L-Histidine
- Iupac Name：(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
- CAS No.: 71-00-1
- Molecular Weight：155.157
- Modify Date.: 2022-10-30 20:05
- Introduction: White, odorless crystals or crystalline powder having a slightlybitter taste. It is soluble in water, very slightly soluble in alcohol, and insoluble in ether. It melts with decomposition between about 277° and 288°C.
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1. Names and Identifiers
- 1.1 Name
- L-Histidine
- 1.2 Synonyms
(s)-1h-imidazole-4-alanin (S)-1H-Imidazole-4-alanine (s)-1h-imidazole-4-propanoicaci (s)-4-(2-amino-2-carboxyethyl)imidazole (S)-a-Amino-1H-imidazole-4-propanoic Acid (s)-alpha-amino-1h-imidazole-4-propanoicacid (S)-histidine 1H-Imidazole-4-propanoic acid, alpha-amino-, (S)- 1H-Imidazole-4-propanoic acid, α-amino-, (S)- 3-(1h-imidazol-4-yl)-l-alanin 3-(1H-imidazol-4-yl)-L-Alanine 4-(2-Amino-2-carboxyethyl)imidazole a-Amino-4(or 5)-Imidazolepropionic Acid d,l-histidine EINECS 200-745-3 FEMA 3694 H-His-OH His Histidin Histidine HISTIDINE, L- H-L-HIS-OH hydrogen L-histidinate L-(15N3)Histidine L-His L-Hisidine L-Histdine L-HISTIDINE BASE L-Histidine-15N3 MFCD00064315 MFCD04118132
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- 1.3 CAS No.
- 71-00-1
- 1.4 CID
- 6274
- 1.5 EINECS(EC#)
- 200-745-3
- 1.6 Molecular Formula
- C6H9N3O2 (isomer)
- 1.7 Inchi
- InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
- 1.8 InChIkey
- HNDVDQJCIGZPNO-YFKPBYRVSA-N
- 1.9 Canonical Smiles
- C1=C(NC=N1)CC(C(=O)O)N
- 1.10 Isomers Smiles
- C1=C(NC=N1)C[C@@H](C(=O)O)N
2. Properties
- 2.1 Density
- 1.423
- 2.1 Melting point
- 282℃
- 2.1 Boiling point
- 458.9oC at 760 mmHg
- 2.1 Refractive index
- 1.731
- 2.1 Flash Point
- 282oC
- 2.1 Precise Quality
- 155.06900
- 2.1 PSA
- 92.00000
- 2.1 logP
- 0.06440
- 2.1 Solubility
- H2O: 50?mg/mL
- 2.2 Appearance
- white crystals
- 2.3 Storage
- Ambient temperatures.
- 2.4 Color/Form
- Needles or plates
COLORLESS
- 2.5 PH
- 7.0-8.0 (25℃, 0.1M in H2O)
- 2.6 pKa
- 1.8(at 25℃)
- 2.7 Water Solubility
- 41.6 g/L (25 oC)
- 2.8 Spectral Properties
- MAX ABSORPTION (WATER, PH= 0): 211 NM (LOG E= 3.8)
Specific optical rotation:(c=0.77 in 0.5N of NaOH): -10.9 deg C at 20 deg C/D; (c=0.75 to 3.77): -38.95 deg C at 25 deg C/D; (c=1.00-4.05 in 6.1N HCl): +13.34 deg C at 25 deg C/D
Specific optical rotation (1.13% in water): -39.7 @ 20 deg C/D
IR: 21318 (Sadtler Research Laboratories IR Grating Collection)
UV: 2-72 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: NIST 26153 (NIST/EPA/MCDC Mass Spectral Database 1990 version)
- 2.9 Stability
- Stable. Incompatible with strong oxidizing agents.
- 2.10 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The L-enantiomer of the amino acid histidine.
