| Identification | More | [Name]
Methyl L-histidinate dihydrochloride | [CAS]
7389-87-9 | [Synonyms]
H-HIS-OME 2HCL
HISTIDINE METHYL ESTER DIHYDROCHLORIDE
HISTIDINE-OME 2 HCL
H-L-HIS-OME 2HCL
L(+)-HISTIDINE METHYL ESTER DIHYDROCHLORIDE
L-HISTIDINE METHYL ESTER DIHYDROCHLORIDE
L-HISTIDINE METHYL ESTER DIHYDROCHLORIDE SALT
L-HISTIDINE METHYL ESTER HYDROCHLORIDE
L-METHYL HISTIDINATE DIHYDROCHLORIDE
H-His-OMe.2HCI
methyl L-histidinate dihydrochloride
L-Histidine Methyl Ester 2HCl
L-HISTIDINE METHYL ESTER DIHCL
L-Histidine methyl ester dihydrochloride, 98+%
Histidine methyl·2hydrochloride
L-Histidine methyl·dihydrochloride | [EINECS(EC#)]
230-973-9 | [Molecular Formula]
C7H13Cl2N3O2 | [MDL Number]
MFCD00012701 | [Molecular Weight]
242.1 | [MOL File]
7389-87-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
207 °C (dec.)(lit.)
| [alpha ]
9 º (c=2 in H2O) | [refractive index ]
10 ° (C=2, H2O) | [storage temp. ]
−20°C
| [solubility ]
100g/l | [form ]
Fine Crystalline Powder | [color ]
White | [Optical Rotation]
[α]20/D +9.0°, c = 2 in H2O | [Water Solubility ]
Soluble in dimethyl sulfoxide, methanol and water. | [Sensitive ]
Hygroscopic | [BRN ]
3572010 | [InChI]
InChI=1/C7H11N3O2.2ClH/c1-12-7(11)6(8)2-5-3-9-4-10-5;;/h3-4,6H,2,8H2,1H3,(H,9,10);2*1H/t6-;;/s3 | [InChIKey]
DWAYENIPKPKKMV-ILKKLZGPSA-N | [SMILES]
C1(N=CNC=1)C[C@H](N)C(=O)OC.Cl.Cl |&1:6,r| | [CAS DataBase Reference]
7389-87-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29332900 |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
Methyl L-histidinate dihydrochloride is used in the preparation of optically pure L-(+)-Ergothioneine.
| [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
Example 1; Synthesis of (R)-2-amino-3-(1H-imidazol-4-yl)propanoic acid methyl ester dihydrochloride was carried out by improving the method reported by Cook et al. In a 200 L Schott glass reactor equipped with an air-driven stirrer, a high-efficiency condenser and a gas introduction port, 12.5 kg of L-histidine hydrochloride monohydrate was suspended in 130 L of methanol. Dry HCl gas was passed into the suspension while the mixture was heated to 55-65 °C until complete dissolution. The passage of HCl gas was continued until saturation, at which point it was stopped. Shortly after the solution was formed, a precipitation of the product began to appear. The mixture is stirred continuously and supplemented with additional passes of HCl gas every 1 hour and 15 minutes; the mixture is heated under mild reflux conditions for 8 hours. After the reaction is complete, it can be kept warm for 6-8 hours. Subsequently, 40 L of ethyl acetate is added, stirred for 1 hour and filtered. The filter cake was washed with 10 L of isopropyl ether and the resulting white crystalline product was air dried. The yield was 95%. The melting point was 102-103 °C (literature value 102-103 °C). Spinodal [α]25D = +3.5° (c=2, H2O).1H NMR (D2O) data: δ 3.4 (t, 2H), 3.9 (s, 3H), 4.5 (s, 2H), 7.4 (s, 1H), 8.5 (s, 1H). | [References]
[1] Tetrahedron Asymmetry, 2008, vol. 19, # 3, p. 273 - 278
[2] Patent: US2009/93642, 2009, A1. Location in patent: Page/Page column 6; 7 |
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