트리메틸아민옥사이드
트리메틸아민N-옥사이드 · 트리메틸아민옥사이드 · 트라이메틸아민옥사이드 · 트라이메틸아민 N-산화물 · TMAO · Trimetlylamine Oxide · N,N-dimethylmethanamine oxide · trimethyloxamine
식별자 및 물리적 특성
| CAS No. | 1184-78-7 |
|---|---|
| 분자식 | C3H9NO |
| 평균 분자량 | 75.11 g/mol |
| 단동위원소 질량 | 75.06841391 g/mol |
| SMILES | C[N+](C)(C)[O-] |
| InChIKey | UYPYRKYUKCHHIB-UHFFFAOYSA-N |
| PubChem CID | 1145 |
| ChEBI | CHEBI:15724 |
| EC No. | 214-675-6 |
| DTXSID | DTXSID8049678 |
| 현지명 | 트리메틸아민옥사이드 |
화학 및 물리적 성질
| XLogP | -0.3 |
|---|---|
| 극성 표면적 | 18.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 5 |
| 형식 전하 | 0 |
| 복잡도 | 28.4 |
| 물질 분류 | Nitrogen Compounds -> Amine Oxides |
| 의약품 | Pharmaceuticals -> Metabolite of Levocarnitine |
| SpringerMaterials Properties | Schoenflies notation |
| LogP(분배 계수) | -2.570 |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 향미제 | EU Flavoring substances |
| 용해도 | 454 mg/mLSoluble in waterSoluble (in ethanol)클로로포름, DMSO, 메탄올(약간 용해됨) |
| 녹는점 | 95 - 99 °C220-222 °C (lit.) |
| Physical Description | LiquidColorless solidHighly hygroscopic[Merck Index]Colourless to yellow solidOdourless |
| 끓는 점 | 133.8°C (rough estimate) |
| 밀도 | 0.9301 (rough estimate) |
| 증기압 | 23.5Pa at 20℃ |
| 굴절률 | 1.4698 (estimate) |
| FEMA | 4245 | TRIMETHYLAMINE OXIDE |
| 저장 조건 | Hygroscopic, Room Temperature, under inert atmosphere |
| pKa(산도 계수) | 4.65(at 25℃) |
| 물리적 상태 | 고체 |
| 색상 | 옅은 노랑 |
| 냄새 | 냄새 없는 |
| 용해도 | 793g/L at 24.5℃ |
| Merck | 14,9711 |
| JECFA Number | 1614 |
| 안정성 | 흡습성 |
| InChI | 1S/C3H9NO/c1-4(2,3)5/h1-3H3 |
| InChIKey | UYPYRKYUKCHHIB-UHFFFAOYSA-N |
| SMILES | C[N+](C)(C)[O-] |
| LogP(분배 계수) | -2.79 |
| EPA | Methanamine, N,N-dimethyl-, N-oxide (1184-78-7) |
화학적 성질
White crystalline powder
안전 및 규제
| GHS 분류 | DangerH302 (71.8%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302+H332 (31.5%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation] |
|---|---|
| 규제 정보 | Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Methanamine, N,N-dimethyl-, N-oxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanamine, N,N-dimethyl-, N-oxide 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: 03-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/25104Methanamine, N,N-dimethyl-, N-oxide: Does not have an individual approval but may be used under an appropriate group standardAmines, C12-16-alkyldimethyl, N-oxides: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| 유해성 요약 | The dihydrate is CAS# 62637-93-8May cause skin, eye, and respiratory tract irritation[Merck Index] Safe when used as a flavoring agent in food[JECFA] A skin and strong eye irritant[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (57.6%)Acute Tox. 4 (71.8%) |
| Minimum Risk Level | >75 uM in blood |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Treatments for atherosclerosis may include lifestyle changes (exercise, eating fruits and vegetables), medicines (statins), and medical procedures or surgery (angioplasty). |
| 건강 영향 |
용도
개요
Trimethylamine N-oxide (TMAO) is a metabolite of choline, phosphatidylcholine, and L-carnitine . It is formed by gut microbiota-mediated metabolism of choline, phosphatidylcholine, and L-carnitine to TMA followed by oxidation of TMA by flavin-containing monooxygenase 3 (FMO3) in the liver. Dietary administration of TMAO (0.12% w/w) increases renal tubulointerstitial fibrosis, collagen deposition, and Smad3 phosphorylation in mice and increases aortic lesion area in atherosclerosis-prone ApoE-/- mice. Plasma levels of TMAO are elevated in patients with chronic kidney disease and decreased in patients with active, compared with inactive, ulcerative colitis. Elevated plasma levels of TMAO are associated with increased risk of cardiovascular disease.
용도
TrimethylamineN-oxide can be used:As a demetallationand decarbonylationreagent for organometallic compounds.To prepare azomethine ylide by reaction with lithium di-isopropylamide. This, in turn, may be reacted with simple alkenes to obtain corresponding pyrrolidines.To mediate the conversion of thiols to disulfides.
일반 설명
TrimethylamineN-oxide is an organic compound that belongs to the class of amine oxides. It is generally found in the tissues of marine organisms, wherein it helps protect them from harsh conditions like salinity, hydrostatic pressure, temperature, and high urea.