Product Name

  • Name

    L-Anserine

  • EINECS 209-545-0
  • CAS No. 584-85-0
  • Article Data10
  • CAS DataBase
  • Density 1.38 g/cm3
  • Solubility
  • Melting Point 268℃ (decomposition)
  • Formula C10H16N4O3
  • Boiling Point 611.3 °C at 760 mmHg
  • Molecular Weight 240.262
  • Flash Point 323.5 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 584-85-0 (L-Anserine)
  • Hazard Symbols
  • Synonyms Anserine(8CI);Histidine, N-b-alanyl-3-methyl-, L- (7CI);L-Histidine, N-b-alanyl-3-methyl-;β-Alanyl-3-methyl-L-histidine;L-Anserine;
  • PSA 110.24000
  • LogP -0.02800

Synthetic route

C15H24N4O5

C15H24N4O5

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 50℃; for 4h;97%
With hydrogenchloride In water at 40 - 50℃; for 8h;5.1 g
C16H20N4O3

C16H20N4O3

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With sodium hydrogencarbonate at 20 - 30℃; for 8h;95%
C25H28N4O5

C25H28N4O5

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With ammonium formate In ethanol at 70 - 80℃; for 12h; Solvent; Reagent/catalyst; Temperature;95%
C12H20N4O3

C12H20N4O3

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With potassium hydroxide at 20 - 30℃; for 8h;93%
β-alanyl-3-methyl-L-histidine methyl ester
1018683-10-7

β-alanyl-3-methyl-L-histidine methyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With potassium hydroxide at 20 - 30℃; for 8h;92%
C14H24N4O3

C14H24N4O3

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With potassium hydroxide at 20 - 30℃; for 8h;91%
C13H22N4O3

C13H22N4O3

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With potassium carbonate at 20 - 30℃; for 8h;90.5%
C17H22N4O3

C17H22N4O3

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 20 - 30℃; for 2h;90%
With palladium 10% on activated carbon; hydrogen at 20 - 30℃; for 2h;4.9 g
C18H24N4O4

C18H24N4O4

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 20 - 30℃; for 2h;90%
phthalyl-L-anserine methylester
848572-83-8

phthalyl-L-anserine methylester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With hydrogenchloride; water; hydrazine for 5h; Heating / reflux;73.8%
N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine methyl ester
952739-81-0

N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine methyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Stage #1: N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine methyl ester With sodium hydroxide In methanol; water at 20℃; for 16h; pH=> 11;
Stage #2: With hydrogenchloride In methanol; water for 15h; pH=< 3;
67%
With sodium hydroxide at 20℃;
Multi-step reaction with 2 steps
1: sodium hydroxide; water / methanol / 6 h / 20 - 30 °C
2: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol; water / 4 h / 20 - 40 °C
2: potassium hydroxide / 8 h / 20 - 30 °C
View Scheme
benzyl N-[2-(hydrazinecarbonyl)ethyl]carbamate
21855-66-3

benzyl N-[2-(hydrazinecarbonyl)ethyl]carbamate

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
With hydrogenchloride; water; acetic acid; sodium nitrite Umsetzen des erhaltenen Azids mit 3-Methyl-L-histidin-methylester,anschliessendes Behandeln mit wss.NaOH und Hydrieren an Palladium in wss.H2SO4;
3-methyl-L-histidine
368-16-1

3-methyl-L-histidine

3-amino propanoic acid
107-95-9

3-amino propanoic acid

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
ueber die enzymatische Synthese;
3-amino propanoic acid
107-95-9

3-amino propanoic acid

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
ueber die enzymatische Synthese;
2-(3-tert-butoxycarbonylaminopropionylamino)-3-(1H-imidazol-4-yl)propionic acid methyl ester
82361-55-5

2-(3-tert-butoxycarbonylaminopropionylamino)-3-(1H-imidazol-4-yl)propionic acid methyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / Et3N / benzene / 1 h / Heating
2: tetrahydrofuran / 1 h / Heating
3: 18.7 g / AgOAc / acetic acid; H2O / 0.08 h
4: aq. NaOH / 20 °C
View Scheme
2-(3-tert-butoxycarbonylaminopropionylamino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid methyl ester
952739-80-9

2-(3-tert-butoxycarbonylaminopropionylamino)-3-(1-trityl-1H-imidazol-4-yl)propionic acid methyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 1 h / Heating
2: 18.7 g / AgOAc / acetic acid; H2O / 0.08 h
3: aq. NaOH / 20 °C
View Scheme
C35H41N4O5(1+)*I(1-)

C35H41N4O5(1+)*I(1-)

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 18.7 g / AgOAc / acetic acid; H2O / 0.08 h
2: aq. NaOH / 20 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide; Et3N / CH2Cl2 / 24 h / 20 °C
2: 98 percent / Et3N / benzene / 1 h / Heating
3: tetrahydrofuran / 1 h / Heating
4: 18.7 g / AgOAc / acetic acid; H2O / 0.08 h
5: aq. NaOH / 20 °C
View Scheme
(S)-methyl 2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoate
72244-50-9

