Hexane (CHEM001992)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-06-30 20:14:11 UTC
Update Date2026-03-26 21:20:57 UTC
Accession NumberCHEM001992
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.
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant 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
ValueSource
CH3-[CH2]4-CH3ChEBI
HexanChEBI
N-HexaneChEBI
HexanesMeSH
IsohexaneMeSH
IsohexanesMeSH
N-Hexane, 2-(13)C-labeled CPDMeSH, HMDB
N-Hexane, 3-(13)C-labeled CPDMeSH, HMDB
N-Hexane, 1-(13)C-labeled CPDMeSH, HMDB
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 KeyVLKZOEOYAKHREP-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
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-8ab77db137ff0d1e75f0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-d534432d96279fe04f73Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-2c1489cf6d4c005a89aeSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-82853202ddc92c8709aeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-8ab77db137ff0d1e75f0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-d534432d96279fe04f73Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-054o-9000000000-2c1489cf6d4c005a89aeSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-82853202ddc92c8709aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0573-9000000000-a5e2bfa74b29082bd5a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-318ef636384b005bc4beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-78a07733b829adaafb09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0c842d507eb6ba1f9733Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c44d91f3b273433a3944Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-72fa4d8dca736350f1a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-05281e623da690ce94a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-f87d58adbe1279a987b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-435e3e4c3711a641d8c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2787044af46be8aa53b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2dd044301debb5ba5b0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-9000000000-eb7db8b7a784233132ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05n0-9000000000-56d8224d6aac80494040Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-3f28cfcd32d6c9e1da29Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (10) ; inhalation (10) ;dermal (10)
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. (10)
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. (10)
Toxicity ValuesLD50: 28 710 mg/kg (Oral, Rat) (13) LC50: 48 000 ppm over 4 hours (Inhalation, Mouse) (9)
Lethal Dose50 grams for an adult human. (14)
Carcinogenicity (IARC Classification)Hexane is found in gasoline, which is possibly carcinogenic to humans (Group 2B). (8)
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. (10)
Minimum Risk LevelChronic Inhalation: 0.6 ppm (7)
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. (11, 12)
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. (10, 1)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029600
FooDB IDFDB000765
Phenol Explorer IDNot Available
KNApSAcK IDC00049006
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDHEX
Wikipedia LinkHexane
Chemspider ID7767
ChEBI ID29021
PubChem Compound ID8058
Kegg Compound IDC11271
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

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

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11292478
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11684179
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11886809
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15325316
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18231777
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19229957
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19384711
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23452516
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23567114
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23620851
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23740543
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23822317
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23931182
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=7612176
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.