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HCID 6305생성일: 2026년 10월 27일

DL-트립토판

DL-트립토판 · 트립토판 · DL-Trp-OH · ryptophan · DL-Trp · DL-3β- · DL-Tryptphan · DL-Trytophan

https://huagongshe.com/ko/chemical/6305

DL-트립토판 분자 구조식

식별자 및 물리적 특성

CAS No.54-12-6
분자식C11H12N2O2
평균 분자량204.22 g/mol
단동위원소 질량204.08987762 g/mol
SMILESN[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
InChIKeyQIVBCDIJIAJPQS-VIFPVBQESA-N
PubChem CID6305
ChEMBLCHEMBL54976
ChEBICHEBI:16828
EC No.200-795-6
DTXSIDDTXSID5021419
현지명DL-트립토판

화학 및 물리적 성질

XLogP-1.1
극성 표면적79.1
수소 결합 공여자 수3
수소 결합 수용자 수3
회전 가능 결합 수3
무거운 원자 수15
형식 전하0
복잡도245
물질 분류Biological Agents -> Amino Acids and Derivatives
의약품Pharmaceuticals -> Listed in ZINC15
화장품Cosmetic ingredients (Tryptophan) -> CIR (Cosmetic Ingredient Review)Antistatic
pHA 1% solution in water has a pH of 5.5 to 7.
LogP(분배 계수)log Kow = -1.06
냄새Odorless냄새 없는
맛FLAT TASTESlightly bitter
식품 첨가물NUTRIENT SUPPLEMENT -> FDA Substance added to food
Color/FormLeaflets or plates from dilute alcoholWhite to slightly yellowish-white ... crystals or crystalline powder
용해도1 to 5 mg/mL at 68 °F (NTP, 1992)Slightly soluble in acetic acid, ethanolinsoluble in ethyl etherSolubility in water: 0.23 g/L at 0 °C, 11.4 g/L at 25 °C, 17.1 g/L at 50 °C, 27.95 g/L at 75 °C, 49.9 g/L at 100 °CSoluble 1 in 100 of watervery slightly soluble in alcoholpractically insoluble chloroform and ethersoluble in hot alcohol and solutions of dilute acids and alkali hydroxides.13.4 mg/mL at 25 °C메탄올: 물(7:3): 용해성
Dietary IngredientsL-tryptophan
DecompositionWhen heated to decomposition it emits toxic fumes of /nitric oxide/.
녹는점289-290 °C (dec.)(lit.)
끓는 점342.72°C (rough estimate)
밀도1.1754 (rough estimate)
굴절률1.5200 (estimate)
저장 조건Keep in dark place,Inert atmosphere,Room temperature
pKa(산도 계수)2.30±0.10(Predicted)
물리적 상태가루
색상흰색에서 밝은 베이지색 또는 밝은 노란색까지
용해도10g/L(20℃)
BRN86196
안정성안정적인. 강한 산화제, 강산과 호환되지 않습니다.
화장품 원료 기능대전방지제헤어 컨디셔닝향기
InChI1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)
InChIKeyQIVBCDIJIAJPQS-UHFFFAOYSA-N
SMILESNC(Cc1c[nH]c2ccccc12)C(O)=O
LogP(분배 계수)1.040 (est)
NISTTryptophane(54-12-6)
EPATryptophan (54-12-6)

화학적 성질

White crystals. Slightly soluble in water; stable in alkaline solution; decomposed by strong acids.

안전 및 규제

GHS 분류This chemical does not meet GHS hazard criteria for 98.7% (222 of 225) of all reports.Not ClassifiedAggregated GHS information provided per 225 reports by companies from 5 notifications to the ECHA C&L Inventory.
규제 정보Chemical: TryptophanChemical: L-TryptophanRegulation (EC) No 1831/2003 (amended)Status: Active Update: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10835Tryptophan: Does not have an individual approval but may be used under an appropriate group standardl-Tryptophan: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보IMAP assessments - DL-Tryptophan: Environment tier I assessmentIMAP assessments - L-Tryptophan: Environment tier I assessment
화재 위험Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
건강 유해성ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
유해성 요약Teratogenic effects observed in experimental animals at high doses[Shepard's Catalog of Teratogenic Agents] No evidence of carcinogenicity in rats or mice[NTP] May cause irritationThe FDA and CDC have established a possible link between L-tryptophan and eosinophilia-myalgia syndrome[Sigma-Aldrich MSDS]
FDA 요건L-Tryptophan is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: tryptophan is included in weight control drug products.

용도

용도

DL-Tryptophan is an amino acid precursor of serotonin and melatonin. It is a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. DL-tryptophan also can be used as feed nutrition enhancer, antioxidants.

일반 설명

Tryptophan is the precursor for 5-hydroxy-tryptamin and an essential α-amino acid. DL-Tryptophan exists as a zwitterion during crystallization.

