L-6-Hydroxydopa

HCID 33755

Substructure search Find similar structures

Basic information

CAS: 27244-64-0
Standard SMILES: N[C@@H](Cc1cc(O)c(O)cc1O)C(=O)O
InChIKey: YLKRUSPZOTYMAT-YFKPBYRVSA-N
Molecular formula: C9H11NO5
Average molar mass: 213.19 g/mol
Monoisotopic mass: 213.06372245

Overview

6-hydroxy-L-dopa is an L-alpha-amino acid that is L-dopa carrying an additional hydroxy substituent at position 6. It is a non-proteinogenic L-alpha-amino acid and a L-phenylalanine derivative. It is functionally related to a L-dopa.

Names & identifiers

Preferred name: L-6-Hydroxydopa
IUPAC: (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
English name: LEVODOPA RELATED COMPOUND A (50 MG) (3-(3,4,6-TRIHYDROXYPHENYL)-ALANINE)
Molecular formula: C9H11NO5
Molecular weight: 213.19

Names & synonyms

27244-64-0L-6-Hydroxydopa6-Hydroxy-L-DOPA2,5-Dihydroxy-L-tyrosine(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acidLevodopa EP Impurity A6-OH-DOPATOPA6-Hydroxydopa, L-2,4,5-trihydroxy-L-phenylalanineL-Tyrosine, 2,5-dihydroxy-L-2,4,5-Trihydroxyphenylalanine

Show more names

Levodopa Related CoMpound ATopaquinone

MFCD22577205(S)-2-Amino-3-(2,4,5-trihydroxyphenyl)propanoic acid2,4,5-trihydroxyphenyl-L-alanine3-(3,4,6-Trihydroxyphenyl)-L-alanineL-Hydroxydopa580PK2O48OHydroxy-L-dopa3-(3,4,6-Trihydroxyphenyl)-alanine

Database identifiers

CAS: 27244-64-0
PubChem CID: 33755
DTXSID: DTXSID90949974
ChEMBL: CHEMBL1256516
ChEBI: CHEBI:72753
UNII: 580PK2O48O
Nikkaji: J90.476G

Properties

Computed structural properties

XLogP: -2.5
Topological polar surface area: 124 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 6
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 235

Physicochemical properties

Melting point: 190 °C · >190°C (dec.)
Boiling point: 515.2 · 515.2±38.0 °C(Predicted)
Density: 1.606 · 1.606±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility: Aqueous Acid (Slightly, Sonicated), Water (Slightly, Heated, Sonicated)
pka: 2.34 · 2.34±0.25(Predicted)
form: Solid
color: Brown to Black
Stability: Air Sensitive, Hygroscopic
Major Application: pharmaceutical (small molecule)
InChI: 1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)/t5-/m0/s1
InChIKey: YLKRUSPZOTYMAT-YFKPBYRVSA-N
SMILES: [N+H3][C@@H](Cc1c(cc(c(c1)O)O)O)C(=O)[O-]
FDA UNII: 580 PK2O48O · 580PK2O48O
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315
Precautionary statements: 264 · P264-P270-P280-P301+P312+P330-P332+P313-P501
WGK Germany: 3 · WGK 3
HS Code: 2922504500 · 2922504500
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralSkin · Acute Tox. 4 OralSkin Irrit. 2

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
hs_code: 2922504500
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315
Hazard Classifications: Acute Tox. 4 OralSkin Irrit. 2
Precautionary statements: P264-P270-P280-P301+P312+P330-P332+P313-P501

Chemistry & industry

Applications · 2 items

Uses6-Hydroxy-L-DOPA (Levodopa EP Impurity A; Levodopa USP Related Compound A) is the 6-hydroxy derivative of the amino acid L-DOPA (D533751) with neurotoxic properties. Studies show that exogenously administered 6-Hydroxy-L-DOPA is biotransformed by amino acid decarboxylase to the highly potent and catecholamine-selective neurotoxin, 6-Hydroxydopamine. The treatment of 6-Hydroxy-L-DOPA in rats resulted in the stimulation of acetylcholinesterase.

Uses6-Hydroxy-L-DOPA is the 6-hydroxy derivative of the amino acid L-DOPA (D533751) with neurotoxic properties. Studies show that exogenously administered 6-Hydroxy-L-DOPA is biotransformed by amino acid decarboxylase to the highly potent and catecholamine-selective neurotoxin, 6-Hydroxydopamine. The treatment of 6-Hydroxy-L-DOPA in rats resulted in the stimulation of acetylcholinesterase.

Suppliers67 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

济南百隆化学有限公司[email protected] · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: An L-alpha-amino acid that is L-dopa carrying an additional hydroxy substituent at position 6.

Related reactions

0 records

New reaction record

No reaction records under the current filter.

Compound notes

Loading…