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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:53 UTC
NP-MRD IDNP0000371
Secondary Accession NumbersNone
Natural Product Identification
Common NamePalmitic acid
DescriptionPalmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126 ), And it is a major, but highly variable, lipid component of human breast milk (PMID: 352132 ). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.
Structure
Thumb
Synonyms
ValueSource
1-Hexyldecanoic acidChEBI
1-Pentadecanecarboxylic acidChEBI
16:00ChEBI
C16ChEBI
C16 Fatty acidChEBI
C16:0ChEBI
Cetylic acidChEBI
CH3-[CH2]14-COOHChEBI
FA 16:0ChEBI
HexadecanoateChEBI
Hexadecoic acidChEBI
Hexadecylic acidChEBI
Hexaectylic acidChEBI
N-Hexadecanoic acidChEBI
N-Hexadecoic acidChEBI
PalmitateChEBI
Palmitinic acidChEBI
PalmitinsaeureChEBI
Pentadecanecarboxylic acidChEBI
1-HexyldecanoateGenerator
1-PentadecanecarboxylateGenerator
CetylateGenerator
Hexadecanoic acidGenerator
HexadecoateGenerator
HexadecylateGenerator
HexaectylateGenerator
N-HexadecanoateGenerator
N-HexadecoateGenerator
PalmitinateGenerator
PentadecanecarboxylateGenerator
Edenor C16HMDB
Emersol 140HMDB
Emersol 143HMDB
Glycon p-45HMDB
Hexadecanoate (N-C16:0)HMDB
Hexadecanoic acid palmitic acidHMDB
HydrofolHMDB
Hydrofol acid 1690HMDB
Hystrene 8016HMDB
Hystrene 9016HMDB
Industrene 4516HMDB
Kortacid 1698HMDB
Loxiol ep 278HMDB
Lunac p 95HMDB
Lunac p 95KCHMDB
Lunac p 98HMDB
PalmitoateHMDB
Palmitoic acidHMDB
PAMHMDB
PLMHMDB
Prifac 2960HMDB
Prifrac 2960HMDB
Pristerene 4934HMDB
Univol u332HMDB
Acid, hexadecanoicHMDB
Acid, palmiticHMDB
FA(16:0)HMDB
Chemical FormulaC16H32O2
Average Mass256.4241 Da
Monoisotopic Mass256.24023 Da
IUPAC Namehexadecanoic acid
Traditional Namepalmitic acid
CAS Registry Number57-10-3
SMILES
CCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
InChI KeyIPCSVZSSVZVIGE-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Acca sellowianaKNApSAcK Database
Acorus calanus L.KNApSAcK Database
Aesculus hippocastanum L.KNApSAcK Database
Ailanthus altissimaKNApSAcK Database
Aleurites moluccanaKNApSAcK Database
Aleurites montanaKNApSAcK Database
Anisomeles indicaKNApSAcK Database
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Averrhoa carambolaKNApSAcK Database
Bauhinia tomentosaKNApSAcK Database
Boehmeria holosericeaKNApSAcK Database
Boehmeria tricuspisKNApSAcK Database
Brassica hirtaKNApSAcK Database
Brassica oleracea var. italicaKNApSAcK Database
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Carica papayaKNApSAcK Database
Cinnamomum subavenium MIQ.KNApSAcK Database
Cinnamomum tenuifoliumKNApSAcK Database
Cistus creticusKNApSAcK Database
Citrus sinensisKNApSAcK Database
Clitoria ternataKNApSAcK Database
Curcuma manggaKNApSAcK Database
Diascia cordataKNApSAcK Database
Diascia integerrimaKNApSAcK Database
Diascia megathuraKNApSAcK Database
Diascia purpureaKNApSAcK Database
Diascia vigilisKNApSAcK Database
Dioscorea oppositaKNApSAcK Database
Drymaria cordataKNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Frullania monoceraKNApSAcK Database
Frullania solanderianaKNApSAcK Database
Haplophyllum acutifoliumKNApSAcK Database
Henriettella fascicularisKNApSAcK Database
Houttuynia cordata Thunb.KNApSAcK Database
Hydrangea chinensisKNApSAcK Database
Isatis tinctoriaKNApSAcK Database
Jasminum auriculatumKNApSAcK Database
Jatropha curcusKNApSAcK Database
Justicia heterocarpa T.ANDERSKNApSAcK Database
Lagerstroemia thomsonilKNApSAcK Database
Laminaria japonicaKNApSAcK Database
Lantana camaraKNApSAcK Database
Lupinus albusKNApSAcK Database
Mandragora autumnalisKNApSAcK Database
Mangifera indicaKNApSAcK Database
Matricaria chamomillaKNApSAcK Database
Murraya paniculataKNApSAcK Database
Nymphaea albaKNApSAcK Database
Oryza sativa cv. HeugjinjubyeoKNApSAcK Database
Panax ginsengKNApSAcK Database
Petasites albusKNApSAcK Database
Phagnalon sordidumKNApSAcK Database
Pinellia pedatisectaKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Piper obliquumKNApSAcK Database
Polygonum minusKNApSAcK Database
Prunus aviumKNApSAcK Database
Punica granatumKNApSAcK Database
Rhaponticum carthamoidesKNApSAcK Database
Rhodiola rosea L.KNApSAcK Database
Santalum albumKNApSAcK Database
Saxifraga stolonifera Meerb.KNApSAcK Database
Senecio vulgarisKNApSAcK Database
Silybum marianumKNApSAcK Database
Solanum tuberosumKNApSAcK Database
Tanacetum macrophyllumKNApSAcK Database
Thymus capitatusKNApSAcK Database
