Showing Compound Card for Hexyl butyrate (CDB000080)

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Record Information
Version1.0
Created at2020-03-18 23:24:02 UTC
Updated at2020-12-07 19:07:04 UTC
CannabisDB IDCDB000080
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHexyl butyrate
DescriptionButanoic acid-hexyl ester or hexyl butyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid consisting of 6 or more carbons. Hexyl butyrate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a clear, colorless liquid obtained by the formal condensation of hexanol with butyric acid. Hexyl butyrate has a sweet, slightly waxy, fruity, apple, and apple peel aroma, with a similar green/soapy taste. Hexyl butyrate occurs naturally in many fruits and has been detected, but not quantified in apples, yellow passion fruit, roman camomiles, pears, sweet cherries, and other fruits. This could make hexyl butyrate a potential biomarker for the consumption of these foods. Hexyl butyrate is one of the main volatile chemicals released by the Tarnished plant bugs, Lygus hesperus and Lygus lineolaris when they are attacked or disturbed ( PMID: 12775153 ). Hexyl butyrate has also been found in Cannabis sativa (PMID: 6991645 , 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Hexyl butanoateChEBI
Hexyl butanoic acidGenerator
Hexyl butyric acidGenerator
1-Hexyl butyrateHMDB
Butanoic acid, hexyl esterHMDB
Butyric acid, hexyl esterHMDB
N-Hexyl butanoateHMDB
N-Hexyl butyrateHMDB
N-Hexyl N-butanoateHMDB
N-Hexyl N-butyrateHMDB
Chemical FormulaC10H20O2
Average Molecular Weight172.26
Monoisotopic Molecular Weight172.1463
IUPAC Namehexyl butanoate
Traditional Namebutanoic acid, hexyl ester
CAS Registry Number2639-63-6
SMILES
CCCCCCOC(=O)CCC
InChI Identifier
InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3
InChI KeyXAPCMTMQBXLDBB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • 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

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-78 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.83ALOGPS
logP3.28ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.72 m³·mol⁻¹ChemAxon
Polarizability21.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHexyl butyrate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c8872258839b61d390dfSpectrum
GC-MSHexyl butyrate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c8872258839b61d390dfSpectrum
Predicted GC-MSHexyl butyrate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9100000000-9f8196fd8fcb4b814812Spectrum
Predicted GC-MSHexyl butyrate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-6900000000-368fabd4b2575589195b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9200000000-27d4a37c4787bf47f7fd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000000000-22561504063c6adcb91a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-8900000000-480bd7612e20fa9239a92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9200000000-73d81bff8e0227cfce5f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-53888f5f63b2eccb81bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0076-9000000000-9c8633e250e33b093eae2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0596-9000000000-8750a7c084310c2d0b792021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-22625670baa9b44593002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c88e28e333946d3bdfd32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-c10c5926a9899a63e0202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9000000000-5bfd33ac1f466ca55d492021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033620
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011708
KNApSAcK IDC00035702
Chemspider ID16570
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17525
PDB IDNot Available
ChEBI ID87559
References
General References
  1. Wardle AR, Borden JH, Pierce HD Jr, Gries R: Volatile compounds released by disturbed and calm adults of the tarnished plant bug, Lygus lineolaris. J Chem Ecol. 2003 Apr;29(4):931-44. doi: 10.1023/a:1022987901330. [PubMed:12775153 ]
  2. 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 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]