- 3.2 Purification Methods
- A likely impurity is arginine. S-Histidine is adsorbed from aqueous solution onto a Dowex 50-H+ ion-exchange resin, washed with 1.5M HCl (to remove other amino acids), then eluted with 4M HCl as the dihydrochloride. This purified dihydrochloride (see below) is finally dissolved in water, the pH adjusted to 7.0, and the free zwitterionic base crystallises out on addition of EtOH. Its solubility in H2O is 4.2% at 25o. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1971-1993 1961, Beilstein 25 III/IV 4344.] L-Histidine Preparation Products And Raw materials Raw materials
- 3.3 Usage
- (1) nutritional supplements. It is the very important components of Amino acid infusion and comprehensive amino acid preparations. It can be used in the treatment of gastric ulcer, anemia, allergies and so on.(2) It is used for biochemical research, medicine for the treatment of gastric ulcer, anemia, allergies and so on.(3) It is used as amino acid drugs. It is the main components of amino acid infusion and amino acid preparations, for the treatment of gastric ulcer, anemia and angina, aortitis, heart failure and other cardiovascular system disorders. Adverse reactions and contraindications: low toxicity, adult poisoning>64g/day, such as the injection of hydrochloric acid histidine with headache, flushing and heat.(4) It is used as a nutrient enhancer, the important component of amino acid infusion and amino acid preparations. It can be used for the treatment of gastric ulcer and biochemical researchment.(5) It is used for pharmaceutical raw materials and food additives.
4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- 22-36/37/38
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- L-Histidine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
- 4.2 Octanol/Water Partition Coefficient
- log Kow= -3.32
- 4.3 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.4 RIDADR
- 25kgs
- 4.4 Formulations/Preparations
- ECRISTIDINE; & LAROSTIDIN. /L-HISTIDINE MONOHYDROCHLORIDE/
Available commercially as L(+)-histidine hydrochloride and as the free base.
Found naturally in the L(-) form.
- 4.5 WGK Germany
- 2
- 4.5 RTECS
- MS3070000
- 4.5 Report
-
Reported in EPA TSCA Inventory.
- 4.6 Safety
-
Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Other safty informations about?Histidine (CAS NO.71-00-1):
Hazard Codes:?Xn
Risk Statements: 22-36/37/38?
R22: Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37-26-22?
S24/25: Avoid contact with skin and eyes.?
S36/37: Wear suitable protective clothing and gloves.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S22: Do not breathe dust.
WGK Germany: 2
RTECS: MS3070000
F: 10-23
HS Code: 29332990
- 4.7 Specification
-
White crystalline powder
Safety Statements:24/25-36/37-26-22
24/25:Avoid contact with skin and eyes
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
22:Do not breathe dust
- 4.8 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
intraperitoneal |
> 10gm/kg (10000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| mouse |
LD50 |
intravenous |
> 2gm/kg (2000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| mouse |
LD50 |
oral |
> 15gm/kg (15000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| mouse |
LD50 |
subcutaneous |
> 10gm/kg (10000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| rat |
LD50 |
intraperitoneal |
> 8gm/kg (8000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| rat |
LD50 |
intravenous |
> 2gm/kg (2000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| rat |
LD50 |
oral |
> 15gm/kg (15000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
| rat |
LD50 |
subcutaneous |
> 10gm/kg (10000mg/kg) |
? |
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 1253, 1981. |
- View all
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
71-00-1Total: 34 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,4720
- 9.1 BRN
- 4673585
- 9.2 Uses
- (1) nutritional supplements. It is the very important components of Amino acid infusion and comprehensive amino acid preparations. It can be used in the treatment of gastric ulcer, anemia, allergies and so on.
(2) It is used for biochemical research, medicine for the treatment of gastric ulcer, anemia, allergies and so on.
(3) It is used as amino acid drugs. It is the main components of amino acid infusion and amino acid preparations, for the treatment of gastric ulcer, anemia and angina, aortitis, heart failure and other cardiovascular system disorders.
Adverse reactions and contraindications: low toxicity, adult poisoning>64g/day, such as the injection of hydrochloric acid histidine with headache, flushing and heat.
(4) It is used as a nutrient enhancer, the important component of amino acid infusion and amino acid preparations. It can be used for the treatment of gastric ulcer and biochemical researchment.
