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{{not to be confused|Caprylic acid|Capric acid}}
{{chembox
{{Chembox
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 443856741
|verifiedrevid = 443856741
| ImageFile_Ref = {{chemboximage|correct|??}}
|ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Caproic acid acsv.svg
|ImageFile = Caproic acid acsv.svg
| ImageName = Skeletal formula
|ImageName = Skeletal formula
| ImageFile1 = Caproic-acid-3D-balls.png
|ImageFile1 = Caproic-acid-3D-balls.png
| ImageName1 = Ball-and-stick model
|ImageName1 = Ball-and-stick model
| IUPACName = Hexanoic acid
|PIN = Hexanoic acid
| OtherNames = Caproic acid; ''n''-Caproic acid; C6:0 ([[Fatty acid#Nomenclature|Lipid numbers]])
|OtherNames = Hexoic acid; Hexylic acid; Butylacetic acid; Pentylformic acid; 1-Pentanecarboxylic acid; C6:0 ([[Fatty acid#Nomenclature|Lipid numbers]])
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8552
|ChemSpiderID = 8552
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1F8SN134MX
|UNII = 1F8SN134MX
|Gmelin = 185066
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01585
|Beilstein = 773837
|EC_number = 205-550-7
⚫
| InChI = 1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
⚫
|KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| InChIKey = FUZZWVXGSFPDMH-UHFFFAOYAY
|KEGG = C01585
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
|InChI = 1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
⚫
| ChEMBL = 14184
⚫
|InChIKey = FUZZWVXGSFPDMH-UHFFFAOYAY
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
|ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| StdInChI = 1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
⚫
|ChEMBL = 14184
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChIKey = FUZZWVXGSFPDMH-UHFFFAOYSA-N
⚫
|StdInChI = 1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo = 142-62-1
⚫
|StdInChIKey = FUZZWVXGSFPDMH-UHFFFAOYSA-N
⚫
| PubChem = 8892
| ChEBI_Ref = {{ebicite|correct|EBI}}
|CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 30776
|CASNo = 142-62-1
⚫
|PubChem = 8892
⚫
| SMILES = CCCCCC(=O)O
⚫
|ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
}}
|ChEBI = 30776
⚫
|SMILES = CCCCCC(=O)O
⚫
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=6 | H=12 | O=2
|C=6 | H=12 | O=2
| Appearance=Oily liquid<ref name=Merck>{{Merck11th}}</ref>
|Appearance=Oily liquid<ref name=Merck>{{Merck11th}}</ref>
| Odor = goat-like
|Odor = goat-like
| Density=0.929 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=28160}}</ref>
|Density=0.929 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=28160}}</ref>
| MeltingPtC=−3.4
|MeltingPtC=−3.4
| MeltingPt_ref = <ref name=Merck/>
|MeltingPt_ref = <ref name=Merck/>
| BoilingPtC=205.8
|BoilingPtC=205.8
| BoilingPt_ref = <ref name=Merck/>
|BoilingPt_ref = <ref name=Merck/>
| Solubility=1.082 g/100 mL<ref name=Merck/>
|Solubility=1.082 g/100 mL<ref name=Merck/>
| SolubleOther = soluble in [[ethanol]], [[ether]]
|SolubleOther = soluble in [[ethanol]], [[diethyl ether|ether]]
| pKa = 4.88
|pKa = 4.88
| RefractIndex = 1.4170
|RefractIndex = 1.4170
| Viscosity = 3.1 mP
|Viscosity = 3.1 mP
|MagSus = −78.55·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
⚫
|NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 0
| MainHazards=
⚫
|FlashPtC =103
⚫
| NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 0
⚫
|FlashPt_ref = <ref name=GESTIS/>
⚫
| FlashPtC =103
⚫
|AutoignitionPtC =380
⚫
| FlashPt_ref = <ref name=GESTIS/>
⚫
|ExploLimits = 1.3-9.3%
⚫
| AutoignitionPtC =380
⚫
|LD50 = 3000 mg/kg (rat, oral)
⚫
| ExploLimits = 1.3-9.3%
|GHSPictograms = {{GHS05}}{{GHS06}}
⚫
| LD50 = 3000 mg/kg (rat, oral)
|GHSSignalWord = Danger
⚫
}}
|HPhrases = {{H-phrases|311|314}}
|PPhrases = {{P-phrases|260|264|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|322|361|363|405|501}}
⚫
}}
|Section4={{Chembox Related
|OtherCompounds = [[Pentanoic acid]], [[Heptanoic acid]]
}}
}}
}}
⚫
'''Hexanoic acid''' ('''caproic acid''') is the [[carboxylic acid]] derived from [[hexane]] with the general formula C<sub>5</sub>H<sub>11</sub>COOH. It is a colorless oily [[liquid]] with an odor that is fatty, cheesy, waxy, and like that of [[goat]]s<ref name=Merck/> or other barnyard [[animal]]s. It is a [[fatty acid]] found naturally in various animal [[fat]]s and [[oil]]s, and is one of the [[chemical]]s that give the decomposing fleshy seed coat of the [[Ginkgo biloba|ginkgo]] its characteristic [[unpleasant odor]].<ref>[http://scidiv.bcc.ctc.edu/rkr/Ginkgo/Ginkgo.html Ginkgo.html<!-- Bot generated title -->]</ref> It is also one of the components of [[vanilla]]. The primary use of hexanoic acid is in the manufacture of its [[ester]]s for artificial flavors, and in the manufacture of hexyl [[derivative (chemistry)|derivatives]], such as [[Alkylphenol|hexylphenols]].<ref name=Merck/>


