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N-Dodecanoyl-L-phenlyalanine
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Name

N-Dodecanoyl-L-phenlyalanine

 EINECS N/A
CAS No. 14379-64-7 Density N/A
PSA 66.40000 LogP 5.11030
Solubility N/A Melting Point N/A
Formula C21H33NO3 Boiling Point N/A
Molecular Weight 347.498 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 14379-64-7 (N-Dodecanoyl-L-phenlyalanine) Hazard Symbols N/A
Synonyms

Alanine,N-lauroyl-3-phenyl- (6CI,7CI);Alanine, N-lauroyl-3-phenyl-, L- (8CI);N-Dodecanoyl-phenylalanine;N-Lauroyl-L-phenylalanine;N-Lauroylphenylalanine;

Article Data 28

N-Dodecanoyl-L-phenlyalanine Synthetic route

112-16-3

n-dodecanoyl chloride

Wang resin-bound Fmoc-L-phenylalanine

Wang resin-bound Fmoc-L-phenylalanine

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
Stage #1: Wang resin-bound Fmoc-L-phenylalanine With piperidine In N,N-dimethyl-formamide at 20℃;
Stage #2: n-dodecanoyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;
Stage #3: With trifluoroacetic acid In dichloromethane at 20℃; for 18h;		99%
122889-27-4

N-n-dodecanoyl methyl (L)-phenylalaninate

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol; water at 0℃; for 2h;98%
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h;
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol / 20 °C
2: hydrogenchloride / water
View Scheme
112-16-3

n-dodecanoyl chloride

63-91-2

L-phenylalanine

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With potassium carbonate In water; acetone at 0 - 20℃;89%
Stage #1: L-phenylalanine With sodium hydroxide In water; acetone for 0.5h; Cooling with ice;
Stage #2: n-dodecanoyl chloride In water; acetone		83%
With sodium hydroxide at 3℃;
75531-12-3

p-nitrophenyl N-dodecanoyl-D-phenylalaninate

A

100-02-7

4-nitro-phenol

B

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With coaggregate system composed of 59 mol percent ditetradecyl-dimethylammonium bromide and 41 mol percent hexadecyltrimethylammonium bromide; tris buffer (μ=0.2 with KCl); water; quercitrin; acetonitrile; Z-Phe-His-Leu at 25℃; Rate constant; enantioselective hydrolysis; var. flavonoids; pH 7.6;
75531-11-2

p-nitrophenyl N-dodecanoyl-L-phenylalanine

A

100-02-7

4-nitro-phenol

B

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With coaggregate system composed of 59 mol percent ditetradecyl-dimethylammonium bromide and 41 mol percent hexadecyltrimethylammonium bromide; tris buffer (μ=0.2 with KCl); water; quercitrin; acetonitrile; Z-Phe-His-Leu at 25℃; Rate constant; enantioselective hydrolysis; var. flavonoids; pH 7.6;
With Tris-KCl buffer; water; N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; MyrHisLeu In acetonitrile at 25℃; Rate constant; pH 7.6; hydrolysis; other catalysts;;
Z-L-Phe-L-His-L-Leu-OH In methanol; water at 25℃; Rate constant; other catalysts (Z-L-His-L-Phe, Z-Phe-L-Phe-L-His, Bz-Gly-L-His-L-Leu, Z-L-Phe-L-His-L-Leu)and by benzylhexadecyldimethylammonium chloride and hexadecyltrimethylammonium chloride;
75531-11-2

p-nitrophenyl N-dodecanoyl-L-phenylalanine

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; N-tetradecanoyl-L-histidyl-L-leucine In water; acetonitrile at 10 - 45℃; Kinetics; Thermodynamic data; ΔG(excit.), other dialkyldimethylammonium bromides;
75531-07-6

