Arachidic acid

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	506-30-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28822 ;
ChEMBL	ChEMBL1173381 ;
ChemSpider	10035 ;
ECHA InfoCard	100.007.302
KEGG	C06425 ;
PubChem CID	10467;
UNII	PQB8MJD4RB ;
CompTox Dashboard (EPA)	DTXSID1060134 ;
	show InChI
	show SMILES
Properties
Chemical formula	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)
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 [77 °F], 100 kPa).
	(what is ?)
	Infobox references

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] It also constitutes 7.08% of the fats from the fruit of the durian species Durio graveolens.^[7] 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[]

^ *Merck Index, 11th Edition, 791
^ 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.
^ 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).^{[permanent dead link]}
^ 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.
^ U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release 20. Nutrient Data Laboratory Home Page
^ USDA nutrient database Archived March 3, 2015, at the Wayback Machine
^ Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.

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[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).^{[permanent dead link]}

[lexicon-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.

[USDA-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

[Nasaruddin-7] Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.

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show v t Lipids: fatty acids
Saturated	Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Heptacosylic (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) (C38) (C39) (C40)
ω−3 Unsaturated	(8:1) (10:1) (10:2) (12:1) (12:2) (14:1) (14:2) (14:3) (16:3) (16:4) α-Linolenic (18:3) Stearidonic (18:4) (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) (24:5) (24:6)
	Myristoleic (14:1) (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) (18:3) (20:3) (20:4)
ω−6 Unsaturated	(14:1) (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) (20:2) Dihomo-γ-linolenic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) (20:3)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) (20:2) Mead (20:3)
	Sapienic (16:1)
	Gadoleic (20:1)
	(16:1) Petroselinic (18:1) (20:1)

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Names


Preferred IUPAC name Icosanoic acid
Other names Eicosanoic acid n-Eicosanoic acid Arachidic acid Arachic acid C20:0 (Lipid numbers)
Identifiers
CAS Number	506-30-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28822^Y
ChEMBL	ChEMBL1173381^Y
ChemSpider	10035^Y
ECHA InfoCard	100.007.302
KEGG	C06425^Y
PubChem CID	10467
UNII	PQB8MJD4RB^Y
CompTox Dashboard (EPA)	DTXSID1060134
show 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)^Y Key: VKOBVWXKNCXXDE-UHFFFAOYSA-N^Y 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
show SMILES O=C(O)CCCCCCCCCCCCCCCCCCC
Properties^[1]
Chemical formula	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)
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 [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references