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Arachidates - salts and esters
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| ImageFile2=Arachidic Acid.png
| ImageFile2=Arachidic Acid.png
| ImageSize2=320px
| ImageSize2=320px
| IUPACName=icosanoic acid
| PIN=Icosanoic acid
| OtherNames=eicosanoic acid<br />''n''-eicosanoic acid<br />arachidic acid<br />arachic acid<br />C20:0 ([[Fatty acid#Nomenclature|Lipid numbers]])
| OtherNames=Eicosanoic acid<br />''n''-Eicosanoic acid<br />Arachidic acid<br />Arachic acid<br />C20:0 ([[Fatty acid#Nomenclature|Lipid numbers]])
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=506-30-9
| CASNo=506-30-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PQB8MJD4RB
| PubChem=10467
| PubChem=10467
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| Appearance=White crystalline solid
| Appearance=White crystalline solid
| Density=0.8240 g/cm<sup>3</sup>
| Density=0.8240 g/cm<sup>3</sup>
| MeltingPtC=75.5
| MeltingPtC=75.4
| BoilingPtC=328
| BoilingPtC=328
| Solubility=Practically insoluble in water
| Solubility=Practically insoluble in water
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|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPtC = 169.7
| FlashPtC = 110
| AutoignitionPtC =
| AutoignitionPtC =
}}
}}
}}
}}


'''Arachidic acid''', also known as '''eicosanoic acid''', is a saturated [[fatty acid]] with a 20-carbon chain. It is a minor constituent of [[cupuaçu]] butter (7%),<ref>{{cite journal |author= Cohen, K. de O. |author2= Jackix, M. de N. H. |last-author-amp= yes | title = Características químicas e física da gordura de cupuaçu e da manteiga de cacau | journal = Document / Embrapa Cerrados |language = Portuguese | year = 2009 | issue = 269 | pages = 1–22| url=http://ainfo.cnptia.embrapa.br/digital/bitstream/CPAC-2010/31579/1/doc-269.pdf }}</ref> [[perilla oil]] (0–1%),<ref>{{Cite book|title=Perilla: The Genus Perilla|last=Shin|first=Hyo-Sun|publisher=CRC Press|year=1997|isbn=9789057021718|editor-last=Yu|editor-first=He-Ci|location=London|pages=93|chapter=9. Lipid Composition and Nutritional and Physiological Roles of Perilla Seed and its Oil|quote=Perilla seed contains about 38-45% of lipid (Sonntag, 1979; Vaughan, 1970).|editor-last2=Kosuna|editor-first2=Kenichi|editor-last3=Haga|editor-first3=Megumi|doi=10.1201/9781439822715}}{{Dead link|date=May 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> [[peanut oil]] (1.1–1.7%),<ref name="lexicon">{{cite journal |year=2001 |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |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> corn oil (3%),<ref name="USDA">U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release 20. [http://www.ars.usda.gov/ba/bhnrc/ndl Nutrient Data Laboratory Home Page]</ref> and [[cocoa butter]] (1%).<ref>[http://www.nal.usda.gov/fnic/foodcomp/search/ USDA nutrient database] {{webarchive |url=https://web.archive.org/web/20150303184216/http://www.nal.usda.gov/fnic/foodcomp/search/ |date=March 3, 2015 }}</ref> It also constitutes 7.08% of the fats from the fruit of the [[durian]] species ''[[Durio graveolens]]''.<ref name="Nasaruddin">{{cite journal|last1=Nasaruddin|first1=Mohd hanif|last2=Noor|first2=Noor Qhairul Izzreen Mohd|last3=Mamat|first3=Hasmadi|title=Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah|journal=Sains Malaysiana|date=2013|volume=42|issue=9|pages=1283–1288|url=http://www.ukm.my/jsm/pdf_files/SM-PDF-42-9-2013/11%20Mohd%20Hanif.pdf|accessdate=28 November 2017|trans-title=Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)|language=Malay|issn=0126-6039|oclc=857479186}}</ref> The salts and esters of arachidic acid are known as '''arachidates'''.
'''Arachidic acid''', also known as '''icosanoic acid''', is a saturated [[fatty acid]] with a 20-carbon chain. It is a minor constituent of [[cupuaçu]] butter (7%),<ref>{{cite journal |author= Cohen, K. de O. |author2= Jackix, M. de N. H. |name-list-style= amp | title = Características químicas e física da gordura de cupuaçu e da manteiga de cacau | journal = Document / Embrapa Cerrados |language = pt | year = 2009 | issue = 269 | pages = 1–22| url=http://ainfo.cnptia.embrapa.br/digital/bitstream/CPAC-2010/31579/1/doc-269.pdf }}</ref> [[perilla oil]] (0–1%),<ref>{{Cite book|title=Perilla: The Genus Perilla|last=Shin|first=Hyo-Sun|publisher=CRC Press|year=1997|isbn=9789057021718|editor-last=Yu|editor-first=He-Ci|location=London|pages=93|chapter=9. Lipid Composition and Nutritional and Physiological Roles of Perilla Seed and its Oil|quote=Perilla seed contains about 38-45% of lipid (Sonntag, 1979; Vaughan, 1970).|editor-last2=Kosuna|editor-first2=Kenichi|editor-last3=Haga|editor-first3=Megumi|doi=10.1201/9781439822715}}</ref> [[peanut oil]] (1.1–1.7%),<ref name="lexicon">{{cite journal |year=2001 |last1=Beare-Rogers |first1=J. |last2=Dieffenbacher |first2=A. |last3=Holm |first3=J.V. |title=Lexicon of lipid nutrition (IUPAC Technical Report) |journal=Pure and Applied Chemistry |volume=73 |issue=4 |pages=685–744 |doi=10.1351/pac200173040685 |doi-access=free |s2cid=84492006 }}</ref> corn oil (3%),<ref name="USDA">U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release 20. [http://www.ars.usda.gov/ba/bhnrc/ndl Nutrient Data Laboratory Home Page]</ref> and [[cocoa butter]] (1%).<ref>[http://www.nal.usda.gov/fnic/foodcomp/search/ USDA nutrient database] {{webarchive |url=https://web.archive.org/web/20150303184216/http://www.nal.usda.gov/fnic/foodcomp/search/ |date=March 3, 2015 }}</ref> The salts and esters of arachidic acid are known as '''arachidates'''.