(S)-methyl 2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoate

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
2.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
2.2: 15 h / pH < 3
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 4 h / 20 - 30 °C
2: sodium hydroxide; water / methanol / 6 h / 20 - 30 °C
3: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / acetonitrile / 4 h / 20 - 30 °C
2: hydrogenchloride / methanol; water / 4 h / 20 - 40 °C
3: potassium hydroxide / 8 h / 20 - 30 °C
View Scheme
3-methyl-3H-imidazole-4-carboxaldehyde trifluoromethanesulfonate

3-methyl-3H-imidazole-4-carboxaldehyde trifluoromethanesulfonate

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N,N,N',N'-tetramethylguanidine / tetrahydrofuran / 25 h / 0 - 20 °C
2.1: (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen / 2,2,2-trifluoroethanol / 10 h / 50 °C / 15514.9 Torr
3.1: hydrogen; palladium(II) hydroxide / methanol / 3 h / 20 °C
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
5.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
5.2: 15 h / pH < 3
View Scheme
Multi-step reaction with 5 steps
1.1: N,N,N',N'-tetramethylguanidine / tetrahydrofuran / 25 h / 0 - 20 °C
2.1: (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen / methanol / 120 °C / 80160.1 Torr
3.1: hydrogen; palladium(II) hydroxide / methanol / 3 h / 20 °C
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
5.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
5.2: 15 h / pH < 3
View Scheme
(Z)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-5-yl)acrylate

(Z)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-5-yl)acrylate

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen / methanol / 120 °C / 80160.1 Torr
2.1: hydrogen; palladium(II) hydroxide / methanol / 3 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
4.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
4.2: 15 h / pH < 3
View Scheme
Multi-step reaction with 4 steps
1.1: (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen / 2,2,2-trifluoroethanol / 10 h / 50 °C / 15514.9 Torr
2.1: hydrogen; palladium(II) hydroxide / methanol / 3 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
4.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
4.2: 15 h / pH < 3
View Scheme
(S)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-5-yl)propanoate

(S)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-5-yl)propanoate

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen; palladium(II) hydroxide / methanol / 3 h / 20 °C
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere
3.1: sodium hydroxide / methanol; water / 16 h / 20 °C / pH > 11
3.2: 15 h / pH < 3
View Scheme
N(τ)-methyl-L-histidine benzyl ester

N(τ)-methyl-L-histidine benzyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate / tetrahydrofuran / 6 h / 20 - 30 °C
2: hydrogenchloride / methanol; water / 8 h / 20 - 50 °C
3: palladium 10% on activated carbon; hydrogen / 2 h / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / tetrahydrofuran / 6 h / 20 - 30 °C
2: palladium 10% on activated carbon; hydrogen / methanol; water / 6 h / 20 - 30 °C
3: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / tetrahydrofuran / 6 h / 20 - 30 °C
2: hydrogenchloride / methanol; water / 8 h / 40 - 50 °C
3: palladium 10% on activated carbon; hydrogen / 2 h / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / tetrahydrofuran / 6 h / 20 - 30 °C
2: palladium 10% on activated carbon; hydrogen / methanol; water / 12 h / 20 - 30 °C
3: hydrogenchloride / water / 8 h / 40 - 50 °C
View Scheme
N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine benzyl ester

N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine benzyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol; water / 8 h / 20 - 50 °C
2: palladium 10% on activated carbon; hydrogen / 2 h / 20 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol; water / 8 h / 40 - 50 °C
2: palladium 10% on activated carbon; hydrogen / 2 h / 20 - 30 °C
View Scheme
N(τ)-methyl-L-histidine isopropyl ester

N(τ)-methyl-L-histidine isopropyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate / toluene / 8 h / 20 - 30 °C
2: hydrogenchloride / water; toluene / 4 h / 30 - 50 °C
3: potassium carbonate / 8 h / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate / toluene / 8 h / 20 - 30 °C
2: formic acid / methanol; water / 6 h / 30 °C
3: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
C18H30N4O5

C18H30N4O5

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; toluene / 4 h / 30 - 50 °C
2: potassium carbonate / 8 h / 20 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: formic acid / methanol; water / 6 h / 30 °C
2: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
N(τ)-methyl-L-histidine phenyl ester

N(τ)-methyl-L-histidine phenyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate / toluene / 4 h / 20 - 30 °C
2: potassium hydrogencarbonate / tetrahydrofuran / 8 h / 20 - 30 °C
3: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate / toluene / 4 h / 20 - 30 °C
2: hydrogenchloride / water; tetrahydrofuran / 4 h / 20 - 50 °C
3: sodium hydrogencarbonate / 8 h / 20 - 30 °C
View Scheme
N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine phenyl ester

N(α)-(3-((tert-butoxycarbonyl)amino)propylcarbonyl)-N(τ)-methyl-L-histidine phenyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; tetrahydrofuran / 4 h / 20 - 50 °C
2: sodium hydrogencarbonate / 8 h / 20 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydrogencarbonate / tetrahydrofuran / 8 h / 20 - 30 °C
2: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
N(τ)-methyl-L-histidine ethyl ester