(5) It is used for pharmaceutical raw materials and food additives. - View all
- 9.3 Content analysis
- Sample is accurately weighed about 105 rag, dried at 105 ℃ for 3h, then dissolved in 3ml formic acid and 50ml glacial acetic acid, and titrated with 0.1mol/L perchloric acid, and the end point was determined by potentiometric method. At the same time a blank test and the necessary amendments should be made. Per Ml0.1mol/L perchloric acid equates to 15.52mg L-histidine (C6H9N3O2).
- 9.4 Toxicity
- It is safe for using in food products (FDA § 172.320, 2000).
- 9.5 Using limits
- Accounting for 2.4% of total protein in food (FDA § 172.320, 2000).
FEMA: bakery products, meat products, dairy products, candy, frosting, are 150mg/kg.
- 9.6 Chemical Properties
- White or almost white, crystalline powder or colourless crystals
- 9.7 Uses
- L-Histidine is an essential amino acid for human development which the body cannot produce on its own. L-Histidine is one of the 22 proteinogenic amino acids. L-Histidine precursor to histamine (H4365 00) and a component of carnosine.
- 9.8 Definition
- ChEBI: The L-enantiomer of the amino acid histidine.
- 9.9 Purification Methods
- A likely impurity is arginine. S-Histidine is adsorbed from aqueous solution onto a Dowex 50-H+ ion-exchange resin, washed with 1.5M HCl (to remove other amino acids), then eluted with 4M HCl as the dihydrochloride. This purified dihydrochloride (see below) is finally dissolved in water, the pH adjusted to 7.0, and the free zwitterionic base crystallises out on addition of EtOH. Its solubility in H2O is 4.2% at 25o. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1971-1993 1961, Beilstein 25 III/IV 4344.]
- 9.10 Usage
- L-Histidine acts as a precursor to histamine and a component of carnosine. It is also used in medicine, feed additive, biochemical research, dietary supplement. It is used in a nutrition enhancer, is the amino acid fluid infusion. It can be used in the treatment of gastric ulcer.
- 9.11 Production methods
- (1) It is eatracted from pig blood, bovine blood. Pig blood is spraied drying and then obtained blood powder, 100kg pig blood have 18kg blood power. L-histidine is commonly used as its hydrochloride salt ([7048-02-4]). The L-histidine containing eluent was concentrated to the appearance of crystals, adjusted to pH 2.5 with hydrochloric acid, and immediately added with 2 times the amount of ethanol in the solution, standing, precipitating and filtering to obtain L-group ammonia Acid hydrochloride crude, after decolorization, recrystallization, drying in the finished product. L-histidine can also be extracted from hydrolysates of defatted soybeans.
There are two main production methods. First one is direct fermentation, with carbon source of glucose and an inducible drug-resistant strain of corynebacterium glutamicum. Second one is protein hydrolysis. The hydrolysis method is described in detail below. Pig and cattle blood , pig hair or hoof were raw materials, hydrolyzed by acid , separated and purificated to get L-histidine.
Hydrolysis:50kg of pig blood powder and 4 times amout of 6mol/L HCl were put into a hydrolysis tank and heated at 110-120 ℃ for 24 hours.
Preparation of the dilution of the column: The hydrolysis solution of the previous step was concentrated under reduced pressure, distilled water was added again, and the acid was repeatedly distilled for 3-4 times until the distillate did not flow out of the hydrochloric acid. Concentrated solution diluted with distilled water to 500L,adjusted pH to 3.5-4 with concentrated ammonia, plused 20% of the amount of blood powder activated carbon, heated, decolorizated and stirred at 90 ℃ for 6h.Then filtered when it is hot, and take the filtrate standing overnight precipitate. Filtering again, the filtrate was diluted with distilled water to 2.5% (according to the blood powder dosage), and adjusted to pH 2.5 with concentrated HCl, which was column dilution.
