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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:59:09 UTC
NP-MRD IDNP0001484
Secondary Accession NumbersNone
Natural Product Identification
Common NamePentadecanoic acid
DescriptionPentadecanoic acid, also known as pentadecylic acid or C15:0, 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. Pentadecanoic acid (its ester is called pentadecanoate) is a saturated fatty acid that has 15 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. Pentadecanoic acid is found in plants and ruminants. Many "odd" length long-chain fatty acids, such as pentadecanoic acid, are derived from the consumption of cattle fats (milk and meat). Pentadecanoic acid constitutes 1.05% Of milk fat and 0.43% Of ruminant meat fat. The content of pentadecanoic 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 ).
Structure
Thumb
Synonyms
ValueSource
15:00ChEBI
C15ChEBI
C15:0ChEBI
N-Pentadecanoic acidChEBI
Pentadecylic acidChEBI
N-PentadecanoateGenerator
PentadecylateGenerator
PentadecanoateGenerator
N-PentadecylateHMDB
N-Pentadecylic acidHMDB
PentadecyclateHMDB
Pentadecyclic acidHMDB
FA(15:0)HMDB
14FAHMDB
Pentadecanoic acidMeSH
Chemical FormulaC15H30O2
Average Mass242.3975 Da
Monoisotopic Mass242.22458 Da
IUPAC Namepentadecanoic acid
Traditional Namepentadecanoic acid
CAS Registry Number1002-84-2
SMILES
CCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Allium cepa L.FooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
AmaranthusFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Armoracia rusticanaFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Belone beloneFooDB
Bertholletia excelsaFooDB
Beta vulgaris ssp. ciclaFooDB
Bos taurusFooDB
BrachyuraFooDB
Brassica hirtaKNApSAcK Database
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
Cantharellus cibariusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
CarideaFooDB
Carthamus tinctoriusFooDB
Carya illinoinensisFooDB
CastaneaFooDB
CervidaeFooDB
Chamaemelum nobileKNApSAcK Database
Chenopodium quinoaFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbidaeFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Crassostrea virginicaFooDB
Cucumis meloFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cynara scolymusFooDB
Daucus carota ssp. sativusFooDB
DioscoreaFooDB
DiospyrosFooDB
ElaeisFooDB
Elettaria cardamomumFooDB
EngraulidaeFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Esox luciusFooDB
EucheumaFooDB
Fagopyrum esculentumFooDB
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
GastropodaFooDB
Glycine maxFooDB
GossypiumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Ictalurus punctatusFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans nigra L.FooDB
Lactuca sativaFooDB
Lagopus mutaFooDB
Lens culinarisFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
MalusFooDB
Malus pumilaFooDB
Mandragora autumnalisKNApSAcK Database
Mangifera indicaFooDB
Manihot esculentaFooDB
Matricaria chamomillaKNApSAcK Database
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Musa x paradisiacaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Nuphar luteaFooDB
Octopus vulgarisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Ovis ariesFooDB
Pandanus conoideus LamKNApSAcK Database
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
PerciformesFooDB
Persea americanaFooDB
Petroselinum crispumFooDB
Phagnalon sordidumKNApSAcK Database
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
PinusFooDB
Pinus sibiricaKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Polygonum minusKNApSAcK Database
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Psidium guajavaFooDB
Punica granatumFooDB
Pyrus communisFooDB
RanidaeFooDB
Raphanus sativus var. longipinnatusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rumex acetosaFooDB
Saccharina japonicaFooDB
Salmo salarFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Santalum albumKNApSAcK Database
