5934-29-2

Basic information

• Product Name: L-Histidine hydrochloride monohydrate
• Synonyms: L-ALPHA-AMINO-4(OR 5)-IMIDAZOLEPROPIONIC ACID MONOHYDROCHLORIDE, MONOHYDRATE;L-ALPHA-AMINO-BETA-(4-IMIDAZOLYL)PROPIONIC ACID MONOHYDROCHLORIDE;L-HIS HCL H2O;L-HISTIDINE MONOHYDROCHLORIDE H2O;L-(+)-HISTIDINE HYDROCHLORIDE MONOHYDRATE;L-HISTIDINE HYDROCHLORIDE MONOHYDRATE;L-HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE;L-HISTIDINE HCL H2O
• CAS NO: 5934-29-2
• Molecular Formula: C₆H₁₀N₃O₂*Cl*H₂O
• Molecular Weight: 209.63
• EINECS: 211-438-9
• Product Categories: Amino Acid Derivatives;alpha-Amino Acids;Amino Acids;Biochemistry;L-Amino Acids
• Mol File: 5934-29-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 254 °C (dec.)(lit.)
• Boiling Point: 458.9 °C at 760 mmHg
• Flash Point: 231.3 °C
• Appearance: White/Solid
• Density: 1.49 g/cm3
• Vapor Pressure: 3.25E-09mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: H2O: 100 mg/mL
• Water Solubility: 169.9 g/L (20 ºC)
• Merck: 14,4720
• BRN: 4168261
• CAS DataBase Reference: L-Histidine hydrochloride monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: L-Histidine hydrochloride monohydrate(5934-29-2)
• EPA Substance Registry System: L-Histidine hydrochloride monohydrate(5934-29-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36/37-26
• WGK Germany: 3
• RTECS: MS3119000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 5934-29-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystals or cryst. or granular powder

Uses

Different sources of media describe the Uses of 5934-29-2 differently. You can refer to the following data:
1. L-Histidine is used in cell culture media formulations used in biomanufacturing. L-Histidine has been used to study cultures of the human T-lymphoblastic leukemia cell line MOLT-4 to study modulation of apoptosis.
2. L-Histidine monohydrochloride, non-animal, is used in cell culture media formulations used in biomanufacturing. The use of non-animal-sourced L-Histidine and other components avoids the risk of contaminating bioproducts with adventitious viruses.
3. L-Histidine Hydrochloride Monohydrate can be used as AhR activators to treat gluten-induced gastrointestinal diseases. It can also be used for hair coloring method.

General Description

Chemicals play an important role in the stabilization of a biologic drug during its manufacturing and formulation process – for instance, by preventing aggregation. We offer a wide range of high-quality stabilizers, buffers and salts to successfully purify and formulate your biomolecules. Specifically developed for high-risk applications, they are low in bioburden and endotoxins.As part of our Emprove? Program, our raw materials are offered with extensive documentation facilitating compliance of your pharma and biopharma product, full supply chain transparency and risk mitigation. Our SAFC? portfolio of high-quality products for biopharmaceutical and pharmaceutical formulation and production withstands strict quality control procedures and is produced according to applicable cGMP guidelines.

Biochem/physiol Actions

L-Histidine is biosynthesized from ATP, 5-phosphoribosyl-1-pyrophosphate (PRPP), and glutamine. This essential amino acid can be degraded to glutamate by histidiase, urocanase and imidazolonepropionase; it is also the precursor of histamine by action of histidine decarboxylase.

Purification Methods

Crystallise the monohydrochloride from aqueous EtOH or 60% aqueous EtOH (m 259odec). Alternatively dissolve 10g in 50mL of H2O, decolourise with Norite, filter, evaporate it in a vacuum to a syrup, cool to room temperature, add 95% EtOH with stirring until slightly turbid, scratch the sides of the vessel until crystals form, then add slowly 40mL of EtOH and keep at 0o overnight, filter the solid off, wash it several times with EtOH and dry it in a vacuum. [Cox J Biol Chem 78 475 1929, Cox et al. J Biol Chem 81 73 1929, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1972, 2098 1961, Beilstein 25 II 407, 25 III/IV 4346.]

InChI:InChI=1/C6H9N3O2.ClH.H2O/c7-5(6(10)11)1-4-2-8-3-9-4;;/h2-3,5H,1,7H2,(H,8,9)(H,10,11);1H;1H2/t5-;;/m0../s1

Synthetic route

L-histidine (71-00-1) → L-histidine hydrochloride monohydrate (5934-29-2)

Conditions	Yield
With hydrogenchloride; water at 26.84℃;

L-histidine hydrochloride monohydrate (5934-29-2) → (S)-4,4-dimethyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridinyl-6-carboxylic acid dihydrochloride + (S)-4,4-dimethyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridinyl-6-carboxylic acid hydrochloride (154056-78-7)