Its name derives from the Latin ''arachis''—peanut. It can be formed by the [[hydrogenation]] of [[arachidonic acid]].
Its name derives from the Latin ''arachis''—peanut. It can be formed by the [[hydrogenation]] of [[arachidonic acid]].

Latest revision as of 17:23, 7 April 2024

Arachidic acid
Names
Preferred IUPAC name
Icosanoic acid
Other names
Eicosanoic acid
n-Eicosanoic acid
Arachidic acid
Arachic acid
C20:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.302 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) checkY
    Key: VKOBVWXKNCXXDE-UHFFFAOYSA-N checkY
  • InChI=1/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)
    Key: VKOBVWXKNCXXDE-UHFFFAOYAB
  • O=C(O)CCCCCCCCCCCCCCCCCCC
Properties[1]
C20H40O2
Molar mass 312.538 g·mol−1
Appearance White crystalline solid
Density 0.8240 g/cm3
Melting point 75.4 °C (167.7 °F; 348.5 K)
Boiling point 328 °C (622 °F; 601 K)
Practically insoluble in water
Hazards
Flash point 110 °C (230 °F; 383 K)
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 ?)

Arachidic acid, also known as icosanoic acid, is a saturated fatty acid with a 20-carbon chain. It is a minor constituent of cupuaçu butter (7%),[2] perilla oil (0–1%),[3] peanut oil (1.1–1.7%),[4] corn oil (3%),[5] and cocoa butter (1%).[6] The salts and esters of arachidic acid are known as arachidates.

Its name derives from the Latin arachis—peanut. It can be formed by the hydrogenation of arachidonic acid.

Reduction of arachidic acid yields arachidyl alcohol.

Arachidic acid is used for the production of detergents, photographic materials and lubricants.

References

[edit]
  1. ^ *Merck Index, 11th Edition, 791
  2. ^ Cohen, K. de O. & Jackix, M. de N. H. (2009). "Características químicas e física da gordura de cupuaçu e da manteiga de cacau" (PDF). Document / Embrapa Cerrados (in Portuguese) (269): 1–22.
  3. ^ Shin, Hyo-Sun (1997). "9. Lipid Composition and Nutritional and Physiological Roles of Perilla Seed and its Oil". In Yu, He-Ci; Kosuna, Kenichi; Haga, Megumi (eds.). Perilla: The Genus Perilla. London: CRC Press. p. 93. doi:10.1201/9781439822715. ISBN 9789057021718. Perilla seed contains about 38-45% of lipid (Sonntag, 1979; Vaughan, 1970).
  4. ^ Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
  5. ^ U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release 20. Nutrient Data Laboratory Home Page
  6. ^ USDA nutrient database Archived March 3, 2015, at the Wayback Machine


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