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
SiluriformesFooDB
Sinapis albaFooDB
Solanum lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumKNApSAcK Database
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
ThunnusFooDB
Thunnus albacaresFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
VacciniumFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
Vigna angularisFooDB
Vigna radiataFooDB
VitisFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
Species Where Detected
Species NameSourceReference
Ganoderma lucidumKNApSAcK Database
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52.3 °CNot Available
Boiling Point257.00 °C. @ 100.00 mm HgThe Good Scents Company Information System
Water Solubility12 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP6.301 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00033 g/LALOGPS
logP10(6.65) g/LALOGPS
logP10(5.81) g/LChemAxon
logS10(-5.9) g/LALOGPS
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
HMDB IDHMDB0000826
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010033
KNApSAcK IDC00007423
Chemspider ID13249
KEGG Compound IDC16537
BioCyc IDNot Available
BiGG ID215864
Wikipedia LinkPentadecanoic_acid
METLIN ID5789
PubChem Compound13849
PDB IDNot Available
ChEBI ID42504
Good Scents IDrw1272411
References
General References
  1. Matsuo S, Nakamura Y, Nakae I, Matsumoto T, Takada M, Murata K, Horie M: Scintigraphic evaluation of cardiac metabolism in multicentric Castleman's disease. Intern Med. 2004 Jun;43(6):490-2. [PubMed:15283185 ]
  2. Nanasato M, Hirayama H, Ando A, Isobe S, Nonokawa M, Kinoshita Y, Nanbu I, Yokota M, Murohara T: Incremental predictive value of myocardial scintigraphy with 123I-BMIPP in patients with acute myocardial infarction treated with primary percutaneous coronary intervention. Eur J Nucl Med Mol Imaging. 2004 Nov;31(11):1512-21. Epub 2004 Jul 1. [PubMed:15232655 ]
  3. Jong MC, Voshol PJ, Muurling M, Dahlmans VE, Romijn JA, Pijl H, Havekes LM: Protection from obesity and insulin resistance in mice overexpressing human apolipoprotein C1. Diabetes. 2001 Dec;50(12):2779-85. [PubMed:11723061 ]
  4. Seki H, Toyama T, Higuchi K, Kasama S, Ueda T, Seki R, Hatori T, Endo K, Kurabayashi M: Prediction of functional improvement of ischemic myocardium with (123I-BMIPP SPECT and 99mTc-tetrofosmin SPECT imaging: a study of patients with large acute myocardial infarction and receiving revascularization therapy. Circ J. 2005 Mar;69(3):311-9. [PubMed:15731537 ]
  5. Akutsu Y, Kodama Y, Nishimura H, Kinohira Y, Li HL, Yamanaka H, Kayano H, Hamazaki Y, Shinozuka A, Katagiri T: Contractile reserve, thallium-201 reverse redistribution and mismatch between perfusion and metabolism in reperfused infarct-related myocardium with delayed and incomplete functional recovery. Jpn Heart J. 2004 Sep;45(5):739-48. [PubMed:15557715 ]
  6. Tani T, Teragaki M, Watanabe H, Muro T, Yamagishi H, Akioka K, Yoshiyama M, Takeuchi K, Yoshikawa J: Detecting viable myocardium and predicting functional improvement: comparisons of positron emission tomography, rest-redistribution thallium-201 single-photon emission computed tomography (SPECT), exercise thallium-201 reinjection SPECT, I-123 BMIPP SPECT and dobutamine stress echocardiography. Circ J. 2004 Oct;68(10):950-7. [PubMed:15459470 ]
  7. Bauwens K, Jacobi CA, Gellert K, Aurisch R, Zieren HU: [Diagnosis and therapy of postoperative chyloperitoneum]. Chirurg. 1996 Jun;67(6):658-60. [PubMed:8767101 ]
  8. Wolk A, Vessby B, Ljung H, Barrefors P: Evaluation of a biological marker of dairy fat intake. Am J Clin Nutr. 1998 Aug;68(2):291-5. [PubMed:9701185 ]
  9. Wolk A, Furuheim M, Vessby B: Fatty acid composition of adipose tissue and serum lipids are valid biological markers of dairy fat intake in men. J Nutr. 2001 Mar;131(3):828-33. [PubMed:11238766 ]