Conditions	Yield
With sodium hydroxide In water; hydrogen; acetone	A 100% B n/a

4-methoxybenzyloxycarbonyl azide (25474-85-5) + L-histidine hydrochloride monohydrate (5934-29-2) → (S)-3-(1H-Imidazol-4-yl)-2-(4-methoxy-benzyloxycarbonylamino)-propionic acid; hydrate

Conditions	Yield
	66%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-histidine hydrochloride monohydrate (5934-29-2) → (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-4-yl)-propionic acid; hydrate

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane for 5h;	62%

bis(L-histidine)ZnCl2 + L-histidine hydrochloride monohydrate (5934-29-2) → (L-histidine)ZnCl2*HCl

Conditions	Yield
In water soln. of ZnCl2 added slowly;; acetone added; crystd. at -27°C; elem. anal.;;	56%

L-histidine hydrochloride monohydrate (5934-29-2) → 2-mercapto-L-histidine (2002-22-4, 13552-61-9, 51302-10-4)

Conditions	Yield
Stage #1: L-histidine hydrochloride monohydrate With bromine In water at -2 - 0℃; for 0.0833333 - 0.116667h; Stage #2: With L-Cysteine In water at 0℃; for 1h; Stage #3: With 3-mercaptopropionic acid at 95℃; for 18h;	49%

S-benzoyl-3-mercaptopropanoyl chloride (67714-30-1) + L-histidine hydrochloride monohydrate (5934-29-2) → N2-(S-benzoyl-3-mercaptopropanoyl)-L-histidine (64991-73-7)

Conditions	Yield
With sodium hydroxide; potassium carbonate In water for 1h;	39%

potassium pentachloronitrosylruthenate(III) + L-histidine hydrochloride monohydrate (5934-29-2) → Ru(NO)Cl2(L-histidine(1-))*0.5H2O

Conditions	Yield
With KCl In water Ru-complex, ligand and KCl dissolved in H2O, pH 4 adjusted by HCl, refluxed for 2 h; evapd. to dryness on rotary evaporator, suspended in H2O, centrifuged, vac. dried; elem. anal.;	37.7%

L-histidine hydrochloride monohydrate (5934-29-2) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → N-(tert-butoxycarbonyl)-L-histidine (17791-52-5)

Conditions	Yield
With Dowex 50; triethylamine 1.) H2O, dioxane, 5 h, pH=8; 2.) MeOH, 0.1M pyridinium acetate buffer; Yield given. Multistep reaction;

L-histidine hydrochloride monohydrate (5934-29-2) + benzyl chloroformate (501-53-1) → N-[(benzyloxy)carbonyl]-L-histidine (14997-58-1)

Conditions	Yield
With sodium hydroxide; Dowex 50 1.) 3 h; 2.) MeOH, 0.1M pyridinium acetate buffer; Yield given. Multistep reaction;

thiobenzoic acid (98-91-9) + L-histidine hydrochloride monohydrate (5934-29-2) + haloacetyl chloride → Nα-benzoylsulfanylacetyl-histidine (64991-72-6)

Conditions	Yield
With 1.) aq. alkali; 2.) aq. alkali Yield given. Multistep reaction;

L-histidine hydrochloride monohydrate (5934-29-2) + fuming hydrochloric acid + concentrated sodium nitrite → α-chloro-β--propionic acid

L-histidine hydrochloride monohydrate (5934-29-2) + benzoyl chloride (98-88-4) + alkali → N-benzoyl-L-histidine (5354-94-9)

L-histidine hydrochloride monohydrate (5934-29-2) + sodium hypochlorite → -acetaldehyde

L-histidine hydrochloride monohydrate (5934-29-2) + methanolic hydrochloric acid → -methyl ester

Conditions	Yield
Reaktion des wasserfreies Salzes;

L-histidine hydrochloride monohydrate (5934-29-2) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + ammonium chloride

Conditions	Yield
at 255℃;

L-histidine hydrochloride monohydrate (5934-29-2) + silver nitrite + water → levorotatory β--lactic acid

L-histidine hydrochloride monohydrate (5934-29-2) + water → NH3

Conditions	Yield
mit Roentgen-Strahlen.Irradiation;
Kathoden-Strahlen;

L-histidine hydrochloride monohydrate (5934-29-2) + water + sensitizer → NH3

Conditions	Yield
UV-Licht;

L-histidine hydrochloride monohydrate (5934-29-2) → N-mercaptoacetyl-L-histidine (62404-82-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. alkali; 2.) aq. alkali 2: 80 percent / aq. NH4OH View Scheme

L-histidine hydrochloride monohydrate (5934-29-2) → Nα-(3-mercaptopropanoyl)-L-histidine (62404-83-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 39 percent / NaOH, K2CO3 / H2O / 1 h 2: 60 percent / aq. ammonia / 1 h / Ambient temperature View Scheme

copper (II) acetate monohydrate + L-histidine hydrochloride monohydrate (5934-29-2) + salicylaldehyde (90-02-8) → Cu(sal-his)*1.5H2O

