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Heptadecanoic acid (FDB004676)

Record Information
Version1.0
Creation date2010-04-08 22:06:21 UTC
Update date2020-09-17 15:33:18 UTC
Primary IDFDB004676
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHeptadecanoic acid
DescriptionHeptadecanoic acid, also known as margaric acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Heptadecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" lengths long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products (PMID: 9701185). It is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid has pheromonic and allomonic properties for insects and reptiles. The subcaudal gland secretions of the European badger (Meles meles) and the occipital gland secretions of male bactrian camels (Camelus bactrianus) contain many pheromonic chemicals, including heptadecanoic acid, that aid in finding and selection of mates (PMID: 24414593). Heptadecanoic acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito (Culex pipiens; doi: 10.5962/bhl.title.49749). Heptadecanoic acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius; PMID 24264893) and the European viper (Vipera berus), where it is used for the identification of sexual partners (doi:10.1007/bf00579807).
CAS Number506-12-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.66ALOGPS
logP6.7ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.68 m³·mol⁻¹ChemAxon
Polarizability36.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H34O2
IUPAC nameheptadecanoic acid
InChI IdentifierInChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
InChI KeyKEMQGTRYUADPNZ-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight270.4507
Monoisotopic Molecular Weight270.255880332
Classification
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Foods
  • Dairy products
    • Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionCryst. (petrol)CCD
    Mass CompositionC 75.50%; H 12.67%; O 11.83%CCD
    Melting PointMp 62 - 63°CCD
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-05fu-9210000000-099bddb00b5e5f57a5912014-09-20View Spectrum
    GC-MSHeptadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-017i-0900000000-ebd7708ca40db1f69377Spectrum
    GC-MSHeptadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-017i-1900000000-140a09beb5b6859644fdSpectrum
    GC-MSHeptadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-017i-0900000000-ebd7708ca40db1f69377Spectrum
    GC-MSHeptadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-017i-1900000000-140a09beb5b6859644fdSpectrum
    GC-MSHeptadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-016r-0900000000-a9975b7f916df9242d31Spectrum
    Predicted GC-MSHeptadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9620000000-2e104e4843f27f81734aSpectrum
    Predicted GC-MSHeptadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bi-9350000000-8e55b03dd2c18c1e3ca7Spectrum
    Predicted GC-MSHeptadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0019000000-83d961b9674b7b1b2a652017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0019000000-83d961b9674b7b1b2a652017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-1e57778151b8b2a053622017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-1e57778151b8b2a053622017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0090000000-1e57778151b8b2a053622017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0090000000-233b71c471008bbed61b2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-94bee87e459e47f84a4d2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-1e57778151b8b2a053622017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-433ed2666c0e940781472017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014i-0900000000-1e14b3fcd14dfdf48cbd2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0uxr-0090000000-de66caaa914ba0366a3d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-233b71c471008bbed61b2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-94bee87e459e47f84a4d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-433ed2666c0e940781472017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0900000000-1e14b3fcd14dfdf48cbd2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0006-0190000000-0d9a873b65555a15a62e2020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-0390000000-c2f846ea7246884b09ed2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-0090000000-7aadc5ba2a6acb7162cf2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-1e14b3fcd14dfdf48cbd2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-3452bef1d9fd1091e3542015-09-15View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi0-4590000000-727243a3559dd7ed991f2015-09-15View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9710000000-f50bf2fb7778841f9f162015-09-15View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-98c6dcf5eaea4132deb72015-09-15View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-1090000000-e7ed55db02f1210fe7e12015-09-15View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-24fa7a34c1095502e7072015-09-15View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
    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, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
    ChemSpider ID10033
    ChEMBL IDCHEMBL1172910
    KEGG Compound IDNot Available
    Pubchem Compound ID10465
    Pubchem Substance IDNot Available
    ChEBI ID32365
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB02259
    CRC / DFC (Dictionary of Food Compounds) IDHCQ70-H:HCQ70-H
    EAFUS IDNot Available
    Dr. Duke IDDATURIC-ACID|MARGARIC-ACID|HEPTADECANOIC-ACID
    BIGG ID215873
    KNApSAcK IDC00007426
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDHeptadecanoic_acid
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    Enzymes
    NameGene NameUniProt ID
    Liver carboxylesterase 1CES1P23141
    Pancreatic triacylglycerol lipasePNLIPP16233
    Hepatic triacylglycerol lipaseLIPCP11150
    Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
    Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
    Gastric triacylglycerol lipaseLIPFP07098
    Endothelial lipaseLIPGQ9Y5X9
    Pancreatic lipase-related protein 2PNLIPRP2P54317
    Lipoprotein lipaseLPLP06858
    Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
    Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
    Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
    CholinesteraseBCHEP06276
    Carboxylesterase 5ACES5AQ6NT32
    60 kDa lysophospholipaseASPGQ86U10
    Fatty acid synthaseFASNP49327
    Galactoside-binding soluble lectin 13LGALS13Q9UHV8
    Eosinophil lysophospholipaseCLCQ05315
    Cocaine esteraseCES2O00748
    Acylphosphatase-2ACYP2P14621
    Acylphosphatase-1ACYP1P07311
    AspartoacylaseASPAP45381
    Aspartoacylase-2ACY3Q96HD9
    Acid ceramidaseASAH1Q13510
    Homeodomain-interacting protein kinase 1HIPK1Q86Z02
    Peroxisome proliferator-activated receptor gammaPPARGP37231
    Long-chain fatty acid transport protein 6SLC27A6Q9Y2P4
    Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
    Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
    Putative neutral ceramidase CASAH2CP0C7U2
    Alkaline ceramidase 2ACER2Q5QJU3
    Neutral ceramidaseASAH2Q9NR71
    Alkaline ceramidase 1ACER1Q8TDN7
    Neuropathy target esterasePNPLA6Q8IY17
    Carboxylesterase 3CES3Q6UWW8
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.