L(-)-триптофан
- английское имяL-Tryptophan
- CAS №73-22-3
- CBNumberCB3750054
- ФормулаC11H12N2O2
- мольный вес204.23
- EINECS200-795-6
- номер MDLMFCD00064340
- файл Mol73-22-3.mol
| Температура плавления | 289-290 °C (dec.)(lit.) |
| альфа | -31.1 º (c=1, H20) |
| Температура кипения | 342.72°C (rough estimate) |
| плотность | 1.34 |
| показатель преломления | -32 ° (C=1, H2O) |
| температура хранения | 2-8°C |
| растворимость | 20% NH3: 0.1 g/mL at 20 °C, clear, colorless |
| форма | powder |
| пка | 2.46(at 25℃) |
| цвет | White to yellow-white |
| РН | 5.5-7.0 (10g/l, H2O, 20℃) |
| Запах | wh. cryst. or cryst. odorless powd., sl. bitter taste |
| оптическая активность | [α]20/D 31.5±1°, c = 1% in H2O |
| Растворимость в воде | 11.4 g/L (25 ºC) |
| Мерк | 14,9797 |
| БРН | 86197 |
| Стабильность | Stable. Incompatible with strong acids, strong oxidizing agents. |
| ИнЧИКей | QIVBCDIJIAJPQS-VIFPVBQESA-N |
| LogP | 0.704 (est) |
| FDA 21 CFR | 582.5915; 172.320; 310.545 |
| Вещества, добавляемые в пищу (ранее EAFUS) | L-TRYPTOPHAN |
| Справочник по базе данных CAS | 73-22-3(CAS DataBase Reference) |
| Рейтинг продуктов питания EWG | 1 |
| FDA UNII | 8DUH1N11BX |
| Код УВД | N06AX02 |
| Справочник по химии NIST | L-Tryptophan(73-22-3) |
| Система регистрации веществ EPA | L-Tryptophan (73-22-3) |
| Коды опасности | Xi | |||||||||
| Заявления о рисках | 33-40-62-41-37/38-36/37/38-22 | |||||||||
| Заявления о безопасности | 24/25-36/37/39-36-26 | |||||||||
| WGK Германия | 2 | |||||||||
| RTECS | YN6130000 | |||||||||
| F | 8 | |||||||||
| TSCA | Yes | |||||||||
| кода HS | 29339990 | |||||||||
| Банк данных об опасных веществах | 73-22-3(Hazardous Substances Data) | |||||||||
| Токсичность | LD508mmol / kg (rat, intraperitoneal injection). It is safe when used in food (FDA, §172.320, 2000). | |||||||||
| NFPA 704: |
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рисовальное письмо(GHS)
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рисовальное письмо(GHS)
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сигнальный язык
опасность
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вредная бумага
H314：При попадании на кожу и в глаза вызывает химические ожоги.
H225：Легковоспламеняющаяся жидкость. Пары образуют с воздухом взрывоопасные смеси.
H290：Может вызывать коррозию металлов.
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оператор предупредительных мер
P210：Беречь от тепла, горячих поверхностей, искр, открытого огня и других источников воспламенения. Не курить.
P233：Держать в плотно закрытой/герметичной таре.
P234：Хранить только в оригинальной упаковке.
P240：Заземлить и электрически соединить контейнер и приемное оборудование.
P241：Использовать взрывобезопасное оборудование и освещение.
P242：Использовать неискрящие приборы.
P243：Принимать меры предосторожности против статических разрядов.
P264：После работы тщательно вымыть кожу.
P280：Использовать перчатки/ средства защиты глаз/ лица.
P301+P330+P331：ПРИ ПРОГЛАТЫВАНИИ: Прополоскать рот. Не вызывать рвоту!
P303+P361+P353：ПРИ ПОПАДАНИИ НА КОЖУ (или волосы): Снять/удалить немедленно всю загрязненную одежду. Промыть кожу водой.
P304+P340+P310：ПРИ ВДЫХАНИИ: Свежий воздух, покой. Немедленно обратиться за медицинской помощью.
P305+P351+P338+P310：ПРИ ПОПАДАНИИ В ГЛАЗА: Осторожно промыть глаза водой в течение нескольких минут. Снять контактные линзы, если Вы ими пользуетесь и если это легко сделать. Продолжить промывание глаз. Немедленно обратиться за медицинской помощью.
P363：Перед повторным использованием выстирать загрязненную одежду.
P370+P378：При пожаре тушить сухим песком, сухим химическим порошком или спиртостойкой пеной.
P390：Локализовать просыпания/проливы/утечки во избежание воздействия.