⚫
'''Caproic acid''', also known as '''hexanoic acid''', is the [[carboxylic acid]] derived from [[hexane]] with the chemical formula {{chem2|CH3(CH2)4COOH}}. It is a colorless oily [[liquid]] with an odor that is fatty, cheesy, waxy, and like that of [[goat]]s<ref name=Merck/> or other barnyard [[animal]]s. It is a [[fatty acid]] found naturally in various animal [[fat]]s and [[oil]]s, and is one of the chemicals that gives the decomposing fleshy seed coat of the [[Ginkgo biloba|ginkgo]] its characteristic [[unpleasant odor]].<ref>{{Cite web |url=http://scidiv.bcc.ctc.edu/rkr/Ginkgo/Ginkgo.html |title=Ginkgo.html<!-- Bot generated title --> |access-date=2007-03-08 |archive-date=2008-12-26 |archive-url=https://web.archive.org/web/20081226065433/http://scidiv.bcc.ctc.edu/rkr/ginkgo/Ginkgo.html |url-status=live }}</ref> It is also one of the components of [[vanilla]] and [[cheese]]. The primary use of caproic acid is in the manufacture of its [[ester]]s for use as artificial flavors, and in the manufacture of hexyl [[derivative (chemistry)|derivatives]], such as [[Alkylphenol|hexylphenols]].<ref name=Merck/> [[Carboxylate salt|Salts]] and [[ester]]s of caproic acid are known as '''caproates''' or '''hexanoates'''. Several [[progestin]] medications are caproate esters, such as [[hydroxyprogesterone caproate]] and [[gestonorone caproate]].
The salts and esters of this acid are known as [[Hexanoate|hexanoates]] or [[Caproate|caproates]].


Two other acids are named after goats: [[caprylic acid|caprylic]] (C8) and [[decanoic acid|capric]] (C10). Along with hexanoic acid, these total 15% in goat milk fat.
Two other acids are named after goats: [[caprylic acid]] (C8) and [[capric acid]] (C10). Along with caproic acid, they account for 15% of the fat in goat's milk.


Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.
Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.


== References ==
==See also==
* [[List of carboxylic acids]]
{{reflist}}
* [[List of saturated fatty acids]]
* [[Caproate fermentation]]


==References==
⚫
{{Fatty acids}}
{{Reflist}}


⚫
{{Fatty acids}}
{{Authority control}}
{{Authority control}}

[[Category:Fatty acids]]
[[Category:Fatty acids]]
[[Category:Alkanoic acids]]
[[Category:Alkanoic acids]]

Latest revision as of 02:57, 22 November 2024

Not to be confused with Caprylic acid or Capric acid.
Caproic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Hexanoic acid
Other names
Hexoic acid; Hexylic acid; Butylacetic acid; Pentylformic acid; 1-Pentanecarboxylic acid; C6:0 (Lipid numbers)
Identifiers
3D model (JSmol)
773837
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.046 Edit this at Wikidata
EC Number
  • 205-550-7
185066
KEGG
UNII
  • InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) checkY
    Key: FUZZWVXGSFPDMH-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
    Key: FUZZWVXGSFPDMH-UHFFFAOYAY
  • CCCCCC(=O)O
Properties
C6H12O2
Molar mass 116.160 g·mol−1
Appearance Oily liquid[1]
Odor goat-like
Density 0.929 g/cm3[2]
Melting point −3.4 °C (25.9 °F; 269.8 K)[1]
Boiling point 205.8 °C (402.4 °F; 478.9 K)[1]
1.082 g/100 mL[1]
Solubility soluble in ethanol, ether
Acidity (pKa) 4.88
−78.55·10−6 cm3/mol
1.4170
Viscosity 3.1 mP
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: Toxic
Danger
H311, H314
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P361, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 103 °C (217 °F; 376 K)[2]
380 °C (716 °F; 653 K)
Explosive limits 1.3-9.3%
Lethal dose or concentration (LD, LC):
3000 mg/kg (rat, oral)
Related compounds
Related compounds
 Pentanoic acid, Heptanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats[1] or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor.[3] It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.[1] Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.

Two other acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat's milk.

Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

See also

[edit]

References

[edit]
  1. ^ a b c d e f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. ISBN 091191028X.
  2. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ "Ginkgo.html". Archived from the original on 2008-12-26. Retrieved 2007-03-08.
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