반응성 그룹Salts, Acidic
Special ReportsNAS, Food and Nutrition Board, Institute of MedicineDietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients). National Academy Press, Washington, D.C. (2009).[Available from, as of March 10, 2010: http://www.nap.edu/catalog/10490.html]DHEW/NCIBioassay of L-Tryptophan for Possible Carcinogenicity CAS No. 73-22-3 (NCI-CG-TR-71) (1978) Technical Report Series No. 71 DHEW Pub No. (NIH) 78-1321[Available from, as of March 29, 2010: http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr071.pdf]
FIFRA 요건Residues of tryptophan are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: synergist. Limit: maximum of 0.5% of formulation.
Reactivity ProfileAcidic salts, such as L-TRYPTOPHAN, are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.
History and IncidentsIn late 1989 the first notification linking the eosinophilia-myalgia syndrome with the use of tryptophan-containing products was made in the USA. There followed a number of similar published case reports from the USA, Europe, and Japan. Reviews of tryptophan-associated eosinophilia-myalgia syndrome have noted that by early 1990 over 1500 cases were known in the USA. In early 1990 the CDC in the USA summarized the features and known reports concerning the syndrome. As the name implies the characteristic features are an intense eosinophilia together with disabling fatigue and muscle pain, although multisystem organ involvement and inflammatory disorders affecting the joints, skin, connective tissue, lungs, heart, and liver have also been recorded. Symptoms have generally developed over several weeks and the syndrome has occurred in patients who had been receiving tryptophan for many years previously with no untoward effect. In most patients slow and gradual improvement in the degree of eosinophilia and other clinical manifestations has followed the withdrawal of tryptophan, but in some patients the disease has progressed despite withdrawal and there have been fatalities. The inflammatory condition has necessitated the use of corticosteroids in some patients. The eosinophilia-myalgia syndrome has been reported in patients taking both tryptophan-containing prescription products for depression and non-prescription dietary supplements for a number of disorders including insomnia, the premenstrual syndrome, and stressit does not appear to have occurred in patients receiving amino-acid preparations containing tryptophan as part of total parenteral nutrition regimens. The recognition of this syndrome led to the withdrawal of tryptophan-containing products or severe restrictions being imposed upon their use in many countries during 1990. Various theories were proposed as to the reason for the association of tryptophan with this syndrome. Confusion existed because the reports implicated a very wide range of products from different manufacturers. However, later evidence appeared to have confirmed that contaminated tryptophan had originated from a single manufacturer in Japan. Bulk tryptophan was imported from Japan for manufacture into finished pharmaceutical dosage forms and it was noted in one of these reports that a single product was often found to contain two or more lots of powdered tryptophan that were blended together during the production of tablets or capsules. Many trace contaminants have been found in batches of tryptophan associated with the syndrome. One contaminant has been identified as 1,1'-ethylidenebis(tryptophan). Its inclusion in bulk tryptophan powder appeared to coincide with alterations in the manufacturing conditions that involved a change in the strain of Bacillus amyloliquefaciens used in the fermentation process and a reduction in the amount of charcoal used for purification. Other investigations indicated the presence of bacitracin-like peptides in batches of the contaminated tryptophan. However, further work has provided only weak support for an association between the syndrome and any one particular contaminant and the causative agent remains to be confirmed. Nonetheless, since the syndrome only appeared to be associated with tryptophan from one manufacturer, tryptophan preparations were reintroduced in the UK in 1994 for restricted use under carefully monitored conditions. In January 2005, the UK requirement for patient registration and monitoring was removed.[Sweetman SC (ed), Martindale: The Complete Drug Reference.
Air and Water ReactionsSlightly soluble in water.
소화Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
응급 처치EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
보관 조건Protect from light
비화재 누출 대응SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
처리 방법SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Allowable TolerancesResidues of tryptophan are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: synergist. Limit: maximum of 5% of formulation.
Personal Protective Equipment (PPE)RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
체내 부담Concentrations of tryptophan (free and protein bound) and its metabolites in plasma of maternal vein at delivery, umbilical vein, umbilical artery, neonatal vein and breast milk were determined by high performance liquid chromatography. The plasma levels of tryptophan and most of its metabolites in umbilical vein and artery were significantly higher than those in maternal vein. The concentration of total tryptophan in plasma of neonatal vein showed marked decrease at 24 h after birth in comparison with that at birth, but the total kynurenine concentration was not decreased in plasma of neonatal vein. The colostrum contained a high level of total tryptophan. There were high ratios of free to total tryptophan in colostrum, transitional and mature milk. In the blood, ratios of free to total of tryptophan and kynurenine were kept at constant level throughout the perinatal period.
