1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)- supplier

Name
L-MIMOSINE
EINECS 207-905-1
CAS No. 500-44-7
Article Data3
CAS DataBase
Density 1.544 g/cm³
Solubility
Melting Point 224-228 °C
Formula C₈H₁₀N₂O₄
Boiling Point 428.6 °C at 760 mmHg
Molecular Weight 198.178
Flash Point 213 °C
Transport Information
Appearance light tan to pink crystalline powder
Safety 22-36
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (S)-;Mimosine (6CI);L-Mimosine;Leucaenine;Leucaenol;Leucenine;Leucenol;Mimosin;NSC 69188;3-(3-hydroxy-4-oxopyridin-1(4H)-yl)alanine;2-Amino-3-(3-hydroxy-4-oxo-1(4H)-pyridinyl)propanoic acid;
PSA 105.55000
LogP -0.33390

Synthetic route

: 10182-48-6
3,4-dihydroxypyridine

: 5147-00-2
O-acetyl-L-serine

: 500-44-7
L-mimosine

Conditions

Conditions	Yield
With gallium(III) nitrate; pyridoxal 5'-phosphate In water at 62 - 65℃; for 0.5h; pH=4.5;	2%
cysteine synthases from Pisum sativum

: 1121-23-9
3-hydroxypyridin-4-one

: 56-45-1
L-serin

: 500-44-7
L-mimosine

Conditions

Conditions	Yield
With acetate buffer; metal ions; pyridoxal 5'-phosphate

: 1121-23-9
3-hydroxypyridin-4-one

: 5147-00-2
O-acetyl-L-serine

: 500-44-7
L-mimosine

Conditions

Conditions	Yield
With acetate buffer; metal ions; pyridoxal 5'-phosphate

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 500-44-7
L-mimosine

: 1271936-31-2
Fmoc-mimosine

Conditions

Conditions	Yield
Stage #1: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; L-mimosine With sodium carbonate In 1,4-dioxane; water at 20℃; for 6h; Stage #2: With sodium carbonate In 1,4-dioxane; water at 20℃; for 6h;	80%
With sodium carbonate In 1,4-dioxane; water at 20℃;	7.108 g
With sodium carbonate In 1,4-dioxane; water at 20 - 26℃; for 27h;
With sodium carbonate In 1,4-dioxane; water at 25℃;	7.108 g
With sodium carbonate In 1,4-dioxane; water at 20 - 26℃; for 27h;

: 77-78-1
dimethyl sulfate

: 500-44-7
L-mimosine

: 50700-62-4
3-methoxy-N-methyl-4-pyridone

Conditions

Conditions	Yield
With sodium hydroxide

: 500-44-7
L-mimosine

: 515-94-6, 1915-96-4, 4033-39-0, 6018-54-8
(S)-2,3-diaminopropionic acid

Conditions

Conditions	Yield
With bromine In water

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 500-44-7
L-mimosine

A: 1271936-31-2
Fmoc-mimosine

B: 1271936-33-4
C38H30N2O8

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 6h;

...Expand

: 18162-48-6
tert-butyldimethylsilyl chloride

: 500-44-7
L-mimosine

: N-α-Fmoc-O-tert-butyldimethylsilyl-L-mimosine

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 45℃;

: 14152-97-7
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

: 500-44-7
L-mimosine

: C23H29N3O13S

Conditions

Conditions	Yield
With sodium alkyl carbonate In water; acetonitrile for 0.5h;

: 88192-19-2
3-azidopropylamine

: 500-44-7
L-mimosine

: C11H16N6O3

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran

: 500-44-7
L-mimosine

: C13H19N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C13H19N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C17H19N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C17H19N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C19H20N4O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C19H20N4O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C13H17N3O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate / water; 1,4-dioxane / 27 h / 20 - 26 °C 2.1: benzotriazol-1-ol; diisopropyl-carbodiimide; dmap / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C 2.2: 0.75 h / 20 °C View Scheme

: 500-44-7
L-mimosine

: C8H10ClN2O3PS

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium tetrahydroborate; ethanol / 5.5 h / Reflux 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice View Scheme

: 500-44-7
L-mimosine

: C8H8(2)H2ClN2O3PS

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium borodeuteride / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C View Scheme
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium borodeuteride; ethanol / 5.5 h / Reflux 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C / Cooling with ice View Scheme

