Hexane (T3D2403)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (6)XML
Targets (6)
Record Information
Version2.0
Creation Date2009-06-30 20:14:11 UTC
Update Date2014-12-24 20:25:27 UTC
Accession NumberT3D2403
Identification
Common NameHexane
ClassSmall Molecule
DescriptionHexane is found in citrus. Hexane is an extraction solvent used in food production Present in volatile fractions of various plant species e.g. apples, orange juice, guava fruit, roasted filberts, porcini (Boletus edulis), shiitake (Lentinus edodes), heated sweet potato and sage. Also present in scallops Hexane has been shown to exhibit hepatoprotective, antibiotic, anti-nociceptive, anti-inflammatory and anti-microbial functions (2, 3, 4, 5, 6). Hexane belongs to the family of Acyclic Alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2.
Compound Type
  • Adhesive
  • Food Toxin
  • Gasoline Additive/Component
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
  • Solvent
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
N-Hexane
Chemical FormulaC6H14
Average Molecular Mass86.175 g/mol
Monoisotopic Mass86.110 g/mol
CAS Registry Number110-54-3
IUPAC Namehexane
Traditional Namehexane
SMILESCCCCCC
InChI IdentifierInChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
InChI KeyInChIKey=VLKZOEOYAKHREP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentAlkanes
Alternative ParentsNot Available
Substituents
  • Acyclic alkane
  • Alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-93.5°C
Boiling PointNot Available
Solubility0.0095 mg/mL at 25°C
LogP3.9
Predicted Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP4.02ALOGPS
logP3.13ChemAxon
logS-3.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.41 m³·mol⁻¹ChemAxon
Polarizability12.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-8ab77db137ff0d1e75f02017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-d534432d96279fe04f732017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-2c1489cf6d4c005a89ae2017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-82853202ddc92c8709ae2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-8ab77db137ff0d1e75f02018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-d534432d96279fe04f732018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-2c1489cf6d4c005a89ae2018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-82853202ddc92c8709ae2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0573-9000000000-a5e2bfa74b29082bd5a92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-318ef636384b005bc4be2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-78a07733b829adaafb092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0c842d507eb6ba1f97332016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c44d91f3b273433a39442016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-72fa4d8dca736350f1a62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-05281e623da690ce94a42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-f87d58adbe1279a987b22021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-435e3e4c3711a641d8c92021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2787044af46be8aa53b12021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2dd044301debb5ba5b0e2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-9000000000-eb7db8b7a784233132cc2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9000000000-56d8224d6aac804940402021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-3f28cfcd32d6c9e1da292014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (12) ; inhalation (12) ;dermal (12)
Mechanism of ToxicityHexane's toxicity is caused by it neurotoxic metabolite, 2,5-hexanedione. It damages the central and peripheral nervous system by causing axonal swelling and degeneration. 2,5-Hexanedione also reacts with lysine side-chain amino groups in axonal cytoskeletal proteins to form pyrroles. This results in neurofilament cross-linking and loss of function. (12)
MetabolismHexane is mainly absorbed via inhalation, as it is readily absorbed by the lungs. It is distributed throughout the body in the blood, and metabolized by mixed function oxidases in the liver to a number of metabolites. The initial reaction is oxidation by cytochrome P-450 isozymes to hexanols, predominantly 2-hexanol. Further reactions convert 2-hexanol to 2-hexanone, 2,5-hexanediol, 5-hydroxy-2-hexanone, 4,5-dihydroxy-2-hexanone and the neurotoxicant 2,5-hexanedione. Hexane metabolites are excreted in the urine, while unchanged hexane is excreted in expired air. (12)
Toxicity ValuesLD50: 28 710 mg/kg (Oral, Rat) (7) LC50: 48 000 ppm over 4 hours (Inhalation, Mouse) (11)
Lethal Dose50 grams for an adult human. (8)
Carcinogenicity (IARC Classification)Hexane is found in gasoline, which is possibly carcinogenic to humans (Group 2B). (15)
Uses/SourcesPure n-hexane is used in laboratories. Most of the n-hexane used in industry is mixed with similar chemicals called solvents. The major use for solvents containing n-hexane is to extract vegetable oils from crops such as soybeans. These solvents are also used as cleaning agents in the printing, textile, furniture, and shoemaking industries. Certain kinds of special glues used in the roofing and shoe and leather industries also contain n-hexane. Several consumer products contain n-hexane, such as gasoline, quick-drying glues used in various hobbies, and rubber cement. (12)
Minimum Risk LevelChronic Inhalation: 0.6 ppm (10)
Health EffectsHexane mainly affects the nervous system. It causes degeneration of the peripheral nervous system (and eventually the central nervous system), starting with damage to the nerve axons. Exposure to hexane may also damage the lungs and reproductive system. (13, 14)
SymptomsBreathing large amounts of hexane causes numbness in the feet and hands, followed by muscle weakness in the feet and lower legs. Continued exposure may lead to paralysis of the arms and legs. However, if removed from the exposure, recovery occurs in 6 months to a year. Inhalation of high concentrations produces first a state of mild euphoria, followed by somnolence with headaches and nausea. (12, 1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02764
HMDB IDHMDB29600
PubChem Compound ID8058
ChEMBL IDCHEMBL15939
ChemSpider ID7767
KEGG IDC11271
UniProt IDNot Available
OMIM ID
ChEBI ID29021
BioCyc IDCPD-8232
CTD IDC026385
Stitch IDn-Hexane
PDB IDHEX
ACToR ID707
Wikipedia LinkHexane
References
Synthesis Reference

Willy D. Kollmeyer, “Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile.” U.S. Patent US4225499, issued August, 1949.

