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472727

Sigma-Aldrich

3-(3,4-Dimethoxyphenyl)-L-alanine

97%, for peptide synthesis

Synonym(s):

(S)-2-Amino-3-(3,4-dimethoxyphenyl)propanoic acid, 3-Methoxy-O-methyl-L-tyrosine, DMPA

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About This Item

Linear Formula:
(CH3O)2C6H3CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
225.24
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

product name

3-(3,4-Dimethoxyphenyl)-L-alanine, 97%

Assay

97%

optical activity

[α]22/D −5°, c = 4 in 1 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

254-257 °C (lit.)

application(s)

peptide synthesis

SMILES string

COc1ccc(C[C@H](N)C(O)=O)cc1OC

InChI

1S/C11H15NO4/c1-15-9-4-3-7(6-10(9)16-2)5-8(12)11(13)14/h3-4,6,8H,5,12H2,1-2H3,(H,13,14)/t8-/m0/s1

InChI key

VWTFNYVAFGYEKI-QMMMGPOBSA-N

Application

3-(3,4-Dimethoxyphenyl)-L-alanine can be used as a reactant to synthesize (2S)-2-amino-3-[3,4-di(methoxy)phenyl]propan-1-ol (β-amino alcohol) for use as a key intermediate to prepare tetracyclic core of the Erythrina alkaloids.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Facile and highly stereoselective synthesis of the tetracyclic erythrinane core
Allin SM, et al.
The Journal of Organic Chemistry, 67, 9464-9467 (2002)

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