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H15403

Sigma-Aldrich

L-Histidine methyl ester dihydrochloride

97%

Sinonimo/i:

(S)-Histidine methyl ester dihydrochloride, Methyl L-histidinate dihydrochloride

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About This Item

Formula empirica (notazione di Hill):
C7H11N3O2 · 2HCl
Numero CAS:
7389-87-9
Peso molecolare:
242.10
Beilstein:
3572009
Numero CE:
230-973-9
Numero MDL:
MFCD00012701
Codice UNSPSC:
12352209
eCl@ss:
32160406
ID PubChem:
24895465
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Attività ottica

[α]20/D +9.0°, c = 2 in H2O

Impiego in reazioni chimiche

reaction type: solution phase peptide synthesis

Colore

white

Punto di fusione

207 °C (dec.) (lit.)

applicazioni

peptide synthesis

Stringa SMILE

Cl.Cl.COC(=O)[C@@H](N)Cc1c[nH]cn1

InChI

1S/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-;;/m0../s1
DWAYENIPKPKKMV-ILKKLZGPSA-N

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Applicazioni

L-Histidine methyl ester dihydrochloride can be used as a reactant to synthesize:
  • Imidazopyridine derivatives by Pictet-Spegler reaction with different aldehydes.
  • A metal-chelating ligand, N-methacryloyl-(l)-histidine methyl ester by reacting with methacryloyl chloride.
  • Zwitterionic polypeptide derivative by amidation reaction with poly (α,β-L-aspartic acid).

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
MKCQ7560
MKCM4499
MKCJ9626
MKCH6408
MKCD3214

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3-Methyl-L-histidine

Sigma-Aldrich

M9005

3-Methyl-L-histidine

L-Istidina European Pharmacopoeia (EP) Reference Standard

H0750000

L-Istidina

L-Histidine dihydrochloride ≥99.0% (AT)

Sigma-Aldrich

53340

L-Histidine dihydrochloride

Xiaoyu Su et al.
Chirality, 21(5), 539-546 (2008-08-14)
Two kinds of novel chiral molecular tweezers containing imidazoliums were synthesized from L-alanine, L-phenylalanine, and L-glutamic acid. They are constructed by the chiral imidazolium pincers and two different spacers which are 1,3-bis (bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine, respectively. The enantioselective recognition of
T A Alston et al.
Biochemistry, 26(13), 4082-4085 (1987-06-30)
L-Histidine methyl ester inactivates histidine decarboxylase in a time-dependent manner. The possibility was considered that an irreversible reaction between enzyme and inhibitor occurs [Recsei, P. A., & Snell, E. E. (1970) Biochemistry 9, 1492-1497]. We have confirmed time-dependent inactivation by
V H Vilchiz et al.
Acta crystallographica. Section C, Crystal structure communications, 52 ( Pt 3), 696-698 (1996-03-15)
The title compound, C7H13N3O2(2+).2Cl-, has distances and angles quite similar to those of histidine hydrochloride monohydrate [Donohue & Caron (1964). Acta Cryst. 17, 1178-1180], except for the distances within the ester functionality.
Scott Worley et al.
Proteins, 46(3), 321-329 (2002-02-09)
Histidine decarboxylase (HDC) from Lactobacillus 30a converts histidine to histamine, a process that enables the bacteria to maintain the optimum pH range for cell growth. HDC is regulated by pH; it is active at low pH and inactive at neutral
Y Oya et al.
Mutation research, 198(1), 233-240 (1988-03-01)
An enhancing effect of L-histidine (L-His) was detected on the induction by hydrogen peroxide (H2O2) of chromosomal aberrations of both the chromosome type and the chromatid type, in human embryonic fibroblasts. The maximum efficiency of induction was about 8-fold higher
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