2-アミノエタンスルホン酸

Taurine

HCID 1123CAS 107-35-7

基本情報

標準SMILES
NCCS(=O)(=O)O
InChIKey
XOAAWQZATWQOTB-UHFFFAOYSA-N
分子式
C2H7NO3S
平均分子量
125.15 g/mol
単同位体質量
125.01466426

名称と識別子

優先名称
Taurine
IUPAC
2-aminoethanesulfonic acid
現地名
2-アミノエタンスルホン酸
英語名
Taurine
分子式
C2H7NO3S
分子量
125.15

名称と別名

taurine2-aminoethanesulfonic acid107-35-7L-TaurineEthanesulfonic acid, 2-amino-tauphon2-Aminoethylsulfonic acidaminoethylsulfonic acid2-SulfoethylamineAminoethanesulfonic acidO-Due2-aminoethane-1-sulfonic acid
名称をさらに表示
2-アミノエタンスルホン酸タウリン【Taurine】アミノエチルスルホン酸2-アミノ-1-エタンスルホン酸β-アミノエタンスルホン酸タウリン2-アミノエタンスルホン酸 タウリン2-アミノエタン-1-スルホン酸βアミノエタンスルホン酸2-アミノエチルスルホン酸2-アミノエタンスルホン酸 タウリンアミノエチルスルホン酸 (JAN)タウリン (JP17)TATUTaurine Powder2-amino-ethanesulfonicaciFEMA 3813TAURINE extrapure CHRTURINTAURINE SYNTHETIC
taufonbeta-Aminoethylsulfonic acidTaurinumTaurinaFEMA No. 3813TaukardNCI-C60606NSC-32428

データベース識別子

CAS
107-35-7
PubChem CID
1123
DTXSID
DTXSID3021304
ChEMBL
CHEMBL239243
ChEBI
CHEBI:15891
UNII
1EQV5MLY3D
EC Number
203-483-8
Nikkaji
J5.056C

物性

構造計算による物性

XLogP
-4.1
極性表面積
88.8 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
2
重原子数
7

実験および物理化学的性質

pHpH = 4.1-5.6 (5% aqueous solution)
Odor · 2 件

Odorless

Almost odorless

TasteSlightly acidic taste
Density · 2 件

Density = 1.7 g/cu cm

Bulk density = 0.65-0.75 g/cu cm

Color/Form · 2 件

Colorless crystals

Monoclinic prisms from water

Solubility · 6 件

50 to 100 mg/mL at 74.3 °F (NTP, 1992)

65

In water, 94.9 g/L at 25 °C

Soluble in 15.5 parts of water at 12 °C; 100 parts of 95% alcohol dissolves 0.004 parts at 17 °C; insoluble in absolute alcohol

80.7 mg/mL

Soluble in water

物理化学的性質

融点
300 °C · >300 °C (lit.)
比重(密度)
1 g/mL · 1.00 g/mL at 20 °C
屈折率
1.513 · 1.5130 (estimate)
FEMA
3813 · 3813 | TAURINE
貯蔵温度
2 · 2-8°C
溶解性
2 O: · H2O: 0.5M at20℃、透明、無色

化学的性質

化学的特性Taurine is a naturally occurring amino acid with a bitter taste and sharp flavor. It is a nonessential amino acid by definition because the body can synthesize it from methionine and cysteine.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 18.5% (307 of 1656) of reports.

Warning

H315 (81.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (81.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (81.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1656 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 307 of 1656 reports by companies.;There are 14 notifications provided by 1349 of 1656 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 5 件

Chemical: Ethanesulfonic acid, 2-amino-

Regulation (EC) No 1831/2003 (amended)

Ethanesulfonic acid, 2-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanesulfonic acid, 2-amino- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 21-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24137;Status: Active Update: 20-08-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6448;Status: Active Update: 30-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26194

Taurine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire HazardsFlash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This material evolves highly toxic fumes when heated to decomposition, and may cause irritation on contact. (NTP, 1992)
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Sigma-Aldrich MSDS]
FDA Requirements · 1 件

The food additive taurine (2-amino-ethanesulfonic acid) may be safely used in feed in accordance with the following prescribed conditions: (a) It is used as a nutritional supplement in the feed of growing chickens. (b) It is added to complete feeds so that the total taurine content does not exceed 0.054 percent of the feed.

