Control Environ Health Hazards): 14-29 (1979)


For more Metabolism/Metabolites (Complete) data for N-HEXANE (8 total), please visit the HSDB record page.


Hexane has known human metabolites that include Hexanol.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.3 Biological Half-Life

Urine (2,5-hexanedione): 15 hours; blood: 2-3 hours; fat: 64 hours; [TDR, p. 769]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 769


5.4 Mechanism of Action

N-hexane ... causes peripheral polyneuropathy and testicular atrophy. The testicular toxicity is separate from its neurotoxicity. /The metabolite, 2,5-hexanedione (HD)/ produces gonadal toxicity by altering testicular tubulin. The HD testicular toxicity results from alterations in Sertoli cell microtubules and the altered microtubules result from pyrole-dependent cross-linking. HD toxicity is slow in onset. Initially, HD affects the cross-linking of cytoskeletal elements leading to altered protein secretions and trafficking in the Sertoli cell. Consequently, there is altered Sertoli cell-germ cell contacts and a loss of Sertoli cell paracrine support of the germ cells.

Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 689


2,5-Hexanedione is the toxic metabolite resulting from oxidation of /n-hexane./ ... Exposure to 2,5-hexanedione or its precursors results in a slowly progressive peripheral polyneuropathy and testicular injury. The chemical basis of the injury involves reaction of 2,5-hexanedione with protein amines, such as the epsilon-amine of lysine, to form pyrroles which further react to form protein-protein crosslinks. The target cell of injury in the testis is the supportive cell in the seminiferous epithelium, the Sertoli cell. A major function of the Sertoli cell is to nurture the dependent germ cell population by secreting seminiferous tubule fluid. 2,5-Hexanedione-induced crosslinking of the microtubule subunit protein, tubulin, leads to altered Sertoli cell microtubule-dependent transport and deficient formation of seminiferous tubule fluid, compromising germ cell viability.

PMID:11764975 Boekelheide K, Schoenfeld HA; Adv Exp Med Biol 500: 421-8 (2001)


n-Hexane's metabolism to 2,5-hexanedione decreases phosphorylation of neurofilaments, which destroys the normal cytoskeletal matrix. Neurofilament proteins are then transported down the axon where they accumulate, crosslink, and produce the giant axonal swelling that characterizes this axonopathy.

Ford MD, Delaney KA, Ling LJ, Erickson T; Clinical Toxicology. W.B. Saunders Company., Philadelphia, PA. 2001, p. 171


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API | Excipient name

Hexane

Synonyms

110-54-3, Esani, Skellysolve b, Gettysolve-b, Hexanes, Hexyl hydride

Cas Number

110-54-3

Unique Ingredient Identifier (UNII)

2DDG612ED8

About Hexane

Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.

Hexane Manufacturers

A Hexane manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Hexane, including repackagers and relabelers. The FDA regulates Hexane manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Hexane API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Hexane Suppliers

A Hexane supplier is an individual or a company that provides Hexane active pharmaceutical ingredient (API) or Hexane finished formulations upon request. The Hexane suppliers may include Hexane API manufacturers, exporters, distributors and traders.

Hexane GMP

Hexane Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Hexane GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Hexane GMP manufacturer or Hexane GMP API supplier for your needs.

Hexane CoA

A Hexane CoA (Certificate of Analysis) is a formal document that attests to Hexane's compliance with Hexane specifications and serves as a tool for batch-level quality control.

Hexane CoA mostly includes findings from lab analyses of a specific batch. For each Hexane CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Hexane may be tested according to a variety of international standards, such as European Pharmacopoeia (Hexane EP), Hexane JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Hexane USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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