Hercynine
- Product Name
- Hercynine
- CAS No.
- 534-30-5
- Chemical Name
- Hercynine
- Synonyms
- Hercynine;Histidine-betaine;
L -Hercynine;N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine;N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+);(S)-3-(1H-Imidazol-5-yl)-2-(trimethylammonio)propanoate;(alphaS)-alpha-Carboxy-N,N,N-trimethyl-1H-imidazole-4-ethanaminium inner salt;(S) -3- (1H imidazol-5-yl) -2-trimethylammonium) propionic acid internal salt - CBNumber
- CB72520909
- Molecular Formula
- C9H15N3O2
- Formula Weight
- 197.24
- MOL File
- 534-30-5.mol
Hercynine Property
- Melting point:
- 237-238° (dec)
- alpha
- D22 +44.5° (5N HCl)
- storage temp.
- 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- Off-White to Pale Yellow
- Stability:
- Hygroscopic
- InChI
- InChI=1/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)/t8-/s3
- InChIKey
- GPPYTCRVKHULJH-SBYBRXNCNA-N
- SMILES
- [C@H](C(=O)[O-])([N+](C)(C)C)CC1NC=NC=1 |&1:0,r|
Safety
- WGK Germany
- WGK 3
- Storage Class
- 11 - Combustible Solids
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- H288900
- Product name
- L-Hercynine
- Packaging
- 250mg
- Price
- $640
- Updated
- 2021/12/16
- Product number
- PXT0002264
- Product name
- HERCYNINE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $505.59
- Updated
- 2021/12/16
Hercynine Chemical Properties,Usage,Production
Uses
L-Hercynine is a precursor of L-(+)-Ergothioneine (E600000); a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential or it may be used as a food additive or in cosmetics.
Definition
ChEBI: N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine is an amino-acid betaine and a member of N(alpha)-methyl-L-histidines. It is a conjugate base of a N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+).
Definition
Hercynine is an intermediate (precursor) in ERGO biosynthesis; thus, fungi and mycobacteria can synthesize hercynine, but animals cannot. A human study showed that hercynine was detected in whole blood, plasma, urine, and saliva, and another clinical study showed that the levels of hercynine correlated with those of ERGO in whole blood, which suggested that hercynine is a metabolite of ERGO. However, the levels of hercynine were lower than those of ERGO, which presented the possibility that hercynine was further oxidized.
Synthesis
A method for producing hercynine on an industrial scale comprises the steps of:
1. reacting L-histidine, in a polar solvent or a mixture of polar solvents, with a methylating agent, MeX, at room temperature under controlled pH conditions;
2. separating the organic products from the inorganic salts formed during the reaction by electrodialysis; and the electrodialysis is carried out on a reaction medium adjusted to a pH between 8.5 to 9.5;
3. recrystallization of L-histidine betaine (hercynine) to eliminate organic impurities.
Hercynine Preparation Products And Raw materials
Raw materials
Preparation Products
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