506-30-9

Basic information

• Product Name: Arachidic Acid
• Synonyms: Eicosansαure;n-Eicosansαure;ARACHIC ACID;ARACHIDIC ACID;ARACHIDINIC ACID;EICOSANOIC ACID;C20:0 FATTY ACID;C20
• CAS NO: 506-30-9
• Molecular Formula: C20H40O2
• Molecular Weight: 312.53
• EINECS: 208-031-3
• Product Categories: Alkylcarboxylic Acids;Biochemistry;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Saturated Higher Fatty Acids
• Mol File: 506-30-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 74-76 °C(lit.)
• Boiling Point: 328 °C
• Flash Point: 110 °C
• Appearance: White/Glistening Powder or Flakes
• Density: d4100 0.8240
• Vapor Pressure: 2.46E-06mmHg at 25°C
• Refractive Index: nD100 1.4250
• Storage Temp.: −20°C
• Solubility: chloroform: 50 mg/mL, clear, colorless
• PKA: 4.78±0.10(Predicted)
• Water Solubility: practically insoluble
• Merck: 14,764
• BRN: 1788211
• CAS DataBase Reference: Arachidic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: Arachidic Acid(506-30-9)
• EPA Substance Registry System: Arachidic Acid(506-30-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• RTECS: JX3780000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 506-30-9(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 506-30-9 differently. You can refer to the following data:
1. white glistening powder or flakes
2. ARACHIDIC ACID is also known as eicosanoic acid, formula CH3(CH2)18COOH. A widely distributed, but minor, component of the fats of certain edible vegetable oils. Shining, white crystalline leaflets; soluble in ether, slightly soluble in water. Decomposes at 328 C. Commercial product derived from groundnut (peanut) oil. Used in organic synthesis, lubricating greases, waxes, and plastics. Source of arachidyl alcohol.

Uses

Different sources of media describe the Uses of 506-30-9 differently. You can refer to the following data:
1. Arachidic acid is used in the manufacture of pharmaceuticals, soaps, cosmetics, and food packaging because of its surfactant-like properties. Arachidic acid is a saturated fatty acid with a 20 carbon chain. Diets rich in saturated fats like arachidic acid are associated with increased levels of serum low density lipoproteins.
2. Arachidic acid is a saturated fatty acid and a minor constituent of peanut oil, coconut oil and corn oil. Arachidic acid is used for the production of detergents, photographic materials and lubricants .

Definition

ChEBI: A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Arachidic acid is a saturated fatty acid with a 20 carbon chain. Arachidic acid occurs naturally in fish and vegetable oils. Diets rich in saturated fats like arachidic acid are associated with increased levels of serum low density lipoproteins.

Purification Methods

Crystallise the C20 acid pKEst
~ from absolute EtOH. [Beilstein 2 IV 1276.]

InChI: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)

Synthetic route

6-bromohexanoic acid (4224-70-8) + n-tetradecylmagnesium chloride → Arachidic acid (506-30-9)

Conditions	Yield
Stage #1: 6-bromohexanoic acid With 1-methyl-pyrrolidin-2-one; tert-butylmagnesium chloride In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: n-tetradecylmagnesium chloride With buta-1,3-diene; nickel dichloride In tetrahydrofuran under 760.051 Torr; for 1h; Inert atmosphere; Cooling with ice;	95%

n-eicosanol (629-96-9) → Arachidic acid (506-30-9)

Conditions	Yield
bei der Oxydation;

gadoleic acid (29204-02-2) → Arachidic acid (506-30-9)

Conditions	Yield
Hydrogenation;

cis-13-docosenoic acid (112-86-7) → Arachidic acid (506-30-9)

Conditions	Yield
With potassium hydroxide; water durch Schmelzen;
With potassium hydroxide

Brassidic acid (506-33-2) → Arachidic acid (506-30-9)

Conditions	Yield
With potassium hydroxide Schmelzen;

n-triacontane (638-68-6) → Arachidic acid (506-30-9)

Conditions	Yield
With terpentine oil; oxygen at 95℃;

eicos-9t-enoic acid (62133-71-5) → Arachidic acid (506-30-9)

Conditions	Yield
Hydrogenation;

behenolic acid (506-35-4) → Arachidic acid (506-30-9)

Conditions	Yield
With nitric acid

4-oxoicosanoic acid (110071-74-4) → Arachidic acid (506-30-9)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; ethylene glycol at 220℃;

octadecyl malonic acid (4475-04-1) → Arachidic acid (506-30-9)

