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{{short description|Saturated fatty acid}} |
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{{not to be confused|Caproic acid|Caprylic acid}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 443683382 |
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|Watchedfields = changed |
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| Name = Decanoic acid |
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|verifiedrevid = 450974113 |
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| ImageFile = Decanoic acid.png |
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|Name = Decanoic acid |
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| ImageSize = 220px |
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|ImageFile = Decanoic acid acsv.svg |
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| ImageName = Skeletal formula |
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|ImageSize = 200px |
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| ImageFile1 = Decanoic-acid-3D-balls.png |
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|ImageName = Skeletal formula of decanoic acid |
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| ImageSize1 = 220px |
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|ImageFile1 = Decanoic-acid-3D-balls.png |
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| ImageName1 = Ball-and-stick model |
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|ImageSize1 = 200px |
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| IUPACName = Decanoic acid |
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|ImageName1 = Ball-and-stick model of decanoic acid |
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| OtherNames = Capric acid<ref>http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=W236403|ALDRICH&N5=Product%20No.|BRAND_KEY&F=SPEC</ref><br />''n''-Capric acid<br />''n''-Decanoic acid<br />Decylic acid<br />''n''-Decylic acid<br />C10:0 (]) |
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|PIN = Decanoic acid |
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| Section1 = {{Chembox Identifiers |
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|OtherNames = Caprinic acid; Caprynic acid; Decoic acid; Decylic acid; <br/>1-Nonanecarboxylic acid; <br/>C10:0 (]) |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|Section1={{Chembox Identifiers |
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| ChEBI = 30813 |
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|IUPHAR_ligand = 5532 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| DrugBank = DB03838 |
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|ChEBI = 30813 |
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| SMILES = O=C(O)CCCCCCCCC |
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|DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|DrugBank = DB03600 |
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| ChemSpiderID = 2863 |
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|SMILES = O=C(O)CCCCCCCCC |
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| PubChem = 2969 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 2863 |
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| UNII = 4G9EDB6V73 |
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|PubChem = 2969 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| KEGG = C01571 |
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|UNII = 4G9EDB6V73 |
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| InChI = 1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
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|UNII1_Ref = {{fdacite|correct|FDA}} |
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| InChIKey = GHVNFZFCNZKVNT-UHFFFAOYAC |
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|UNII1 = 4I820XKV2A |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|UNII1_Comment = (sodium salt) |
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| ChEMBL = 107498 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = C01571 |
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| StdInChI = 1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
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|InChI = 1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GHVNFZFCNZKVNT-UHFFFAOYSA-N |
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|InChIKey = GHVNFZFCNZKVNT-UHFFFAOYAC |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| CASNo = 334-48-5 |
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|ChEMBL = 107498 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = |
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|StdInChI = 1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) |
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}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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|StdInChIKey = GHVNFZFCNZKVNT-UHFFFAOYSA-N |
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| Formula = C<sub>10</sub>H<sub>20</sub>O<sub>2</sub> |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| MolarMass = 172.26 g/mol |