安全と保護具

Fire FightingFires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: 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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Fire Fighting Procedures · 2 件

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup MethodsPick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Nonfire Spill Response · 1 件

SMALL 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 strong 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.;STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

毒性情報

Body BurdenTaurine is a major constituent of bile and can be found in the large intestine and accounts for approximately 0.1% of total human body weight(1).
Interactions · 5 件

It prevented the development of ethanol-induced hypertension in rats.

In animal studies, taurine was found to ameliorate the pulmonary side effects (pulmonary fibrosis) of bleomycin.

...Three fatalities occurred after "energy" drinks had been consumed in combination with alcohol, whereby the forensic examinations including autopsy yielded negative results concerning medicaments and drugs, values between 0.59 and 0.87 parts per thousand of ethanol in blood samples, but no clear causes of death.

...Severe adverse effects arose after consumption of an "energy" drink in combination with physical efforts: A 31-year old regularly trained man consumed 750 mL of an "energy" drink while taking part in a 3,000 m competition. He developed a poor general condition with a rhabdomyolysis and acute kidney failure with tubular necrosis diagnosed one week after the competition.

For more Interactions (Complete) data for Taurine (10 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that taurine is expected to have very high mobility in soil(SRC). Taurine has pKa values of 1.05 (the acid) and 9.06 (the amine)(3) indicating that this compound will exist as a zwitterion having both a cation and anion form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of taurine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Taurine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.7X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Various species of bacteria and fungi are capable of degrading taurine and using taurine as a sole source of sulfur, carbon and energy(5,6), therefore, biodegradation may be an important fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that taurine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.7X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Taurine has pKa values of 1.05 (the acid) and 9.06 (the amine)(4) indicating that this compound will exist as a zwitterion having both a cation and anion form in the environment that also suggests volatilization from water will not be an important fate process(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -3.36(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Taurine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Various species of bacteria and fungi are capable of degrading taurine and using taurine as a sole source of sulfur, carbon and energy(5,6), therefore, biodegradation may be an important fate process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), taurine, which has an estimated vapor pressure of 1.7X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase taurine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12 hrs(SRC), calculated from its rate constant of 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase taurine may be removed from the air by wet and dry deposition(SRC).

Food Survey Values · 1 件

Taurine is found in animal protein such as seafood, beef and chicken and nearly absent from vegetarian foods; the synthetic form has been petitioned for use in infant formula because insufficient taurine could result in subpar fat digestion and absorption in infants(1). The taurine concentration of various samples of fresh prune juice ranged from 16-155 mg/L of juice(2).

Milk ConcentrationsTaurine is the primary free amino acid in the milk of most mammals, including humans(1); taurine is present in human breast milk, and has been added to many infant formulas since the early 1980s(1).
Average Daily Intake · 1 件

The mean daily intake of taurine from omnivore diets was determined to be around 58 mg (range from 9 to 372 mg) and to be low or negligible from a strict vegan diet(1). In another study taurine intake was estimated to be generally less than 200 mg/day, even in individuals eating a high meat diet(1). According to another study, taurine consumption was estimated to vary between 40 to 400 mg/day(1).

法規制情報

Regulatory Information · 5 件

Chemical: Ethanesulfonic acid, 2-amino-

Regulation (EC) No 1831/2003 (amended)

Ethanesulfonic acid, 2-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanesulfonic acid, 2-amino- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 21-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24137;Status: Active Update: 20-08-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6448;Status: Active Update: 30-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26194

Taurine: Does not have an individual approval but may be used under an appropriate group standard

FDA Requirements · 1 件

The food additive taurine (2-amino-ethanesulfonic acid) may be safely used in feed in accordance with the following prescribed conditions: (a) It is used as a nutritional supplement in the feed of growing chickens. (b) It is added to complete feeds so that the total taurine content does not exceed 0.054 percent of the feed.

安全データ

wgk
2
tsca
TSCA listed
rtecs
WX0175000
毒性
LD50 orally in Rabbit: > 5000 mg/kg
hs_code
29211980
risk_code
36/37/38

化学と産業

薬理情報

Bionecessity · 5 件

Taurine is involved in the pre-and post-natal development of CNS and visual system...

