Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:46 UTC |
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Update date | 2020-09-17 15:42:18 UTC |
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Primary ID | FDB011679 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Hexadecanoic acid |
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Description | Palmitic acid, also known as palmitate or C16, 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. Palmitic acid is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Palmitic 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). In humans and other mammals, 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 lipid 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 has been detected, but not quantified in, several different foods, such as sea-buckthornberries, avocado, star fruits, babassu palms, and acerola. 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 triglycerides, rendered from palm trees (species Elaeis guineensis), are 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 word’s naphthenic acid and palmitic acid. Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. |
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CAS Number | 57-10-3 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Hexyldecanoic acid | ChEBI | 1-Pentadecanecarboxylic acid | ChEBI | 16:00 | ChEBI | C16 | ChEBI | C16 Fatty acid | ChEBI | C16:0 | ChEBI | Cetylic acid | ChEBI | CH3-[CH2]14-COOH | ChEBI | FA 16:0 | ChEBI | Hexadecanoate | ChEBI | Hexadecoic acid | ChEBI | Hexadecylic acid | ChEBI | Hexaectylic acid | ChEBI | N-Hexadecanoic acid | ChEBI | N-Hexadecoic acid | ChEBI | Palmitate | ChEBI | Palmitinic acid | ChEBI | Palmitinsaeure | ChEBI | Pentadecanecarboxylic acid | ChEBI | 1-Hexyldecanoate | Generator | 1-Pentadecanecarboxylate | Generator | Cetylate | Generator | Hexadecanoic acid | Generator | Hexadecoate | Generator | Hexadecylate | Generator | Hexaectylate | Generator | N-Hexadecanoate | Generator | N-Hexadecoate | Generator | Palmitinate | Generator | Pentadecanecarboxylate | Generator | Edenor C16 | HMDB | Emersol 140 | HMDB | Emersol 143 | HMDB | Glycon p-45 | HMDB | Hexadecanoate (N-C16:0) | HMDB | Hexadecanoic acid palmitic acid | HMDB | Hydrofol | HMDB | Hydrofol acid 1690 | HMDB | Hystrene 8016 | HMDB | Hystrene 9016 | HMDB | Industrene 4516 | HMDB | Kortacid 1698 | HMDB | Loxiol ep 278 | HMDB | Lunac p 95 | HMDB | Lunac p 95KC | HMDB | Lunac p 98 | HMDB | Palmitoate | HMDB | Palmitoic acid | HMDB | PAM | HMDB | PLM | HMDB | Prifac 2960 | HMDB | Prifrac 2960 | HMDB | Pristerene 4934 | HMDB | Univol u332 | HMDB | Acid, hexadecanoic | HMDB | Acid, palmitic | HMDB | FA(16:0) | HMDB | Aethalic acid | db_source | C16 fatty acid | biospider | FEMA 2832 | db_source | Glycon P-45 | HMDB | Hexadecanoic acid (9CI) | biospider | Lunac P 95 | HMDB | Lunac P 95kc | HMDB | Lunac P 98 | HMDB | Palmitic acid | biospider | Palmitic acid, USAN | db_source |
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Predicted Properties | |
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Chemical Formula | C16H32O2 |
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IUPAC name | hexadecanoic acid |
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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) |
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InChI Key | IPCSVZSSVZVIGE-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCCCCCCCCCCCCC(O)=O |
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Average Molecular Weight | 256.4241 |
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Monoisotopic Molecular Weight | 256.240230268 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.94%; H 12.58%; O 12.48% | DFC |
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Melting Point | Mp 63-64° | DFC |
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Boiling Point | Bp15 215° | DFC |
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Experimental Water Solubility | 4e-05 mg/mL at 25 oC | ROBB,ID (1966) |
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Experimental logP | 7.17 | SANGSTER (1993) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-06xx-9100000000-7ac9cd088cb9cb9f7560 | 2014-09-20 | View Spectrum | GC-MS | Hexadecanoic acid, 1 TMS, GC-MS Spectrum | splash10-014i-0901000000-51ee83f9462d25fa4045 | Spectrum | GC-MS | Hexadecanoic acid, 1 TMS, GC-MS Spectrum | splash10-0100-9700000000-3d8b6cf4736afa482b57 | Spectrum | GC-MS | Hexadecanoic acid, 1 TMS, GC-MS Spectrum | splash10-0159-2901000000-fb423e89a78708021db1 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0abc-9110000000-6d7f0dbe5b588850b941 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-014i-0901000000-51ee83f9462d25fa4045 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0100-9700000000-3d8b6cf4736afa482b57 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0159-2901000000-fb423e89a78708021db1 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-0159-2901000000-fb423e89a78708021db1 | Spectrum | GC-MS | Hexadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-014i-1900000000-d7638a578d846871e670 | Spectrum | Predicted GC-MS | Hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9610000000-f75185fa40c090817f46 | Spectrum | Predicted GC-MS | Hexadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-022i-9440000000-7d3a81432d58729f9f98 | Spectrum | Predicted GC-MS | Hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hexadecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0a4i-0090000000-39c3a0e17432781e9760 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-0090000000-8ec1a6953701fc22ce27 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0fba-9200000000-23c995bf81d5ef609489 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0abc-9110000000-12f1884d67998fb924a5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0091010000-6922411e48d747e592b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0091000000-4f6858c1cc0f04cbabf5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0090000000-14e58eecd83ba52123c2 