Conditions	Yield
With NaOH In ethanol; water EtOH soln. of salicylaldehyde was added to aq. soln. of histidine hydrochloride with stirring; aq. soln. of Cu salt was added to prepd. soln. with stirring, soln. of NaOH was added and the soln. was heated at 70°C for 30 min; filtration, washing with water, EtOH, Et2O, drying in vac.; elem. anal.;

methanol (67-56-1) + Mo3S4(4+)*9H2O = {Mo3S4(H2O)9}(4+) + L-histidine hydrochloride monohydrate (5934-29-2) → [Mo3(L-histidinato)3(μ-S)3(μ3-S)]Cl*KCl*6H2O + [Mo3(L-histidinato)3(μ-S)3(μ3-S)]Cl*0.5KCl*MeOH*6H2O

Conditions	Yield
With KOH In hydrogenchloride byproducts: KCl; to a soln. of Mo-contg. compd. in aq. HCl, L-Hhis*HCl*H2O was added; Ph = ca. 7; the ppt. was removed by filtration; MeOH was added to deposit KCl; KCl was removed by filtration; the filtrate was evapd.; MeOH was added; recrystn. from a hot satd. KCl aq. soln.; elem. anal.;

isovanillin (621-59-0) + uranyl nirate hexahydrate + 1,10-phenanthroline hydrate (5144-89-8) + L-histidine hydrochloride monohydrate (5934-29-2) → UO2(N-o-vanillylidene-L-histidinate)(1,10-phenanthroline) * H2O

Conditions	Yield
With KOH In methanol; water treatment of aminoacid with aldehyde in presence of KOH, evapn., addn. of 1 equiv. UO2-salt and 1,10-phenanthroline; elem. anal.;

isovanillin (621-59-0) + uranyl nirate hexahydrate + L-histidine hydrochloride monohydrate (5934-29-2) → UO2(N-o-vanillylidene-L-histidinate)(2,2'-bipyridyl) * 3 H2O

Conditions	Yield
With KOH; 2,2'-bipyridyl In methanol; water treatment of aminoacid with aldehyde in presence of KOH, evapn., addn. of 1 equiv. UO2-salt and 2,2'-bipyridine; elem. anal.;

uranyl nirate hexahydrate + 1,10-phenanthroline hydrate (5144-89-8) + L-histidine hydrochloride monohydrate (5934-29-2) + salicylaldehyde (90-02-8) → UO2(salicylidene-L-histidinate)(1,10-phenanthroline) * 4 H2O

Conditions	Yield
With KOH In methanol; water treatment of aminoacid with aldehyde in presence of KOH, evapn., addn. of 1 equiv. UO2-salt and 1,10-phenanthroline; elem. anal.;

uranyl nirate hexahydrate + L-histidine hydrochloride monohydrate (5934-29-2) + salicylaldehyde (90-02-8) → UO2(salicylidene-L-histidinate)(2,2'-bipyridyl) * 2 H2O

Conditions	Yield
With KOH; 2,2'-bipyridyl In methanol; water treatment of aminoacid with aldehyde in presence of KOH, evapn., addn. of 1 equiv. UO2-salt and 2,2'-bipyridine; elem. anal.;

L-histidine hydrochloride monohydrate (5934-29-2) + copper dichloride → copper(L-histidine)2

Conditions	Yield
With NaOH; H2SO4 In water soln. stirred for an hour at room temp.; pH adjusted to 7.3 using NaOH or H2SO4;

chromium(III) chloride (10025-73-7) + L-histidine hydrochloride monohydrate (5934-29-2) → Cr(3+) doped (L)-histidine hydrochloride monohydrate

Conditions	Yield
In water aq. soln. contg. CrCl3 (0.01 mol%) slowly evapd. at room temp. for 15-20d;

Upstream product

• 71-00-1 L-histidine 

Downstream Products

• 5354-94-9 N-benzoyl-L-histidine 
• 1175619-51-8 Cu(OCOCH(NH₂)CH₂(C₃H₃N₂))2 
• 2002-22-4 2-mercapto-L-histidine 
• 14997-58-1 N-[(benzyloxy)carbonyl]-L-histidine 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 

Relevant articles and documents

Investigations on the growth aspects and characterization of semiorganic nonlinear optical single crystals of l-histidine and its hydrochloride derivative

Semiorganic single crystals of l-histidine and l-histidine hydrochloride monohydrate have been obtained in a single solution prepared from the mixture of l-histidine and hydrochloric acid in 1:2 M ratio. Growth aspects of the single crystals have been discussed along with characterization studies. Crystal system and lattice parameters have been identified by X-ray diffraction analyses. It has been observed that the grown crystals possess orthorhombic system but with different set of lattice parameters. Presence of various functional groups has been identified and formation of two different crystals has been confirmed by Fourier transform infrared spectral analyses and FT-Raman studies. Linear and nonlinear optical properties have been studied by UV-Vis spectral analyses and Kurtz-Perry powder technique respectively. The thermal stability of the grown crystals was determined by thermal analyses. From the characterization studies it is found that both the crystals are useful for second harmonic generation applications.