상호 작용Acetylsalicylic acid reduced serum-protein binding of tryptophan in man, causing rise in free serum tryptophan. Changes in metabolic pattern also occurred, with increased urinary excretion of xanthurenic acid and 3-hydroxylkynurenine and decreased excretion of 3-hydroxyanthranilic acid.Although tryptophan has been given to patients receiving MAOIs in the belief that clinical efficacy may be improved, it should be noted that the adverse effects may also be potentiated.Use of tryptophan with drugs that inhibit the reuptake of serotonin may exacerbate the adverse effects of the latter and precipitate the serotonin syndrome.There have been occasional reports of sexual disinhibition in patients taking tryptophan with phenothiazines or benzodiazepines.For more Interactions (Complete) data for (L)-Tryptophan (16 total), please visit the HSDB record page.
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 320(SRC), determined from a log Kow of -1.06(2) and a regression-derived equation(3), indicates that (L)-tryptophan is expected to have moderate mobility in soil(SRC). The pKa values of pKa1 2.38 (carboxylic acid) and pKa2 9.39 (primary amine)(4) indicate that this compound will exist as a zwitterion which may affect its adsorption to soils and sediments(SRC). Volatilization from moist soil is not expected because ions do not volatilize(SRC). Volatilization from moist soil is not expected because the acid/base exists as an anion/cation and anions/cations do not volatilize. (L)-Tryptophan is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Using the Warburg respirometer test, a theoretical BOD value of 4.6% in 24 hours(6) suggests that biodegradation is not expected to be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 320(SRC), determined from a log Kow of -1.06(2) and a regression-derived equation(3), indicates that (L)-tryptophan may adsorb to suspended solids and sediment(SRC). The pKa values of pKa1 2.38 (carboxylic acid) and pKa2 9.39 (primary amine)(4) indicate (L)-tryptophan will exist as a zwitterion at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using the Warburg respirometer test, a theoretical BOD value of 4.6% in 24 hours(8) suggests that biodegradation is not expected to be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), (L)-tryptophan, which has an estimated vapor pressure of 2.1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase (L)-tryptophan may be removed from the air by wet or dry deposition(SRC). Photooxidation proceeds primarily by a singlet-oxygen mechanism(3). The oxidation products kynurenine and N-formylkynurenine accumulated most readily at pH 4-7.5 following irradiation of solutions of tryptophan containing riboflavin(4).
Milk ConcentrationsConcentrations of tryptophan (free and protein bound) and its metabolites in ... breast milk were determined by high performance liquid chromatography. ... The colostrum contained a high level of total tryptophan. There were high ratios of free to total tryptophan in colostrum, transitional and mature milk. ...
독성 요약Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgA number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD<sup>+</sup> and NADP<sup>+</sup>.
Plant ConcentrationsPlant species with highest amount of tryptophan(1). /Tryptophan/ [Table#4826]
Signs and SymptomsSymptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=73-22-3]
Soil Adsorption/MobilityThe Koc of (L)-tryptophan is estimated as 320(SRC), using a log Kow of -1.06(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that (L)-tryptophan is expected to have moderate mobility in soil. The pKa values of pKa1 2.38 (carboxylic acid) and pKa2 9.39 (primary amine)(4) indicate that this compound will exist as a zwitterion which may affect its adsorption to soils and sediments(SRC).
Natural Pollution Sources(L)-Tryptophan is an essential amino acid for human development and a precursor of serotonin(1).MILK & EGGS ... HAVE HIGH TRYPTOPHAN CONTENT.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Serotonin and its metabolite 5-hydroxyindoleacetic acid (5-HIAA) in human blood and brain cerebrospinal fluid (CSF) increase /were found/ after tryptophan loading, which is similar to the effects of L-tryptophan in animals. ... Elevations in blood and 5-HIAA and CSF serotonin after single doses of 3 or 6 g of L-tryptophan. However, ... a double-blind, placebo-controlled trial in six normal men fed 3 g/day of L-tryptophan in divided doses with meals for 3 days, found a 113% elevation in plasma tryptophan, but no changes in platelet or plasma serotonin or in plasma catecholamines. ... No changes in urinary catecholamines /were found/. Additionally, no changes in blood pressure, heart rate, plasma sodium levels or 24-hour sodium excretion in urine /were found/./HUMAN EXPOSURE STUDIES/ L-Tryptophan administration (2 g) as a single dose before a meal has been found to decrease subjective hunger ratings, food intake, and alertness in men, but not women./HUMAN EXPOSURE STUDIES/ 15 humans /were tested/ only once with 0, 1, 2, and 3 g of L-tryptophan. Individuals receiving 2 and 3 g of L-tryptophan had decreased hunger and alertness and increased faintness and dizziness. Administration of 1 g of L-tryptophan with 10 g of carbohydrates before each meal (3 g L-tryptophan/d) for 3 months did not affect body weight of obese humans./HUMAN EXPOSURE STUDIES/ Daily doses of 2.4 g of L-tryptophan for 2 weeks did not produce a significant reduction in the consumption of carbohydrate snacks in the majority of the 24 individuals.For more Human Toxicity Excerpts (Complete) data for (L)-Tryptophan (19 total), please visit the HSDB record page.
Artificial Pollution Sources(L)-Tryptophan's production and use in nutrition and research, in medicine, as a dietary supplement, and in cereal enrichment(1) may result in its release to the environment through various waste streams(SRC).
수질 위해 등급(WGK)1
TSCA 등재 상태TSCA listed
RTECS 번호YN6129200
관세 코드29339990
위험 문구(R)22-36/37/38-37/38-41
위험 표시Xi
안전 문구(S)24/25-36/37/39-36-26
기존화학 물질2014-3-5933
F 고인화성물질8
저장 분류11 - Combustible Solids