5-ヒドロキシトリプトファン

定義

本品は、次の化学式で表される有機化合物である。

解説

5-ヒドロキシトリプトファン，C11H12N2O3(220.23)．ウシの血清より結晶として単離される．4-アセチルアミノフェノールから合成もされている．L-体は分解点273 ℃．[α]²⁰_D－32.5°(水)，＋16°(4 mol L－1 塩酸)．λmax 275 nm(ε 5300，0.1 mol L－1 塩酸)．DL-体は分解点298～300 ℃．λmax 278，298 nm(ε 5300，4300)．蛍光極大波長540～550 nm．水溶性．空気中で酸化されやすい．動物体内でトリプトファンからセトロニンやメラトニンが生成する際の中間体である．ただし，ヒトでは投与してもそれらの現象はみられない．

化粧品の成分用途

皮膚コンディショニング剤

説明

5-Hydroxytryptophan (5-HTP) is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan (LT). Produced commercially by extraction from the seeds of the African plant, Griffonia simplicifolia, 5-HTP has been used clinically for over 30 years. The clinical efficacy of 5-HTP is due to its ability to increase production of serotonin in the brain.

化学的特性

Off-White to Pale Beige Solid, slightly salty in taste, soluble in methanol, ethanol, DMSO and other organic solvents, derived from African Ghana seeds.

使用

5-Hydroxytryptophan (5-HTP) is an intermediate in the natural synthesis of the essential amino acid, tryptophan, to serotonin. Clinical studies suggest that 5-HTP supports healthy serotonin levels. In the body, 5-HTP converts to serotonin with the enzymatic removal of a carboxyl group (COOH). Serotonin is an important neurotransmitter involved in the regulation of endocrine and brain activity responsible for emotion, appetite and sleep/wake cycles.

定義

ChEBI: 5-hydroxytryptophan is a tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. It has a role as a human metabolite and a neurotransmitter.

主な応用

5-hydroxytryptophan is a dietary supplement made from the seeds of the African plant Griffonia simplicifolia.
5-hydroxytryptophan has been used in alternative medicine as a possibly effective aid in treating depression or fibromyalgia.
Other uses not proven with research have included insomnia, alcohol withdrawal, headaches, premenstrual syndrome, binge-eating related to obesity, attention deficit disorder, and muscle spasms in the mouth.
5-hydroxytryptophan is often sold as an herbal supplement. There are no regulated manufacturing standards in place for many herbal compounds and some marketed supplements have been found to be contaminated with toxic metals or other drugs. Herbal/health supplements should be purchased from a reliable source to minimize the risk of contamination.

製造方法

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)

生合成

5-Hydroxytryptophan, an intermediate molecule in the serotonin biosynthesis pathway, is formed by the addition of a hydroxyl (OH) group to the fifth carbon of the indole ring of tryptophan. It is used as an antiepileptic and antidepressant.