ChemicalBook CAS DataBase List 5-Hydroxytryptophan

5-Hydroxytryptophan synthesis

4synthesis methods

Product Name:5-Hydroxytryptophan
CAS Number:56-69-9
Molecular formula:C11H12N2O3
Molecular Weight:220.22

The synthesis of 5-hydroxytryptophan (5-HTP) by the condensation of 5-benzyloxygramine with diethyl formaminomalonate, followed by saponification, decarboxylation, and hydrogenolysis was described in 1951 and 1954 and was an application of gramine synthesis, developed by Snyder and Smith ten years before. A few years later, another application of gramine synthesis was reported. In the same year, Frangatos and Chubb reported an application of the convenient tryptophan synthesis developed ten years before by eliminating the difficult and tedious preparation of 5-benzyloxyindole. The p-benzyloxyphenylhydrazone of γ,γ-dicarbethoxy-γ-acetamido-butyraldehyde (I) was prepared and cyclized, without isolation, to form ethyl β-(5-benzyloxyindol-3-)-αcarbethoxy-α-acetamidopropioilate (II). Saponification and partial decarboxylation of II, followed by hydrolysis of the acetamido group, gave 5-benzyloxytryptophan (III). 5-HTP was obtained by hydrogenolysis of III (Figure 1). However, this synthetic method suffers from the difficulty involved in the regioselective hydroxylation of tryptophan.

synthesis of 5-hydroxytryptophan (5-HTP)

619-60-3 Synthesis

619-60-3
112 suppliers
$9.00/250mg

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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56-69-9
417 suppliers
$25.00/10g

Yield:-

Reaction Conditions:

with potassium hydroxide in waterRate constant;Equilibrium constant;Irradiation;

References:

Steenken, S.;Neta, P. [Journal of Physical Chemistry,1982,vol. 86,p. 3661 - 3667]

N,N,N',N'-Tetramethyl-1,4-phenylenediamine

100-22-1
126 suppliers
$10.00/1g

1000210-73-0
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100-22-1
126 suppliers
$10.00/1g

56-69-9
417 suppliers
$25.00/10g

References

1000210-73-0
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150-76-5 Synthesis

150-76-5
733 suppliers
$5.00/5 g

1000210-73-0
0 suppliers
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56-69-9
417 suppliers
$25.00/10g

References

1000210-73-0
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108-46-3 Synthesis

108-46-3
733 suppliers
$10.00/10g

1000210-73-0
0 suppliers
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56-69-9
417 suppliers
$25.00/10g

References

5-Hydroxytryptophan Related Search:

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