基本情報
- 標準SMILES
CNCC(=O)O- InChIKey
FSYKKLYZXJSNPZ-UHFFFAOYSA-N- 分子式
- C3H7NO2
- 平均分子量
- 89.09 g/mol
- 単同位体質量
- 89.04767846
概要
Deliquescent crystals or powder. Has a sweetish taste. (NTP, 1992)
名称と識別子
- 優先名称
- Sarcosine
- IUPAC
- 2-(methylamino)acetic acid
- 現地名
- サルコシン
- 英語名
- Sarcosine
- 分子式
- C3H7NO2
- 分子量
- 89.09
名称と別名
名称をさらに表示
データベース識別子
- CAS
107-97-1、25951-24-0、68411-97-2- PubChem CID
- 1088
- DTXSID
DTXSID1047025- ChEMBL
CHEMBL304383- ChEBI
CHEBI:15611- UNII
- Z711V88R5F
- EC Number
- 203-538-6
- Nikkaji
- J5.067I
物性
構造計算による物性
- XLogP
- -2.8
- 極性表面積
- 49.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 52.8
実験および物理化学的性質
Cosmetics
Cosmetic ingredients (Cocoyl Sarcosine) -> CIR (Cosmetic Ingredient Review)
Cleansing; Surfactant; Skin conditioning
Personal care product
Solubility
greater than or equal to 100 mg/mL at 61 °F (NTP, 1992)
300.0 mg/mL
5.6 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
406 °F (Decomposes) (NTP, 1992)
208 °C
Physical Description
Deliquescent crystals or powder. Has a sweetish taste. (NTP, 1992)
Deliquescent solid; [Merck Index] Cream-colored hygroscopic solid; [NTP] White odorless crystalline powder; Hygroscopic; [Alfa Aesar MSDS]
Solid
物理化学的性質
- 融点
- 208 · 208-212 °C (dec.)(lit.)
- 沸点
- 165.17 °C · 165.17°C (rough estimate)
- 比重(密度)
- 1.1948 · 1.1948 (rough estimate)
- 屈折率
- 1.4368 · 1.4368 (estimate)
- 闪点
- 100 ℃ · >100℃
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 2 O: · H2O: 1M at20℃
- 酸解離定数(Pka)
- 2.21 · 2.21(at 25℃)
- 外見
- 結晶または粉末
- 色
- 無色または白から黄色
- PH
- 6.1 · 6.1 (100g/l, H2O, 20℃)
- 水溶解度
- 1480 g/L · 1480g/L(20℃)
- Merck
- 14 · 14,8373
- BRN
- 1699442 · 1699442
- 主な用途
- ペプチド合成
- 化粧品成分の機能
- スキンコンディショニング
- InChI
- 1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)
- InChIKey
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N
- SMILES
- CNCC(O)=O
- CAS データベース
- 107 · 107-97-1(CAS DataBase Reference)
- NISTの化学物質情報
- Sarcosine(107-97-1)
- EPAの化学物質情報
- Sarcosine (107-97-1)
- CAS Number Unlabeled
- 107 · 107-97-1
化学的性質
化学的特性White crystalline powder
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 98.7% (149 of 151) of all reports.
Not Classified
Aggregated GHS information provided per 151 reports by companies from 3 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Glycine, N-methyl-
Status: Active Update: 20-12-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18702
Glycine, N-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
SARCOSINE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical is incompatible with acids. (NTP, 1992).
安全と保護具
First Aid
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.
Nonfire Spill Response
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 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.
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)
毒性情報
Treatment
Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Health Effects
Acyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (A2881)
Acute Exposure: Can lead to eye and skin irritation. Chronic Exposure: High levels of sarcosine in prostate tissues are associated with aggressive prostate tumors. In this regard, sarcosine appears to function as an oncometabolite. High levels of sarcosine are also seen in patients with sarcosinemia. Sarcosinemia is a rare inborn error of metabolism that is characterized by an increased level of sarcosine (N-methylglycine) in the plasma and urine. The enzymatic block results from a deficiency of sarcosine dehydrogenase (SarDH), a liver mitochondrial matrix enzyme that converts sarcosine into glycine. The disease is mostly characterized by mental delay, cardiomyopathy, deafness and visual disturbance.
Exposure Routes
Oral (A2881) ; inhalation (A2881) ; dermal (A2881)
Endogenous, Eye contact, Ingestion.
Toxicity Summary
The CIR Expert Panel concluded that the following ingredients are safe as used in cosmetics when formulated to be non-irritating. The Expert Panel cautions that these ingredients should not be used in cosmetic products in which N-nitroso compounds can be found...Cocoyl Sarcosine...
Safe for use in cosmetics, with qualifications
While acyl sarcosines themselves are not toxic, they are nitrosating agents. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (L1889, L1890, A2878, A2879, A2880, A2881)
Sarcosine is an oncometabolite. Sarcosine appears to upregulate the expression of the potent oncoprotein called human epidermal growth factor receptor 2 (HER2/neu) in androgen-dependent prostate cancer cells upon exposure to exogenous sarcosine. Thus, sarcosine may induce prostate cancer progression by increased HER2/neu expression.