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|CASNo = 334-48-5 |
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| Appearance = White crystals with strong smell |
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|CASNo1_Ref = {{cascite|correct|CAS}} |
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| Density = 0.893 g/cm<sup>3</sup>, ? |
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|CASNo1 = 1002-62-6 |
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| Solubility = immiscible |
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|CASNo1_Comment = (sodium salt) |
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| MeltingPt = 31.6 °C (304.8 K) <ref name="lexicon">{{cite journal |year=2001 |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |url=http://iupac.org/publications/pac/73/4/0685/ |doi=10.1351/pac200173040685 }}</ref> |
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|RTECS = HD9100000 |
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| BoilingPt = 269 °C (542 K) |
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| pKa = |
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|EINECS = 206-376-4 |
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}} |
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| Viscosity = |
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|Section2={{Chembox Properties |
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}} |
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|C=10 | H=20 | O=2 |
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| Section7 = {{Chembox Hazards |
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|Appearance = White crystals |
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| ExternalMSDS = |
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|Odor = Strong rancid and unpleasant<ref name=pubchem /> |
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| MainHazards = Medium toxicity<br />May cause respiratory irritation<br />May be toxic on ingestion<br /> May be toxic on skin contact |
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|Density = 0.893 g/cm<sup>3</sup> (25 °C)<ref name="sigma" /><br/> 0.8884 g/cm<sup>3</sup> (35.05 °C)<br/> 0.8773 g/cm<sup>3</sup> (50.17 °C)<ref name=edm /> |
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| RPhrases = {{R36}} {{R38}} |
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|Solubility = 0.015 g/100 mL (20 °C)<ref name="clcl" /> |
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| SPhrases = {{S24}} {{S25}} {{S26}} {{S36}} {{S37}} {{S39}} |
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|SolubleOther = Soluble in ], ], ], ], ], ]<ref name=pubchem /> |
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}} |
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|MeltingPtC = 31.6 |
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| Section8 = {{Chembox Related |
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|MeltingPt_ref = <ref name="lexicon">{{cite journal |last1=Beare-Rogers |first1=J. L. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |date=1 January 2001 |volume=73 |issue=4 |pages=685–744 |doi=10.1351/pac200173040685 |doi-access=free |s2cid=84492006}}</ref> |
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| OtherCpds = ]<br />] |
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|BoilingPtC = 268.7 |
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| Function = ]s |
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|BoilingPt_ref = <ref name="clcl" /> |
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| OtherFunctn = ]<br />] |
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|Viscosity = 4.327 cP (50 °C)<ref name=clcl>{{CRC90}}</ref><br/> 2.88 cP (70 °C)<ref name=edm /> |
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}} |
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|VaporPressure = 4.88·10<sup>−5</sup> kPa (25 °C)<ref name=pubchem /><br/> 0.1 kPa (108 °C)<ref name="clcl" /><br/> 2.03 kPa (160 °C)<ref name=nist>{{nist|name=n-Decanoic acid| id= C334485|accessdate=2014-06-15|mask=FFFF|units=SI}}</ref><ref name="sigma" /> |
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|ThermalConductivity = 0.372 W/m·K (solid)<br/> 0.141 W/m·K (liquid)<ref name=edm>{{cite book|last1 = Mezaki|first1 = Reiji|last2 = Mochizuki|first2 = Masafumi|last3 = Ogawa|first3 = Kohei|year = 2000|title = Engineering Data on Mixing|publisher = Elsevier Science B.V.|isbn = 978-0-444-82802-6|page = 278|url = https://books.google.com/books?id=6PDnxdmwlKUC&pg=PA278|edition = 1st}}</ref> |
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|LogP = 4.09<ref name="clcl" /> |
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|pKa = 4.9<ref name=pubchem>{{PubChemLink|2969}}</ref> |
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|RefractIndex = 1.4288 (40 °C)<ref name=pubchem /> |
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}} |
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|Section3={{Chembox Structure |