4-(5-dodecyl-[2]thienyl)-butyric acid → Arachidic acid (506-30-9)

Conditions	Yield
With nickel

adipic acid monomethyl ester (627-91-8) + 1-hexadecylcarboxylic acid (57-10-3) → Arachidic acid (506-30-9)

Conditions	Yield
With methanol; sodium Electrolysis.und Behandlung des Reaktionsprodukts mit methanol.Natronlauge;

succinic acid monobenzyl ester (103-40-2) + stearic acid (57-11-4) → Arachidic acid (506-30-9)

Conditions	Yield
With methanol; sodium Electrolysis.und Hydrierung des Reaktionsprodukts an Palladium/Kohle und an Palladium/Strontiumcarbonat in Aethylacetat;

N-Isobutyleicosansaeure (63647-45-0) → Arachidic acid (506-30-9)

Conditions	Yield
With hydrogenchloride In methanol

17-hydroxy-13,14-dihydrokolavenol arachidate → Arachidic acid (506-30-9) + 17-hydroxy-13,14-dihydrokolavenol

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; methanol at 70℃; for 3h; Yield given;

lup-20(29)-ene-7β,15α-diol-3β-fatty acid ester mixture (III) → Arachidic acid (506-30-9) + lup-20(29)-ene-3β,7β,15α-triol (115498-81-2) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4)

Conditions	Yield
With hydrogenchloride; potassium hydroxide; ethanol for 2h; Heating; Further byproducts given;	A 38 % Chromat. B 36 mg C 17 % Chromat. D 6 % Chromat.
With potassium hydroxide; ethanol for 2h; Heating; Further byproducts given;	A 38 % Chromat. B 36 mg C 17 % Chromat. D 6 % Chromat.

6-oxo-arachic acid → Arachidic acid (506-30-9)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2,5-dihydroxy-3-methyl-6-nonadecyl-[1,4]benzoquinone (2654-76-4) + aqueous KMnO4 → Arachidic acid (506-30-9)

2,5-dihydroxy-3-methyl-6-nonadecyl-[1,4]benzoquinone (2654-76-4) + dihydrogen peroxide (7722-84-1) + aqueous KOH → Arachidic acid (506-30-9)

arachic acid nitrile → Arachidic acid (506-30-9)

Conditions	Yield
With sodium hydroxide

arachidonic acid → Arachidic acid (506-30-9)

Conditions	Yield
With ethanol; palladium Hydrogenation;

arachis oil → Arachidic acid (506-30-9)

Conditions	Yield
With sodium hydroxide man digeriert die mit Salzsaeure freigemachten Fettsaeuren mit kaltem Alkohol, presst ab und krystallisiert den Rueckstand mehrmals aus viel Alkohol um;

benzyleicosanoate → Arachidic acid (506-30-9)

Conditions	Yield
With potassium hydroxide

11-eicosenoic acid (5561-99-9) + nickel → Arachidic acid (506-30-9)

Conditions	Yield
at 180℃; Reaktion der Alkylester; nachfolgende Hydrolyse.Hydrogenation;

octadecylacetoacetic acid ester → Arachidic acid (506-30-9)

Conditions	Yield
With potassium hydroxide

paraffin → Arachidic acid (506-30-9)

Conditions	Yield
With manganese compounds; oxygen at 150℃;

Brassidic acid (506-33-2) + potash → Arachidic acid (506-30-9)

Conditions	Yield
beim Schmelzen;

11-eicosenoic acid (5561-99-9) + concentrated HI + red phosphorus → Arachidic acid (506-30-9)

15-hydroxyimino-tetratriacontanoic acid + sulfuric acid (7664-93-9) → pentadecanedioic acid (1460-18-0) + 1-nonadecanamine (n-nonadecylamine) (14130-05-3) + 14-aminotetradecanoic acid (17437-20-6) + Arachidic acid (506-30-9)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit konz. HCl auf 180grad;

di(succinimido) carbonate (74124-79-1) + Arachidic acid (506-30-9) → N-(eicosanoyloxy)succinimide (69888-87-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 1h;	100%

Arachidic acid (506-30-9) + acetone oxime (127-06-0) → eicosanoic acid acetoxime ester (1544620-07-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	99%

Arachidic acid (506-30-9) → Eicosanylamide (51360-63-5)

Conditions	Yield
With titanium(IV) isopropylate; ammonia at 165℃; for 7.5h; Reagent/catalyst;	98%
Multi-step reaction with 2 steps 1: SOCl2 2: NH3 View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: ammonia gas / CHCl3 View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h / Reflux 2: ammonia / water / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / Inert atmosphere 2: ammonium hydroxide View Scheme

Arachidic acid (506-30-9) + (-)-6-O-allyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol (154372-20-0) → C58H80O8 (867062-60-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	98%

Arachidic acid (506-30-9) + Methyl 2,5-dihydroxybenzoate (2150-46-1) → methyl 2-hydroxy-5-(icosanoyloxy)benzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 1h;	98%

Arachidic acid (506-30-9) + ethyl iodide (75-03-6) → ethyl eicosanoate (18281-05-5)

Conditions	Yield
With caesium carbonate In acetonitrile for 2h; Heating;	97%
With cesium fluoride In acetonitrile for 1.5h; Heating;	96%

Arachidic acid (506-30-9) + para-nitrobenzenethiol (1849-36-1) → S-arachidoyl-p-nitrothiophenol (168907-23-1)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 8h;	95%

2,4-Dinitrophenol (51-28-5) + Arachidic acid (506-30-9) → O-arachidoyl-2,4-dinitrophenol (168907-26-4)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h;	93.5%

1-O-(4-methoxybenzyl)-3-O-stearyl-sn-glycerol (1037195-33-7) + Arachidic acid (506-30-9) → 1-O-(4-methoxybenzyl)-2-O-arachidyl-3-O-stearyl-sn-glycerol (1037195-77-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	93%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	93%

Arachidic acid (506-30-9) + tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine (155021-56-0) → N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]eicosanamide (1042940-11-3)

Conditions	Yield
Stage #1: Arachidic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine With dmap In dichloromethane for 2h;	93%

Arachidic acid (506-30-9) → n-nonadecane (629-92-5) + carbon monoxide (201230-82-2)

Conditions	Yield
With hydrogen at 200℃; under 7500.75 Torr; for 24h; Microwave irradiation;	A 93% B n/a

Arachidic acid (506-30-9) + isopropyl alcohol (67-63-0) → isopropyl arachidate (26718-90-1)

Conditions	Yield
With toluene-4-sulfonic acid at 60℃; for 72h;	92.3%
With sulfuric acid In benzene Heating;

methanol (67-56-1) + Arachidic acid (506-30-9) → methyl arachidate (1120-28-1)

Conditions	Yield
With silphos at 20℃; for 0.0833333h; Neat (no solvent);	90%
With hydrogenchloride
With sulfuric acid

Arachidic acid (506-30-9) + (R)-3-(4-methoxybenzyloxy)propane-1,2-diol (109786-74-5) → (R)-1,2-di-eicosyloxycarbonyl-3-(p-methoxybenzyl)-sn-glycerol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 22h;	90%

5''-amino-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin + Arachidic acid (506-30-9) → 5''-N-(nonadecanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin (1067241-24-0)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	89%

[1,2']bipyridinyl-2-one (3480-65-7) + Arachidic acid (506-30-9) → 6-nonadecyl-2H-[1,2'-bipyridin]-2-one

Conditions	Yield
With di(rhodium)tetracarbonyl dichloride; di-tert-butyl dicarbonate; Trimethylacetic acid In 1,4-dioxane at 130℃; for 8h; Schlenk technique; Sealed tube; regioselective reaction;	89%

doxorubicin (23214-92-8) + Arachidic acid (506-30-9) → (8S,10S)-10-((2R,4S,5S,6S)-4-(icosanoylamido)-5-hydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione (1310544-49-0)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	88.2%

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) + Arachidic acid (506-30-9) → N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosanamide (21249-34-3)

Conditions	Yield
With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent;	88%

2,6-Diaminopyridine (141-86-6) + Arachidic acid (506-30-9) → N-(6-aminopyridin-2-yl)icosanamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 20h;	87%

Arachidic acid (506-30-9) + (2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane (1082745-96-7) → C47H101NO4Si3 (1176281-05-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride	86%

Arachidic acid (506-30-9) + dasatanib (302962-49-8) → 2-(4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl icosanoate

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; Inert atmosphere; Cooling with ice;	85.3%

Arachidic acid (506-30-9) + zinc(II) oxide → zinc(II) eicosanoate

Conditions	Yield
In ethanol prepn. by refluxing ZnO with excess of carboxylic acid in EtOH for about2 h; cooled; ppt. filtered off; washed (EtOH) repeatedly; collected; kept over silica gel in vac. desiccator; elem. anal.;	85%

Arachidic acid (506-30-9) → nonadec-1-ene (18435-45-5)

Conditions	Yield
With bis(triphenylphosphine)iridium(I) carbonyl chloride; acetic anhydride; potassium iodide at 160℃; for 5h; Inert atmosphere;	84%
With carbon monoxide; 1,5-bis-(diphenylphosphino)pentane; acetic anhydride; potassium iodide; iron(II) chloride at 240℃; under 15201 Torr; for 3h;	78%
With sodium phosphite; phosphite dehydrogenase; OleTJE decarboxylase/P450BM3 reductase domain fusion protein; oxygen; NADPH; catalase In water at 20℃; for 12h; Green chemistry; Enzymatic reaction;	70 %Chromat.

Arachidic acid (506-30-9) + 2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose (1427716-38-8) → 6,6′-di-O-eicosanoyl-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose (1427716-40-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	84%

Arachidic acid (506-30-9) + 4-amino-4-(2-tert-butoxycarbonylethyl)heptanedioic acid di-tertbutyl ester (136586-99-7) → di-tert-butyl 4-(2-(tert-butoxycarbonyl)ethyl)-4-(1-oxoicosylamino)heptanedioate

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 168h;	82%

3-O-(4-methoxybenzyl)-1-O-stearyl-sn-glycerol (1037195-26-8) + Arachidic acid (506-30-9) → 2-O-arachidyl-3-O-(4-methoxybenzyl)-1-O-stearyl-sn-glycerol (1037195-80-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	82%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	82%

Upstream product

• 638-68-6 n-triacontane 
• 62133-71-5 eicos-9t-enoic acid 
• 506-35-4 behenolic acid 
• 627-91-8 adipic acid monomethyl ester 
• 57-10-3 1-hexadecylcarboxylic acid 
• 2654-76-4 2,5-dihydroxy-3-methyl-6-nonadecyl-[1,4]benzoquinone 
• 7722-84-1 dihydrogen peroxide 
• 5561-99-9 11-eicosenoic acid 
• 506-33-2 Brassidic acid 
• 7664-93-9 sulfuric acid 
• 103799-79-7 11-hydroxyimino-triacontanoic acid 
• 112-86-7 cis-13-docosenoic acid 
• 112-89-0 1-Bromooctadecane 
• 1120-28-1 methyl arachidate 

Downstream Products

• 504-56-3 Ginnon 
• 506-48-9 octacosanoic acid 
• 69888-87-5 N-(eicosanoyloxy)succinimide 
• 131933-60-3 rac-1-eicosanamido-2-ethoxy-3-(trityloxy)propane 
• 168907-23-1 S-arachidoyl-p-nitrothiophenol 
• 620-64-4 1,2,3-tris-eicosanoyloxy-propane 
• 149576-20-5 rac-3-eicosanamido-2-ethoxypropylphosphocholine 
• 1037195-80-4 2-O-arachidyl-3-O-(4-methoxybenzyl)-1-O-stearyl-sn-glycerol 
• 1037195-77-9 1-O-(4-methoxybenzyl)-2-O-arachidyl-3-O-stearyl-sn-glycerol 
• 1067241-24-0 5''-N-(nonadecanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin 
• 629-92-5 n-nonadecane 
• 617703-96-5 N-arachidoyl glycine 
• 404918-73-6 Icosanoic acid (2R,3R,4R,5R)-4-icosanoyloxy-5-methoxy-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 50906-68-8 glyceryl-1-eicosanoate 

Relevant articles and documents

Neutral components of the genus Corydalis

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PROCESS FOR PREPARATION OF ARACHIDIC ACID

The present application relates to an improved process for preparation of arachidic acid.

Anti-H5N1 virus new diglyceride ester from the Red Sea grass Thallasodendron ciliatum

Some Egyptian plants were screened against highly pathogenic avian influenza strain H5N1 using plaque inhibition assay in Madin-Darby canine kidney. The results indicated that the extracts of Red Sea grass Thallasodendron ciliatum possessed potent antiviral activity (100% inhibition at the concentration of 1mgmL21). The bioactivityguided fractionations led to the isolation of a new diglyceride ester (1) along with asebotin (2) for the first time from the plant. The two isolates showed reduction of virus titre by 67.26% and 53.81% inhibition at concentration of 1 ngmL21, respectively.