Product Name

  • Name

    N-Dodecanoyl-L-phenlyalanine

  • EINECS
  • CAS No. 14379-64-7
  • Article Data28
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point
  • Formula C21H33NO3
  • Boiling Point
  • Molecular Weight 347.498
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 14379-64-7 (N-Dodecanoyl-L-phenlyalanine)
  • Hazard Symbols
  • Synonyms Alanine,N-lauroyl-3-phenyl- (6CI,7CI);Alanine, N-lauroyl-3-phenyl-, L- (8CI);N-Dodecanoyl-phenylalanine;N-Lauroyl-L-phenylalanine;N-Lauroylphenylalanine;
  • PSA 66.40000
  • LogP 5.11030

Synthetic route

n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

Wang resin-bound Fmoc-L-phenylalanine

Wang resin-bound Fmoc-L-phenylalanine

N-dodecanoyl-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%
N-n-dodecanoyl methyl (L)-phenylalaninate
122889-27-4

N-n-dodecanoyl methyl (L)-phenylalaninate

N-dodecanoyl-L-phenylalanine
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
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

L-phenylalanine
63-91-2

L-phenylalanine

N-dodecanoyl-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℃;
p-nitrophenyl N-dodecanoyl-D-phenylalaninate
75531-12-3

p-nitrophenyl N-dodecanoyl-D-phenylalaninate

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

N-dodecanoyl-L-phenylalanine
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;
p-nitrophenyl N-dodecanoyl-L-phenylalanine
75531-11-2

p-nitrophenyl N-dodecanoyl-L-phenylalanine

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

N-dodecanoyl-L-phenylalanine
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;
p-nitrophenyl N-dodecanoyl-L-phenylalanine
75531-11-2

p-nitrophenyl N-dodecanoyl-L-phenylalanine

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;
p-nitrophenyl n-dodecanoyl-D(L)-phenylalaninate
75531-07-6

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

A

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

B

n-dodecanoyl-D-phenylalanine
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;
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

N-dodecanoyl-L-phenylalanine
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
L-phenylalanine
63-91-2

L-phenylalanine

N-dodecanoyl-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
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

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

N-dodecanoyl-L-phenylalanine
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
C40H45ClNO3Pol

C40H45ClNO3Pol

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane 2-chlorotrityl chloride resin;34.3 mg
methyl (2S)-2-amino-3-phenylpropanoate
2577-90-4

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

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 20 °C / Cooling with ice
2: sodium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 18 h / 0 °C
2: sodium hydroxide / methanol / 20 °C
3: hydrogenchloride / water
View Scheme
N-dodecanoyl-L-phenylalanine

N-dodecanoyl-L-phenylalanine

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water1.37 g
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

L-proline methyl ester monohydrochloride
2133-40-6

L-proline methyl ester monohydrochloride

C27H42N2O4

C27H42N2O4

Conditions
ConditionsYield
Stage #1: N-dodecanoyl-L-phenylalanine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: L-proline methyl ester monohydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 17h;		44%
Stage #1: N-dodecanoyl-L-phenylalanine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In tetrahydrofuran; N,N-dimethyl-formamide for 0.166667h;
Stage #2: L-proline methyl ester monohydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 17h;		44%
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C13H21N3O2*BrH

C13H21N3O2*BrH

C34H52N4O4

C34H52N4O4

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;32%
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

L-Histidine methyl ester
1499-46-3

L-Histidine methyl ester

N-lauroyl-L-phenylalanyl-L-histidine methyl ester
79416-20-9

N-lauroyl-L-phenylalanyl-L-histidine methyl ester

n-Dodecylamine
124-22-1

n-Dodecylamine

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

N-lauroyl-L-phenylalanine-n-dodecyl amide

N-lauroyl-L-phenylalanine-n-dodecyl amide

Conditions
ConditionsYield
With boron trioxide; propylene glycol monoethyl ether at 125℃; for 10h;
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C25H36N2O5

C25H36N2O5

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In chloroform at 20℃; for 12h;
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C25H39N3O5

C25H39N3O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
2: sodium carbonate / water; acetone / 20 °C
View Scheme
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C29H42N4O7

C29H42N4O7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
2: sodium carbonate / water; acetone / 20 °C
3: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
View Scheme
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C30H47N5O7

C30H47N5O7

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
2: sodium carbonate / water; acetone / 20 °C
3: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
4: sodium carbonate / water; acetone / 20 °C
View Scheme
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C49H73BN10O12

C49H73BN10O12

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
2.1: sodium carbonate / water; acetone / 20 °C
3.1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
4.1: sodium carbonate / water; acetone / 20 °C
5.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide
5.2: 20 °C
View Scheme
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C44H65BN10O12

C44H65BN10O12

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
2.1: sodium carbonate / water; acetone / 20 °C
3.1: dicyclohexyl-carbodiimide / chloroform / 12 h / 20 °C
4.1: sodium carbonate / water; acetone / 20 °C
5.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide
5.2: 20 °C
6.1: water; hydrogenchloride / water / 24 h / 20 °C
View Scheme
N-dodecanoyl-L-phenylalanine
14379-64-7

N-dodecanoyl-L-phenylalanine

C26H40N2O4

C26H40N2O4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 17 h / 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water; methanol / 20 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h
1.2: 17 h / 20 °C
2.1: lithium hydroxide; water / tetrahydrofuran; methanol / 20 h / 0 - 20 °C
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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