Showing Compound Card for Octacosanoic acid (CDB005782)

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Record Information
Version1.0
Created at2020-04-27 16:56:03 UTC
Updated at2021-01-04 18:49:16 UTC
CannabisDB IDCDB005782
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOctacosanoic acid
DescriptionOctacosanoic acid, also known as Montanic acid is a 28-carbon, long-chain unsaturated fatty acid. It belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Octacosanoic acid exists as a white solid and is a very hydrophobic molecule that is practically insoluble in water. Octacosanoic acid is mainly found in montan wax, beeswax and Chinese wax. Montan wax is a hard wax normally obtained by solvent extraction of certain types of lignite or brown coal. Montan wax is used for making car and shoe polishes, paints, phonograph records, and as a lubricant for molding paper and plastics. About a third of the world’s total production of montan wax is used in car polish. Formerly, montan wax’s main use was making carbon paper. Montanic acid is found in many living organisms, ranging from plants, to insects to mammals. It has even been found in the human brain and several visceral organs (PMID: 2474624 ). In the body, octacosanoic acid is formed from octacosanol via beta-oxidation (PMID: 15847942 ). Octacosanoic acid has also been detected in a number of plants and foods including sugar-cane (Saccharum officinarum L.) wax, chickweed, box-holly, horseradish tree and potato leaves (white, yellow and Irish). Octacosanoic acid has been shown to inhibit platelet aggregation that was induced by the addition of agonists to platelet-rich plasma (PRP) of rats, guinea pigs, and healthy human volunteers (PMID: 5099499 ). Octacosanoic acid is one of several acidic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octacosanoic acidChEBI
CH3-[CH2]26-COOHChEBI
Montanic acidChEBI
N-Octacosanoic acidChEBI
N-Octaeicosanoic acidChEBI
OctacosancarbonsaeureChEBI
OctacosansaeureChEBI
Octacosoic acidChEBI
Octaeicosanoic acidChEBI
1-OctacosanoateGenerator
MontanateGenerator
N-OctacosanoateGenerator
N-OctaeicosanoateGenerator
OctacosoateGenerator
OctaeicosanoateGenerator
OctacosanoateGenerator
Octacosanoic acid, 1-2 calcium saltMeSH, HMDB
Octacosanoic acidMeSH
Chemical FormulaC28H56O2
Average Molecular Weight424.74
Monoisotopic Molecular Weight424.428
IUPAC Nameoctacosanoic acid
Traditional Nameoctacosanoic acid
CAS Registry Number506-48-9
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C28H56O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28(29)30/h2-27H2,1H3,(H,29,30)
InChI KeyUTOPWMOLSKOLTQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.11ALOGPS
logP11.59ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity132.3 m³·mol⁻¹ChemAxon
Polarizability60.17 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)splash10-05fu-9200100000-a1e6c74a1e455906fd842014-09-20View Spectrum
GC-MSOctacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-015a-1900000000-58c72f07b64a0561338dSpectrum
GC-MSOctacosanoic acid, 1 TMS, GC-MS Spectrumsplash10-0159-3900100000-34225aef9330c47437c0Spectrum
GC-MSOctacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-015a-1900000000-58c72f07b64a0561338dSpectrum
GC-MSOctacosanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-3900100000-34225aef9330c47437c0Spectrum
Predicted GC-MSOctacosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7970000000-c94a43bb5bc46c5071ccSpectrum
Predicted GC-MSOctacosanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g0-9550000000-1dbd0ba0052b40b0cb0cSpectrum
Predicted GC-MSOctacosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0020900000-38ac2a13b58f10f626f72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002b-0942700000-00dc2499f3a7191748fb2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00r2-8900000000-a826aa016c3aee7f31642012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0002900000-5053554af4cc5fc398352017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-3449400000-423526b92fd641c6bf0f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-7974000000-400dfc77ba97ac62ae002017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-aaf485cd3e6ba25073192017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-1003900000-b15c91e2c70889b2f2092017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9113000000-2b4dc4a33e559f5501312017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-3002900000-b5c62f7b0c138068c4ba2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9027600000-dda5ed1ff49b80af804a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9010000000-2badc125175359e5b85b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-b9024a8d18f6acb5ce372021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1000900000-0508eeb1764771afaf8a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9001100000-51b30ca86b20536752de2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002348
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007128
KNApSAcK IDC00051638
Chemspider ID10038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMontanic_acid
METLIN ID6638
PubChem Compound10470
PDB IDNot Available
ChEBI ID31001
References
General References
  1. Molzer B, Kainz-Korschinsky M, Sundt-Heller R, Bernheimer H: Phytanic acid and very long chain fatty acids in genetic peroxisomal disorders. J Clin Chem Clin Biochem. 1989 May;27(5):309-14. [PubMed:2474624 ]
  2. Menendez R, Marrero D, Mas R, Fernandez I, Gonzalez L, Gonzalez RM: In vitro and in vivo study of octacosanol metabolism. Arch Med Res. 2005 Mar-Apr;36(2):113-9. doi: 10.1016/j.arcmed.2004.12.006. [PubMed:15847942 ]
  3. Lankin VZ, Sadovnikova IP: [Simple quantitative method of direct transesterification of higher fatty acid in biological samples]. Vopr Med Khim. 1971 May-Jun;17(3):331-5. [PubMed:5099499 ]