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Pentadecanoic acid (FDB010033)

Record Information
Version1.0
Creation date2010-04-08 22:08:55 UTC
Update date2019-11-26 03:03:35 UTC
Primary IDFDB010033
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePentadecanoic acid
DescriptionA fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05% of milk fat and 0.43% 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; PMID 11238766). Pentadecanoic acid is found in many foods, some of which are common bean, coriander, pepper (c. annuum), and hamburger.
CAS Number1002-84-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00033 g/LALOGPS
logP6.65ALOGPS
logP5.81ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity72.48 m³·mol⁻¹ChemAxon
Polarizability32.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H30O2
IUPAC namepentadecanoic acid
InChI IdentifierInChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)
InChI KeyWQEPLUUGTLDZJY-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCCCCCCCC(O)=O
Average Molecular Weight242.3975
Monoisotopic Molecular Weight242.224580204
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

Industrial application:

Biological role:

Foods
  • Dairy products
    • Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point52.3 oC
    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)splash10-06xx-9100000000-5bd17e6ee11dac1f2a7f2014-09-20View Spectrum
    GC-MSPentadecanoic acid, 1 TMS, GC-MS Spectrumsplash10-015a-2910000000-7f0113961bc4f281b68dSpectrum
    GC-MSPentadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-015a-2910000000-7f0113961bc4f281b68dSpectrum
    GC-MSPentadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-d69aa674fba2ef153294Spectrum
    Predicted GC-MSPentadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9700000000-5fdb791c98a3d1afb3f2Spectrum
    Predicted GC-MSPentadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ds-9440000000-c48712b46200e1d92783Spectrum
    Predicted GC-MSPentadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSPentadecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a92017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a92017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0900000000-6ec01ce9b8fdc68d94a92017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0090000000-e497b3530081726e5ced2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0006-0090000000-15d18c0525685af6dade2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0090000000-72b33052a241e98e015e2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d592017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0090000000-e497b3530081726e5ced2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0090000000-15d18c0525685af6dade2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0090000000-72b33052a241e98e015e2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-1416cf4e0892e7961cf52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9100000000-7afbfa184267e53ce7242021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9550000000-66ce9961a17feae488d92021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066r-9000000000-d53184bd1b3b6d6a3eb52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0090000000-cb5c25c7dcdbbb67eb602021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0090000000-30f81c19c47194f754c52021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052f-9100000000-250dbe37e10809fe36162021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-bf26bddfb84b56f5d5ef2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0290000000-e7342714318939c2be522016-06-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-4930000000-0b5a7be5eba92f8945172016-06-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-4a20037c0dd6bfa5cd452016-06-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-af3122f573a9dcce90402016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-1590000000-76597eec59d238b7eb312016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-5852258bf4f39de4722e2016-08-03View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 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
    ChemSpider ID13249
    ChEMBL IDCHEMBL460025
    KEGG Compound IDC16537
    Pubchem Compound ID13849
    Pubchem Substance IDNot Available
    ChEBI ID42504
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB00826
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS ID2893
    Dr. Duke IDPENTADECANOIC-ACID
    BIGG ID215864
    KNApSAcK IDC00007423
    HET IDF15
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1272411
    SuperScent IDNot Available
    Wikipedia IDNot Available
    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
    Flavours
    FlavorCitations
    waxy
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    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).
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — 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.