Taurine deficiency in cats can result in a variety of clinical abnormalities, including central retinal degeneration, dilated cardiomyopathy and platelet function abnormalities.

Taurine is a nonprotein amino acid. It is an end product of L-cysteine metabolism and the principal free intracellular amino acid in many tissues of human and other animal species... It is classified as a conditionally essential amino acid because it is necessary to be supplied in the diet of infants for normal retinal and brain development.

Taurine is an essential beta-amino acid for some species. Taurine is not incorporated into proteins and is found in the tissues of most animal species in its free form. Taurine is involved in a number of physiological processes including bile acid conjugation, osmoregulation, neuronal excitability, inflammatory reactions and glucose metabolism. In some animal species, low dietary levels of taurine have been associated with retinal degeneration, dilated cardiomyopathy and growth retardation.

For more Bionecessity (Complete) data for Taurine (9 total), please visit the HSDB record page.

Protein BindingTaurine is highly bound to plasma proteins and retained in the plasma fraction.
Pharmacodynamics · 1 件

The diet supplements containing taurine are formulated as a well-tolerated nitrogen source for nutritional support. Administration of diet supplements regulates the level of plasma amino acid concentration, nitrogen balance, weight and serum protein concentration to reach normal values, thus improving the nutritional status.

Mechanism of Action · 1 件

The diet supplements containing taurine function by replacing the missing nutriments in the body. Taurine, as a single agent, presents different functions like substrate for formation of bile salts, cell volume regulation, modulation of intracellular calcium, cytoprotection of central nervous system, etc.

Biological Half-LifeOral administration of taurine in healthy individuals gave a plasma elimination half-life that ranged from 0.7-1.4 h.
Metabolism/Metabolites · 4 件

Taurine can be metabolized by diverse organisms to form different types of metabolites derived from the original form of taurine. In the human, the pathways that form the metabolism of taurine are divided in the formation of 5-glutamyl-taurine by the action of the enzyme gamma-glutamyltransferase 6 or the formation of taurocholate by the action of the bile acid-CoA:amino acid N-acyltransferase.

There are two sources of taurine in the body: dietary and endogenous. In mammals, taurine is synthesised in many tissues; the main sites are liver, brain and pancreas, predominantly in alpha-islets. Taurine is synthesised from cysteine and methionine in a few steps, one of which requires pyridoxal-5-phosphate (vitamin B6) as coenzyme of cysteine sulphinate decarboxylase. In species other than mammals, the biosynthesis of taurine has been poorly studied. The extent of synthesis varies widely between species. An adult rat consuming standard laboratory food produces about 80 % of its total body taurine and obtains the remainder from the diet. However, if required, rats can obtain all body taurine from biosynthesis, since rats fed taurine-free diets for extended periods do not exhibit any decrease in tissue taurine concentrations. Cats have low levels of activity of cysteine sulphinate decarboxylase, the rate-limiting enzyme for taurine biosynthesis, and are, therefore, dependent on a dietary source to maintain their body pool of this amino acid. Thus, taurine is an essential nutrient in cats.

Taurocholate, the bile salt conjugate of taurine and cholic acid, is the principal conjugate formed via the action of the enzyme choloyl-CoA N-acyltransferase.

In all vertebrates except mammals, taurine is the sole amino acid conjugated to form bile salts. Among the mammals, carnivores also tend to be conjugators of taurine only, whereas other species tend to conjugate both taurine and glycine. High concentrations of taurine are present in retina, liver, pancreas, central nervous system and white blood cells. The largest pools of taurine are found in skeletal and cardiac muscles, where it regulates intracellular Ca2+ concentration...

用途と製造

Uses · 6 件

A conditionally essential amino acid; Used as a nutritional supplement; [Merck Index] Used in biochemical research, pharmaceuticals, and as a wetting agent; [NTP]

Derivatives of taurine, especially fatty acid derivatives, are important wetting, washing, and dispersion agents in body and household cleaning agents, and also in textile processing.

Biochemical research, pharmaceuticals, wetting agents

Nutritional supplement

Cosmetic compositions

For more Uses (Complete) data for Taurine (10 total), please visit the HSDB record page.