N(τ)-methyl-L-histidine ethyl ester

L-anserine
584-85-0

L-anserine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 20 - 30 °C
2: hydrogenchloride / water; ethanol / 4 h / 20 - 50 °C
3: potassium hydroxide / 8 h / 20 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 20 - 30 °C
2: sodium carbonate / 8 h / 20 - 30 °C
3: hydrogenchloride / water / 4 h / 20 - 50 °C
View Scheme
2I-O-(p-toluenesulfonyl)-β-cyclodextrin
84216-71-7

2I-O-(p-toluenesulfonyl)-β-cyclodextrin

L-anserine
584-85-0

L-anserine

(2AS,3AR)-3A-[(3-{[(1S)-1-carboxy-2-(1-methyl-1H-imidazol-5-yl)ethyl]amino}-3-oxopropyl)amino]-3A-deoxy-β-cyclodextrin

(2AS,3AR)-3A-[(3-{[(1S)-1-carboxy-2-(1-methyl-1H-imidazol-5-yl)ethyl]amino}-3-oxopropyl)amino]-3A-deoxy-β-cyclodextrin

Conditions
ConditionsYield
Stage #1: 2I-O-(p-toluenesulfonyl)-β-cyclodextrin With sodium hydrogencarbonate In water
Stage #2: L-anserine In water at 60℃; for 40h; Further stages.;
37%
L-anserine
584-85-0

L-anserine

soda lime

soda lime

1,2-dimethylimidazole
10447-93-5

1,2-dimethylimidazole

L-anserine
584-85-0

L-anserine

barytes water

barytes water

B

3-amino propanoic acid
107-95-9

3-amino propanoic acid

Conditions
ConditionsYield
at 140℃;
L-anserine
584-85-0

L-anserine

A

3-methyl-Nα-<N-phosphono-β-alanyl>-L-histidine

3-methyl-Nα-<N-phosphono-β-alanyl>-L-histidine

B

5-<(S)-2-carboxy-2-<(N-phosphono-β-alanyl)-amino>-ethyl>-3-methyl-1-phosphono-imidazolium

5-<(S)-2-carboxy-2-<(N-phosphono-β-alanyl)-amino>-ethyl>-3-methyl-1-phosphono-imidazolium

C

Nα-β-alanyl-3-methyl-1-phosphono-L-histidine

Nα-β-alanyl-3-methyl-1-phosphono-L-histidine

Conditions
ConditionsYield
ueber die Phosphorylierung;
L-anserine
584-85-0

L-anserine

NaHPO3(NH2)

NaHPO3(NH2)

A

3-methyl-Nα-<N-phosphono-β-alanyl>-L-histidine

3-methyl-Nα-<N-phosphono-β-alanyl>-L-histidine

B

5-<(S)-2-carboxy-2-<(N-phosphono-β-alanyl)-amino>-ethyl>-3-methyl-1-phosphono-imidazolium

5-<(S)-2-carboxy-2-<(N-phosphono-β-alanyl)-amino>-ethyl>-3-methyl-1-phosphono-imidazolium

C

Nα-β-alanyl-3-methyl-1-phosphono-L-histidine

Nα-β-alanyl-3-methyl-1-phosphono-L-histidine

Conditions
ConditionsYield
ueber die Phosphorylierung;
methanol
67-56-1

methanol

L-anserine
584-85-0

L-anserine

β-alanyl-3-methyl-L-histidine methyl ester
1018683-10-7

β-alanyl-3-methyl-L-histidine methyl ester

Conditions
ConditionsYield
With hydrogenchloride at 0℃;
L-anserine
584-85-0

L-anserine

C10H16N4O4

C10H16N4O4

Conditions
ConditionsYield
With oxygen; copper(II) sulfate; ascorbic acid In aq. phosphate buffer at 20℃; for 0.5h; pH=7.2;

L-Histidine, β-alanyl-3-methyl- Specification

The L-Histidine, β-alanyl-3-methyl-, with the CAS registry number 584-85-0, is also known as L-Anserine. It belongs to the product categoy of Chiral heterocyclic compounds. Its EINECS number is 209-545-0. This chemical's molecular formula is C10H16N4O3 and molecular weight is 240.26. What's more, its systematic name is β-alanyl-3-methyl-L-histidine.

Physical properties of L-Histidine, β-alanyl-3-methyl- are: (1)ACD/LogP: -2.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -5.63; (4)ACD/LogD (pH 7.4): -4.88; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 67.67 Å2; (13)Index of Refraction: 1.615; (14)Molar Refractivity: 60.43 cm3; (15)Molar Volume: 173.1 cm3; (16)Polarizability: 23.95×10-24cm3; (17)Surface Tension: 57.1 dyne/cm; (18)Density: 1.38 g/cm3; (19)Flash Point: 323.5 °C; (20)Enthalpy of Vaporization: 95.43 kJ/mol; (21)Boiling Point: 611.3 °C at 760 mmHg; (22)Vapour Pressure: 8.52E-16 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@H](NC(=O)CCN)Cc1cncn1C
(2)InChI: InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
(3)InChIKey: MYYIAHXIVFADCU-QMMMGPOBSA-N

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