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Arachidic acid: Difference between revisions

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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 412505292 | verifiedrevid = 443396639
|ImageFile=Arachinsäure.svg | ImageFile=Arachinsäure.svg
|ImageSize=320px | ImageSize=320px
|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 (]) | OtherNames=Eicosanoic acid<br />''n''-Eicosanoic acid<br />Arachidic acid<br />Arachic acid<br />C20:0 (])
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06425 | KEGG = C06425
| 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) | 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)
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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}}
⚫ | PubChem=10467
| UNII = PQB8MJD4RB
⚫ | PubChem=10467
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=10035 | ChemSpiderID=10035
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28822 | ChEBI = 28822
| SMILES = O=C(O)CCCCCCCCCCCCCCCCCCC | SMILES = O=C(O)CCCCCCCCCCCCCCCCCCC
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Reference = <ref>*''Merck Index'', 11th Edition, '''791'''</ref> | Properties_ref = <ref>*''Merck Index'', 11th Edition, '''791'''</ref>
| C=20|H=40|O=2 | C=20 | H=40 | O=2
| 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
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPtC = 110
| FlashPt=169.7 °C
| AutoignitionPtC =
| Autoignition=
}} }}
}} }}


'''Arachidic acid''', also called '''eicosanoic acid''', is the saturated ] with a 20 carbon chain. It is as a minor constituent of ] 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> and corn oil (3%).<ref name="USDA">U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release 20. </ref> Its name derives from the Latin ''arachis'' — peanut. It can be formed by the ] of ]. '''Arachidic acid''', also known as '''icosanoic acid''', is a saturated ] with a 20-carbon chain. It is a minor constituent of ] 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> ] (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> ] (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. </ref> and ] (1%).<ref> {{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 ] of ].


Reduction of arachidic acid yields ]. Reduction of arachidic acid yields ].
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{{Fatty acids}} {{Fatty acids}}

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{{organic-compound-stub}} {{organic-compound-stub}}

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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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.302 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: VKOBVWXKNCXXDE-UHFFFAOYSA-N
  • 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
SMILES
  • O=C(O)CCCCCCCCCCCCCCCCCCC
Properties
Chemical formula C20H40O2
Molar mass 312.538 g·mol
Appearance White crystalline solid
Density 0.8240 g/cm
Melting point 75.4 °C (167.7 °F; 348.5 K)
Boiling point 328 °C (622 °F; 601 K)
Solubility in water 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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%), perilla oil (0–1%), peanut oil (1.1–1.7%), corn oil (3%), and cocoa butter (1%). 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

  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
Lipids: fatty acids
Saturated
ω−3 Unsaturated
ω−5 Unsaturated
ω−6 Unsaturated
ω−7 Unsaturated
ω−9 Unsaturated
ω−10 Unsaturated
ω−11 Unsaturated
ω−12 Unsaturated


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