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| CrystalStruct = ] (−3.15 °C)<ref name=adb>{{cite journal |last1=D. Bond |first1=Andrew |title=On the crystal structures and melting point alternation of the n -alkyl carboxylic acids |journal=New Journal of Chemistry |date=2004 |volume=28 |issue=1 |pages=104–114 |doi=10.1039/B307208H }}</ref> |
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|SpaceGroup = P2<sub>1</sub>/c<ref name=adb /> |
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|LattConst_a = 23.1 Å |
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|LattConst_b = 4.973 Å |
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|LattConst_c = 9.716 Å<ref name=adb /> |
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|LattConst_beta = 91.28 |
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}} |
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|Section4={{Chembox Thermochemistry |
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|DeltaHc = 6079.3 kJ/mol<ref name=nist /> |
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|HeatCapacity = 475.59 J/mol·K<ref name=nist /> |
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|DeltaHf = −713.7 kJ/mol<ref name="clcl" /> |
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}} |
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|Section5={{Chembox Hazards |
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|ExternalSDS = |
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|MainHazards = Medium toxicity |
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|GHSPictograms = {{GHS07}}<ref name="sigma">{{Sigma-Aldrich| id= w236411|name=Decanoic acid|accessdate=2014-06-15}}</ref> |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|315|319|335}}<ref name="sigma" /> |
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|PPhrases = {{P-phrases|261|305+351+338}}<ref name="sigma" /> |
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|InhalationHazard = May cause irritation |
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|IngestionHazard = May be toxic |
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|SkinHazard = May be toxic on contact |
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|FlashPtC = 110 |
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|FlashPt_ref = <ref name="sigma" /> |
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|NFPA-H = 2 |
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|NFPA-F = 1 |
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|NFPA-R = 0 |
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|NFPA_ref = <ref name=cheml /> |
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|LD50 = 10 g/kg (rats, oral)<ref name=cheml /> |
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}} |
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|Section6={{Chembox Related |
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|OtherCompounds = ]<br />] |
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|OtherFunction_label = ]s |
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|OtherFunction = ], ] |
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}} |
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}} |
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}} |
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'''Capric acid''', also known as '''decanoic acid''' or '''decylic acid''', is a ], ] (MCFA), and ]. Its formula is {{chem2|CH3(CH2)8COOH}}. ] and ]s of decanoic acid are called '''caprates''' or '''decanoates'''. The term capric acid is derived from the Latin "''caper / capra''" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.<ref>{{cite web|url=http://wordinfo.info/unit/371|title=capri-, capr- +|access-date=2012-09-28|archive-date=2017-12-23|archive-url=https://web.archive.org/web/20171223161349/http://wordinfo.info/unit/371|url-status=live}}</ref> |
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'''Decanoic acid''', or '''capric acid''', is a saturated ]. |
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Its formula is CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COOH. ] and ]s of decanoic acid are called '''decanoates'''. The term capric acid arises from the Latin "''capric''" which pertains to goats due to their olfactory similarities.<ref>http://www.wordinfo.info/words/index/info/view_unit/371</ref> |
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==Occurrence== |
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Capric acid occurs naturally in ] and ], as well as in the ] of various mammals and to a lesser extent in other animal fats.<ref name="lexicon" /> |
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Capric acid occurs naturally in ] (about 10%) and ] (about 4%), otherwise it is uncommon in typical seed oils.<ref name=Ullmann>David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_245.pub2}}</ref> It is found in the ] of various mammals and to a lesser extent in other animal fats.<ref name="lexicon" /> |