P403+P235：Хранить в прохладном, хорошо вентилируемом месте.
P405：Хранить в недоступном для посторонних месте.
L(-)-триптофан химические свойства, назначение, производство
Химические свойства
Appearance: white crystalline powder. Odorless, slightly bitter taste;Solubility: slightly soluble in water (1.14%, 25 ℃), insoluble in ethanol; soluble in dilute acid or dilute alkali. mp 289 ° C (decomposition).
Isoelectric point: 5.89. [α] D + 2.8 (5 mol / L HCl), [α] D + 6.2 (0.5 mol / L NaOH).
It can be colored upon long-term exposure to light. Its co-heating reaction with water will generate a small amount of indole while heating in the presence of sodium hydroxide and copper sulfate will produce a large amount of indole. It is stable upon heating together with acid in the dark, but is easily to be decomposed when heated together with other amino acids, carbohydrates and aldehydes. L-tryptophan will be completely decomposed when applying acid to break down the protein.
Использование
L-tryptophan is an essential amino acid which is necessary for normal growth in infants and for nitrogen balance in adults. It acts as a natural dietary supplement and used as an antidepressant, anxiolytic and sleep aid. It is used as a precursor to niacin, indole alkaloids and serotonin. It acts as an important intrinsic fluorescent probe, which finds to estimate the nature of microenvironment of the tryptophan.Определение
ChEBI: L-tryptophan is the L-enantiomer of tryptophan. It has a role as an antidepressant, a nutraceutical, a micronutrient, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tryptophan and a L-alpha-amino acid. It is a conjugate base of a L-tryptophanium. It is a conjugate acid of a L-tryptophanate. It is an enantiomer of a D-tryptophan. It is a tautomer of a L-tryptophan zwitterion.Методы производства
The most attractive production processes for tryptophan are based on microorganisms used as enzyme sources or as overproducers: Enzymatic production from various precursors; Fermentative production from precursors; Direct fermentative production from carbohydrates by auxotrophic and analogue resistant regulatory mutants. L-tryptophan is synthesized from indole, pyruvate, and ammonia by the enzyme tryptophanase or from indole and L-serine/D,L-serine by tryptophan synthase these process variants were not economic due to the high costs of the starting materials. The microbial conversion of biosynthetic intermediates such as indole or anthranilic acid to L-tryptophan has also been considered as alternative for production.However, the manufacturer using genetically modified strains derived fromBacillus amyloliquefaciens IAM 1521 was forced to stop Ltryptophan production. L-Tryptophan produced by this process was stigmatized because of side products found in the product causing a new severe disease termed eosinophilia-myalgia syndrome (EMS). One of the problematic impurities, "Peak E", was identified as 1,10-ethylidene- bis-(L-tryptophan), a product formed by condensation of one molecule acetaldehyde with two molecules of tryptophan.
Всемирная организация здравоохранения(ВОЗ)
L-tryptophan, an essential aminoacid and precursor of serotonin, was introduced into medicine in 1963 for the treatment of depression and sleep disorders. Its effectiveness in these conditions has, however, never been convincingly demonstrated. It is also widely used in dietary supplements, parenteral nutrition preparations and dietary products for children with phenylketonuria. In 1989, reports from the USA showed an association between the consumption of L-tryptophan containing preparations and the development of eosiniphilia-myalgia syndrome (EMS), a condition characterized by intense eosinophilia, severe muscle and joint pain, swelling of the arms and legs, skin rashes and possible fever. Some of the reported cases have been fatal. Since it is not yet clear whether L-tryptophan itself or an unidentified contaminant is the cause of the EMS, many drug regulatory authorities have suspended the marketing authorization of products containing tryptophan pending further investigation, whereas others have withdrawn these products or restricted their use.Общее описание
White powder with a flat taste. An essential amino acid; occurs in isomeric forms.Реакции воздуха и воды
Slightly soluble in water.Профиль реактивности
Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.Угроза здоровью
ACUTE/CHRONIC HAZARDS: When heated to decomposition L-Tryptophan emits toxic fumes.Пожароопасность
Flash point data for L-Tryptophan are not available. L-Tryptophan is probably combustible.Профиль безопасности
Moderately toxic by intraperitoneal route. Experimental teratogenic and reproductive effects. Human mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of NOx.Методы очистки
Crystallise L-tryptophan from H2O/EtOH, wash it with anhydrous diethyl ether and dry it at room temperature in a vacuum over P2O5. It sublimes at 220-230o/0.03mm with 99% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Cox & King Org Synth Coll Vol II 612 1943, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2316-2345 1961, Beilstein 22 IV 6765.]L(-)-триптофан запасные части и сырье
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