Impurities · 1 件

Taurine is a white crystalline powder that is almost odourless but with a slightly acidic taste. It contains by specification at least 98.0 % taurine in dried substance. Analysis of five batches of the active substance showed an average content of 99.5 +/- 0.1 % taurine and a loss on drying of 0.07 +/- 0.01 %.11 The final additive may be formulated by adding a maximum 0.8 % of an anti-caking agent (SiO2). Three batches of the additive were analysed for impurities, one batch with six replicate samples and another batch with three replicate samples. In all batches, sulphated ash was < 0.06 % (in one batch residue on ignition 0.06 %), chloride < 0.01 %, sulphate < 0.01 %, ammonium salt < 0.02 %, related substances < 0.2 %, heavy metals (expressed as lead) < 10 mg/kg and arsenic < 1.0 mg/kg (two batches).

U.S. Production · 3 件

2023: 35,273 lb;2021: 35,273 lb;2020: 35,274 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8141]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethanesulfonic acid, 2-amino-. Aggregated National Production Volume: < 500,000 pounds.

Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 2 件

Taurine is synthesised starting from ethylene oxide and sodium bisulphite. Subsequently, liquid ammonia and sulphuric acid are added. The product is then decolorised, purified, crystallised, centrifuged, dried, sieved and blended with the carrier to obtain the additive.

Ethyleneimine reacts rapidly with sulfurous acid to give taurine in high yield.

Formulations/Preparations · 4 件

Diabetic Support Formula Tablets: Taurine 50 mg /and minerals, vitamins, herbs/

Diabetiks Tablets: Taurine 375 mg /and vitamins, minerals, herb extracts/

Enfamil Kindercal Liquid with Fiber: Taurine 15 mg /and vitamins, minerals, fiber/

Enfamil Kindercal Liquid: Taurine 15 mg /with vitamins and minerals/

応用分野 · 6 件

解説2-aminoethanesulfonic acid.C2H7NO3S(125.15).NH2CH2CH2SO3H.生物界,とくに軟体動物の肉エキス中に遊離の形で広く分布しており,またコール酸と結合して胆汁中にタウロコール酸として存在している.生体内ではシステインから生合成され,化学的にはエテンやニトロエテンから容易に合成される.単斜晶系プリズム状結晶.分解点約300 ℃.pK1 1.5,pK2 8.74.水に易溶,有機溶媒に不溶.胆汁の分泌や脂肪の吸収をよくし,制汗作用がある.高級脂肪酸とのアミドは浸透剤として用いる.LD50 > 64 mg/kg(マウス,腹腔内).[CAS 107-35-7]森北出版「化学辞典(第2版)

用途医薬品用N-置換タウリンと高級脂肪酸とのアミドは合成浸透剤(表面活性剤)となる。

天然物の起源Reported found in beef, black beans, chicken, chick peas, clams, cod, fish, lamb, milk, octopus, oysters, pistachios, pork, scallops, shrimp and other natural sources.

使用Taurine is an organic acid found in animal tissues and is a major constituent of bile. Taurine has many biological roles such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization and modulation of calcium signaling. It is an amino acid nutritional supplement that is used to treat taurine-deficiency diseases such as dilated cardiomyopathy, a type of heart disease.

一般的な説明Taurine, which has chemistry similar to other amino acids, is important in several of the body's metabolic processes. Taurine is thought to have antioxidant properties. But little is known about the effects of long-term supplemental taurine use.

使用用途タウリンの使用用途は幅広く、主に医薬品や食品添加物、保湿剤に使用されます。 その他、粉ミルクやペットフード、工業用の触媒、界面活性剤などにも、タウリンは多用途に使われています。

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補足説明 · 2 件

定義本品は、次の化学式で表されるアミノスルホン酸化合物である。

定義ChEBI: Taurine is an amino sulfonic acid that is the 2-amino derivative of ethanesulfonic acid. It is a naturally occurring amino acid derived from methionine and cysteine metabolism. An abundant component of fish- and meat-based foods, it has been used as an oral supplement in the treatment of disorders such as cystic fibrosis and hypertension. It has a role as a human metabolite, an antioxidant, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a glycine receptor agonist, a nutrient and a radical scavenger. It is a conjugate acid of a 2-aminoethanesulfonate. It is a tautomer of a taurine zwitterion.

関連反応

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