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Two other acids are named after goats: ] (a C6:0 fatty acid) and ] (a C8:0 fatty acid). Along with capric acid, these total 15% in goat milk fat.<ref>{{cite journal |last1=Hilditch |first1=T. P. |last2=Jasperson |first2=H. |title=The component acids of milk fats of the goat, ewe and mare |journal=Biochemical Journal |date=1944 |volume=38 |issue=5 |pages=443–447 |doi=10.1042/bj0380443 |pmid=16747831 |pmc=1258125 }}</ref> |
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It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.<ref>http://www.chemicalland21.com/industrialchem/organic/CAPRIC%20ACID.htm</ref> |
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Two other acids are named after goats: ] (C6) and ] (C8). Along with decanoic acid, these total 15% in goat milk fat. |
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==Production== |
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==Production== |
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Decanoic acid can be prepared from ] of ] ], by using ] (CrO<sub>3</sub>) ] under acidic conditions in an ] solvent. This will give decanoic acid in up to 93% yield.<ref>{{cite book | title = Organic Chemistry 7th edition| publisher = Thompson - Brooks/Cole| author= John McMurry| year=2008}} Page 624</ref> |
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Capric acid can be prepared from ] of the primary alcohol ] by using ] ({{chem2|CrO3}}) ] under acidic conditions.<ref>{{cite book | title = Organic Chemistry | edition = 7th | publisher = Thompson - Brooks/Cole | first = John | last = McMurry| year = 2008 | page = 624 | author-link = John E. McMurry}}</ref> |
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Neutralization of capric acid or ] of its ] esters with ] yields sodium caprate, {{chem2|CH3(CH2)8CO2-Na+}}. This ] is a component of some types of ]. |
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==Pharmaceuticals== |
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Decanoate salts and esters of various drugs are available. Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its ] and its affinity for ]. Since ] of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a ]) by using its decanoate form. Some examples of drugs available as a decanoate ester or salt include ], ], ], ] and ]. |
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==Use== |
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==Uses== |
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Capric acid is used in the manufacture of ] for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.<ref name=cheml>{{cite web |url=http://www.chemicalland21.com/industrialchem/organic/CAPRIC%20ACID.htm |title=CAPRIC ACID |publisher=AroKor Holdings |website=chemicalland21.com |access-date=2014-06-15 |archive-date=2018-10-19 |archive-url=https://web.archive.org/web/20181019110735/http://chemicalland21.com/industrialchem/organic/CAPRIC |url-status=live }}</ref> |
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Manufacturing of esters for artificial fruit flavors and perfumes. Also as an intermediate in chemical syntheses. |
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===Pharmaceuticals=== |
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Caprate ester ]s of various pharmaceuticals are available. Since capric acid is a fatty acid, forming a salt or ester with a drug will increase its ] and its affinity for ]. Since ] of a drug from ] is usually slow, one may develop a long-acting injectable form of a drug (called a ]) by using its caprate form. Some examples of drugs available as a caprate ester include ] (as ]),<ref>{{Cite web |title=ROLON 250mg/ml Solution for Injection - Summary of Product Characteristics (SmPC) - (emc) |url=https://www.medicines.org.uk/emc/product/5374/smpc#gref |archive-url=https://web.archive.org/web/20200922210716/https://www.medicines.org.uk/emc/product/5374/smpc#gref |archive-date=2020-09-22 |access-date=2020-10-09 |website=www.medicines.org.uk}}</ref> ] (as fluphenazine decanoate),<ref name="AHFS2015">{{cite web |title=fluphenazine decanoate |url=https://www.drugs.com/monograph/fluphenazine-decanoate.html |url-status=live |archive-url=https://web.archive.org/web/20151208191534/http://www.drugs.com/monograph/fluphenazine-decanoate.html |archive-date=8 December 2015 |access-date=1 December 2015 |publisher=The American Society of Health-System Pharmacists}}</ref> ] (as ]),<ref name="Elks2014">{{cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA182 |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies |date=14 November 2014 |publisher=Springer |isbn=978-1-4757-2085-3 |editor=J. Elks |pages=182– |oclc=1058412474}}</ref> and ] (as ]).<ref name="Elks2014" /> |
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==Effects== |