MSDST3D2403.pdf
General References
  1. Meulenberg CJ, Vijverberg HP: Selective inhibition of gamma-aminobutyric acid type A receptors in human IMR-32 cells by low concentrations of toluene. Toxicology. 2003 Aug 28;190(3):243-8. [12927378 ]
  2. Rathi A, Srivastava AK, Shirwaikar A, Singh Rawat AK, Mehrotra S: Hepatoprotective potential of Fumaria indica Pugsley whole plant extracts, fractions and an isolated alkaloid protopine. Phytomedicine. 2008 Jun;15(6-7):470-7. doi: 10.1016/j.phymed.2007.11.010. Epub 2008 Mar 4. [18164606 ]
  3. Wiart C, Hannah A, Yusof M, Hamimah H, Sulaiman M: Growth inhibition of foodborne and nosocomial pathogens by aqueous fraction of bearded Argostemma (Argostemma involucratum Hemsl., Rubiaceae). J Herb Pharmacother. 2005;5(3):97-102. [16520301 ]
  4. Freitas CS, Baggio CH, Dos Santos AC, Mayer B, Twardowschy A, Luiz AP, Marcon R, Soldi C, Pizzolatti MG, Dos Santos EP, Marques MC, Santos AR: Antinociceptive properties of the hydroalcoholic extract, fractions and compounds obtained from the aerial parts of Baccharis illinita DC in mice. Basic Clin Pharmacol Toxicol. 2009 Apr;104(4):285-92. doi: 10.1111/j.1742-7843.2008.00367.x. Epub 2009 Mar 5. [19281601 ]
  5. Villena C, Vivas JM, Villar AM: Suppression of croton oil-induced rabbit corneal edema by sideritis javalambrensis. J Ethnopharmacol. 2000 Jul;71(1-2):301-5. [10904177 ]
  6. Kunle O, Okogun J, Egamana E, Emojevwe E, Shok M: Antimicrobial activity of various extracts and carvacrol from Lippia multiflora leaf extract. Phytomedicine. 2003 Jan;10(1):59-61. [12622465 ]
  7. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  8. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  10. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  11. ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for toluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  12. Wikipedia. Methanol. Last Updated 19 May 2009. [Link]
  13. Wikipedia. Hexane. Last Updated 15 June 2009. [Link]
  14. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for n-hexane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  15. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

Target Details
1. Trypsin-1
General Function:
Serine-type endopeptidase activity
Specific Function:
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates.
Gene Name:
PRSS1
Uniprot ID:
P07477
Molecular Weight:
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
2. Glycolipid transfer protein
General Function:
Lipid binding
Specific Function:
Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides.
Gene Name:
GLTP
Uniprot ID:
Q9NZD2
Molecular Weight:
23849.6 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Target Details
3. Myelin basic protein
General Function:
Structural constituent of myelin sheath
Specific Function:
The classic group of MBP isoforms (isoform 4-isoform 14) are with PLP the most abundant protein components of the myelin membrane in the CNS. They have a role in both its formation and stabilization. The smaller isoforms might have an important role in remyelination of denuded axons in multiple sclerosis. The non-classic group of MBP isoforms (isoform 1-isoform 3/Golli-MBPs) may preferentially have a role in the early developing brain long before myelination, maybe as components of transcriptional complexes, and may also be involved in signaling pathways in T-cells and neural cells. Differential splicing events combined with optional post-translational modifications give a wide spectrum of isomers, with each of them potentially having a specialized function. Induces T-cell proliferation.
Gene Name:
MBP
Uniprot ID:
P02686
Molecular Weight:
33116.855 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]
Target Details
4. Neurofilament heavy polypeptide
General Function:
Toxic substance binding
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber. NF-H has an important function in mature axons that is not subserved by the two smaller NF proteins.
Gene Name:
NEFH
Uniprot ID:
P12036
Molecular Weight:
112477.915 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. [Link]
Target Details
5. Neurofilament light polypeptide
General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFL
Uniprot ID:
P07196
Molecular Weight:
61515.95 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. [Link]
Target Details
6. Neurofilament medium polypeptide
General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFM
Uniprot ID:
P07197
Molecular Weight:
102471.425 Da
References
  1. Wikipedia. Methanol. Last Updated 19 May 2009. [Link]