Basic information
- CAS
534-30-5- Standard SMILES
C[N+](C)(C)[C@@H](Cc1cnc[nH]1)C(=O)[O-]- InChIKey
GPPYTCRVKHULJH-QMMMGPOBSA-N- Molecular formula
- C9H15N3O2
- Average molar mass
- 197.23 g/mol
- Monoisotopic mass
- 197.11642673
Overview
N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine is a member of N(alpha)-methyl-L-histidines and an amino-acid betaine. It is a conjugate base of a N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+).
Names & identifiers
- Preferred name
- Histidine-betaine
- IUPAC
- (2S)-3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
- English name
- Hercynine
- Molecular formula
- C9H15N3O2
- Molecular weight
- 197.24
Names & synonyms
Hercynine534-30-5HISTIDINE-BETAINEM8MWM6K25V(S)-alpha-Carboxy-N,N,N-trimethyl-1H-imidazole-4-ethanaminium hydroxide, inner salt(2S)-3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoateNalpha,Nalpha,Nalpha-Trimethyl-L-histidineRefChem:145780(1-carboxy-2-imidazol-4-ylethyl)ammonium hydroxide /OD/ histidine-betaineL-Hercynine(S)-3-(1H-Imidazol-5-yl)-2-(trimethylammonio)propanoateUNII-M8MWM6K25V
Show more names
N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+)(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
N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine1H-Imidazole-4-ethanaminium, a-carboxy-N,N,N-trimethyl-, inner salt,(aS)-MFCD34596650(2S)-3-(1H-imidazol-4-yl)-2-(trimethylammonio)propanoate1H-Imidazole-4-ethanaminium, alpha-carboxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-HERCYNINE [MI]orb3142021SCHEMBL1331027
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 68.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 207
Physicochemical properties
- Melting point
- 237 · 237-238° (dec)
- alpha
- 22 · D22 +44.5° (5N HCl)
- storage temp.
- 2 · 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|
- FDA UNII
- 8 MWM6K25V · M8MWM6K25V
- UNSPSC Code
- 41116105 · 41116105
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesL-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.
Upstream & downstream products
Upstream raw materials
Suppliers52 total
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
曼顿生物科技（深圳）有限公司+86-75589664337 +86-15112661142 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
上海药诚医药科技合伙企业（有限合伙）400-6181121 18616381138 · [email protected]
上海康恩博科技有限公司（科小研试剂）400-1388-521 17673770086 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）
Related reactions
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Compound notes
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