Showing Compound Card for Hentriacontane (CDB000355)

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Record Information
Version1.0
Created at2020-03-19 00:32:37 UTC
Updated at2020-12-07 19:07:23 UTC
CannabisDB IDCDB000355
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHentriacontane
DescriptionHentriacontane, also known as untriacontane, is a long-chain hydrocarbon containing 31 carbons. It 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. Thus, hentriacontane is considered to be a hydrocarbon lipid molecule. Hentriacontane is a very hydrophobic molecule, insoluble in water, and fully neutral. It exists as a clear, waxy solid. Hentriacontane is found naturally in a number of common plants and foods including the common pea, gum arabic (acacia senegal), grapes, watermelons, papaya, coconuts, and sunflowers. It also comprises about 8-9% of beeswax. Hentriacontane has also been found to be a major component of Candelilla wax. Candelilla wax is a wax derived from the leaves of the small Candelilla shrub native to northern Mexico and the southwestern United States. The Candelilla shrub is a member of the Euphorbia plant genus, from the family Euphorbiaceae. Candelilla wax is used as a food additive and is used as a glazing agent. It also used in cosmetic industry, as a component of lip balms and lotion bars. One of its major uses is as a binder for chewing gums. Candelilla wax can be used as a substitute for carnauba wax and beeswax. It is also used for making varnish. Hentriacontane is one of many alkanes that are known in cannabis plants (PMID: 6991645 ). Hentriacontane is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). Hentriacontane has been shown to have anti-inflammatory effects. In particular, hentriacontane ameliorates the expression of inflammatory mediators (TNF-α, IL-6, PGE(2), COX-2 and iNOS) and the activation of NF-κB and caspase-1 in LPS-stimulated peritoneal macrophages (PMID: 21394806 ). Hentriacontane is also thought to have antitumor and antimicrobial activities (PMID: 28549290 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CH3-[CH2]29-CH3ChEBI
HentriacontanChEBI
N-HentriacontaneChEBI
Chemical FormulaC31H64
Average Molecular Weight436.84
Monoisotopic Molecular Weight436.5008
IUPAC Namehentriacontane
Traditional Namehentriacontane
CAS Registry Number630-04-6
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C31H64/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-31H2,1-2H3
InChI KeyIUJAMGNYPWYUPM-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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point67.9 °CNot Available
Boiling Point458 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP11.01ALOGPS
logP14.25ChemAxon
logS-8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity144.43 m³·mol⁻¹ChemAxon
Polarizability65.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-9100000000-e2e1b3c01c61d96faf792015-03-01View Spectrum
GC-MSHentriacontane, non-derivatized, GC-MS Spectrumsplash10-00dr-9400000000-0110d9d07cbae4ff1cbaSpectrum
GC-MSHentriacontane, non-derivatized, GC-MS Spectrumsplash10-00dr-9400000000-0110d9d07cbae4ff1cbaSpectrum
Predicted GC-MSHentriacontane, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0076-9877000000-d212ea79de06006da97cSpectrum
Predicted GC-MSHentriacontane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHentriacontane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-9c9a5dada8c1882393682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6888900000-ae7041af8be0733916732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-8689000000-53058733d9f596c79c4d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-212b65f9b9745ef447fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-76a2da826326b0928a332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-4669500000-f666714c0cb703ae23e22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2000900000-025f489cf7bd87ef5fdf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-9001300000-8f20c95e0fcf2e42fdaa2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-c23bf4669608ebce00902021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-0032af527bd01e0b58332021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-0032af527bd01e0b58332021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3207900000-a44c1991b0ebf3c6e5642021-09-24View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0030092
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001480
KNApSAcK IDC00001250
Chemspider ID11904
KEGG Compound IDC08376
BioCyc IDCPD-7937
BiGG IDNot Available
Wikipedia LinkHentriacontane
METLIN IDNot Available
PubChem Compound12410
PDB IDNot Available
ChEBI ID5659
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Kim SJ, Chung WS, Kim SS, Ko SG, Um JY: Antiinflammatory effect of Oldenlandia diffusa and its constituent, hentriacontane, through suppression of caspase-1 activation in mouse peritoneal macrophages. Phytother Res. 2011 Oct;25(10):1537-46. doi: 10.1002/ptr.3443. Epub 2011 Mar 11. [PubMed:21394806 ]
  3. Khajuria V, Gupta S, Sharma N, Kumar A, Lone NA, Khullar M, Dutt P, Sharma PR, Bhagat A, Ahmed Z: Anti-inflammatory potential of hentriacontane in LPS stimulated RAW 264.7 cells and mice model. Biomed Pharmacother. 2017 Aug;92:175-186. doi: 10.1016/j.biopha.2017.05.063. Epub 2017 May 23. [PubMed:28549290 ]