Signs and Symptoms
Acyl sarcosines may cause irritation to the skin and eyes. (A2881)
Acute Exposure: eye irritation and skin irritation Chronic Exposure: sarcosinemia is associated with mental delay, cardiomyopathy, deafness and visual disturbance. In individuals with prostate cancer, high prostate tissue levels of sarcosine promote aggressive, rapidly growing prostate tumors.
Carcinogen Classification
No indication of carcinogenicity (not listed by IARC). (L135)
Not listed by IARC. Has been implicated in oncogenesis (A15089).
Toxicity Data
LD50: 2.1 g/kg (Oral, Mouse) (A2881)
NA
安全データ
- F
- 3
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- VQ2897000
- hs_code
- 29224995
- risk_code
- 36/37/38
- 化審法
- (2)-1205
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
Acyl sarcosines can be absorbed following oral or dermal contact, while nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase. (A2878, A2879, L1892)
Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine.
用途と製造
Uses
CIR ingredient: Cocoyl Sarcosine
Used as an intermediate in synthesis of toothpaste antienzyme agents; [Merck Index] An amino acid intermediate in the metabolism of choline. [ChemIDplus] Used to make antienzyme agents for cosmetics and pharmaceuticals; [NTP]
Acyl sarcosines are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines and their sodium salts are also used in the metal finishing and processing industries for their crystal modifying, anti-rust, and anti-corrosion properties. (A2881)
Sarcosine can be used as a cognitive enhancer and to treat schizophrenia.
応用分野
解説サルコシン略号Sar.ヒトデ,ウニ,ウミザリガニGasus lalandii,ハナゴケなどに遊離の形で存在する.アクチノマイシン,エタマイシンなどの抗生ペプチドの構成アミノ酸であるが,タンパク質中には存在しない.カフェインを水酸化バリウムで分解すると生成する.ホルムアルデヒド,シアン化ナトリウム,メチルアミンから合成される.実験室的には,モノクロロ酢酸とメチルアミンからつくられる.分解点212 ℃.pK1 2.23,pK2 10.01.甘味がある.
用途界面活性剤及び有機合成原料。
使用Sarcosine can improve people's intelligence, especially for exams such as the students need to temporarily increase the effectiveness of intelligence is more obvious. sarcosine can increase muscle strength and anaerobic explosiveness.To prevent damage caused by the brain injury. Sarcosine can effectively improve athletic performance,power, and shorten muscle recovery time.
使用Sarcosine is an important component for the production of the amino acid glycine and a byproduct of glycine breakdown. In the body, it is produced by converting dietary choline to glycine or breaking down methionine into glycine. It can also be synthesized in the laboratory with chloroacetic acid and methylamine. Sarcosine has a unique mild sweetness. Since a derivative of creatine helps prevent tooth decay and causes foam, it acts as an ingredient in toothpaste. Sarcosine can also be used as a drug, and research over the past 20 years has revealed its role in treating mental health disorders such as schizophrenia and depression.
一般的な説明Deliquescent crystals or powder. Has a sweetish taste.
使用用途1. 界面活性剤の原料 サルコシンは、練り歯磨き粉や生分解性界面活性剤の原料として、幅広く使用されてきました。例えば、窒素上にラウリン酸が付加したラウロイルサルコシンのナトリウム塩は、皮膚への刺激性が低く、硬水を用いた場合も洗浄力に優れ、泡立ちの良い界面活性剤です。 これらの優れた洗浄効果から、シャンプーを始めとし、ボディーソープや洗顔料、歯磨き粉などによく用いられます。 2. 医療分野 最近の研究では、前立腺がんのバイオマーカーとなる可能性が高いことや、うつ病や統合失調症などの精神疾患に効果があるとの結果も示されています。また、サルコシンの重合体 (ポリマー) であるポリサルコシンは、DDS (ドラッグデリバリーシステム) 製剤として利用する研究も進められています。
調製方法
純化方法Crystallise sarcosine from absolute EtOH, 95% EtOH or H2O. It sublimes at 180-185o/0.3mm with 99.1% recovery [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Cocker & Harris J Chem Soc 1291 1940, Cocker & Lapworth J Chem Soc 1897 1931, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2750 1961, Beilstein 4 III 1121, 4 IV 2363.]
上流・下流製品情報
上流原料
下流製品
サプライヤー9 社
補足説明
定義本品は、次の化学式で表されるアミノ酸である。
定義ChEBI: Sarcosine is a N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. It has a role as a glycine transporter 1 inhibitor, a glycine receptor agonist, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a N-alkylglycine, a N-methyl-amino acid and a member of N-methylglycines. It is a conjugate base of a sarcosinium. It is a conjugate acid of a sarcosinate. It is a tautomer of a sarcosine zwitterion.
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