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0a4i-0090000000-c3f9f4d5c336137b7fcf | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0090000000-47919da3faa8e0f52bbc | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4i-0090000000-fdd9e98416da12470fe9 | 2017-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-26bb4965a56ab0e82b49 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06rj-5790000000-251700f3edf9a5af04cd | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9600000000-5b75a67e276017f221b8 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-26bb4965a56ab0e82b49 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06rj-5790000000-251700f3edf9a5af04cd | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9600000000-5b75a67e276017f221b8 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-e4a4200bd25f8fa480cc | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bti-1090000000-768a48058fc0a2d7a877 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9320000000-c9714c7ffdc804bf9323 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-e4a4200bd25f8fa480cc | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bti-1090000000-768a48058fc0a2d7a877 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9320000000-c9714c7ffdc804bf9323 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 960 |
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ChEMBL ID | CHEMBL82293 |
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KEGG Compound ID | C00249 |
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Pubchem Compound ID | 985 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15756 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03796 |
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HMDB ID | HMDB00220 |
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CRC / DFC (Dictionary of Food Compounds) ID | GXZ18-W:GXZ18-W |
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EAFUS ID | 2858 |
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Dr. Duke ID | HEXADECANOIC-ACID|PALMITIC-ACID |
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BIGG ID | 34386 |
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KNApSAcK ID | C00030479 |
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HET ID | PLM |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1009101 |
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SuperScent ID | Not Available |
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Wikipedia ID | Palmitic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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5alpha-reductase inhibitor | 50781 | An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone. | DUKE | anti alopecic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti androgenic | 35497 | A compound which inhibits or antagonises the biosynthesis or actions of androgens. | DUKE | anti fibrinolytic | | | DUKE | antioxidant | 22586 | 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 | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | hemolytic | | | DUKE | hypercholesterolemic | | | DUKE | lubricant | | | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | propecic | | | DUKE | soap | | | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Bile acid-CoA:amino acid N-acyltransferase | BAAT | Q14032 | Liver carboxylesterase 1 | CES1 | P23141 | Pancreatic triacylglycerol lipase | PNLIP | P16233 | Hepatic triacylglycerol lipase | LIPC | P11150 | Inactive pancreatic lipase-related protein 1 | PNLIPRP1 | P54315 | Patatin-like phospholipase domain-containing protein 3 | PNPLA3 | Q9NST1 | Gastric triacylglycerol lipase | LIPF | P07098 | Endothelial lipase | LIPG | Q9Y5X9 | Pancreatic lipase-related protein 2 | PNLIPRP2 | P54317 | Lipoprotein lipase | LPL | P06858 | Patatin-like phospholipase domain-containing protein 4 | PNPLA4 | P41247 | Patatin-like phospholipase domain-containing protein 2 | PNPLA2 | Q96AD5 | Pancreatic lipase-related protein 3 | PNLIPRP3 | Q17RR3 | Cholinesterase | BCHE | P06276 | Carboxylesterase 5A | CES5A | Q6NT32 | 60 kDa lysophospholipase | ASPG | Q86U10 | Fatty acid synthase | FASN | P49327 | Galactoside-binding soluble lectin 13 | LGALS13 | Q9UHV8 | Eosinophil lysophospholipase | CLC | Q05315 | Cocaine esterase | CES2 | O00748 | Acylphosphatase-2 | ACYP2 | P14621 | Acylphosphatase-1 | ACYP1 | P07311 | Aspartoacylase | ASPA | P45381 | Aspartoacylase-2 | ACY3 | Q96HD9 | Lysosomal thioesterase PPT2 | PPT2 | Q9UMR5 | Acid ceramidase | ASAH1 | Q13510 | Homeodomain-interacting protein kinase 1 | HIPK1 | Q86Z02 | Peroxisome proliferator-activated receptor gamma | PPARG | P37231 | Long-chain fatty acid transport protein 6 | SLC27A6 | Q9Y2P4 | Long-chain fatty acid transport protein 3 | SLC27A3 | Q5K4L6 | Long-chain fatty acid transport protein 4 | SLC27A4 | Q6P1M0 | Putative neutral ceramidase C | ASAH2C | P0C7U2 | Alkaline ceramidase 2 | ACER2 | Q5QJU3 | Neutral ceramidase | ASAH2 | Q9NR71 | Alkaline ceramidase 1 | ACER1 | Q8TDN7 | Neuropathy target esterase | PNPLA6 | Q8IY17 | Carboxylesterase 3 | CES3 | Q6UWW8 | S-acyl fatty acid synthase thioesterase, medium chain | OLAH | Q9NV23 | Cytosolic acyl coenzyme A thioester hydrolase | ACOT7 | O00154 | Acyl-coenzyme A thioesterase 2, mitochondrial | ACOT2 | P49753 | Acyl-coenzyme A thioesterase 4 | ACOT4 | Q8N9L9 | Acyl-coenzyme A thioesterase 8 | ACOT8 | O14734 | Acyl-coenzyme A thioesterase 1 | ACOT1 | Q86TX2 | Acyl-protein thioesterase 1 | LYPLA1 | O75608 | Acyl-protein thioesterase 2 | LYPLA2 | O95372 | Palmitoyl-protein thioesterase 1 | PPT1 | P50897 | Cytosolic acyl coenzyme A thioester hydrolase-like | ACOT7L | Q6ZUV0 | Long-chain-fatty-acid--CoA ligase ACSBG2 | ACSBG2 | Q5FVE4 | Long-chain-fatty-acid--CoA ligase ACSBG1 | ACSBG1 | Q96GR2 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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slightly waxy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fatty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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