Tilia cordata Mill.KNApSAcK Database
Tipuana tipuKNApSAcK Database
Triticum aestivumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Skin)KNApSAcK Database
Sargassum crassifolium J.AsgardhKNApSAcK 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 Point61.8 °CNot Available
Boiling Point204.00 to 220.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.0e-05 mg/mLNot Available
LogP7.17Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility0.00041 g/LALOGPS
logP7.23ALOGPS
logP6.26ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.08 m³·mol⁻¹ChemAxon
Polarizability34.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000220
DrugBank IDDB03796
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031084
KNApSAcK IDC00001233
Chemspider ID960
KEGG Compound IDC00249
BioCyc IDPALMITATE
BiGG ID34386
Wikipedia LinkPalmitic_acid
METLIN ID187
PubChem Compound985
PDB IDNot Available
ChEBI ID15756
Good Scents IDrw1009101
References
General References
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  2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  3. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  4. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [PubMed:16351159 ]
  5. Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
  6. Lloyd B, Halter RJ, Kuchan MJ, Baggs GE, Ryan AS, Masor ML: Formula tolerance in postbreastfed and exclusively formula-fed infants. Pediatrics. 1999 Jan;103(1):E7. [PubMed:9917487 ]
  7. Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
  8. Mensink RP: Nutrition in lipid disorders. Ther Umsch. 1995 Aug;52(8):509-14. [PubMed:7676394 ]
  9. Mesiha MS, Ponnapula S, Plakogiannis F: Oral absorption of insulin encapsulated in artificial chyles of bile salts, palmitic acid and alpha-tocopherol dispersions. Int J Pharm. 2002 Dec 5;249(1-2):1-5. [PubMed:12433429 ]
  10. Dubinin DM, Naidina VP, Zaloguev SN: [Evaluation of human skin function in a sealed room by a chromatographic method]. Kosm Biol Aviakosm Med. 1985 Nov-Dec;19(6):69-73. [PubMed:2868151 ]
  11. Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
  12. Otsuki T, Oku M: [A study on the effect of cortisol and progesterone on cytosolic arachidonic and palmitic acid concentrations in cultured human myometrial cells]. Nihon Sanka Fujinka Gakkai Zasshi. 1995 Jun;47(6):531-8. [PubMed:7608616 ]
  13. Draisey TF, Gagneja GL, Thibert RJ: Pulmonary surfactant and amniotic fluid insulin. Obstet Gynecol. 1977 Aug;50(2):197-9. [PubMed:577607 ]
  14. Florentin E, Athias A, Lagrost L: Modulation of the activity of the human cholesteryl ester transfer protein by carboxylated derivatives. Evidence for 13-cis-retinoic acid as a potent activator of the protein's activity in plasma. Eur J Biochem. 1996 Sep 15;240(3):699-706. [PubMed:8856073 ]
  15. Urien S, Morin D, Tillement JP: Effect of alpha-1-acid glycoprotein, albumin and palmitic acid on the brain and salivary gland extraction of warfarin in rats. J Pharmacol Exp Ther. 1989 Feb;248(2):781-5. [PubMed:2918479 ]
  16. Wang J, Zhu F, Pan G: [Diagnosis of chylous ascites with oral administration of 13C-palmitic acid]. Zhonghua Nei Ke Za Zhi. 1996 Jun;35(6):382-4. [PubMed:9387625 ]
  17. Ip MP, Draisey TF, Thibert RJ, Gagneja GL, Jasey GM: Fetal lung maturity, as assessed by gas-liquid chromatographic determination of phospholipid palmitic acid in amniotic fluid. Clin Chem. 1977 Jan;23(1):35-40. [PubMed:832370 ]
  18. Messner T, Erkstam UB, Gustafsson IB, Nilsson SB, Vessby B: Diet and dietary markers in Kiruna and Uppsala, Sweden--a comparison. Int J Circumpolar Health. 1997 Apr;56(1-2):21-9. [PubMed:9300843 ]
  19. Vessby B, Tengblad S, Lithell H: Insulin sensitivity is related to the fatty acid composition of serum lipids and skeletal muscle phospholipids in 70-year-old men. Diabetologia. 1994 Oct;37(10):1044-50. [PubMed:7851683 ]
  20. Liau YH, Slomiany BL, Slomiany A, Piasek A, Palmer D, Rosenthal WS: Identification of mucus glycoprotein fatty acyltransferase activity in human gastric mucosa. Digestion. 1985;32(1):57-62. [PubMed:4018446 ]
  21. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  22. KINGSBURY KJ, PAUL S, CROSSLEY A, MORGAN DM: The fatty acid composition of human depot fat. Biochem J. 1961 Mar;78:541-50. [PubMed:13756126 ]
  23. Jensen RG, Hagerty MM, McMahon KE: Lipids of human milk and infant formulas: a review. Am J Clin Nutr. 1978 Jun;31(6):990-1016. doi: 10.1093/ajcn/31.6.990. [PubMed:352132 ]