: 500-44-7
L-mimosine

: mimosinol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 5.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium tetrahydroborate; ethanol / 5.5 h / Reflux View Scheme

: 500-44-7
L-mimosine

: d2-mimosinol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium borodeuteride / ethanol / 5.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium borodeuteride; ethanol / 5.5 h / Reflux View Scheme

: 500-44-7
L-mimosine

: 3-hydroxy-1-(((4S)-2-methoxy-2-sulfanylidene-1,3,2-oxazaphospholidin-4-yl)methyl)pyridin-4(1H)one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice 4: sodium methylate / 0.17 h View Scheme
Multi-step reaction with 4 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium tetrahydroborate; ethanol / 5.5 h / Reflux 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice 4: sodium methylate / 0.17 h View Scheme

: 500-44-7
L-mimosine

: 3-hydroxy-1-(((4S)-2-ethoxy-2-sulfanylidene-1,3,2-oxazaphospholidin-4-yl)methyl)pyridin-4(1H)one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice 4: sodium methylate / 0.17 h View Scheme

: 500-44-7
L-mimosine

: 3-hydroxy-1-(((4S)-2-propoxy-2-sulfido-1,3,2-oxazaphospholidin-4-yl)methyl)pyridin-4(1H)-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 1 h / Cooling with ice 4: sodium methylate / 0.17 h View Scheme

: 500-44-7
L-mimosine

: d2-3-hydroxy-1-(((4S)-2-methoxy-2-sulfanylidene-1,3,2-oxazaphospholidin-4-yl)methyl)pyridin-4(1H)one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium borodeuteride / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C 4: triethylamine / 1,4-dioxane / 1.67 h View Scheme
Multi-step reaction with 4 steps 1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: sodium borodeuteride; ethanol / 5.5 h / Reflux 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C / Cooling with ice 4: triethylamine / 1,4-dioxane / 1.67 h View Scheme

: 500-44-7
L-mimosine

: d2-3-hydroxy-1-(((4S)-2-ethoxy-2-sulfanylidene-1,3,2-oxazaphospholidin-4-yl)methyl)pyridin-4(1H)one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium borodeuteride / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C 4: triethylamine / 1,4-dioxane / 1.67 h View Scheme

: 500-44-7
L-mimosine

: C11H15(2)H2N2O4PS

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1H-imidazole / N,N-dimethyl-formamide; dichloromethane / 2 h / 0 - 20 °C 2: sodium borodeuteride / ethanol / 5.5 h / 20 °C 3: triethylamine; trichlorothiophosphine / 1,4-dioxane / 0.17 h / 10 °C 4: triethylamine / 1,4-dioxane / 1.67 h View Scheme

: tris(triethylsilyl)silyl triflate

: 500-44-7
L-mimosine

: mimosine tris(triethylsilyl)silyl ester

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;

1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)- Specification

The 1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)-, with the CAS registry number 500-44-7 and EINECS registry number 207-905-1, has the systematic name of 3-(3-hydroxy-4-oxopyridin-1(4H)-yl)alanine. It is a kind of light tan to pink crystalline powder, and belongs to the product category of Alkaloids. And the molecular formula of the chemical is C₈H₁₀N₂O₄.

The characteristics of 1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)- are as followings: (1)ACD/LogP: -1.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.57; (4)ACD/LogD (pH 7.4): -3.71; (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: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 59.08 Å²; (13)Index of Refraction: 1.645; (14)Molar Refractivity: 46.56 cm³; (15)Molar Volume: 128.3 cm³; (16)Polarizability: 18.46×10^-24cm³; (17)Surface Tension: 85.8 dyne/cm; (18)Density: 1.544 g/cm³; (19)Flash Point: 213 °C; (20)Enthalpy of Vaporization: 78.95 kJ/mol; (21)Boiling Point: 428.6 °C at 760 mmHg; (22)Vapour Pressure: 3.84E-09 mmHg at 25°C.

You should be cautious while dealing with this chemical. It is harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Do not breathe dust, and wear suitable protective clothing.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)C(N)CN/1/C=C\C(=O)C(\O)=C\1
(2)InChI: InChI=1/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)
(3)InChIKey: WZNJWVWKTVETCG-UHFFFAOYAK

Product Name

L-MIMOSINE

Synthetic route

1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)- Specification

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