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Capric acid acts as a non-competitive ] antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its ] effects.<ref name= awv325>{{cite journal |last1=Chang |first1=Pishan |last2=Augustin |first2=Katrin |last3=Boddum |first3=Kim |last4=Williams |first4=Sophie |last5=Sun |first5=Min |last6=Terschak |first6=John A. |last7=Hardege |first7=Jörg D. |last8=Chen |first8=Philip E. |last9=Walker |first9=Matthew C. |last10=Williams |first10=Robin S. B. |title=Seizure control by decanoic acid through direct AMPA receptor inhibition |journal=Brain |date=February 2016 |volume=139 |issue=2 |pages=431–443 |doi=10.1093/brain/awv325 |pmc=4805082 |pmid=26608744 }}</ref> This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the ] effect of the ] ].<ref name=awv325/> Decanoic acid and the AMPA receptor antagonist drug ] act at separate sites on the AMPA receptor, and so it is possible that they have a cooperative effect at the AMPA receptor, suggesting that perampanel and the ketogenic diet could be synergistic.<ref name=awv325/> |
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Capric acid may be responsible for the mitochondrial proliferation associated with the ], and that this may occur via ] agonism and its target genes involved in ].<ref name="pmid24383952">{{cite journal |last1=Hughes |first1=Sean David |last2=Kanabus |first2=Marta |last3=Anderson |first3=Glenn |last4=Hargreaves |first4=Iain P. |last5=Rutherford |first5=Tricia |last6=Donnell |first6=Maura O’ |last7=Cross |first7=J. Helen |last8=Rahman |first8=Shamima |last9=Eaton |first9=Simon |last10=Heales |first10=Simon J. R. |title=The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells |journal=Journal of Neurochemistry |date=May 2014 |volume=129 |issue=3 |pages=426–433 |doi=10.1111/jnc.12646 |pmid=24383952 |s2cid=206089968 |doi-access=free }}</ref><ref name="pmid22039047">{{cite journal |last1=Malapaka |first1=Raghu R. V. |last2=Khoo |first2=SokKean |last3=Zhang |first3=Jifeng |last4=Choi |first4=Jang H. |last5=Zhou |first5=X. Edward |last6=Xu |first6=Yong |last7=Gong |first7=Yinhan |last8=Li |first8=Jun |last9=Yong |first9=Eu-Leong |last10=Chalmers |first10=Michael J. |last11=Chang |first11=Lin |last12=Resau |first12=James H. |last13=Griffin |first13=Patrick R. |last14=Chen |first14=Y. Eugene |last15=Xu |first15=H. Eric |title=Identification and Mechanism of 10-Carbon Fatty Acid as Modulating Ligand of Peroxisome Proliferator-activated Receptors |journal=Journal of Biological Chemistry |date=2 January 2012 |volume=287 |issue=1 |pages=183–195 |doi=10.1074/jbc.M111.294785 |pmid=22039047 |pmc=3249069 |doi-access=free }}</ref> |
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] activity of the ] is substantially elevated by decanoic acid treatment.<ref name="pmid24383952" /> |
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It should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the ], and are quickly metabolized via ] intermediates through ] and the ] to produce ], ] and ].<ref name=PMC3625124>{{cite journal |last1=Chang |first1=Pishan |last2=Terbach |first2=Nicole |last3=Plant |first3=Nick |last4=Chen |first4=Philip E. |last5=Walker |first5=Matthew C. |last6=Williams |first6=Robin S.B. |title=Seizure control by ketogenic diet-associated medium chain fatty acids |journal=Neuropharmacology |date=June 2013 |volume=69 |pages=105–114 |doi=10.1016/j.neuropharm.2012.11.004 |pmid=23177536 |pmc=3625124 }}</ref> Whether the ketones, β-hydroxybutyrate and ] have direct antiseizure activity is unclear.<ref name=awv325/><ref>{{cite journal |last1=Viggiano |first1=Andrea |last2=Pilla |first2=Raffaele |last3=Arnold |first3=Patrick |last4=Monda |first4=Marcellino |last5=D׳Agostino |first5=Dominic |last6=Coppola |first6=Giangennaro |title=Anticonvulsant properties of an oral ketone ester in a pentylenetetrazole-model of seizure |journal=Brain Research |date=August 2015 |volume=1618 |pages=50–54 |doi=10.1016/j.brainres.2015.05.023 |pmid=26026798 |doi-access= }}</ref><ref>{{cite journal |last1=Rho |first1=Jong M. |last2=Anderson |first2=Gail D. |last3=Donevan |first3=Sean D. |last4=White |first4=H. Steve |title=Acetoacetate, Acetone, and Dibenzylamine (a Contaminant in l-(+)-β-Hydroxybutyrate) Exhibit Direct Anticonvulsant Actions in Vivo |journal=Epilepsia |date=22 April 2002 |volume=43 |issue=4 |pages=358–361 |doi=10.1046/j.1528-1157.2002.47901.x |pmid=11952765 |s2cid=31196417 }}</ref><ref>{{cite journal |last1=Ma |first1=Weiyuan |last2=Berg |first2=Jim |last3=Yellen |first3=Gary |title=Ketogenic Diet Metabolites Reduce Firing in Central Neurons by Opening KATP Channels |journal=The Journal of Neuroscience |date=4 April 2007 |volume=27 |issue=14 |pages=3618–3625 |doi=10.1523/JNEUROSCI.0132-07.2007 |pmid=17409226 |pmc=6672398 }}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ], a medium-chain fatty acid, also with antiseizure activity |
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==References== |
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==References== |
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{{reflist|30em}} |
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<references/> |
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{{Fatty acids}} |
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{{Fatty acids}} |
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{{Authority control}} |
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{{DEFAULTSORT:Decanoic Acid}} |
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