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Heptanal (FDB008048)

Record Information
Version1.0
Creation date2010-04-08 22:07:54 UTC
Update date2020-09-17 15:30:13 UTC
Primary IDFDB008048
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHeptanal
DescriptionHeptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is a fatty aldehyde lipid molecule. It is an endogenous aldehyde resulting from membrane lipid oxidation. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor with an aldehydic, citrus, and fat taste. It is miscible with alcohols and practically insoluble in water. Heptanal is very hydrophobic and is relatively neutral. Heptanal exists in all eukaryotes, from yeast to humans. It is found in highest concentrations in corns, tea, and sweet oranges and in a lower concentrations in lemons, wild carrots, and carrots. Heptanal was detected in horned melons, common beets, dills, red bell peppers, and malus (crab apple) making it a potential biomarker for the consumption of these foods. Heptanal was distilled from castor oil and first described in 1878 ( https://pubs.rsc.org/en/content/articlelanding/1878/an/an878030329a#!divAbstract). Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus) ( https://www.routledge.com/Fenarolis-Handbook-of-Flavor-Ingredients/Burdock/p/book/9781420090772). Because of heptanal’s strong fruity odor, it is used as precursor to components in perfumes and lubricants ( https://doi.org/10.1002/14356007.a01_321.pub2). For example, heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to alpha-pentylcinnamaldehyde, which is also called jasmine aldehyde (because of the typical jasmine odor). This jasmine aldehyde has been used in fragrances. Heptanal may be a potential biomarker of lung cancer as it was found in the blood of lung cancer patients (PMID:28366212).
CAS Number111-71-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP2.59ALOGPS
logP2.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.75 m³·mol⁻¹ChemAxon
Polarizability14.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H14O
IUPAC nameheptanal
InChI IdentifierInChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3
InChI KeyFXHGMKSSBGDXIY-UHFFFAOYSA-N
Isomeric SMILESCCCCCCC=O
Average Molecular Weight114.1855
Monoisotopic Molecular Weight114.10446507
Classification
Description Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.63%; H 12.36%; O 14.01%DFC
Melting PointMp -43.3°DFC
Boiling PointBp30 59.6°DFC
Experimental Water Solubility1.25 mg/mL at 25 oCSUZUKI,T (1991)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd20 0.82DFC
Refractive Indexn20D 1.4133DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-781fd8622d3cd4023d6f2014-09-20View Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSHeptanal, non-derivatized, GC-MS Spectrumsplash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
Predicted GC-MSHeptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056u-9000000000-721c1006ed41ad91802fSpectrum
Predicted GC-MSHeptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-66f451ed07dec07dc2bd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9300000000-f683fbeaae9661c3375f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-62e7748838e417c074ba2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-242e518285d8711c88d32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-2b9ed46fa89f52e6874e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-614ce9045eac88449a8a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-9000000000-e5c26cac568c7e70be7f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9000000000-0497fb39284b3eae18e72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7f7db6b93b3268b348982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-87ba7764343ecec4c93f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-baad9901fa250e031cb52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-8ffddb005d2cb639ad092021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID7838
ChEMBL IDCHEMBL18104
KEGG Compound IDC14390
Pubchem Compound ID8130
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31475
CRC / DFC (Dictionary of Food Compounds) IDDBL19-A:DBL19-A
EAFUS ID1570
Dr. Duke IDHEPTANAL|HEPTAN-1-AL
BIGG IDNot Available
KNApSAcK IDC00034880
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID111-71-7
GoodScent IDrw1014291
SuperScent IDNot Available
Wikipedia IDHeptanal
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
citrus
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
rancid
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
aldehydic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wine-lee
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ozone
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).