ChemicalBook > CAS DataBase List > H-His(Trt)-OH

H-His(Trt)-OH

Product Name: H-His(Trt)-OH
CAS No.: 35146-32-8
Chemical Name: H-His(Trt)-OH
Synonyms: His(Trt);L-His(Trt);L-His(Trt)-OH;H-HIS(TRT)-OH;L-His(Trt)·H2O;H-L-HIS(TRT)-OH;H-HIS(T-TRT)-OH;H-HIS(1-TRT)-OH;H-His(tau-Trt)-OH;HISTIDINE(1-TRT)-OH
CBNumber: CB9185713
Molecular Formula: C25H23N3O2
Formula Weight: 397.47
MOL File: 35146-32-8.mol

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H-His(Trt)-OH Property

Melting point:: 210℃
Boiling point:: 584.8±50.0 °C(Predicted)
Density: 1.19±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,Store in freezer, under -20°C
pka: 1.78±0.10(Predicted)
form: Solid
color: White to off-white
InChI: InChI=1S/C25H23N3O2/c26-23(24(29)30)16-22-17-28(18-27-22)25(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,17-18,23H,16,26H2,(H,29,30)/t23-/m0/s1
InChIKey: BSZQZNOAYQCQFZ-QHCPKHFHSA-N
SMILES: C(O)(=O)[C@H](CC1N=CN(C(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=1)N

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Safety

WGK Germany: 3
F: 10

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: T808775
Product name: 1-(Triphenylmethyl)-L-histidine
Packaging: 10g
Price: $120
Updated: 2021/12/16

Usbiological

Product number: 285606
Product name: Nim-Trityl-histidine
Packaging: 2g
Price: $333
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: AAA0002849
Product name: H-HIS(TRT)-OH
Purity: 95.00%
Packaging: 1G
Price: $151.83
Updated: 2021/12/16

ChemScene

Product number: CS-W013871
Product name: H-His(Trt)-OH
Purity: 99.41%
Packaging: 25g
Price: $120
Updated: 2021/12/16

Activate Scientific

Product number: AS102790
Product name: H-His(Trt)-OH
Purity: 97%
Packaging: 1g
Price: $23
Updated: 2021/12/16

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H-His(Trt)-OH Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

1-(Triphenylmethyl)-L-histidine is a reactant in the synthesis of falcitidin acyl tetrapeptides as antimalarial agent.

Preparation

The amino acid N(im)-trityl-D-histidine was dissolved in dichloromethane, followed by the addition of triethylamine and trimethylsilyl chloride (3.5 equivalents). After 2 hours of gentle reflux, the mixture was ready to be used for in situ coupling to the anhydride of the carboxylic acid. Thus, isovaleric acid was separately dissolved in THF and maintained at -20 ℃ using an ice-salt bath. N-methyl morpholine (1.2 equivalents) was added, followed by the addition of ethyl chloroformate (1.0 equivalent). After 15-20 minutes at -20 ℃, the bis-TMS amino acid reaction mixture was added directly to the anhydride solution and left stirring at room temperature overnight. After 8 hours, the reaction mixture was concentrated in vacuo. Finally, H-His(Trt)-OH was obtained after purification.

Definition

H-His(Trt)-OH, also known as 1-(Triphenylmethyl)-L-histidine, is a histidine derivative. It can be obtained by removing fmoc group protection from Fmoc-His(Trt)-OH. L-histidine (HIS) is an essential amino acid with unique roles in proton buffering, metal ion chelation, scavenging of reactive oxygen and nitrogen species, erythropoiesis, and the histaminergic system.

Synthesis

109425-51-6

35146-32-8

General procedure for the synthesis of N'-(triphenylmethyl)-L-histidine from N-Fmoc-N'-trityl-L-histidine: Fmoc-His(Trt)-OH (100 g, 0.161 mol, 1 eq.) was dissolved in THF (2000 mL) and piperidine (140 g, 1.614 mol, 10 eq.) was added under stirring conditions. The reaction mixture was stirred for 2 hours using a mechanical stirrer. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm the complete removal of the Fmoc protecting group. Subsequently, water (~4 L) was added to the reaction system and stirring was continued for 30 min. The precipitate was collected by filtration. The filtrate was concentrated to remove THF completely. pH of the solution was adjusted to 2.5 with dilute hydrochloric acid and the mixture was stirred overnight. Filtration yielded 53 g of colorless crystals (83% yield) and the product was dried in air overnight.

References

[1] Patent: WO2012/136604, 2012, A1. Location in patent: Page/Page column 42-43
[2] Tetrahedron Letters, 2014, vol. 55, # 11, p. 1949 - 1951

H-His(Trt)-OH Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from H-His(Trt)-OH manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd

Product: H-L-His(trt)-OH 35146-32-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%;99%
Supply Ability: 1T+
Release date: 2023-09-08

Sichuan Jiaying Lai Technology Co.,LTD

Product: H-His(trt)-OH 35146-32-8
Price: US $1.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 100KG
Release date: 2019-07-25

Career Henan Chemical Co

Product: H-HIS(TRT)-OH 35146-32-8
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1kg,5kg,100kg
Release date: 2019-07-04

35146-32-8, H-His(Trt)-OHRelated Search:

Methyl L-histidinate dihydrochloride H-HIS(BZL)-OH 3-METHYL-L-HISTIDINE H-His(Trt)-OMe · HCl 3,5-DIIODO-D-TYROSINE HYDROCHLORIDE Fmoc-His(Trt)-OH N-Fmoc-N'-Trityl-L-histidine pentafluorophenyl ester H-His(Trt)-OH Boc-His(Trt)-OH TRT-OH N-Boc-S-Trityl-L-cysteine N-Boc-N'-trityl-L-glutamine N-FMOC-GLY(TRT)-OH Z-GLN(TRT)-OH,Z-GLUTAMINE(TRT)-OH FMOC-D-PEN(TRT)-OH Z-ASN(TRT)-OH Fmoc-Asn(Trt)-OH H-GLN(TRT)-OH

N-τ-Trityl-L-histidine

1-(Triphenylmethyl)-L-histidine

L-His(Trt)·H2O

L-His(Trt)-OH

Nim-Trityl-histidine≥ 98% (HPLC)

(2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoicacid

1-Trityl-L-histidine, 98%

H-L-HIS(TRT)-OH

HISTIDINE(1-TRT)-OH

H-HIS(1-TRT)-OH

H-HIS(T-TRT)-OH

H-HIS(TRT)-OH

RARECHEM AL BE 1480

N-IM-TRITYL-HISTIDINE

N-IM-TRITYL-L-HISTIDINE

N-TAU-TRITYL-L-HISTIDINE

His(Trt)

N<T/(IM)>-TRITYL-L-HISTIDINE

H-His(tau-Trt)-OH

(2S)-2-amino-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanoic acid

(2S)-2-amino-3-[1-(triphenylmethyl)-4-imidazolyl]propanoic acid

L-His(Trt)

(2S)-2-ammonio-3-(1-trityl-1H-imidazol-4-yl)propanoate

(S)-2-Amino-3-(1-trityl-1H-imidazol-4-yl)propanoicacid

L-Histidine, 1-(triphenylmethyl)-

(2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoicaci

H-HIS(TRT)-OH USP/EP/BP

1-Trityl-L-histidine, 98%

35146-32-8

C25H23N3O2

Histidine

Peptide Synthesis

Specialty Synthesis

Amino Acid Derivatives

Histidine [His, H]

Amino Acids and Derivatives

Amino Acid Derivatives

Histidine

Peptide Synthesis