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Monatin
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Name

Monatin

 EINECS N/A
CAS No. 146142-94-1 Density 1.526 g/cm3
PSA 136.64000 LogP 1.02840
Solubility N/A Melting Point N/A
Formula C14H16N2O5 Boiling Point 656.358 °C at 760 mmHg
Molecular Weight 292.291 Flash Point 350.753 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 146142-94-1 (Monatin) Hazard Symbols N/A
Synonyms

(2S,4S)-Monatin;L-Glutamicacid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (S)-;(2S,4S)-2-Amino-4-carboxy-4-hydroxy-5-(3-indolyl)pentanoic acid;L-Glutamic acid,4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-;

Article Data 12

Monatin Synthetic route

(2S,4S)-4-Amino-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol92%
With sodium hydroxide In methanol; water at 20℃; for 6h;54 mg
Stage #1: (2S,4S)-4-Amino-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid With water; potassium hydroxide In methanol at 25℃; for 1h; Inert atmosphere; Large scale reaction;
Stage #2: With acetic acid In methanol pH=6.5; Large scale reaction;
Stage #3: With acetic acid In methanol pH=6.5; Large scale reaction; optical yield given as %ee;		193 g
855433-72-6

4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid

A

400769-77-9

(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

B

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
RP18-HPLC resolution;
551958-84-0

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Aeromonas hydrophila IFO3820 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Agrobacterium tumefaciens IFO3058 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Alcaligenes faecalis ATCC8750 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;
73-22-3

L-Tryptophan

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water for 27 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water for 27 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;
73-22-3

L-Tryptophan

A

914081-89-3

(S)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid

B

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 3 - 5h; pH=7.5 - 7.8; Product distribution / selectivity; Enzymatic reaction;
56-41-7

L-alanin

A

914081-89-3

(S)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid

B

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
Stage #1: L-Tryptophan With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 3 - 5h; pH=7.5 - 7.8; Enzymatic reaction;
Stage #2: L-alanin; HIS6-HEXaspC aminotransferase In water at 30℃; pH=7.5 - 7.8; Product distribution / selectivity; Enzymatic reaction;
113-24-6

sodium pyruvate

73-22-3

L-Tryptophan

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 21 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;

3-((2S,4S)-4-Amino-2-hydroxymethyl-5-oxo-tetrahydro-furan-2-ylmethyl)-indole-1-carboxylic acid tert-butyl ester

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
2: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
3: HCO2H; HCl / 4 h / 20 °C
4: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme
645396-51-6

2-[(indol-3-yl)methyl]prop-2-en-1-ol

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: CH2Cl2 / 360 h / 20 °C
2: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C
3: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
4: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
5: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
6: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
7: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
8: HCO2H; HCl / 4 h / 20 °C
9: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: 98 percent / MgBr2*OEt2 / CH2Cl2 / 84 h / 20 °C
2: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C
3: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
4: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
5: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
6: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
7: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
8: HCO2H; HCl / 4 h / 20 °C
9: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: CH2Cl2 / 360 h / 20 °C
2: 97 percent / imidazole / dimethylformamide
3: 97 percent / DMAP / acetonitrile
4: 100 percent / HF*pyridine / tetrahydrofuran
5: H2 / Pd(OH)2/C / methanol
6: acetonitrile
7: 69 percent / PDC / dimethylformamide
8: HCl; HCOOH
9: 92 percent / NaOH / methanol
View Scheme
Multi-step reaction with 9 steps
1: 98 percent / MgBr2*OEt2 / CH2Cl2 / 72 h / 20 °C
2: 97 percent / imidazole / dimethylformamide
3: 97 percent / DMAP / acetonitrile
4: 100 percent / HF*pyridine / tetrahydrofuran
5: H2 / Pd(OH)2/C / methanol
6: acetonitrile
7: 69 percent / PDC / dimethylformamide
8: HCl; HCOOH
9: 92 percent / NaOH / methanol
View Scheme
87438-91-3

ethyl 2-((1H-indol-3-yl)methyl)acrylate

146142-94-1

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 85 percent / DIBAL-H / CH2Cl2; hexane / -78 - 20 °C
2: CH2Cl2 / 360 h / 20 °C
3: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C
4: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
5: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
6: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
7: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
8: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
9: HCO2H; HCl / 4 h / 20 °C
10: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: 85 percent / DIBAL-H / CH2Cl2; hexane / -78 - 20 °C
2: 98 percent / MgBr2*OEt2 / CH2Cl2 / 84 h / 20 °C
3: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C
4: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
5: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
6: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
7: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
8: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
9: HCO2H; HCl / 4 h / 20 °C
10: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1: 97 percent / Et3N; 4-DMAP / CH2Cl2 / 20 °C
2: 72 percent / DIBAL-H / CH2Cl2 / -78 °C
3: MgBr2*OEt2 / CH2Cl2 / 96 h / 20 °C
4: 97 percent / imidazole / dimethylformamide
5: 97 percent / DMAP / acetonitrile
6: 100 percent / HF*pyridine / tetrahydrofuran
7: H2 / Pd(OH)2/C / methanol
8: acetonitrile
9: 69 percent / PDC / dimethylformamide
10: HCl; HCOOH
11: 92 percent / NaOH / methanol
View Scheme

Monatin Specification

The Monatin, with the CAS registry number 146142-94-1, is also known as L-Glutamic acid,4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-. This chemical's molecular formula is C14H16N2O5 and molecular weight is 292.29. What's more, its IUPAC name is (2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid. It is a naturally-occurring, high intensity sweetener isolated from the plant sclerochiton ilicifolius. It contains no carbohydrate or sugar, and nearly no food energy, unlike sucrose or other nutritive sweeteners.

Physical properties of Monatin are: (1)ACD/LogP: 0.90; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -3; (4)ACD/LogD (pH 7.4): -3; (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: 6; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 136.64 Å2; (13)Index of Refraction: 1.708; (14)Molar Refractivity: 74.733 cm3; (15)Molar Volume: 191.575 cm3; (16)Polarizability: 29.626×10-24cm3; (17)Surface Tension: 88.913 dyne/cm; (18)Density: 1.526 g/cm3; (19)Flash Point: 350.753 °C; (20)Enthalpy of Vaporization: 101.55 kJ/mol; (21)Boiling Point: 656.358 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@@H](N)C[C@](O)(C(=O)O)Cc2c1ccccc1nc2
(2)InChI: InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1
(3)InChIKey: RMLYXMMBIZLGAQ-HZMBPMFUSA-N

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