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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:33 UTC
Update Date2019-07-23 21:44:56 UTC
HMDB IDHMDB0031475
Secondary Accession Numbers
  • HMDB31475
Metabolite Identification
Common 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 considered to be a fatty aldehyde lipid molecule. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Heptanal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Heptanal exists in all eukaryotes, ranging from yeast to humans. Heptanal is an aldehydic, citrus, and fat tasting compound. Outside of the human body, heptanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and sweet oranges and in a lower concentration in lemons, wild carrots, and carrots. heptanal has also been detected, but not quantified in, several different foods, such as horned melons, common beets, dills, red bell peppers, and malus (crab apple). This could make heptanal a potential biomarker for the consumption of these foods. The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid ester (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):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). Heptanal is a potentially toxic compound. Heptanal has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, uremia, and nonalcoholic fatty liver disease; also heptanal has been linked to the inborn metabolic disorders including celiac disease. The compound has a flash point of 39.5 °C. The explosion range is between 1.1% by volume as the lower explosion limit (LEL) and 5.2% by volume as the upper explosion limit. Heptanal or heptanaldehyde is an alkyl aldehyde. Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol. A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal. Heptanal forms flammable vapor-air mixtures. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, which is miscible with alcohols and practically insoluble in water. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to alpha-pentylcinnamaldehyde (also called jasmine aldehyde because of the typical jasmine odor), which is mostly used in many fragrances as a cis/trans isomer mixture.
Structure
Data?1563862130
Synonyms
ValueSource
Aldehyde C-7ChEBI
EnanthalChEBI
EnanthaldehydeChEBI
Enanthic aldehydeChEBI
HeptaldehydeChEBI
HeptanaldehydeChEBI
Heptyl aldehydeChEBI
HeptylaldehydeChEBI
N-C6H13CHOChEBI
N-HeptaldehydeChEBI
N-HeptanalChEBI
N-HeptylaldehydeChEBI
OenanthalChEBI
OenanthaldehydeChEBI
Oenanthic aldehydeChEBI
OenantholChEBI
1-HeptaldehydeHMDB
1-HeptanalHMDB
Aldehyde C7HMDB
EnantholeHMDB
FEMA 2540HMDB
Heptan-1-alHMDB
OenantholeHMDB
HeptanalMeSH
Chemical FormulaC7H14O
Average Molecular Weight114.1855
Monoisotopic Molecular Weight114.10446507
IUPAC Nameheptanal
Traditional Nameheptanal
CAS Registry Number111-71-7
SMILES
CCCCCCC=O
InChI Identifier
InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3
InChI KeyFXHGMKSSBGDXIY-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-43.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.25 mg/mL at 25 °CNot Available
LogPNot 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-183283cb2427145b7678Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-aedf02ade0aa5bd82d71Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a85809c1e2c6b7471781Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-d026c39b0c01ca9d12eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-721c1006ed41ad91802fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-66f451ed07dec07dc2bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9300000000-f683fbeaae9661c3375fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-62e7748838e417c074baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-242e518285d8711c88d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4900000000-2b9ed46fa89f52e6874eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-614ce9045eac88449a8aSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-781fd8622d3cd4023d6fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.45 +/- 0.10 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Female
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-11501.752 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.54 +/- 0.39 uMAdult (>18 years old)Bothuremia details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
details
FecesDetected and Quantified0-27878.613 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008048
KNApSAcK IDC00034880
Chemspider ID7838
KEGG Compound IDC14390
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeptanal
METLIN IDNot Available
PubChem Compound8130
PDB IDNot Available
ChEBI ID34787
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .