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% |
Conditions | Yield |
---|---|
bei der Oxydation; |
gadoleic acid
Arachidic acid
Conditions | Yield |
---|---|
Hydrogenation; |
Conditions | Yield |
---|---|
With potassium hydroxide; water durch Schmelzen; | |
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide Schmelzen; |
Conditions | Yield |
---|---|
With terpentine oil; oxygen at 95℃; |
eicos-9t-enoic acid
Arachidic acid
Conditions | Yield |
---|---|
Hydrogenation; |
Conditions | Yield |
---|---|
With nitric acid |
4-oxoicosanoic acid
Arachidic acid
Conditions | Yield |
---|---|
With sodium hydroxide; hydrazine hydrate; ethylene glycol at 220℃; |
Arachidic acid
Conditions | Yield |
---|---|
With nickel |
Conditions | Yield |
---|---|
With methanol; sodium Electrolysis.und Behandlung des Reaktionsprodukts mit methanol.Natronlauge; |
Conditions | Yield |
---|---|
With methanol; sodium Electrolysis.und Hydrierung des Reaktionsprodukts an Palladium/Kohle und an Palladium/Strontiumcarbonat in Aethylacetat; |
N-Isobutyleicosansaeure
Arachidic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol |
A
Arachidic acid
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane; methanol at 70℃; for 3h; Yield given; |
A
Arachidic acid
B
lup-20(29)-ene-3β,7β,15α-triol
C
1-hexadecylcarboxylic acid
D
stearic acid
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. |
Arachidic acid
Conditions | Yield |
---|---|
With sodium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol |
2,5-dihydroxy-3-methyl-6-nonadecyl-[1,4]benzoquinone
dihydrogen peroxide
Arachidic acid
Arachidic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
Arachidic acid
Conditions | Yield |
---|---|
With ethanol; palladium Hydrogenation; |
Arachidic acid
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; |
Arachidic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
at 180℃; Reaktion der Alkylester; nachfolgende Hydrolyse.Hydrogenation; |
Arachidic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
Arachidic acid
Conditions | Yield |
---|---|
With manganese compounds; oxygen at 150℃; |
Conditions | Yield |
---|---|
beim Schmelzen; |
sulfuric acid
A
pentadecanedioic acid
B
1-nonadecanamine (n-nonadecylamine)
C
14-aminotetradecanoic acid
D
Arachidic acid
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts mit konz. HCl auf 180grad; |
di(succinimido) carbonate
Arachidic acid
N-(eicosanoyloxy)succinimide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 99% |
Arachidic acid
Eicosanylamide
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
(-)-6-O-allyl-1-O-(p-methoxybenzyl)-3,4,5-tri-O-benzyl-myo-inositol
C58H80O8
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 1h; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 2h; Heating; | 97% |
With cesium fluoride In acetonitrile for 1.5h; Heating; | 96% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 8h; | 95% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 12h; | 93.5% |
1-O-(4-methoxybenzyl)-3-O-stearyl-sn-glycerol
Arachidic acid
1-O-(4-methoxybenzyl)-2-O-arachidyl-3-O-stearyl-sn-glycerol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 93% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 93% |
Arachidic acid
tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine
N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]eicosanamide
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% |
Conditions | Yield |
---|---|
With hydrogen at 200℃; under 7500.75 Torr; for 24h; Microwave irradiation; | A 93% B n/a |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 60℃; for 72h; | 92.3% |
With sulfuric acid In benzene Heating; |
Conditions | Yield |
---|---|
With silphos at 20℃; for 0.0833333h; Neat (no solvent); | 90% |
With hydrogenchloride | |
With sulfuric acid |
Arachidic acid
(R)-3-(4-methoxybenzyloxy)propane-1,2-diol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 22h; | 90% |
Arachidic acid
5''-N-(nonadecanoyl)-1,3,2',6',2''',6'''-hexa-N-(tert-butoxycarbonyl)-5''-deoxy-neomycin
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% |
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
Arachidic acid
(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
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
Arachidic acid
N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosanamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; Solvent; | 88% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 20h; | 87% |
Arachidic acid
(2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane
C47H101NO4Si3
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride | 86% |
Arachidic acid
dasatanib
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% |
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
nonadec-1-ene
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
2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose
6,6′-di-O-eicosanoyl-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 84% |
Arachidic acid
4-amino-4-(2-tert-butoxycarbonylethyl)heptanedioic acid di-tertbutyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 168h; | 82% |
3-O-(4-methoxybenzyl)-1-O-stearyl-sn-glycerol
Arachidic acid
2-O-arachidyl-3-O-(4-methoxybenzyl)-1-O-stearyl-sn-glycerol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 82% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; | 82% |
Molecule structure of Eicosanoic acid (CAS NO.506-30-9):
IUPAC Name: Icosanoic acid
Molecular Weight: 312.5304 g/mol
Molecular Formula: C20H40O2
Density: 0.884 g/cm3
Melting Point: 74-76 °C(lit.)
Storage Temp.: −20 °C
Solubility: chloroform: 50 mg/mL, clear, colorless
Water Solubility: practically insoluble
Boiling Point: 376.4 °C at 760 mmHg
Flash Point: 169.7 °C
Index of Refraction: 1.457
Molar Refractivity: 96.27 cm3
Molar Volume: 353.2 cm3
Polarizability: 38.16×10-24 cm3
Surface Tension: 33.4 dyne/cm
Enthalpy of Vaporization: 65.83 kJ/mol
Vapour Pressure: 2.46E-06 mmHg at 25 °C
XLogP3: 8.5
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 18
Exact Mass: 312.302831
MonoIsotopic Mass: 312.302831
Topological Polar Surface Area: 37.3
Heavy Atom Count: 22
Complexity: 226
Canonical SMILES: CCCCCCCCCCCCCCCCCCCC(=O)O
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)
InChIKey: VKOBVWXKNCXXDE-UHFFFAOYSA-N
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
Eicosanoic acid (CAS NO.506-30-9) is used for the preparation of detergent, photographic materials, lubricants, etc.
1. | imp-mus TDLo:1000 mg/kg:NEO | CNREA8 Cancer Research. 26 (1966),105. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi, Xn
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RTECS: JX3780000
HazardClass: IRRITANT
Questionable carcinogen with experimental neoplastigenic data by implant route. When heated to decomposition it emits acrid smoke and fumes.
Eicosanoic acid (CAS NO.506-30-9) is also named as Arachic acid ; Arachidic acid ; Icosanoic acid ; NSC 93983 ; n-Eicosanoic acid . Eicosanoic acid (CAS NO.506-30-9) is white glistening powder or flakes.
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