p-nitrophenyl n-dodecanoyl-D(L)-phenylalaninate

A

14379-64-7

N-dodecanoyl-L-phenylalanine

B

56211-88-2

n-dodecanoyl-D-phenylalanine

Conditions
ConditionsYield
With N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; Z-L-Phe-L-His-L-Leu-OH In water; acetonitrile at 25℃; Rate constant; Product distribution; enantioselective hydrolysis; var. ionic strenght, pH 7.6;
With MES buffer; copper(II) ion; (4R,14R)-9-dodecyl-4,14-dihydroxymethyl-6,12-dithia-3,9,15,18-tetraazabicyclo[15.3.1]heneicosa-1(18),17(19),20-triene-2,16-dione In acetonitrile at 25℃; Rate constant; var. macrocyclic ligands and metal ions;
Z-Phe-His-Leu In various solvent(s) at 10 - 35℃; pH=7.6; Kinetics; Further Variations:; Temperatures; composition of coaggregates; ionic strength; Hydrolysis;
With L-tartaric acid co-embedded with bis-zinc-cyclen complex Zn2Cy into 1,2-dioleoyl-sn-glycero-3-phosphocholine membrane In aq. buffer at 20℃; pH=7.4; Kinetics; Reagent/catalyst;
112-16-3

n-dodecanoyl chloride

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / KHCO3; triethylamine / H2O; CHCl3 / 5 h / 0 °C
2: 98 percent / NaOH / methanol; tetrahydrofuran; H2O / 2 h / 0 °C
View Scheme
63-91-2

L-phenylalanine

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 6 h
2: 83 percent / KHCO3; triethylamine / H2O; CHCl3 / 5 h / 0 °C
3: 98 percent / NaOH / methanol; tetrahydrofuran; H2O / 2 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride / 10 h / 0 °C / Reflux
2: triethylamine / dichloromethane / 20 °C / Cooling with ice
3: sodium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / 18 h / 0 °C
2: sodium hydrogencarbonate
3: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 18 h / 0 °C
4: sodium hydroxide / methanol / 20 °C
5: hydrogenchloride / water
View Scheme
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / KHCO3; triethylamine / H2O; CHCl3 / 5 h / 0 °C
2: 98 percent / NaOH / methanol; tetrahydrofuran; H2O / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium hydrogencarbonate
2: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 18 h / 0 °C
3: sodium hydroxide / methanol / 20 °C
4: hydrogenchloride / water
View Scheme

N-Dodecanoyl-L-phenlyalanine Specification

The N-Dodecanoyl-L-phenlyalanine with the cas number 14379-64-7 is also called L-Phenylalanine,N-(1-oxododecyl)-. The systematic name is (2S)-2-(dodecanoylamino)-3-phenylpropanoic acid. Its molecular formula is C21H33NO3.

Physical properties about N-Dodecanoyl-L-phenlyalanine are: (1)XLogP3-AA 6.3 ; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 3; (4)Rotatable Bond Count: 14; (5)Tautomer Count: 2; (6)Exact Mass: 347.246044; (7)MonoIsotopic Mass: 347.246044; (8)Topological Polar Surface Area: 66.4; (9)Heavy Atom Count: 25; (10)Formal Charge: 0; (11)Complexity: 364; (12)Isotope Atom Count: 0; (13)Defined Atom StereoCenter Count: 1; (14)Undefined Atom StereoCenter Count: 0; (15)Defined Bond StereoCenter Count: 0; (16)Undefined Bond StereoCenter Count: 0; (17)Covalently-Bonded Unit Count: 1.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCCCCCCCC(=O)NC(CC1=CC=CC=C1)C(=O)O;
(2)InChI: InChI=1S/C21H33NO3/c1-2-3-4-5-6-7-8-9-13-16-20(23)22-19(21(24)25)17-18-14-11-10-12-15-18/h10-12,14-15,19H,2-9,13,16-17H2,1H3,(H,22,23)(H,24,25)/t19-/m0/s1;
(3)InChIKey: RKQUHHNIJVGMIG-IBGZPJMESA-N;

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