The column dilution was separated, washed with water and eluted. Column is Ф300mm×2000 mm, PVC material, packed with 001 × 7 (732) strong acidic styrene cation exchange resin 1730mm, flow rate 1L/ min, stopping to upper column until the outflow of L histidine. Washing with water 500L, flow rate 1.5L /min. The pH 7.0-10.0 fraction was collected. After the collection, the resin was recoated for 15 min, and then regenerated with twice the amount of 1.5-2 mol/L HCl, the flow rate was 5-13 L/min. After regeneration, Washing with water untill PH 4 or so, waiting for the next column.
Purification: L-histidine acid eluent, removing ammonia with vacuum, concentrated to dry, and then dissolved with 40L distilled water, adjusted pH with 3-3.26 mol/L HCl, add 1kg activated carbon, heated and decolorizated at 90 ℃ for 30min.The filtrate was concentrated in a thin film evaporator and allowed to stand for 48 hours to precipitate crystals. The crystals were collected by filtration, washed with 95% ethanol and dried at 80 oC with vacuum for 4 hours to give L-histidine hydrochloride.
(2) Dry flour and hydrochloric acid as raw material reflux for several hours, filtrated,washed and handled with activated carbon to get L-histidine monohydrochloride crude, then purified to obtain the pure product.
(3) separated with ion exchange resin from the protein hydrolyzate of the basic amino acid. - View all
- 9.12 Toxicity
- It is safe for using in food products (FDA § 172.320, 2000).
- 9.13 Using limits
- Accounting for 2.4% of total protein in food (FDA § 172.320, 2000).
FEMA: bakery products, meat products, dairy products, candy, frosting, are 150mg/kg.
- 9.14 Description
- White, odorless crystals or crystalline powder having a slightly bitter taste. It is soluble in water, very slightly soluble in alcohol, and insoluble in ether. It melts with decomposition between about 277° and 288°C.
- 9.15 Chemical Properties
- L-Histidine is an odorless powder with slightly bitter taste
- 9.16 Occurrence
- Reported found in water bread, macaroni, egg noodles, corn flakes, corn grits, oatmeal, wheat bran, wheat flakes, shredded wheat, barley, brown rice, rye flour, whole grain wheat flour, buttermilk, blue cheese, cheddar cheese, cottage cheese, cream cheese, Parmesan cheese, bacon, cured ham, frankfurters, pork sausage, canned red kidney beans, canned sweet corn, canned peas, canned lima beans, canned potatoes, almonds, cashews, peanuts, dates, beef, lamb, veal, chicken, turkey and other natural sources
- 9.17 Uses
-
L-Histidine has been used for characterization of ZnO nanorod in an attempt to develop a technique for the ultra-low level detection of l-histidine.
10. Computational chemical data
- Molecular Weight: 155.157g/mol
- Molecular Formula: C6H9N3O2
- Compound Is Canonicalized: True
- XLogP3-AA: -3.2
- Exact Mass: 155.069476538
- Monoisotopic Mass: 155.069476538
- Complexity: 151
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 92
- Heavy Atom Count: 11
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBjMAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHgAQCAAACCjBlgQtmBbJkgCoART3bAAAgC2xEqABUYG4cAiCaBJA2QGUQAAMkAJAQCC8EQIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
L-Histidine, chemically known as L-alpha-amino-p-imidazolepropionic acid, is a basic amino acid containing an imidazole nucleus in its molecule. It has various physiological functions and is widely us..
-
L-Histidine Biosynthesis L-Histidine, an essential protein amino acid with various medical applications, is efficiently biosynthesized by a recombinant strain of Corynebacterium glutamicum. To overcom..
-
L-Histidine is an important amino acid with a wide range of applications in the pharmaceutical field. However, how can we evaluate the quality of the L-Histidine raw material used in the pharmaceutica..
-
Description L-Histidine (L-His, L-H) is an essential amino acid utilized in protein production and commonly found at protein active sites. It possesses anti-inflammatory, antioxidant, and antisecretor..
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L-Histidine
- Purity:99%Packing: 200kg/bag FOB
- Price: 1 USD/kilogram
- Time: 2024/11/14
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